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Holiday Rentals in Siesta Key

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    ₹ 11,519 Average
    ₹ 65,000+
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    Travellers to Siesta Key are booking July dates now. Secure your holiday home today, and have the perfect trip.
    1 / 12
    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    1 / 9
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 24
    5 of 5 bubbles (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 24
    4.5 of 5 bubbles (7) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Grill
    • Satellite TV
    • Balcony
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    • Ocean Views
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    • x
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    About this property
    Split floor plan with each bedroom having a private full bath, tv and access to the lanai. New bathroom floors installed in October 2016 and new tile in master bath/tub. New king size mattress as of May 2017. Secure Wi-fi Relaxing lanai with couch, two chairs and three end tables to enjoy a book... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 bubbles Reviewed 1 week ago
    We absolutely loved our rental condo in the Crescent Arms community. The condo was clean, comfortable, and fully stocked with all the basic necessities. The owner provides a fully...
    5 of 5 bubbles Reviewed 2 weeks ago
    Nothing beats this condo--the décor, the comfortable beds, the beautiful beach view, the location! Everything we could ever imagine was here in this condo and surrounding areas...
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    1 / 24
    5 of 5 bubbles (5) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Wi-Fi
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    • Waterfront
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    • Ocean Views
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    • Child-friendly
    • x
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    About this property
    - Expansive, panoramic gulf view from every room of this 6th floor condo. -Crescent Arms is a quiet, beach front, high rise condominium building that is ideally located for maximum fun and relaxation. -Right on the beach with lounge chairs provided. As close as you can get to the Gulf without... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 bubbles Reviewed 1 March 2017
    We really enjoyed our stay. The unit has been thoughtfully equipped with dishes, containers and beach items. The space was perfect for my husband and I to share with another...
    5 of 5 bubbles Reviewed 13 February 2017
    Second time we have stayed in this unit. Perfect for us and everything continues to be first class. Unit is well appointed and VERY clean. Impressed with the new carports...
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    1 / 24
    5 of 5 bubbles (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
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    About this property
    I have tried to make this apartment as comfortable as your own home only at the beach. This unit has two bedrooms and two baths. It can accommodate six people with a king bed and two double beds. There are plenty of closet and dresser space, a fully-equipped kitchen, color TV's, VCR and/or DVD and... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 bubbles Reviewed 28 January 2017
    The condo was everything and more in ad. Very close to the beach. I plan on booking again next year. Rooms were spacious, bedding was comfortable and the kitchen was was awesome...
    5 of 5 bubbles Reviewed 9 August 2016
    This condo was very nice. Steps away from the gorgeous white sandy beach and convenient to shopping and restaurants. We were very impressed with not only the condition of the...
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    1 / 33
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Unit #100 was renovated in 2016! This condo is a 2 bedroom, 2 bath garden view unit located in the quiet area of Jamaica Royale Condominiums! Jamaica Royale is located directly on the Gulf of Mexico along the white sands of world-famous Siesta Key Beach in Sarasota, Florida. A barrier island on... View all property information
    Location Information
    Siesta Key, Florida 34242
    1 / 22
    4.5 of 5 bubbles (4) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Wi-Fi
    • Air Conditioning
    • Washer
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    • Ocean Views
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    LAST MINUTE DEALS NOW AVAILABLE AUGUST - JANUARY at our luxurious Villa#4 (on Crystal Sands, 6300 Midnight Pass Rd, Sarasota, Florida) - sleeps 6 and includes everything your family needs for your stay at the #1 beach in the USA. This Villa has easy access to the beach without leaving the property... View all property information
    Location Information
    Siesta Key, Florida 34242
    4 of 5 bubbles Reviewed 7 September 2016
    The two bedroom cottage is nice. Not luxury, but absolutely adequate. The beach is spectacular. The biggest drawback from the rental was the lack of any sort of outdoor...
    4 of 5 bubbles Reviewed 30 November 2015
    Villa was nice. It had all of the amenities needed for a comfortable stay. It was clean. It was only a short walk to the beach. It was close to town center.
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    1 / 30
    5 of 5 bubbles (14) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Balcony
    • Air Conditioning
    • DVD Player
    • Grill
    • Satellite TV
    • Washer
    • Secure Parking
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    “Pristine sand, blue skies - 'Number 1 Beach'” <BR><BR>The Best Thing to Come Home to after a Day on the Beach Is...<BR> ...a vacation home as comfortable as your own home. <BR><BR>Just a walk across the street to Siesta Key's world famous #1 Beach.<BR><BR> This split-level townhouse, has 2... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 bubbles Reviewed 5 weeks ago
    The town home was in the perfect location, just a three minute walk to the the beautiful beach of Siesta Key. The owners had every possible beach amenity you could ask for, beach...
    5 of 5 bubbles Reviewed 5 April 2017
    Beautiful townhouse located across from Siesta Beach. Great location! The unit was equipped with everything needed for a wonderful vacation. Owner Michelle was very warm and...
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    1 / 31
    3.5 of 5 bubbles (2) Average
    2 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Balcony
    • Ocean Views
    • Patio
    • Terrace
    • Waterfront
    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Great first impressions are evident from the moment you enter this lovely condo and enjoy the breathtaking ocean views from our private oversized lanai. We know you'll adore our comfortably decorated oceanfront condo and have the relaxing vacation you've been dreaming of. This unit unfolds as you... View all property information
    Location Information
    Siesta Key, Florida 34242
    3 of 5 bubbles Reviewed 12 February 2017
    This condo is just feet away from waves slapping against the shore. It is well stocked with everything you would need while vacationing. It could use a deep cleaning, But...
    4 of 5 bubbles Reviewed 31 January 2017
    Great week in Siesta Key as always! Thanks! Will visit again in the near future. Would definitely recommend the Key!
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    1 / 17
    5 of 5 bubbles (10) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Grill
    • Wi-Fi
    • Parking
    • Private Garden
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    This luxurious one story townhouse was newly renovated and has its own private access to the #1 beach in the US merely steps away from the front door. It boasts all the luxury you'd expect from a beach house! Modern kitchen, contemporary bathroom with walk in rain shower, luxurious bedroom and... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 bubbles Reviewed 4 February 2017
    Very impressive space and proximity to everything that was important to me. I felt welcomed from the first moment I entered this beautifully appointed beach condo. Steps away are...
    5 of 5 bubbles Reviewed 5 November 2016
    Very well located property. Fixtures and fittings of a high standard. Near all amenities. Definitely to be recommended
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    1 / 17
    5 of 5 bubbles (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • Parking
    • Washer
    • Internet Access
    • Balcony
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    • Terrace
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Just across the street from sun kissed Siesta Beach, acclaimed as the Number One Beach in the United States. Noted for “The Whitest sand in the world”, set your sites for your next vacation at Our House At the Beach! Enjoy spectacular sunsets and Gulf views from 2 over-sized balconies in this... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 bubbles Reviewed 6 days ago
    This is our 3rd time renting this beautiful condo. Diane could not be more accomodating and welcoming. The unit was spotless and stocked with all the basics. The location is...
    5 of 5 bubbles Reviewed 1 week ago
    We just got back from a week full of fun. The condo was beautiful with a wonderful view. It was our first time to Siesta Key, our granddaughters love it as much as we did!! When...
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    1 / 24
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Satellite TV
    • Air Conditioning
    • Balcony
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    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    ***ONLY ONE WEEK AVAILABLE UNTIL AUGUST 2017*** Steps to Siesta Beach and a Gorgeous Condo, Bring the Entire Family! #1 Beach in the US (2017) : Siesta Key is the United States #1 Beach Boasting Miles of Powder White Sand and a Charming Village loaded Shopping, Dining and Ice Cream :) This 2... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 bubbles Reviewed 4 weeks ago
    I have to admit I wasn't expecting our stay to be anything special. We had been to Sarasota and Siesta Key before and stayed in a nice hotel. I wanted to do that again, but my...
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    1 / 19
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Wi-Fi
    • Patio
    • DVD Player
    • Air Conditioning
    • Secure Parking
    • Grill
    • Washer
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Jamaica Royale Condominiums are located directly on the Gulf of Mexico along the white sands of world-famous Siesta Key Beach in Sarasota, Florida. A barrier island on Florida’s West coast, considered the most beautiful of Florida’s barrier islands, Siesta Key’s beach boasts “the world’s finest... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 bubbles Reviewed 7 March 2017
    Truly awesome experience. Quiet garden sid. A home away from home. Nice sheets & new towels. Everything we needed. Very responsive & helpful owner Beach side, 3 pools, helpful...
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    1 / 31
    4.5 of 5 bubbles (11) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Air Conditioning
    • Patio
    • Waterfront
    • Satellite TV
    • Private Outdoor...
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    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Welcome to our Condo in Siesta Key ! Located on the inter-coastal Waterway and a short walk to the whitest sand and the # 1 beach in the USA. This 1 bedroom Condo is a great retreat for anyone looking for a beautiful Island getaway! Our condo is on the 2nd floor (sleeps 4) We are on Siesta... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 bubbles Reviewed 2 February 2017
    Thank you for allowing me to rent your beach themed condo. It was more than my expectations. Newly remodeled and furnished. The backyard is flat and offers lots of chaise...
    5 of 5 bubbles Reviewed 30 August 2016
    Thank you so much for the chance to stay in your condo. It was clean and had everything we needed for our 5 day stay. Siesta Key is a beautiful beach and we can't wait to...
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    1 / 12
    5 of 5 bubbles (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Grill
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    • Air Conditioning
    • Satellite TV
    • Porch
    • Patio
    • DVD Player
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Jamaica Royale condo #92 on the #1 beach in the USA, This 2 bedroom 2 bath garden view unit is located in the garden area of our beautifully landscaped property. This unit is on the first floor and reserved parking is right outside the front door. This unit has a full size washer and dryer for... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 bubbles Reviewed 29 December 2014
    Just returned from our first trip to Siesta Key. Had my wife and two adult sons with us. Unit was very clean and ready upon our arrival. Beds were extremely comfortable...
    5 of 5 bubbles Reviewed 11 May 2014
    My husband and I stayed here with our five children. This place was perfect for us. It was clean and comfortable. I was surprised to find every single thing I needed in the...
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    1 / 18
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Adorable, quiet, and clean home away from home on the South end of Siesta Key. Only a short five minute walk to private beach at access 13, a more secluded area and away from the public beaches. The king sized bed is extra comfortable with a new flat screened tv, dressers, nightstands, fan, and... View all property information
    Location Information
    Siesta Key, Florida 34242
    1 / 37
    5 of 5 bubbles (3) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Waterfront
    • Air Conditioning
    • DVD Player
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    • Hot Tub
    • Private Outdoor...
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 bubbles Reviewed 23 June 2016
    For our first time in Florida we have been looking for the perfect house to rent and we couldn't have made a better choice!! We were 5 in total and the house is just perfect...
    5 of 5 bubbles Reviewed 18 April 2016
    We have been in search of the 'perfect' family holiday since our twin daughters were born 6 years ago, and we can finally say we have found it!! We have just returned from an 11...
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    1 / 24
    5 of 5 bubbles (42) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Very clean, bright, airy 1 bedroom, single- story cottage. Ebb Tide #1 offers all you need for a wonderful vacation at the beach. - Beautiful, large, heated, saltwater pool. - Private, gated access to world renowned Crescent Beach, famous for its powdery, white, quartz sand and gorgeous sunsets! -... View all property information
    Location Information
    Siesta Key, Florida 34242
    3 of 5 bubbles Reviewed 5 weeks ago
    EBB TIDE #1 is perfect for gated access to the award winning white sand beach that's literally a 3 minute walk away. There's also a gated, heated pool available for use on the way...
    5 of 5 bubbles Reviewed 8 January 2017
    Ebb Tide #1 is a great little cottage for a couple or a couple with a small child. It is in my favorite area of Siesta Key and is a short walk to restaurants, shops, the pool and...
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    1 / 11
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Private Garden
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    • Pet-friendly
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    • x
    • Smoking allowed
    • x
    About this property
    Our 3 Bed 2 bath home is on the Gulf coast of Florida. Sleeps 6 in beds. We are on the Island of Siesta Key. The number 1 beach in the USA. Great location, a short walk to everything. Lots of restatuants, bars, shops, And the beach It has a private back yard overlooking a small pond. The home is... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 bubbles 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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    1 / 27
    4.5 of 5 bubbles (21) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Available APRIL 2018 GOING FAST-BOOK NOW! FALL SPECIALS - BOOK NOW! One Bedroom with TWO (2) BATHROOMS! PRIVACY of-- 2ND floor END unit! No one walking past door all day and night!! TWO (2) OUTDOOR common areas -BALCONY for morning coffee SHADED by Palm... View all property information
    Location Information
    Siesta Key, Florida 34242
    4 of 5 bubbles Reviewed 24 March 2017
    This unit is located just south of Highway 72 on Midnight Pass Road. It's walking distance to some nice restaurants and shopping. The condo itself is located on the second floor...
    5 of 5 bubbles Reviewed 9 February 2017
    The location of the condo couldn't be more convenient--near the beach, with restaurants (don't miss the one offering German food and bakery), a drug store, a grocery story, and...
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    1 / 14
    4.5 of 5 bubbles (18) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Newly furnished, newly renovated 2BR (one king size & 2 single beds) + convertible sofa bed, 2 Bathrooms 2nd floor condo (sleeps 4-6), and with all the amenities of a comfortable home. Located in White Sands Village with 7 acres of lush tropical surroundings, our air-conditioned condo offers two... View all property information
    Location Information
    Siesta Key, Florida 34242
    3 of 5 bubbles Reviewed 21 April 2017
    We stayed at the apartment for 2 weeks during Easter holidays with our 2 girls (aged 1 and 4). We had a lovely holiday. We felt there was some positives and negatives with the...
    5 of 5 bubbles Reviewed 31 January 2017
    Everything about this condo was fantastic! The beautiful two bedroom/ two bathroom, spacious, quiet, the large swimming pool and two gas grills which we used often, we will...
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    1 / 40
    4.5 of 5 bubbles (5) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Ocean Views
    • Washer
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    • Satellite TV
    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Leave your worries behind... If you're looking for a relaxing beachfront condo that's been totally remodeled you've come to the right place. Our ground-level oceanfront condo is the perfect place to unwind unplug and recharge the batteries. Fisherman's Cove is a quiet and relaxed complex on the... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 bubbles Reviewed 5 September 2016
    If you are an avid beach goer, you're average rental experience probably includes lifting and lugging a million beach accessories and toys (if you have kids) for what seems like a...
    5 of 5 bubbles Reviewed 16 August 2016
    This unit is literally 200 steps to the water. Fantastic ocean front appeal and it had literally the best master suite mattress that we've had in years for a vacation property...
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    1 / 16
    4.5 of 5 bubbles (9) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    GREAT Value !!! MVPROPERTIES AT SIESTA KEY Recently renovated and very conveniently located duplex villas at beautiful Crescent Beach on Siesta Key. We have (2) 2 bedroom 1 bath apartments. Each apartment sleeps up to 5 persons. Rent 1 apartment or both. The units are bright, updated, very clean... View all property information
    Location Information
    Siesta Key, Florida 34242
    4 of 5 bubbles Reviewed 15 August 2015
    Ideally situated 2 minutes from the beach, restaurants,shops and 7 eleven. Very clean accommodation has everything that you need but does need a little refurb ie furniture...
    5 of 5 bubbles Reviewed 10 August 2015
    We had a great stay here. The owners were VERY pleasant. Everything that you would need for a beach vacation with a toddler was included and readily available. The place was...
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    1 / 10
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    2 bedroom/2 bath top-floor end unit steps from the #1 beach in the County and #3 in the World (voted by Trip Advisor Feb. 2016). Sarasota County spent almost $30 million renovating all of the public facilities - new concession, bathrooms, SunDeck Restaurant, playground equipment and picnic... View all property information
    Location Information
    Siesta Key, Florida 34242
    1 / 25
    5 of 5 bubbles (6) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Air Conditioning
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    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
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    About this property
    Beach and water front on Gulf Of Mexico. A block from Siesta Key Village for lite and fine dinning, fun, shopping and nightlife. Two Master Suite King Bedrooms with Master Bath for each. Sauna, four Mexican tiled decks with panoramic views of the Gulf and beaches. Fishing Pier. Leather, stone... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 bubbles Reviewed 28 March 2017
    The location is fabulous! A wonderful view with so much privacy as well as close to great shopping in the village shops. We should also complement the great food served at the...
    5 of 5 bubbles Reviewed 6 January 2016
    THE best spot in the US to see the sunset over the Gulf of Mexico! A starting point for a long beach walk on Siesta Key's white sands as it is just steps to the beach. A short...
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    1 / 40
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Gorgeous 2 bedroom condo across the street from #1 voted beach Siesta Key. We have everything for your home away from home. The beauty of Sarasota will get your attention on your first visit. Siesta Beach is one of the top ranked beaches in the world! Its fine quartz white sand has a silky,... View all property information
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    Siesta Key, Florida 34242
    1 / 19
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Siesta Key Vacation Condo all new, and an easy walk over to the #1 Beach in America. Complex has Pool, Covered Parking, Clubhouse, Marina. Two Bedrooms, Two full Bathrooms, Completely renovated Kitchen, all new Tile flooring throughout Condo, back Lanai catches glimpse of Sunsets, and front... View all property information
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    Siesta Key, Florida 34242
    5 of 5 bubbles Reviewed 28 August 2016
    we stayed here in mid July 2016, Sue was very helpful on answering all my questions and I had a few .she's a very nice professional lady and that makes easier to communicate .the...
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    1 / 10
    4.5 of 5 bubbles (2) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Half Mile to the Beach This recently remodeled Beach house has both inside and outside living spaces. There is a combination Kitchen/dining/living area with windows on every wall allowing in loads of the wonderful Florida natural light. The kitchen is all white with stainless appliances and... View all property information
    Location Information
    Siesta Key, Florida 34242
    4 of 5 bubbles Reviewed 3 February 2017
    It was like home away from home. Glad we were able to take our dog and cottage was fully equipped with everything necessary for our stay.
    5 of 5 bubbles Reviewed 31 May 2016
    The space seems bigger than the pictures lead it on to be which is a plus! We really enjoyed our stay as the master bedroom was very spacious. We visit Siesta Key almost every...
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    1 / 19
    5 of 5 bubbles (7) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Pet-friendly
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    About this property
    This vacation rental offers a full view of Siesta Key Beach/ The Gulf upon entry; relax and enjoy from your lanai or master bedroom. The property has been newly transformed to accommodate our guests best welcome to Siesta. From the comfort of the home décor to your fully stocked kitchen: cookware,... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 bubbles Reviewed 13 March 2017
    The lanai was our favorite space because of the wide view of the beach and ocean. We even saw dolphins during breakfast one day and twice at lunch time!!! With the beach being...
    5 of 5 bubbles Reviewed 6 March 2015
    What an awesome condo. Unit was furnished beautifully and very up to date. Couldn't have has asked for more. Location was great. Great views of the ocean and less than 20 minute...
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    1 / 21
    5 of 5 bubbles (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Our 2nd floor, end unit condo was completely renovated over the winter of 2012– 2013. The floor plan was opened up to provide a nice airy feel and to enjoy the water view. All furniture, flooring and fixtures are new. The entry hall has a bench to store your flip-flops and other beach gear and... View all property information
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    Siesta Key, Florida 34242
    5 of 5 bubbles Reviewed 17 April 2017
    This is a wonderful 2-bedroom, 2 bath condo overlooking the bay. The nicely decorated lanai is a great place to relax with your morning coffee. The kitchen is wonderfully equipped...
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    1 / 42
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    About this property
    Cozy Cove is a small condominium complex of six total units, located on the south end of Siesta Key in Sarasota, Florida. The complex sits on the Gulf side of the Key along Blind Pass. The complex itself is on the inlet with a dock at the back of the property where you will often see fish jump and... View all property information
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    Siesta Key, Florida 34242
    1 / 40
    5 of 5 bubbles (9) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    About this property
    -Accommodations: Condo, 2 Bedrooms + Convertible Bed, 2 Baths (Sleeps 4-6) -Expansive, panoramic gulf view from every room of this 7th (top) floor condo. -Crescent Arms is a quiet, beach front, high rise condominium building that is ideally located for maximum fun and relaxation. -Right on the... View all property information
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    Siesta Key, Florida 34242
    5 of 5 bubbles Reviewed 2 March 2017
    The condo was clean, cozy and well-equipped. The beach sand is almost pure white quartz crystal and it feels like powder or flour on your feet. I couldn’t believe that it never...
    5 of 5 bubbles Reviewed 1 March 2017
    Stunning views, comfortable, and exceptionally clean property. Pools had lots of room for kids and adults. Unit was more than accommodating for a family of 4. Thank you so very...
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    1 / 42
    3 of 5 bubbles (2) Average
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Waterfront
    • Patio
    • Porch
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    YOUR PRIVATE GETAWAY ON THE KEY ASK ABOUT OUR SUMMER SPECIALS!!!!!!!!! Does not include Weekends or Holidays!!! Looking to relax, Flip Flop Cottages is the place to be for a quaint and private vacation in Siesta Key, Florida. Come and stay at our serene environment and enjoy and visit all the... View all property information
    Location Information
    Siesta Key, Florida 34242
    4 of 5 bubbles Reviewed 23 May 2015
    Nice overall for what we needed-good location for beach hoppers like ourselves. Could get to Lido beach and turn around and go to Venice beach with still many beaches between...
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    1 / 12
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    • x
    About this property
    Siesta Sun Villas Sand dollar villa is a 2 Bedroom 1 bathroom. A short walk to the number 1 beach in the USA. Our villa is fully furnished and ready to start your vaction Full Kitchen. Free wifi. Free parking. Located within walking distance to almost everything. The beach is just down the street.... View all property information
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    Siesta Key, Florida 34242
    1 / 17
    5 of 5 bubbles (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    Island House Beach Resort, Siesta key, Crescent Beach!New improvements in 2014! 60" tv and entertainment center ( netflix reaady), new ac unit, new dishwasher and ceiling fans in bedrooms. Professionally decorated in October 2011. This large 2 bedrooms, 2 bath unit is approx 1000 sq. ft. It has a... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 bubbles Reviewed 23 May 2015
    A wonderful place to stay! Clean and updated. King bed was very comfortable. Problems with the wifi is my only complaint. Wifi is available, but not dependable. Couldn't...
    5 of 5 bubbles Reviewed 24 June 2014
    Our stay was fantastic, very clean, quiet ... the spectacular beaches, pool spotlessly clean condo. We were in town .. 39 is very comfortable and cozy, had everything we needed...
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    1 / 18
    4.5 of 5 bubbles (2) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    About this property
    2 bedroom, 2 bathroom on 4th floor, lovely view...<BR><BR>Enjoy the best that beautiful Bay Oaks has to offer. This 4th floor corner condo has been remodeled. With 1101 square feet, this 2BR/2BA condo has a living room, dining room, kitchen and screened lanai where you can enjoy morning coffee or... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 bubbles Reviewed 27 March 2017
    The location is very nice and close to everything from the beach to the shops and restaurants with free rides to all, if needed. The condo is very clean and has many extras to...
    4 of 5 bubbles Reviewed 24 March 2017
    Nice clean unit with screened patio. Everything needed for a comfortable vacation...washer/dryer, beach towels,chairs even a fish pole and tackle for hubby! Very friendly condo...
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    1 / 28
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    This gorgeous townhouse is located 2 short blocks from Siesta Key Village and a block from the white sands of Siesta Key Beach. VIew the gorgeous sunset and Gulf and beach views from the Master Bedroom on the top level. This unit is immaculately appointed and will make your Siesta Key Vacation... View all property information
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    Siesta Key, Florida 34242
    1 / 21
    5 of 5 bubbles (5) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • x
    • ?
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    About this property
    Villa Palma is a stand-alone single story villa located in the beautiful Polynesian Gardens community, on the beautiful barrier island of Siesta Key, Fl. The home is chic and hip in its mid-century modern beach cottage decor and style. The newly renovated kitchen is sleek in design and... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 bubbles Reviewed 8 November 2016
    We had a great time at Villa Palma. The villa is very clean and it has everything you need for your stay. It is very close to the beach, we ended up only going to the beach. The...
    5 of 5 bubbles Reviewed 11 August 2016
    What a LOVELY place to stay!!! Sean was flexible, attentive and accommodating, and there was even fresh fruit, sparkling water and a personalized welcome sign waiting on the...
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    1 / 30
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
    About this property
    If you have a boat, bring it along, because this 4 bedroom, two bath pet friendly home has it's own boat dock!! Want to hit the beach? No problem because you're a short walk from access #5 to Siesta Key Beach, voted #1 beach in the USA. Just steps from Siesta Key village where you can dine in one... View all property information
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    Siesta Key, Florida 34242
    1 / 26
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
    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... View all property information
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    Siesta Key, Florida 34242
    1 / 15
    4.5 of 5 bubbles (2) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    About this property
    Island House Beach Resort, Siesta Key Florida, Crescent Beach - This large 2 bedrooms, 2 bath villa is approx. 1000 sq. ft. It has a large living area, dining area, fully equipped kitchen, screened lanai, covered parking, central heat/air, 3 tvs, dvd, free wi-fi in unit, washer/dryer. It has a king... View all property information
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    Siesta Key, Florida 34242
    1 / 19
    5 of 5 bubbles (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Satellite TV
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    • x
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    • x
    About this property
    Island House Beach Resort! Crescent Beach, Siesta Key Florida. This beautifully maintained complex is located on the widest part of one of the best beaches in Florida. This condos offers a view of the palm trees, white sand and turquoise waters of the Gulf of Mexico. The view is picturesque and the... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 bubbles Reviewed 1 October 2013
    Stayed in 9N and loved it. Could not say enough good things. But beware: the mattress beds are in need of replacing.
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    1 / 18
    5 of 5 bubbles (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    Island House Beach Resort - Crescent Beach, Siesta Key Florida. 2nd Floor unit, 2 bedrooms, 2 baths. This beautifully maintained complex is located on one of the best beaches in Florida. This condo offers a view of palm trees, white sand and the turquoise waters of the Gulf of Mexico. The view is... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 bubbles Reviewed 3 August 2012
    4S was an awesome apartment/condo. It was on the second floor right off the beach . Very clean and stocked with everything you can think of that you would need to stay for a...
    5 of 5 bubbles Reviewed 13 June 2012
    I had an impossible time finding a beachfront condo to rent for just two nights. We would have loved to stay a week but we didn't have the time this trip. All I got from other...
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    1 / 41
    5 of 5 bubbles (61) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • x
    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.... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 bubbles Reviewed 4 weeks ago
    Perfect property for our annual family vacation. Close proximity to the Village and easy access to the beach. Lots of sand toys for the little ones and nice beach chairs for the...
    5 of 5 bubbles Reviewed 11 April 2017
    We've been coming to Siesta Key for several years and this was our first time staying at The Shells Villa. What a fantastic vacation home. The entire place was very clean...
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    1 / 20
    4.5 of 5 bubbles (12) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Island House Beach Resort! Crescent Beach, Siesta key Florida. This beautifully maintained complex is located on the widest part of one of the best beaches in central florida. This unit is one bedroom and 2 full baths. It is 1300 sq. ft, King, queen sleeper, Central heat/ac. The unit has large... View all property information
    Location Information
    Siesta Key, Florida 34242
    4 of 5 bubbles Reviewed 3 September 2012
    My immediate and extended family have been coming to Siesta Key for our family/friends vacation for over 22 years! We we first came years ago we fell in love with another resort...
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    1 / 18
    5 of 5 bubbles (5) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    • x
    About this property
    Island House Beach Resort!! Siesta Key Florida. This 2 bedrooms, 2 bath unit is 1300 sq. ft. and is located on one the finest beaches in Florida. It has a large living area, dining area, 2 lanais, central heat/ac, fully equipped kitchen, ( all appliances) 3 tvs, dvd and is located on the 3rd floor.... View all property information
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    Siesta Key, Florida 34242
    1 / 15
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    Island House Beach Resort - Siesta Key Florida, Crescent Beach. This bright spacious villa is approx. 1000 sq. ft., non-carpeted and has all the comforts and luxuries of home. Enjoy the significant renovations done including a newly renovated, fully-equipped kitchen with granite counter top, brand... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 bubbles Reviewed 15 September 2015
    My husband and I really enjoyed this villa, so close to the beach, and close to a small town feel. We took our three sons here between 35-40 years ago and were pleasantly...
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    1 / 18
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    Island House Beach Resort!! Crescent Beach, Siesta Key Florida! Direct Gulf Front - Panoramic Views. This beautifully mainained complex is located on the widest part of one of the best beaches in central florida. It is 1300 sq. ft, non carpeted, 2 bedrooms, 2 baths.King, 2 twins. The unit has a... View all property information
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    Siesta Key, Florida 34242
    1 / 22
    5 of 5 bubbles (18) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • x
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    About this property
    The condo benefits from its own private pool. The living room, master bedroom, and lanai (balcony) all have stunning ocean views. The lanai, with over $10,000 of new doors and windows, is furnished with a table and chairs to enable you to dine al fresco. There is also a comfortable couch to... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 bubbles Reviewed 20 January 2017
    This was our 6th year staying at Fishermans Cove in Siesta Key, Unit 208, 8900 Blindmans Pass. We become very comfortable during our three weeks in this waterfront condo. The...
    5 of 5 bubbles Reviewed 26 June 2016
    This condo was perfect for relaxing beachfront in a beautiful, secluded location. The view was amazing, with the gorgeous gulf beach out back and the bay out front! And the...
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    Siesta Key Holiday Rentals

    Looking for world class powdery white quartz sand beaches, a relaxed low-rise life style, and about 100 nearby golf courses on Florida’s South Gulf Coast? This plus bay- and ocean-side views can be yours with a money-saving Siesta Key holiday rental. From Siesta Key cross Roberts or Little Sarasota Bay to Sarasota for museums, art, wildlife, circuses, opera, ballet, symphonies, theatre, film festivals, botanical gardens, baseball spring training, and polo, cricket, and lawn bowling clubs.

    Lions, Tigers & Circuses

    When you need a break from basking in the sun or seashell collecting around Siesta Key, it’s Ringling Brothers and Barnum & Bailey Circus time at Circus Sarasota (Feb., March) and the Museum of the Circus (year-round) at the old Ringling wintering grounds. Visit the Ringling’s bayside winter mansion, Ca d'Zan, and savor their extensive art collection at the recently expanded John and Mable Ringling Museum of Art. The nearby Big Cat Habitat is a sanctuary for lions, tigers, bears and other animals. Hike or take a swamp buggy eco-tour with the kids at Babcock Wilderness in Punta Gorda, and see Florida’s native plants and animals in their natural habitats.

    Gardens & Aquariums

    Let the whole family enjoy the mazes, pirates ships, colorful flowers, and tropical birds at the Sarasota Children's Garden. Marvel at the orchids, bromeliads, and Sarasota Bay views at Selby Gardens. Enjoy the Parker Manatee Aquarium, plus the Bishop Planetarium’s digital projections of the heavens with Dolby surround sound at the South Florida Museum, near the Manatee River in downtown Bradenton. Schedule a Monday, Wednesday, or Friday morning for Mote Aquarium’s Narrated Shark Training Sessions; and visit Molly the Mollusk, a 27-foot pickled New Zealand giant squid.

    Locomotives & Science

    Learn some science and technology with the family at downtown Sarasota’s bay-front G.WIZ (Gulfcoast Wonder & Imagination Zone). In the evening, treat the family to Broadway theatre, dance, or a jazz, pop, or rock concert at the Van Wezel Performing Arts Hall, next door to G.WIZ. Make a weekend visit to the Florida Railroad Museum, 45 minutes north of Siesta Key in Parrish, where you can get hands-on-training, take over the controls, and even rent a locomotive.

    History & Baseball

    From your money-saving Siesta Bay holiday rental home, apartment or condo, take Stickney Point Road across Little Sarasota Bay to the Tamiami Trail (U.S. 41) and Historic Spanish Point. This unusual museum and archaeological site has an intact prehistoric village with middens, as well as a pioneer home, citrus packing house, and old boatyard. In 1924, the New York Giants began a spring training tradition in Sarasota that is being continued by the Baltimore Orioles and the Grapefruit League in Ed Smith Stadium.