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Holiday Rentals with Pools in Sarasota

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    Travellers to Sarasota are booking December dates now. Secure your holiday home today, and have the perfect trip.
    181 Matching Rentals in SarasotaView all 322 rentals
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    Executive 2 Bed 3 Bath Pool Home near Siesta Key1 / 90
    (25)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Walk to beach & St Armand's Circle !!!1 / 10
    (29)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 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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    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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    • Washer
    • Wi-Fi
    • Air Conditioning
    • Porch
    • Patio
    • Cable/satellite TV
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    Our family had a wonderful vacation,Yvonne ' s house was lovely, clean and just perfect. Thanks for making our trip memorable! !
    Reviewed 4 weeks ago
    This place had it all! Great location, numerous amenities, lovely home with almost everything we could have wanted. The owner was very nice.Our only negative feedback would be...
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    About this property
    This home is in walking distance to all facilities, 2 car drive/ car port, lanai. Manured garden and trees. Area for BBQ and out door eating. Located ideally for easy access to Sarasota's famous 'Siesta Beach' Downtown and St. Armands Circle have many restaurants to suit all eclectic tastes....
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    Sarasota, Southwest Gulf Coast 34233
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedroom Family friendly Coastal Manor of Sarasota1 / 22
    (19)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 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...
    Reviewed 7 March 2017
    Located at a quiet, lovely place, this location offers everything you need for a relaxing stay. Amazing hosts make a stay an unforgettable experience.
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    Sarasota, Southwest Gulf Coast 34231
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    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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    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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    Sarasota, Southwest Gulf Coast 34232
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Beautiful 3 bedms/2 bathms with pool close to Downtown1 / 22
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Washer
    • Air Conditioning
    • Grill
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 May 2018
    Great place conveniently located at 15 minutes to Siesta Key,Lido Key.The only thing that would have been better was for Alberto storm to choose a different path,but we were...
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    About this property
    This is spacious house, located in Novus Place, close to downtown and beaches. With 3 bedrooms, 2 bathrooms, a private swimming pool, equipped kitchen and TV equipped living room, it can perfectly accommodate a family or group of friends of 6 guests. The house is located in a residential area,...
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    Location Information
    Sarasota, Southwest Gulf Coast 34237
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Superb Village Des Pins Sarasota vacation villa near Siesta Key1 / 25
    (10)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Washer
    • Grill
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • Hot Tub
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    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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    Location Information
    Sarasota, Southwest Gulf Coast 34232
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Washer
    • Waterfront
    • Grill
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    Suitability
    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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    Elegant 4 Bedroom 3 bath Executive Home - HEATED POOL near Siesta Key Beaches!!!1 / 34
    (10)Excellent
    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 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...
    Reviewed 21 December 2017
    The house was very spacious and accommodating. The location was near the beach and local eateries and grocery stores.
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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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    Location Information
    Sarasota, Southwest Gulf Coast 34231
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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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
    • Washer
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Balcony
    • Patio
    • Shared Outdoor Pool (Unheated)
    Suitability
    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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    Sarasota, Southwest Gulf Coast 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Waterfront 2BR 2 Bath Suite at the Sara Bay Marina1 / 16
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Private Garden
    • Cable/satellite TV
    • Waterfront
    • Patio
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 March 2015
    My wife and I stayed here for 5 nights - friends joined us for 3 nights. Lots of room, well appointed through out with a view out over the water. Great location for travelling...
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    About this property
    PLEASE EMAIL ME FOR A LINK TO PREFERRED LISTING ADDRESS, VACATION RENTAL BY OWNER LISTING: 442427 THIS IS A PRIVATELY OWNED CONDOMINIUM AT THE RAMADA INN, 7150 N Tamiami Trail, SARASOTA, Directly on the Sara Bay Marina with direct access to the Gulf of Mexico. Yacht rentals are available on...
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    Location Information
    Sarasota, Southwest Gulf Coast 34243
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Steps from White Sands of Siesta Beach-Best Beach1 / 17
    (17)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Balcony
    • Patio
    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    • Internet Access
    • Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 March 2018
    We had a wonderful two week stay at Sea Winds. Lionel and Sally were wonderful hosts and were very accessible. They were very good about communicating with us before and...
    Reviewed 26 June 2016
    Lionel's apartment is very nice, clean and felt like a home away from home. Comfortable enough for me, my wife and our 3yr old son (who loved the big queen-size sofabed). The is...
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    About this property
    This may be the most updated apartment on Siesta Key! Newly remodeled one-bedroom, one bath ground-floor apartment with ceramic tile and enclosed backyard/garden for lounging and barbecuing. New cabinets and granite counter tops were installed in the kitchen in 2016 along with new ceramic top...
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    Sarasota, Southwest Gulf Coast 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Secure Parking
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Private Garden
    • Private Outdoor Pool (Unheated)
    • Grill
    • Patio
    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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    bring A Boat, 12 Minutes To Sarasota Bay1 / 11
    (15)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • 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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    New in Southgate:Lovely remodeled 3 bedroom pool villa 2.5 Miles from Siesta Key1 / 25
    (1)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 6 July 2018
    This house blew us away. I can’t believe we got such a wonderful property for less than a Hotel Room! This house is amazing. I wish my house was half as nice as this! It had...
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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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    Location Information
    Sarasota, Southwest Gulf Coast 34239
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Tulip House - 1 mile to Siesta Key1 / 40
    (1)Average
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Pool home: This extraordinary 3 bedroom + / 2 baths designer remodeled single family home (1,826 sq/ft) is located on the mainland close to the worlds famous Siesta Key. The home offers a new pool (baby fence available upon request) and is located within approx. 1 mile of the Siesta Key...
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    Location Information
    Sarasota, Southwest Gulf Coast 34239
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Air Conditioning
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    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Private Garden
    • Washer
    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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    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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    • Cable/satellite TV
    • Parking
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Firethorn unit has 2 bedrooms, one and one half baths, full galley kitchen with all appliances, a breakfast bar, living room w/sleeper, dining room as well as an oversized lanai with a large dining set for open air meals. Large flat screen TV in the living room with high-speed internet included....
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    Location Information
    Sarasota, Southwest Gulf Coast 34242
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Luxury Condominium at Siesta Dunes Beachside Pool Hot Tub Tennis Sun Deck1 / 58
    (12)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Grill
    • Balcony
    • Air Conditioning
    • Hot Tub
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 April 2018
    Beautiful condo overlooking the pool. Able to see the ocean from the sliding doors. We enjoyed wonderful weather. Just a few steps from the washer and dryer and elevator...
    Reviewed 22 May 2017
    Perfect location & beautiful condo many amenities. Would highly recommend staying at this condo. Steps away from the beach & stunning pool. We will vist again.
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    About this property
    Hi, I have several weeks available this April. I’ve reduced the rate to $1,395 with the only additional fee being sales tax and the resort booking fee, $100. Let me know if you would like to set up a reservation. Thank You. WE ARE HAVING A LAST MINUTE SALE FOR THE REMAINING OPEN WEEKS OF APRIL...
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    Location Information
    Sarasota, Southwest Gulf Coast 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Pet Friendly Pool Home Close to Beaches & Town1 / 28
    (4)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Grill
    • Air Conditioning
    • Patio
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    • Private Outdoor Pool (Heated)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 May 2017
    Booked to stay for a weekend with visiting family. Beautiful spacious home with a great pool. I have two young daughters so the size of the pool is perfect to be able to keep an...
    Reviewed 16 April 2017
    Let me start with what was most important to us - the pool. It is very small; you can't swim in it. and it is cold! even tho it is heated (barely). even the kids complained...
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    About this property
    Southgate house description We refer to this Florida Home as 'Goldy Lox's West Wing on Bermuda Brook.' This comfortable mid-century Florida home is located central to all things Sarasota. We chose this home for its location and ease of access to beaches, downtown, shopping and restaurants. The home...
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    Location Information
    Sarasota, Southwest Gulf Coast 34239
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Family friendly house with pool/spa1 / 29
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • DVD Player
    • Washer
    • Air Conditioning
    • Housekeeping Included
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Hot Tub
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 August 2016
    The owners are great, very friendly and helpful. The house was clean and almost everything needed was supplied. The rooms are nice and clean. The pool was the main focus of the...
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    About this property
    We want you to enjoy, staying here this year & be back with your friends/family. Beautiful house on 1 acre lot, close to everything located in one of the best and desirable area in south Sarasota. This property offers easy access to all local attractions and beaches. Only a short drive to the...
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    Location Information
    Lido Key, Sarasota 34233
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Star Fish Casita - 2 BR Casita, Heated Pool, 4 Min Walk to Beach [Sleeps 6]1 / 20
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
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    Reviewed 5 May 2018
    We thoroughly enjoyed our stay at the Star Fish Casita. We have previously always stayed in a hotel, but decided to give a rental a try. We were not disappointed! Every...
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    About this property
    The Star Fish and Coral Reef casitas are two separate units which can be uniquely configured to create Villa Dom Brisa, features its own brand new, private heated pool with “sun shelf” and a three minute walk to the Nation’s finest beach [no major streets to cross]. Please Note: These units...
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    Location Information
    Sarasota, Southwest Gulf Coast 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Midnight Cove: Living on the Water1 / 16
    (12)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 October 2016
    This was our third time our family has stayed here and we love it. Everything you need and right across the street from the beach. Looking forward to next year.
    Reviewed 21 April 2016
    This place is a home away from home. You have the best of the bay and beach life. Being about to walk our your door and fish of the dock or take a short walk over to the beach...
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    About this property
    Step out the back door of your ground floor apartment and in seconds you're standing on a boating and fishing dock, surrounded by lush tropical foliage. This breathtakingly beautiful two bedroom, 1½ bath unit is located in Midnight Cove, one of the best complexes on Siesta Key. Since Midnight Cove...
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    Location Information
    Sarasota, Southwest Gulf Coast 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Renovated ! Heated pool! House Close To USA's Best Beach! Great Rates!1 / 19
    (1)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 April 2018
    We traveled with another family. 4 kids and 4 Adults all together. The house was set up perfect. TV's in every room was a nice bonus as well. The pool provided hours of...
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    About this property
    Villa Siesta Sunset-The Ultimate Vacation Home Rental. The first thing you will do when you open the front door is smile. This is a happy place! You will find peace and tranquility in this spacious friendly home. This home has been redone from top to bottom, everything is brand new! You will be...
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    Location Information
    Sarasota, Southwest Gulf Coast 34231
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Amazing  Location-Short Walk to Beach!!!1 / 61
    (8)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
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    • Balcony
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    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 February 2017
    Awesome get away. Everything was found to be as described. Perfect weather, close enough to the trolley and the beach for us. Safe neighborhood, too!
    Reviewed 16 October 2016
    It was a nice stay in a very well equipped appartment.You can really walk to the beach, wonderful!We enjoyed very much our stay and contact to the owner, nice people!
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    About this property
    Discount for 3 months or more!!! Walk less than 10 minutes to the white sands of Siesta beach (Gulf of Mexico) just over the bridge, or to many island restaurants, marina and shops where you can rent absolutely anything for your outdoor activities and adventures. Walk to the opposite direction and...
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    Location Information
    Sarasota, Southwest Gulf Coast 34231 3847
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 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
    Newly renovated, this spectacular 2-bedroom, 2-bathroom Sarasota vacation rental house provides the perfect Florida home base for up to 6 guests! Live the dream while retreating at this abode boasting numerous amenities including a lavish screened lanai with a heated pool and outdoor furniture....
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    Location Information
    Sarasota, Southwest Gulf Coast 34231
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    The Bedroom Cottage with an Old Florida feel.The unit has full kitchen, and Queen size bed plus queen size sleeper sofa. The beach is a 6 minute walk and St. Armands 14 minutes, according to Google Maps. The unit has private patio and separate screen porch. The complex has a heated pool. The unit...
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    Location Information
    Lido Key, Sarasota 34236
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Las Flores, our newest and most gorgeous 3 bedroom 2 bathroom villa, is one of two special vacation homes (the other unit is called Luna Nueva both properties combined are called Luna Flores) that are located mid-town with easy access to Siesta Key - approximately 5 minutes away via car. All...
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    Location Information
    Sarasota, Southwest Gulf Coast 34231
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Newly Remodeled 3 Bed 2 Bath Bungalow Block to Beach Heated Pool & Spa FREE WiFi1 / 23
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Private Outdoor Pool (Heated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 December 2017
    This place was so cute... we didn't want to leave. We were 4 ladies away celebrating birthdays and this home was everything we could have possibility hoped for. Amazing...
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    About this property
    This newly remodeled home has all the amenities you need while on vacation and still manages to maintain its beachy charm. Professionally decorated this home has an airy feel with top of the line finishings. At 3 bedrooms and 2 full bathrooms, this is one of the best little rentals on Lido Key....
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    Location Information
    Lido Key, Sarasota 34236
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    6 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Luna Flores, a gorgeous 6 bedroom, 4 bathroom uniquely configured villa featuring a combination of two special vacation homes. Luna Flores is specially configured to include two separated living areas, Villa Las Flores and Luna Nueva. Located just off island with easy access to Siesta Key...
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    Location Information
    Sarasota, Southwest Gulf Coast 34231
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 16
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    • Private Outdoor Pool (Unheated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Make a splash in the private screened-in pool at this winning 4BR/4BA home. Play a game of ping-pong or fire up the BBQ for an al fresco meal. You’re a quick walk to Lido Beach and an array of shopping, casual eateries, and fine dining. Sleeps 8. Long Description: Make a splash in the private...
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    Location Information
    Sarasota, Southwest Gulf Coast 34236
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Coastal breezes await on the screened front porch of your 4BR/2BA Sarasota rental. Enjoy professionally decorated interiors and comfortable accommodations for eight people. Discover a wide variety of dining options within walking distance, and catch a film at the local movie theater. When you’re...
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    Location Information
    Sarasota, Southwest Gulf Coast 34239
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Timberwoods Vacation Villas Best Value in Sarasota1 / 18
    (20)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 March 2016
    We enjoyed our stay--especially the ease of getting anyplace we were interested in. A Publix grocery store is a short drive away, It was easy to drive down to Venice and up to...
    Reviewed 9 August 2015
    Wonderfully relaxing and well maintained complex of villas. Villa was spacious and well appointed. Master bedroom was huge - with a suitably massive bed. Lovely bathrooms. Pool...
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    About this property
    Are you looking for a Sarasota Vacation Rental close to all of the local attractions and beaches, but want peace & quiet at affordable prices? Then, Timberwoods is the perfect place for your next vacation! This vacation rental has 2 bedrooms, 2 bathrooms, kitchen, washer, dryer, living & dining,...
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    Location Information
    Sarasota, Southwest Gulf Coast 34238
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    House in Florida Bradenton, 4 Bedroom sleeps 8 persons, Private Heated pool1 / 12
    (1)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    Reviewed 30 April 2018
    We booked our stay at the Tara House for 3 weeks. Prior to our stay I had lots of questions for the owners, and Padraig and Jessica were always extremely helpful. The villa's...
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    About this property
    Luxury house with private pool situated on Tara golf and country club in Florida Bradenton. Our house is bright, spacious and fully air-conditioned. The house is furnished to a high standard throughout. There is a lounge with dining area. There is a large bright fully equipped kitchen with...
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    Location Information
    Sarasota, Southwest Gulf Coast 34203
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Garden
    • Parking
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    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Situated a short 5-minute drive from the cool emerald waters of Siesta Key Beach, on the North edge of Palmer Ranch. This tropical resort community is a relaxing oasis under the warm skies of the Gulf Coast. With its swaying palms, shimmering lake views and world-class resort amenities. This...
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    Location Information
    Sarasota, Southwest Gulf Coast 34231
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    PROPERTY OVERVIEW Experience luxury living at its finest in this stunning 4BR/3.5BA home known as Casa Azul. Recently renovated, this modern gem boasts 3,346 sq. ft. of refined living space across two floors. Enjoy entertaining outside with a lush fenced backyard complete with a private pool,...
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    Location Information
    Sarasota, Southwest Gulf Coast 34239
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    Sarasota Florida Paradise!1 / 19
    (15)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Private Outdoor Pool (Unheated)
    • Internet Access
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 February 2016
    Beautiful home! Suitable for a family vacation.I really liked the master suite being in one end of the house.It would be a great idea for grandparents and families.Owner super...
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    About this property
    Sarasota Florida great beaches, nice gulf area - on the West coast of FL...perfect fun-filled getaway! FREE Beach parking!!! Amazing Sunsets!!! Summer Savings!!! Spring & Fall Specials Relaxing, 3b2b home with in ground pool and private fenced back yard and just a few minutes walk to bay...
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    Location Information
    Sarasota, Southwest Gulf Coast 34243
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    Stunning Beach Front Pool Home (Sand Castle Unit)1 / 27
    (7)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 11 Quick View
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    • Waterfront
    • Private Outdoor Pool (Unheated)
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    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Directly overlooking breathtaking views of privately owned beach on North end of Siesta Key. Just renovated everything brand new. Four bedrooms, 2 baths, sleeps 11, living room, dining room, full kitchen and game room. Flat screen TVs in living room, game room, and each bedroom with DVD players,...
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    Location Information
    Sarasota, Southwest Gulf Coast 34242
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 11
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    Late SALE Sep/Oct only -Lakeside villa Uni. Park,golf,cycles,pool, beach1 / 33
    (14)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Private Outdoor Pool (Heated)
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    • Waterfront
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    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 April 2018
    I just completed a 3 week stay at this home in University Park, Bradenton Florida. The home exceeds its representation. It was very clean, well appointed and a very comfortable...
    Reviewed 20 May 2011
    My husband and I and 2 other couples stayed here for a week...really comfortable, clean home. Excellent friendly communication with the owner who made it easy for us to get the...
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    About this property
    SALE LAST AVAILABILITY - $999/week (was $1250). Please note we only have 2-18 September dates and 29 Sep - 9 October left. We may be able to offer a further reduction for 2 week stays in early September (if dates available). Please inquire for rate. Enjoy the ultimate vacation in our luxury...
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    Location Information
    Sarasota, Southwest Gulf Coast 34201
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 4
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    Romantic Retreat with your own Private Pool1 / 25
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Romantic vintage pool side 2 bedroom apartment. Freshly remodeled in 2015. Tropical Chic decor, quality furnishings, lush tropical landscaping. Old Florida neighborhood close to downtown. Alternative lifestyle friendly allows you the freedom to totally be yourself many miles from your home town....
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    Location Information
    Sarasota, Southwest Gulf Coast 34234
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
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    • Balcony
    • Private Outdoor Pool (Unheated)
    • Terrace
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa on Siesta Key is located in luxury development with easy access to the beach. Has 2 floors. First floor has living room, open kitchen, half bath and laundry. Second floor has two bedrooms and 2 bathrooms. Master bedroom has queen size bed, second bedroom two twins bed. You can accommodate 6...
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    Location Information
    Sarasota, Southwest Gulf Coast 34242
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    *****September 2018 30% off****** Great Location   Private beach access1 / 15
    (21)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
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    • Porch
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 April 2017
    It had all the basics you need for a relaxing beach vacation. Very clean and always worried about getting all the WHITE in the room dirty. However, we were hardly there...
    Reviewed 16 September 2014
    My husband and I met at this lovely resort on Saturday night. I went from home, my husband went from work. It took each of us just over a half hour to get there. As soon as we...
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    About this property
    Why stay across the street from the beach when you can stay beachside for the same price or less Enjoy your stay 100 yds from the NUMBER 1 beach in the US see Trip Advisor 2015. No streets to cross no driving to the beach just a short walk and your on the beach. My unit is fully furnished and...
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    Location Information
    Sarasota, Southwest Gulf Coast 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Deluxe Bungalow on Lido Key by St. Armands1 / 39
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    Smoking allowed
    Reviewed 5 September 2014
    Great service and very easy rental for this simple one room efficiency. Room was clean and the location was great. Just a short 4-6 block walk to Lido Beach. Lido is great! The...
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    About this property
    Delightful Studio Cottage tucked away on exciting Lido Key, the Lido Islander. Nestled amid a tropical garden, the units are steps from the beautiful white sands of Lido beach, with the turquoise waters of the Gulf of Mexico just beyond. The beach is a 6 minute walk and St. Armands 14 minutes,...
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    Location Information
    Sarasota, Southwest Gulf Coast 34236
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Built in June 2017, this tri-level home completely captures the true essence of living the luxurious Florida lifestyle. No expense was spared to create this luxurious haven of elegance, with a heated beach-style entry access pool with picturesque water features including a spillover waterfall and...
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    Location Information
    Sarasota, Southwest Gulf Coast 34242
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    Casita Sol- Beautiful 2 BR, Heated Pool, w/Spa, Private Beach Access [Sleeps 4]1 / 30
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 May 2016
    It was absolutely paradise. When we arrived they had three cupcakes waiting for us on the counter . Everything was very clean and had plenty of towels and clean sheets. The...
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    About this property
    Welcome to Casita Sol of Sol y Mar. This COMPLETELY RENOVATED, single level (2 Bedroom / 1 Bathroom - Master BR/1 Queen & 2nd BR/2 twins -sleeps 4) vacation home features private, gated beach access, a sparkling clean hot tub in a private, lush setting, a communal heated swimming pool with plenty...
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    Location Information
    Sarasota, Southwest Gulf Coast 34242
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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