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Siesta Key House Rentals

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    ₹ 19,750 Average
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    Travellers to Siesta Key are booking December dates now. Secure your holiday home today, and have the perfect trip.
    142 Matching Rentals in Siesta KeyView all 881 rentals
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    Siesta Key Beach Condo, 2Br/2Ba Direct Beach Front1 / 20
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    2 Bedroom  2 Bath  Home in Siesta Village1 / 9
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Sandy Toes Siesta Key Florida  (6796)1 / 40
    (23)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    The Top  Location on Siesta Key - Gertrude's Village House1 / 50
    (30)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Waterfront
    • Patio
    • Wi-Fi
    • Cable/satellite TV
    • Balcony
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 May 2017
    My son booked this for his whole family. There were nine of us. The beach was just a half block away. It was beautiful with cool white sand, aqua water with warm rolling...
    Reviewed 25 September 2016
    Stayed there, the location is great. Everything in walking distance. The kitchen was supplied with everything you need. The positives beyond location varied, quiet, lots of room...
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    About this property
    A Gertrude Rentals property! Our Top Location! Leave the car behind. Richly furnished, perfectly nestled between the best beaches, shopping and dining on the Island, and sure to provide a combination of fun and rejuvenation you won't find in other getaways. Our living room, master bedroom and...
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    8 Steps to the Sand of Siestas Best Beach! - Old Man and the Sea Inn (3)1 / 42
    (21)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Wi-Fi
    • Cable/satellite TV
    • Waterfront
    • Patio
    • Washer
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 June 2018
    This place was amazing and could not have been more perfect to stay at for an extended vacation!!!! The unit was cozy and comfortable- it had everything that you could possibly...
    Reviewed 9 April 2018
    Great location! Only steps to beach access. Our unit was very clean and had all we needed for 2 people. The owner Daniel, was great to work with. He always replied to any...
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    About this property
    1BR (sleeps 4)- Perfect for travelers in search of uncomplicated seclusion. Brought to you by Gertrude Rentals! Located in the most “private” non-private beach neighborhood in Siesta Key, The Old Man and the Sea Inn can accommodate up to 24 guests and is a four unit Key West style home located...
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    Siesta Key, Florida 34242
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Palm Oasis - Relax in Comfort - 1 Month Minimum1 / 35
    (3)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Cable/satellite TV
    • Parking
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Wi-Fi
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 August 2018
    This was a family vacation that had been planned for months. We were unaware of the red tide until a few weeks before leaving for our trip. Not spending any time at what was...
    Reviewed 6 August 2018
    For a large family that has not been on vacation sometime, this was ideal. Walking distance to beach and to village as well as the amazing salt water pool. With 3 children under...
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    About this property
    The Palm Oasis is a 4-bed single family home with 2,000 sq. ft. located only 1 block away from Siesta Key Beach. This home is on one level and has all the amenities including a brand new salt-water pool which is the center of the backyard and a outdoor BBQ grill with a bar to enjoy your fabulous...
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    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    8 Steps to the Sand of Siestas Best Beach! - Old Man and the Sea Inn (2)1 / 43
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Washer
    • Grill
    • Air Conditioning
    • Waterfront
    • Balcony
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 February 2017
    What a wonderful stay! To start, Daniel is a very down-to-earth guy....ALWAYS responded promptly to phone calls and emails, and always was always courteous and complete in...
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    About this property
    1BR (sleeps 4)- Perfect for travelers in search of uncomplicated seclusion. Brought to you by Gertrude Rentals! Located in the most “private” non-private beach neighborhood in Siesta Key, The Old Man and the Sea Inn can accommodate up to 24 guests and is a four unit Key West style home located...
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    Siesta Key, Florida 34242
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Fido Friendly, Saltwater Pool, Only 1 mile to SK Beach, Close to the Village, Sh1 / 36
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    • Grill
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 September 2018
    The house was beautiful and very spacious. Great proximity to the beach and town center, and the kids loved Glebe Park, which was located a short walk down the street. We are...
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    About this property
    On Siesta Key we offer a high-end gorgeous, Fido friendly, Key West style 3 bedroom, 2.5 bath custom home. Desire a private saltwater heated pool while vacationing on Siesta Key? Then this vacation home will be your home away from home in tropical paradise…..just minutes from the village and...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Our Beach House1 / 17
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 June 2016
    Just back from our trip to Siesta Key with my Husband and 4 kids where we spent a lovely relaxed week at 'our beach house'. The house was fully equipped with everything a...
    Reviewed 8 May 2016
    "Our Beach house" on Siesta Key is a very comfortable, very clean and well taken care of property. It is in a quiet residential neighborhood with beach access just...
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    About this property
    OUR BEACH HOUSE (right behind the Cottage) (sleeps 6) Fully renovated in the late summer of 2013, this spacious, enchanting 3 bedroom/2 full baths ground-level property of 1,100sq/feet offers 1 King, 1 Queen and 2 Twin beds. You will be in close proximity to Siesta Beach and to Siesta Village. The...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Private Siesta Key House - Walk to Village & Beach - Heated Pool/Spa - No Stairs1 / 26
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Patio
    • Grill
    • Parking
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 January 2018
    I stayed over the winter holiday with my husband and other adult family.It was the perfect place to have a pleasant vacation. Close to all shops and downtown and also a short...
    Reviewed 5 September 2017
    What a beautiful modern and superbly located house. Immaculate and well maintained with everything you could possibly need. Our host Randy was excellent and answered our...
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    About this property
    Steps from the islands best restaurants, shops (in the Village area) and a short walk to the #1 beach in the USA! Great home with 2 car and 1 car private garages. Recently renovated including a screened in patio, hot tub and pool. Brand new appliances making this home a great place for monthly...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    8 Steps to Sand Path of Siesta's Best Beach! - Old Man and the Sea Inn (4)1 / 141
    (34)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Patio
    • Balcony
    • Washer
    • Cable/satellite TV
    • Waterfront
    • Wi-Fi
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 April 2018
    Great location. Steps away from beach, short walk to restaurants, free shuttles to the village. Clean condo.
    Reviewed 12 September 2017
    We stayed for a long weekend and couldn't have been more pleased. Their team has thought of everything- all you need to do is sit back and enjoy the amazing location and town...
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    About this property
    A Gertrude Rentals Property! Rated 'The World's Finest, Whitest Sand' at the Great International Sand Challenge. Perfect for travelers in search of uncomplicated seclusion. Residing in Siesta Keys most 'private' non-private beach neighborhood and just one marlin's length (5 steps) from yard to...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    Best in Siesta Village! 1.5 blocks to best beaches! - Casa Van Lopik (Canal)1 / 48
    (19)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • Grill
    • Cable/satellite TV
    • Balcony
    • Wi-Fi
    • Waterfront
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 April 2018
    This was the perfect place for eight fabulous women who were celebrating life. The beds were comfortable and the rooms spacious. The hot water plenty. It was a plus to have...
    Reviewed 6 March 2017
    Location is the best thing about this condo -- short walk to beach and to Siesta Key Village. Very convenient. Another big "pro" was Daniel. The owner is very...
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    About this property
    A Gertrude Rentals property! Large 3BR home perfectly located between the best beaches, shopping dining and entertainment on Siesta. Leave the car behind. After the beach, you could wander to town for fresh oysters and seafood, drinks, live music or ice cream, or just relax in a tropical garden...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • DVD Player
    • Patio
    • Air Conditioning
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Blue Mermaid is located less then 1/2 mile and less than a 10 minute stroll from Siesta Key Village. It's just a short hop from there (6 minutes or so) to the beach and the crystal sands and sparkling waters of the Gulf of Mexico on Siesta Key. Walk to our local gourmet grocery store for...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    Dog-Friendly Siesta Key Bungalow, Wifi, Adorable Cottage Close to Siesta Key Bea1 / 26
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 July 2017
    The house was nice, large size, comfortable, nice neighborhood close to the beaches, shopping and restaurants. Perfect for our family and dogs that we brought along on our...
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    About this property
    Totally renovated adorable Siesta Key bungalow nestled on a shaded street just minutes from Siesta Key beach and the village of Siesta Key with a variety of shops, restaurants and nightlife. Drive into the circular driveway and park your car under the covered parking to be away from the 10 minute...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Sarasota-Siesta Key Coastal Five Bedroom with Pool and Spa1 / 38
    (7)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 13 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Secure Parking
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 July 2018
    My family with extended family(total of 8) shared this large home with 5 bedrooms and we had plenty of room and at same time all had our privacy when we wanted it. The kitchen...
    Reviewed 1 April 2018
    Perfect location. Very close to the beach and downtown. The sliding kitchen windows opening to the counter bar in the screened in pool and hot tub area made eating in so fun...
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    About this property
    Excellent location at only 120 Yards To The Cool White Quartz Sand Of Siesta Beach! ?This Home Has Water Frontage, Pool, Hot Tub And BBQ Area Within A Screen Enclosure. There Is A Nice Sized Sunning Patio As Well With Views Down The Waterway. This Home Entertains Excellent Because The Pool Area Is...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 13
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    Top in Siesta Village at Best Beaches, Food & Entertainment! - Casa Van Lopik(J)1 / 49
    (17)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Waterfront
    • Balcony
    • Patio
    • Wi-Fi
    • Porch
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 June 2016
    While ratings and reviews are subject to personal taste, we found this property average at best. The positives included a nice size home, 3BR, 2BA, 2 blocks to the beach and...
    Reviewed 4 December 2015
    Our extended family of 7 with 4 adults and 3 children, stayed 4 nights at this property. We were thrilled to see that the grocery store was at the end of the street, as were all...
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    About this property
    Casa Van Lopik (jardin), our garden facing suite, is a large 3BR home. Brought to you by Gertrude Rentals! Perfectly located between the best beaches, shopping dining and entertainment on the island. It was named for our father who was a ships captain and sailed the world for 30 years but always...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    The Banyan - A Tropical Retreat in Paradise1 / 25
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • Grill
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 April 2018
    The Banyon is a remarkably beautiful and comfortable home. There are many private seating areas inside and out. The kitchen is fully equipped; the beds are very comfortable and...
    Reviewed 12 August 2017
    We loved this place! It was so private you felt like you were in your own world with the surrounding trees and tropical landscaping, yet close to most everything. The home was...
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    About this property
    View of Roberts Bay / Near Beaches / Great Shopping & Dining Get lost in the intoxicating relaxation of Siesta Key, in this luxurious private home. This tropical retreat is a single-family residence located at the end of a secluded dead end street in the opulent neighborhoods of northern Siesta...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    8 Steps to the Sand of Siestas Best Beach! - Old Man and the Sea Inn (1)1 / 47
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Balcony
    • Patio
    • Cable/satellite TV
    • Washer
    • Grill
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 July 2017
    Wonderful, relaxing, perfect location! On the quiet side of the key, easy close access to gorgeous crescent Beach. Easy quick walk to bus stop and local market, restaurants as...
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    About this property
    Old Man and the Sea Inn - 1 marlin to the sand! 2BR (sleeps 8). Brought to you by Gertrude Rentals! Perfect for travelers in search of uncomplicated seclusion. Located in the most “private” non-private beach neighborhood in Siesta Key, The Old Man and the Sea Inn can accommodate up to 24 guests...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Grill
    • Cable/satellite TV
    • Hot Tub
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Vacation on Siesta Key in this newly built 4 bedroom custom pool & spa home just a 600 ft. away from Shell Beach. Across the street and down the small drive is the gulf. Shell Beach has a very small sandy beach. It's on Big Pass and looks out to Lido Key. Here the water has a current so little...
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    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Patio
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You will Never Want to Leave this Upscale, Mid-Century Modern, 4 bedroom Pool home with Salt-Water Canal Views and Boat Dock on Siesta Key!!! This unique 1950's built, partially renovated, 4 bedroom, 3 full bath, 'Sarasota School of Architecture style' pool home is conveniently located...... only...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 6
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    Sandy Toes Siesta Key Florida   (6798)1 / 37
    (22)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Cable/satellite TV
    • Grill
    • Internet Access
    • Air Conditioning
    • Balcony
    • Washer
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 August 2018
    The house was nice and spacious along with a garage for your car. You are walking distance to restaurants and stores. And just a couple minute walk to white sand beach. They had...
    Reviewed 22 June 2018
    Had everything we needed. We appreciate Joe the maintenance guy checking on us. He was very helpful. Would stsy here again.
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    About this property
    A short stroll down a private road to the #1 Beach in the US. You will love the location - you are located in the Resorts of the SaraSea community and can walk to everything you might need or want... Grocery, restaurants, ice cream, pizza, sports rentals, drugstore or boat rental. You have your...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Lovely Siesta Key & Sarasota 3 bedroom home - Less than 3 miles to Siesta Key1 / 23
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Parking
    • Private Garden
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 July 2018
    There couldn't be a better house or location to stay at! It's only a short 10 minute drive from Turtle Beach and Siesta Key Beach and dead in the middle of everything that you'd...
    Reviewed 6 July 2017
    Perfect location for SIESTA KEY and THE Greater SARASOTA area. Shopping Centers, Restaurants , and The Beach are nearby. The Home is Great and Modern . Perfect for Families...
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    About this property
    From the beautifully landscaped front yard with the unique Rainbow Eucalyptus Tree to the spacious living areas, and the fantastic layout. As you enter this home, you will be impressed with the lovely touches this home has. It is tastefully updated, with recently installed new laminate floors, new...
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    Location Information
    Siesta Key, Florida 34231
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Luxury Siesta Key Four Bedroom,Five Bathroom Pool Home,180 Yards to Siesta Beach1 / 23
    (1)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Parking
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 August 2018
    Our family looked at several homes in Siesta Key and settled on this one due to its convenient location to the public beach entrance along with direct access to the canal. We...
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    About this property
    This Luxury Four Bedroom, Four and a Half Bathroom Home will leave you breathless as you enter. There are not many large rental homes, this close to Siesta Beach, that live like this home. Most Rentals by the beach have their living area 16 feet above the ground level and the pool below, which is...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 12
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    The Palm Island House - a Shangri-La! 1.5 blocks to Siesta Keys best beaches!1 / 34
    (14)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Waterfront
    • Balcony
    • Patio
    • Grill
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 July 2017
    Palm Island was a DREAM home for us!! My bf and I were the only ones that went on this vacation so we had the WHOLE house to ourselves!! It was amazing!! A perfect location...
    Reviewed 5 December 2015
    We loved this home! We had a large group and it never felt crowded. The house is lovely and very convenient to everything! Highly recommend this rental!
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    About this property
    Prominently featured in the 2013 and 2014 in NYJL House Tour Magazine and winner Spring of 2014 Top Auction Item. Brought to you by Gertrude Rentals! This Spanish revival home is located on Palm Island, the heart shaped island within the island of Siesta Key, just steps from the beach and one...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 14
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Hot Tub
    • Grill
    • Washer
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    In the middle of Siesta Key, tucked away on a shaded and quiet canopy lane is this bright and open air 3 bedroom 3 bath home less than one mile from the world famous Siesta Key beach. Plenty of space to spread out and enjoy your vacation, whether it be out on the pool deck, in the hot tub,...
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    NEW POOL! 3 Bed 2 Bath on Siesta Key  JULY 4TH  AVAILABLE  Walk to beach POOL1 / 18
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 March 2017
    This three bedroom two bath house is located on Siesta Key near the South Bridge. It has great beach access near several fun restaurants. The owners were very supportive and...
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    SIESTA SUN VILLAS - BRAND NEW POOL! 3 Bed 2 bath home on Siesta Key in Sarasota, FL Sleeps 6 people in beds. We are on the beautiful Island of Siesta Key. Walking distance to the number 1 beach in the USA. Full kitchen with oven, microwave, fridge, freezer, coffee maker & toaster. Large HDTV in...
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    8 Steps to Sand Path! Best Value on Siesta Key! - The Siesta Key Poor Boy1 / 44
    (1)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A Gertrude Rentals Property! Rated 'The World's Finest, Whitest Sand' at the Great International Sand Challenge! Just 8 steps from the yard to the sand of the beach path! The Poor-Boy unit is perfect for travellers in search of all the best the island of Siesta Key has to offer but on a limited...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    Stay on Siesta - SEA - ESTA HOUSE1 / 37
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Outdoor Dining Area
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 July 2017
    "Avenida Del Mare" was the perfect vacation rental for my family. The home is well appointed, all renovated with comfy beds and amazing bathrooms (love the rainshower...
    Reviewed 8 November 2016
    Convenient location, just a short stroll to beautiful Siesta Beach. Beach gear available, we left some sand toys for the kids.Very well equipped and beautifully decorated. All...
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    About this property
    This Siesta Key 3 Bedroom 2 Bath Home has been completely remodeled. This home is 1 block from the Famous Siesta Key Beach. Granite counter tops, to accent the new white cabinetry. Beautifully tiled bathrooms with all new hardware. All walls beautifully textured. Screened Lanai. Nice back yard. 1...
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Washer
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    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Grill
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spread out and enjoy this wonderfully appointed and tastefully decorated 3/2 home with private pool just steps away from powder white sands of Siesta Key Beach. Not far from Siesta Key village too where you can eat out in one of the many restaurants, have a drink and dance the night away, grab a...
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    The Shells Villa - Next to Beach & Village1 / 41
    (66)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Washer
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    • Waterfront
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    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 March 2018
    My family and I just returned from a week at the Shells Villa. We had a wonderful time there and hope to return in the future. Our group consisted of our three grown daughters...
    Reviewed 23 February 2018
    This villa is a medium-sized 3 story house with an Italian flair. Its a 5 minute , pleasant walk to the best beach in Sarasota, and just a few minutes more to a bustling, fun...
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    About this property
    3 Bedroom, 2.5 Bath Beach Villa (Sleeps 8-10) What makes us different than other homes you may be considering: · The Beach - The home is located on the ocean side of Beach Rd., so you just walk out your door and through our private access path. It’s literally 230 feet to Siesta Key Beach....
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    Luxury Condo Ground Floor Across the Street1 / 18
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 June 2018
    This condo was perfect. It had everything we needed to feel right at home. It was clean and well-maintained and the owner was very responsive. Beaches were within walking...
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    About this property
    Location! Location! Location! Walk out the door, across the street and onto the # 1 ranked beaches in America! This beautiful condo is on the ground floor, no steps, with a tropical enclosed lanai. It features 3 televisions, Tommy Bahama furnishings, a barbecue grill and high speed internet for...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Parking
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    • Private Outdoor Pool (Heated)
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    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Cascada is a uniquely configured private home featuring a heated pool/waterfall, 4 bedrooms, 4 bathrooms that sleeps 12, with 2 living areas and 2 kitchens and an almost unbelievable pool courtyard surrounded by lush gardens and a tall privacy wall enclosing the entire property. Each of the...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    Crescent Cottage1 / 38
    (6)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 November 2016
    Very cozy but good for 1-2 people. Walk to private beach and pool. Only thing - can be quite noisy at night with the bar across the street but otherwise great
    Reviewed 5 July 2016
    Old Florida vibe, love it. Short walk to beach! Perfect size place for my husband and I and our 60 lb lab. The private fenced grassy area in backyard was perfect for our dog...
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    About this property
    PET Friendly! This one bedroom and one bathroom beach bungalow is located 150 yards away from the beach. You can walk to restaurants, shops and a great pool area. Queen bed and a sleeper sofa make it possible to sleep four. Enjoy your morning coffee on your private screened porch or while you walk...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Siesta Key 3 Bdrm Private House with Heated Pool minutes from village and beach1 / 20
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • Grill
    • Private Outdoor Pool (Heated)
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    • Patio
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 August 2017
    I travelled to Florida with my fiancee for work and decided to extend our stay to enjoy a little R & R. We have used AirB&B in the past and we found this gorgeous home to...
    Reviewed 10 April 2017
    This is a beautiful home a short bike ride to Siesta Beach. It comfortably sleeps 8 on beds in 3 large rooms. 2 of the rooms have a glass door that opens up to the pool and...
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    About this property
    Surrounded by lush, tropical garden, our private villa is situated on a quiet cul-de-sac bordered on two sides by Lake Nancy. A birdwatchers and nature lovers delight! Sip your coffee in your PJs on the private, sunny terrace or enjoy a dip in the large heated pool. Walk for miles on the beach...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Siesta Key Beachfront 3 Bedroom Home, Sarasota1 / 33
    (4)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Washer
    • Cable/satellite TV
    • Internet Access
    • Grill
    • DVD Player
    • Air Conditioning
    • Patio
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    We had a wonderful stay at Siesta Keys Florida. David ‘s home is beautiful and well maintained. It does have several bests of steps if you have any kind of handicap. My husband...
    Reviewed 30 January 2018
    This is a very nice three story three bedroom house. The first floor includes two separate garages with the house entrance in between. The second floor includes a spacious...
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    About this property
    Description:Walk out the back door to the clean white sand of Siesta Key Beach. This home has private Siesta Key beach frontage on the prime section of beach, there are no homes between you and the beach. Nearly every room has a full view of the beach. The entire back of this house opens with...
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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    1 Block to the Beach on Siesta Key Vacation Rental Home with Swimming Pool1 / 24
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Cape Aqua! This single family vacation rental home on Siesta Key has 3 bedrooms 2 1/2 baths and pool. Located on the closest private street to America's #1 named.The two large double doors with decorative frosted glass welcome you into this spacious home. The floor plan offers a very...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Casa Ohana! Our newly constructed luxury cottage (completion date of June 2017) has all the amenities your large group [up to 12!!!] can fathom. The location is THE premier location in the heart of Siesta Key Village, just behind Gilligan's and Lelu's Coffee Shop! Inside you’ll enjoy...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    Casa Junonia - 4BR/3BA Private Home, Heated Pool, Private Cabana, Walk to Beach1 / 39
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
    • Washer
    • Cable/satellite TV
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    • Patio
    • Balcony
    • Private Outdoor Pool (Heated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    This home was absolutely stunning and beautifully furnished throughout. Only a couple of minutes walk to the beach. The private pool was a real bonus. The free trolley service...
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    About this property
    Welcome to Casa Junonia! Our newly constructed luxury cottage has all the amenities your large group [up to 12!!!] can fathom. Inside you’ll enjoy contemporary porcelain wood style flooring throughout the entire three-story building, an elevator to access each landing from the ground floor,...
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    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    PRISTINE SIESTA KEY VILLAGE HOME1 / 28
    (5)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Air Conditioning
    • DVD Player
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Hot Tub
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 August 2017
    Beautiful accommodation, superbly located and very well equipped. The new swimming pool is the jewel in the crown, and Cydney was a pleasure to deal with. We would hope to go back.
    Reviewed 20 July 2017
    I can't say enough wonderful comments about this house. It's charming, comfortable, gorgeous, adorable, lovely....I could go on and on. My family has enjoyed walking to...
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    About this property
    Hidden behind a contemporary privacy wall, enter into our front yard oasis. The perfect setting for tanning, dining and entertaining alongside the waterfall feature. Extensive renos offering a stunning gourmet kitchen, updated bathrooms, flat screen tv's in bedrooms and the most appealing Lanai...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Children's Pool
    • Balcony
    • Washer
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    • Hot Tub
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Quiet and serene, but close to local attractions, you will love this large 4 bedroom, family friendly home with 2 kitchens, new appliances, modern furnishings, and beach buggy with all the gear! Separate living areas can accommodate one large family or two smaller ones. Each living area has its...
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    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located just over the bridge from Siesta Key and minutes away from Sarasota’s thriving dining and arts districts, our sunny and cheerful tiny house, Red Lifeguard Stand, sleeps four. With the convenience of a hotel, the comfort of a vacation home, and the cool factor of a tiny house, make staying...
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    Location Information
    Siesta Key, Florida 34231
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Casita Playa- Playful 2BR, Private Beach Access, Communal Heated Pool [Sleeps 4]1 / 22
    (1)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 May 2018
    Overall went very well, do note that the whole backyard and Landry area are not exclusive to your rental unless you rent the whole home. Not a deal breaker at all, as we will...
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    About this property
    Welcome to Casita Playa of Playa y Blanca. This single level (2 BR/1BA - Master BR/1 Queen & 2nd BR/2 twins -sleeps 4) vacation home features private, gated beach access, a sparkling clean hot tub in a private, lush setting, a communal heated swimming pool with plenty of pool furniture and a...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Villa Vista Mare - Luxurious 3BD/3BA Beachfront, Heated Pool1 / 25
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • Washer
    • Cable/satellite TV
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    • Ocean Views
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 April 2017
    Great spot right across from the beach - which is about the best beach you'll ever see. Pool offers a nice change of pace. Panaramic view from the entire living area and the...
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    About this property
    Welcome to Villa Vista Mare! This beautiful and luxurious 3 bedroom, 3 bathroom, heated pool, townhome boasts the best views of the world famous No. 1 Siesta Key Beach Access! With absolutely unobstructed views, this home is part of only a handful of private residences that can claim such gorgeous...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    6 Bedroom 4 Bathroom house   New pool  Siesta Key Florida  Walk to the Beach1 / 32
    (1)Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 July 2017
    Excellent all-around. Owner was very responsive and friendly. House was clean and in great condition upon arrival, and even bigger than expected! To top it all off, it was...
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    About this property
    Siesta Sun Villa Our home is one large house that has a 3 bed 2 bath unit. A 2 bed 1 bath unit and a 1 bed 1 bath unit. All with connecting doors so you can rent the whole house to sleep 12 guests all in beds. It is perfect for large familys, Weddings and reunions. Private back yard, Overlooking a...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    Beach House Bungalow #11 / 9
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Terrace
    • Parking
    • Balcony
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 April 2015
    Very nice accommodations. Gulf side of Midnight Pass. Five minute walk to beach. Quiet Crescent Beach.
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    About this property
    Located near the South Village of Siesta Key. This newly updated 2 bedroom duplex has it all. A new dipping pool to cool off the hot summer days, along with a BBQ and fire pit for the winter. Lots of space, all new furnishings throughout the home, the large eat in kitchen has plenty of room for...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • Grill
    • Wi-Fi
    • Private Outdoor Pool (Heated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Casa Coquina! Our newest luxury cottage has all the amenities your large group [up to 12!!!] can fathom. Inside you’ll enjoy contemporary porcelain wood style flooring throughout the entire three-story building, an elevator to access each landing from the ground floor, gorgeous and...
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    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 14
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    The Coral Reef and Star Fish Casitas are two separate units which can be uniquely configured to create Villa Dom Bisa, features its own brand new, private heated pool with “sun shelf” and a three minute walk to the Nation’s finest beach [no major streets to cross]. Please Note: These units [Coral...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Welcome to Casita Mar of Sol y Mar. This single level (2 Bedroom / 1 Bathroom - Master BR/1 Queen & 2nd BR/2 twins -sleeps 4) vacation home features private, gated beach access, a sparkling clean hot tub in a private, lush setting, a communal heated swimming pool with plenty of pool furniture and a...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Stay on Siesta - Beach Rd -Step out to the Sand1 / 37
    (6)Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Ocean Views
    • Air Conditioning
    • Patio
    • Waterfront
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 February 2017
    We have visited siesta key many times and loved the location and atmosphere of this condo. It was clean and newly remodeled. The staff was friendly and helpful. Great place to...
    Reviewed 7 February 2017
    Looking forward to coming back. Perfect location for our stay. Nice people and accommodation . Great rates for what you get
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    About this property
    3 bedroom on Beach Rd. with Gulf view This updated townhouse is a one of a kind property. Three bedrooms with king, queen, 2 double beds and living room sleeper sofa. This is a step out to the sand property just north of Siesta Key Beach. Walk to Siesta Village. Views of the Gulf from almost every...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    Welcome to The Canopy Cottage! Nestled deep into a beautifully canopied tree neighborhood, this lovely 4 bedroom, 3 bathroom home features a heated pool and spa under a screened in lanai just a few minutes from Siesta Key's #1 Beach! Take a moment to breathe in the peace and serenity under the...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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