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Holiday Rentals in Sarasota

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    Travellers to Sarasota are booking December dates now. Secure your holiday home today, and have the perfect trip.
    All 338 Rentals in Sarasota
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    Siesta Key Voted #1 Beach, Lovely Home 10 min away1 / 24
    (9)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Canal Pool Home with Free Golf Aug - Nov '18  (15 mins to Siesta Key Beach)1 / 44
    (24)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Executive 2 Bed 3 Bath Pool Home near Siesta Key1 / 45
    (25)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Lovely Lido Key Villa - away from it all but close to the BEACH -1 / 25
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 February 2017
    Lido Key is a perfect getaway for locals and visitors from distant locations alike. This rental comfortably sleeps 5, with all of the amenities for a perfect vacation at an...
    Reviewed 19 February 2017
    My husband and I stayed at this fantastic villa in July 2016. We were pleasantly surprised at how beautifully decorated and conveniently located this little gem is. The...
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    About this property
    This newly remodeled villa will delight you with it's contemporary charm and pristine interior. Featuring a master bedroom with king-sized bed and a loft bedroom with queen bed, it has two full baths, a deluxe kitchen and high-end furnishings throughout. Among Lido Key’s premier vacation rentals...
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    Lido Key, Sarasota 34236
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    New in Southgate:Lovely remodeled 3 bedroom pool villa 2.5 Miles from Siesta Key1 / 25
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Private Outdoor Pool (Unheated)
    • Washer
    • Grill
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    Our family of four had a wonderfully relaxing time here. The house is airy, spacious and comfortable. It has just been renovated so everything is clean and new. The kids...
    Reviewed 3 weeks ago
    We had a great break at this 3 bedroom villa, which has a lovely pool and is really well located for the restaurants, beaches and amenities of Sarasota and surrounds. Everything...
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    About this property
    Magnolia Breeze Welcome to this one-of-a kind 3 bedroom and 2-bathroom pool villa in the acclaimed Southgate community in Sarasota. Nostalgic style with brick exterior detail. This home was recently remodeled and newly furnished to the owners exact taste, style and detail. As you enter this...
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    Sarasota, Southwest Gulf Coast 34239
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Charming 'Old Florida' one bed apartment, Sarasota1 / 24
    (3)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Grill
    • Balcony
    • Hot Tub
    • Parking
    • Air Conditioning
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 April 2018
    We enjoyed our stay at this Sarasota apartment. The outside is very enjoyable in the evening. The hot tub was pleasant and private. We used Uber for our trip to Siesta Key...
    Reviewed 7 October 2017
    We had a great time on our first visit to Sarasota. Our stay was amazing, it had all the comforts of home. We were minutes from the best beach I have ever been too and very...
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    About this property
    This property is attached to the main house but has a private entrance with a private patio and back yard which is fully fenced in. A 10 minute drive to either Siesta Key or Lido Beach and minutes from downtown Sarasota, this charming 'Old Florida' one bedroom apartment is available for weekends,...
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    Sarasota, Southwest Gulf Coast 34239
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Luxury Condo 2 blocks from Siesta Key Beach1 / 24
    (14)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
    • Cable/satellite TV
    • Washer
    • Parking
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 January 2018
    Love the trolley service close to many beaches,restaurants and shops.the accommodations were fantastic could use a new mattress in master bedroom other than that everything was...
    Reviewed 13 December 2017
    6703 Midnight Pass Siesta Key #215 it was ok for the December special price just a little dusty and musty smelling, beach was farther then we were told, a senior condo complex...
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    About this property
    This 2 bedroom, 2 bath unit is in the quiet complex of Sea Winds. It is one of the most updated and best units in this complex. All NEW Tile floors, and ALL NEW Stainless appliances. New living room furniture. Located just 2 blocks South of the South Bridge on Siesta Key, it is within walking...
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    Sarasota, Southwest Gulf Coast 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Hot Tub
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Simply paradise. We're located in the highly desirable Kingston Arms complex in one of the few coveted end units on Lido Key just steps from St. Armand's Circle. Lido Key is surrounded by the beautiful gentle, clear waters of the Gulf of Mexico. The complex sits on a prime location just a few...
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    Sarasota, Southwest Gulf Coast 34236
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Walk to beach & St Armand's Circle !!!1 / 20
    (29)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 August 2018
    Best vacation ever! Beyond lovely apartment/pool/yard/neighborhood. So peaceful. Minutes to great beach. Gracious hostess. Absolutely everything we needed was in that apartment...
    Reviewed 28 June 2018
    Just returned from 2 weeks staying in this fantastic location. Joyce and Jeff were perfect hosts and made us feel very welcome from the minute we arrived. St Armands Circle was...
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    About this property
    Be swept away to luxurious Spain in this beautiful one bedroom guesthouse overlooking a lovely pool. Relax and sip your morning coffee as you take in the peaceful surroundings and bay breezes, with a private entrance, spacious outdoor dining room in tropical paradise. Features include:Mexican...
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    Sarasota, Southwest Gulf Coast 34236
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Siesta Beach Cottage1 / 13
    (4)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • Parking
    • Private Garden
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 January 2016
    I spent the weekend to celebrate my birthday with some friends. The rooms were very nice and very comfortable and the owner was so accommodating. She made sure we had...
    Reviewed 16 December 2015
    The location was awesome, close to the beach and lots of options for fun local activities. It was so nice to have a kitchen and access to a washer and dryer. The rooms were...
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    About this property
    Your 'Beach Cottage' is a private super cute clean & comfy 2 bdr apt just off Siesta Key beach! Perfect for families or 2 couples. Pretty pool shared w/1 other apt Outdoor kitchen bbq & dining. Beach chairs, umbrella, free wifi & laundry. You have two cute bedrooms with comfy queen beds and a...
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    Location Information
    Sarasota, Southwest Gulf Coast 34231
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    bring A Boat, 12 Minutes To Sarasota Bay1 / 11
    (16)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Waterfront
    • Hot Tub
    • Wi-Fi
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 May 2018
    We (2) were guests at Jim‘s house for 6 days and we liked the place very much. The house is very clean and good equipped. Jim is a very kind host and gives good recommendations...
    Reviewed 7 April 2018
    A very clean and updated home. We enjoyed our stay here. We spent a week, family of four with two teens. We all enjoyed the pool and hot tub. The home is very convenient and...
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    About this property
    Clean and spacious, 3/4 of the house is yours, kitchen and laundry, 2 bedroom with 1 and 1/2 bath, pool and spa, on the canal that leads to Sarasota bay, offering morning coffee, light breakfast and an occasional visit from the manatees off the dock. Bedroom 1, has a double bed, bedroom 2, has a...
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    Location Information
    Sarasota, Southwest Gulf Coast 34243
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Fido Friendly w/Fenced Yard, Spa/Swimming Pool,  Wifi, Large Ranch Home, Large L1 / 31
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Hot Tub
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Patio
    • Air Conditioning
    • Wi-Fi
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 April 2018
    We stayed here as an extended family: grandparents, parents, and a 2 year old.The property is located near to the north end of Sarasota–Bradenton Airport just off the I-41...
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    About this property
    This is a beautiful, large 3 bedroom, 2 bath ranch home on the Northside of Sarasota with a heated (optional) swimming pool and jetted spa. (See below for more details) With a two car garage, it's conveniently close to the Sarasota/Bradenton airport and just 10 minutes to downtown Sarasota. Walk...
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    Sarasota, Southwest Gulf Coast 34243
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Private Garden
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 3 bedroom, 2 bath Pet Friendly renovated and fenced 1900 sq. ft BEACH COTTAGE has an iconic Sarasota feel upon pulling up and entering the home. This cozy home is newly renovated and is a short five minute drive or 20 minute bike ride to the #1 beach in the US or the incredible restaurants and...
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    Sarasota, Southwest Gulf Coast 34239
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedroom Family friendly Coastal Manor of Sarasota1 / 22
    (20)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Porch
    • Balcony
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Waterfront
    • Private Outdoor Pool (Heated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 weeks ago
    Stayed all over Florida in many rentals,this one is amazing the house its self felt more like a home,so much room inside and out all the rooms were very nice decor different...
    Reviewed 22 March 2017
    Perfect stay in an amazing Southern State style house. Lovely apartment, well equipped and a lot of space. Wonderful surrounding with pool at Phillipi creek. Best place for...
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    Sarasota, Southwest Gulf Coast 34231
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Spacious Apt. #1 Historic Walkable Downtown, between Siesta & Lido Beach1 / 30
    (2)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 February 2016
    We just spent a delightful 4 days in the heart of historic Burns Court. This renovated apartment was so wonderfully located in it's proximity to historic Sarasota. Everything is...
    Reviewed 19 August 2015
    We had a great stay here, the apartment was right downtown, it was very comfortable, and we hope to return soon!Denise was very helpful.
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    About this property
    Historic 1920's Mediterranean & 1950’s Historic mixed-use building in Burns Square, downtown Sarasota, safely nestled between high-end residential neighborhoods of Palm Avenue, Laurel Park and Hudson Bayou. Apartment is private and secure, located on the second floor (stairs) with original hardwood...
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    Location Information
    Sarasota, Southwest Gulf Coast 34236
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Elegant 4 Bedroom 3 bath Executive Home - HEATED POOL near Siesta Key Beaches!!!1 / 34
    (11)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Internet Access
    • Hot Tub
    • Washer
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 August 2018
    We booked this villa from trip advisor But it didn’t show floor plan we assumed it would have had on suite bathrooms to at least 2 bedrooms it only had one bed room with onsuite...
    Reviewed 10 June 2018
    We rented this house for the last seven days with a very large group. This house is perfect for multiple families staying together. The house had an abundance of everything from...
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    About this property
    Heated Pool with therapy jets. You will Love this Large 4 bedrooms Home situated within minutes to #1 Siesta Key Beaches, Downtown, Live Entertainment, Fine Dinning, Shopping, etc.... The home has a oversized covered Lanai, A screened in Pool and a 2 Car Attached Garage. #1 -'Master Bedroom Suite'...
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    Sarasota, Southwest Gulf Coast 34231
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Newly Updated 3 Bedroom Pool Home - Close to Beach1 / 16
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Wi-Fi
    • Parking
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • DVD Player
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 June 2017
    We were in Florida for my nieces wedding. The location was perfect for us. Nice quite neighborhood, close to grocery stores and shopping. We really enjoyed the back yard and pool.
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    About this property
    Enjoy your time in Sarasota in this newly renovated 3 bedroom 2 bathroom pool home. Located in a quiet family neighborhood just minutes to shopping, dining, golf courses and of course the #1 Beach in the USA along with multiple other beautiful beaches including Lido Key, Casey Key, Turtle Beach...
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    Sarasota, Southwest Gulf Coast 34232
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Washer
    • Balcony
    • Patio
    • Cable/satellite TV
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Embrace the tropical climate and active outdoor lifestyle of Siesta Key in this nearly 2,000 sq.ft., home! This is a 3 bedroom, 2.5 bath light and bright, modern, town home and just a short bike ride to our beloved Crescent Beach! With the patios, there is more than 2,500 sq. feet of living...
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    Sarasota, Southwest Gulf Coast 34231
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    Walk to Crescent Beach, Upgraded Sea Winds Condo1 / 19
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Parking
    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 February 2016
    This condo is an end unit, so one less neighbor to worry about, noise wise, and nice and bright - 3 walls with plantation shuttered windows. The location is perfect, only a...
    Reviewed 3 August 2015
    The condo was a walking distance to the private beach (belonged to other resorts, but no one cared if you accessed it as well.) it was clean and exactly how you see it on the...
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    About this property
    Siesta Key located on the Gulf of Mexico. Tropical beauty with white powder sand, gorgeous sunsets, pristine waters and expansive wide beaches. Beach shops, restaurants, ice cream shops and nightlife all can be found on the palm tree paradise, Siesta Key. The city of Sarasota is just over the...
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    Sarasota, Southwest Gulf Coast 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Oceanfront home w/sunset views of Sarasota Bay1 / 37
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Ocean Views
    • Waterfront
    • Washer
    • Wi-Fi
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 March 2018
    Beautifully remodelled, 3 bedroom, 2 bathroom home located about 10 to 15 minute drive from Siesta Key beach. The backyard is directly on the Sarasota Bay so you can see the...
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    About this property
    Treat your family, friends, and beloved small dogs to an unforgettable oceanfront getaway in sunny Florida! Conveniently located near plenty of Sarasota's shopping and dining, your new home away from home is nice and isolated, surrounded by gorgeous views and just a quick walk from the waters of...
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    Location Information
    Sarasota, Southwest Gulf Coast 34231
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in a quiet family neighborhood just minutes to shopping, dining, golf courses and of course the #1 Beach in the USA along with multiple other beautiful beaches including Lido Key, Casey Key, Turtle Beach and more. This is a 1000 square foot newly renovated two bedroom apartment with 1 car...
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    Sarasota, Southwest Gulf Coast 34232
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    St.Armands Circle condo ( Kingston Arms )1 / 9
    (7)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Terrace
    • Balcony
    • DVD Player
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 April 2018
    We stayed in this condo at Kingston Arms for a week! It is beautiful! I cannot say enough great things about it! It is a short blocks walk to St. Armand’s Circle and 3 blocks...
    Reviewed 10 July 2017
    This is a very nice unit in an older condo facility. We loved how close to the shops and restaurants we were. The walk to the beach is also not bad at all. We never used the...
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    About this property
    2 bedroom,2 bathrooms,modern updated condo.Walking distance to Lido Beach. Fully furnished,microwave,A/C,cable,local phone only,dishwasher, 3 new LCD TV's ,Stereo,Laundry (common area) Beautiful heated pool ,hot tub, all in common area Great shopping,excellent restaurants,great entertainment in St....
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    Location Information
    Sarasota, Southwest Gulf Coast 34232
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Walk to Everything Downtown, Bring Fido, Wifi, Huge Screened Lanai, Extensive Ou1 / 24
    (1)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 June 2018
    This location is within walking distance of downtown. My family used to live a few blocks away so I was very familiar with the area. This is a beautiful place to stay. Very...
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    About this property
    Bring Fido to this dog friendly 2 bedroom, 1 bath duplex in downtown Sarasota near Gillespie Park. Downtown Sarasota and all it has to offer is just blocks away from this adorable cottage like duplex! Feel free to leave your car under your covered carport because you can walk to many downtown...
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    Location Information
    Sarasota, Southwest Gulf Coast 34236
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Secure Parking
    • Air Conditioning
    • Washer
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in the heart of Sarasota City, just minutes to shopping, dining, golf courses and of course the #1 Beach in the USA along with multiple other beautiful beaches including Lido Key, Casey Key, Turtle Beach and more. This is a 1000 square foot two bedroom apartment with 1 car garage, offers a...
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    Location Information
    Lido Key, Sarasota 34236
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Cable/satellite TV
    • Housekeeping Included
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We are in the heart of historic Burns Square in downtown Sarasota, nestled between high end residential neighborhoods S. Palm Avenue, Laurel Park and Hudson Bayou. The property is a mixed-use historic property with residential on the second floor with stairs. You do not need a car as we are in...
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    Sarasota, Southwest Gulf Coast 34236
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Beautiful Main Street Loft Apartment1 / 8
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    This location was just what I looking for. The loft was very cozy and neat. I loved the jazz artwork on the walls which fits right into the locale setting of art galleries...
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    About this property
    The front door of our 1920 vintage loft apartment opens directly onto Main Street... You will be surrounded with all the world-class attractions Sarasota, Florida has to offer - from beaches and boating to arts and culture. When you stay here, each day dawns with endless possibilities, many of the...
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    Location Information
    Lido Key, Sarasota 34236
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    This small loft apartment is on the third floor and perfect for a single, couple or close friends. It is decorated beautifully, simply and clean. The property is a historic building in the heart of historic Burns Square and walking distance to tons of amenities, centrally located to Siesta and Lido...
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    Sarasota, Southwest Gulf Coast 34236
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
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    • Shared Outdoor Pool (Unheated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Imagine combining privacy of staying in a private home with the resort amenities of a fine hotel matched with a fantastic location, just 5 minutes from the beach and very easy access to Sarasota sporting cultural amenities and an array of dining options. Enjoy all that Sarasota has to offer while...
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    Location Information
    Sarasota, Southwest Gulf Coast 34231
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Terrace
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    Pet friendly
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    About this property
    Stay at this beautiful 2 bedroom, condo minutes (by car less than 1 minute) from Crescent Beach and Siesta Key. Looking for a perfect getaway? This is the place for you. This unit is located in a very quiet, quaint, tight-knit community. Perfect for couples who are looking to get away but not be...
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    Sarasota, Southwest Gulf Coast 34231
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Superb Village Des Pins Sarasota vacation villa near Siesta Key1 / 24
    (10)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Reviewed 29 December 2014
    We had a wonderful week in this villa. I am sorely tempted to go live there. It's enormous! There were only the 2 of us, but even for a family there was loads of room. The...
    Reviewed 16 June 2014
    My wife and I stayed here on our recent honeymoon and absolutely loved it. It's a really lovely villa with large rooms, very modern furniture, and plenty of useful appliances...
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    About this property
    Thanks for considering our property. If you have stayed with us before, let us know for a loyalty discount! We would be happy to answer any questions on any aspect of the rental. This top quality spacious modern corner villa is set in an award winning, safe, semi gated community, and are the...
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    Location Information
    Sarasota, Southwest Gulf Coast 34238
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Location Location Location,The 'NEST' west of Tamiami Trl close to everything.1 / 14
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Reviewed 11 May 2018
    This a very clean two-bedroom second-floor apartment with all the amenities of home. Great location, close to a fabulous gourmet market, excellent restaurants, shopping, and...
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    About this property
    THE SARASOTA 'NEST', West Of Tamiami Trail This vacation getaway is an immaculate, 2 bed room upstairs apartment, located in the heart and soul of old Sarasota. Walk to Sarasota's most desired locations, including Shelby Gardens, Bay Front Park, Southside Village (has everything, best restaurants,...
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    Location Information
    Sarasota, Southwest Gulf Coast 34239
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You will love our beautifully maintained and clean Villa Youppie in Sarasota. It is located at the corner of a lake which provides lots of privacy and thanks to a southern exposure you have sun in the pool and on the patio all day long. New travertine tiles on the patio, granite counter tops in the...
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    Location Information
    Sarasota, Southwest Gulf Coast 34238
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Washer
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    About this property
    Located in the heart of Sarasota City, just minutes to shopping, dining, golf courses and of course the #1 Beach in the USA along with multiple other beautiful beaches including Lido Key, Casey Key, Turtle Beach and more. This is a 1000 square foot two bedroom apartment with 1 car garage, offers a...
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    Location Information
    Lido Key, Sarasota 34236
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 7
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    Great Location and Best Price in Sarasota1 / 34
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Parking
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    Pet friendly
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    Reviewed 8 July 2018
    This review is not on McIntosh road but on 626 s Osprey ave in downtown Sarasota...as we were upgraded. Andrey gave us another 2 bedroom apartment available, which had just been...
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    About this property
    Great private cozy apartment with a nice outdoor terrace / bbq area Located in a quiet family neighborhood just minutes to shopping, dining, golf courses and of course the #1 Beach in the USA along with multiple other beautiful beaches including Lido Key, Casey Key, Turtle Beach and more. This is...
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    Location Information
    Sarasota, Southwest Gulf Coast 34232
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Gulf Beach, Pool  And Walk To Siesta Key Village1 / 35
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    What a great location! Walk to Siesta Key village or relax on your small Gulf Beach or fishing on the pier at Sandy Cove. This renovated 2 bedroom 2 bath unit is a 2nd level condo with pool views from the balcony. Enjoy breakfast after a short walk at one of the villages' quite restaurants...
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    Location Information
    Sarasota, Southwest Gulf Coast 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Downtown Apartment in Historic Burns Square downtown Sarasota1 / 21
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Wi-Fi
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    Pet friendly
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    Reviewed 25 January 2017
    My husband and I stayed here for a long weekend in January and really enjoyed. The place is very cozy! Very clean! The bed was extremely comfortable! I loved the fact there...
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    About this property
    My historic building was built in the 1950's and has clean character and ambiance. Walking distance to Whole Foods/Publix, fabulous restaurants, diverse shopping options, performance theaters, movie theaters, nightlife, public transport, boat/water activity rentals, parks, spas, and a short...
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    Location Information
    Sarasota, Southwest Gulf Coast 34236
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Studio, 1 Bathroom, Sleeps 3 Quick View
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    About this property
    1920's mixed-use building in historic area that is nestled between high-end residential neighborhoods. The studio apartment is super nice, safe and secure in a quaint shopping/theater area and walking distance to marina, fishing, supermarkets, transportation, theaters, opera, library, parks and...
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    Location Information
    Sarasota, Southwest Gulf Coast 34236
    Condo/Apartment - 1 Bathroom, Sleeps 3
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Fantastic Sarasota location close to everything... 4 minutes to the Ed Smith Oriole's stadium, 5 minutes to Marina Jacks, 4 minutes to the Hillview section of Sarasota by Sarasota Memorial Hospital, 12 minutes to St. Armands Circle on Lido Key and 15 minutes to Siesta Key Beach. Nicely...
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    Location Information
    Sarasota, Southwest Gulf Coast 34237
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Patio
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Uplands Oasis Find your Oasis in the relaxing global stylings of this unique 2bedrooms/2 baths, single-family ranch style house. Located in the quaint northern Sarasota neighborhood of the Uplands, the Uplands Oasis home provides all the features and amenities to make Sarasota your next home...
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    Location Information
    Sarasota, Southwest Gulf Coast 34243
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the pond view and bird life from the patio area. With 4 bedrooms, 2 bathrooms, 2 car garage and pool, the house can accommodate up to 8 persons The houseis located in a wonderful and quiet area of Sarasota. Within a ten minutes you are on one of our many beaches long on one of our 3 islands...
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    Location Information
    Sarasota, Southwest Gulf Coast 34232
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Smoking allowed
    About this property
    This is a 2 bedroomed, one bath house, centrally located near downtown Sarasota, pet friendly within walking distance to a great dog and family park that also has free yoga, tennis, and an Olympic size heated pool. Siesta Key beach and Lido Beach are both a 15 minute drive away or you can take the...
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    Location Information
    Sarasota, Southwest Gulf Coast 34239
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
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    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stoneybrook in Palmer Ranch is a condo in a gated community of upscale homes. Surrounded by lush vegetation, a golf course, lighted 'har tru' tennis courts, clubhouse with restaurant and activities and a beautiful community pool, there is plenty of open space as well as peace, quiet and...
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    Location Information
    Sarasota, Southwest Gulf Coast 34238
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    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 15 February 2016
    Must admit that I was nervous before my arrival, there was no reviews for that location, usually I take them in consideration. Was very pleased, answers were given fast, easy to...
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    About this property
    Great private cozy apartment with a nice outdoor terrace / bbq area Located in a quiet family neighborhood just minutes to shopping, dining, golf courses and of course the #1 Beach in the USA along with multiple other beautiful beaches including Lido Key, Casey Key, Turtle Beach and more. This is...
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    Location Information
    Sarasota, Southwest Gulf Coast 34232
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bring your well-behaved dog along with you and stay just off Siesta Key in the Southgate area. Here you can walk to the Westfield Southgate Mall, complete with restaurants, shopping and the brand new CinéBistro movie & dining venue or walk to the many other restaurant choices close by. Completely...
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    Location Information
    Sarasota, Southwest Gulf Coast 34239
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sarasota has so much to offer and this condo makes access easy for virtually everything you might want to enjoy. Right off of University Parkway, centrally located near the brand new University Town Center Mall and 2 exits from the Ellenton Outlet center, you can shop to your hearts content....
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    Location Information
    Sarasota, Southwest Gulf Coast 34243
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Secure Parking
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The house is located in a wonderful and quiet area of Sarasota. Within a ten-fifteen minutes you are on one of our many beaches long on one of our 3 islands Siesta Key, Lido Key and Longboat Key with a total of 64 km of white sandy beaches. Our beaches are clean and running at all times. There is...
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    Location Information
    Sarasota, Southwest Gulf Coast 34234
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Patio
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    • Private Garden
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3.5 miles to Siesta Key, North Bridge Dawson House is closely located within a few miles to Siesta Key and close to downtown Sarasota. This home offers an open kitchen that is truly 'the heart of the home.' Completely remodeled with custom wood cabinets, a cast Iron farm sink, Granite Counter tops,...
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    Location Information
    Sarasota, Southwest Gulf Coast 34239
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Gorgeously decorated 3/2 renovated condo with expansive views of the intracoastal waterway and Harbor Tower's marina right on Siesta Key close to the beach. Watch the dolphins frolic in the water right from the privacy of your beautiful condo. The fine white sands of Siesta Key Beach are just a...
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    Location Information
    Sarasota, Southwest Gulf Coast 34242
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Air Conditioning
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    Smoking allowed
    About this property
    My historic building was built in the 1950's and has clean character and ambiance. Walking distance to Whole Foods/Publix, fabulous restaurants, diverse shopping options, performance theaters, movie theaters, nightlife, public transport, boat/water activity rentals, parks, spas, and a short...
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    Location Information
    Sarasota, Southwest Gulf Coast 34236
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Siesta Dunes is where you want to stay on your next vacation and every vacation thereafter! We are offering a 3 bedroom, 2 bath (over 1500 climate controlled sq. ft) 4th floor condo with ocean gulf views at one of Siesta Key's premier complexes. Siesta Dunes is a gated complex with their own...
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    Sarasota, Southwest Gulf Coast 34242
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1
    Sarasota Holiday Rentals

    Encompassing some of the state’s most impressive cultural attractions, world-class beaches and a slew of eco-tourism activities, Sarasota and its surrounding islands, is the perfect destination to unwind in style. If you want to luxuriate in style, you should consider a holiday rental. From roomy, beachside homes to sophisticated high-rise condos, quaint cottages and classy villas and town homes, the selection in the Sarasota area is appealing to a range of tastes and desires. Amenities like fully equipped kitchens and spacious indoor and outdoor dining areas make holiday rentals perfect for families seeking to prepare their own meals and save money.

    Sarasota attractions and activities

    You’ll have access to one of the world’s great beaches. Siesta Key Beach, which was included in Dr. Beaches’ Top 10 “Best Beaches in America” in 2007 & 2008, is a don’t miss experience. While beach activities like parasailing, snorkelling and sailing are popular pastimes, away from the sands, cultural attractions are big draws in Sarasota. A great family outing is the John and Mable Ringling Estate, a Venetian-inspired mansion along Sarasota Bay featuring an art museum, circus museum, a Circus Ring of Fame and the Flying Trapeze and The Flying Fantasy Circus. When it’s time to shop and dine, head to St. Armands Circle on Lido Key, a classy area with a European charm featuring bistros with outdoor dining and a plethora of boutiques, art galleries, speciality shops and restaurants. Popular outdoor activities in the Sarasota area include kayaking at Myakka River State Park, playing golf at top-notch layouts like the Arnold Palmer designed Legacy Golf Club at Lakewood Ranch and the Scottish links-style Tatum Ridge Golf Links and hiking the newly opened Legacy Trail, which stretches more than 12 miles from Sarasota to Venice.

    Family holiday rentals in Sarasota

    From beachfront bungalows to golf course villas and everything in between, the Sarasota area has holiday rentals in a variety of settings. Sarasota is a great destination for kids. It boasts attractions like the Mote Aquarium, Marie Selby Botanical Gardens and Sarasota Jungle Gardens. After a long day of sunbathing, shopping, playing golf or visiting attractions, you can return to a holiday rental that gives your family room to spread out instead of a cramped, mundane hotel room.

    Saving money on Sarasota holiday rentals

    We have a long list of money saving holiday rental options. Regardless of your price range and budget, we have special deals and discounts on all types of properties in different settings in the Sarasota area.

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