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Holiday Homes near Legacy Trail

Train Depot, Sarasota, Florida
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    Travellers to Sarasota are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    All 100 Rentals in Sarasota
    Walk to beach & St Armand's Circle !!!1 / 10
    (27)Excellent
    5.7 kilometres from Legacy Trail
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Waterfront 2BR 2 Bath Suite at the Sara Bay Marina1 / 16
    (2)Very good
    5.6 kilometres from Legacy Trail
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Fido Friendly w/Fenced Yard, Spa/Swimming Pool,  Wifi, Large Ranch Home, Large L1 / 31
    (1)Excellent
    4.5 kilometres from Legacy Trail
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Five star Downtown Sarasota tropical garden Cottage1 / 44
    (17)Excellent
    4.9 kilometres from Legacy Trail
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • DVD Player
    • Wi-Fi
    • Secure Parking
    • Patio
    • Outdoor Dining Area
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 March 2017
    Maureen, our host, was super helpful and her place was a peaceful sanctuary, close to everything downtown. We have a toddler and it was great for him too.
    Reviewed 26 February 2017
    We have rented more than 20 homes and apartments in lieu of staying in hotels. My husband and I were very comfortable at this cottage and look forward to renting it again next...
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    About this property
    This location is central to everything and everywhere in Downtown Sarasota, near all area Beaches, Marinas, Golf courses, YMCA and Sarasota Bayfront. Only 7.5 miles to the 2017 World Rowing Championships at Benderson Park. This Charming Florida style home has been totally updated and stylishly...
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    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Charming 'Old Florida' one bed apartment, Sarasota1 / 24
    (3)Very good
    6.0 kilometres from Legacy Trail
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Grill
    • Balcony
    • Hot Tub
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    • 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 8 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
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    St.Armands Circle condo ( Kingston Arms )1 / 9
    (7)Very good
    6.0 kilometres from Legacy Trail
    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
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3.4 kilometres from Legacy Trail
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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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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    Lido Key, Sarasota
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    bring A Boat, 12 Minutes To Sarasota Bay1 / 11
    (15)Excellent
    5.9 kilometres from Legacy Trail
    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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    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Romantic Retreat with your own Private Pool1 / 25
    (1)Excellent
    0.5 kilometres from Legacy Trail
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
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    • Hot Tub
    • Grill
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    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Patio
    Suitability
    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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    Sarasota, Southwest Gulf Coast
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Beautiful 3 bedms/2 bathms with pool close to Downtown1 / 22
    (1)Excellent
    5.3 kilometres from Legacy Trail
    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 3 weeks ago
    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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3.2 kilometres from Legacy Trail
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Downtown Sarasota five star home1 / 55
    (7)Excellent
    4.7 kilometres from Legacy Trail
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 June 2017
    Loved our visit to this beautifully renovated home! It was just right for 2 couples and 2 boys. Convenient location on a quiet street, with great amenities. Enjoyed the...
    Reviewed 7 June 2017
    Great cozy stay. well kept and very close to everything. they even offered to come over and clean the grill and checked up to make sure we were enjoying our time! Def recommend...
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    About this property
    Our guests say this home is where you want to be ! Very central Downtown Sarasota near all area Beaches, Marinas, Golf courses, and Sarasota Bay front. Only 7.5 miles to the 2017 World Rowing Championships at Benderson Park.. This Charming Florida style 3 bedroom, 2 bath home has been newly...
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    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Tropical Escape Sarasota1 / 26
    (1)Excellent
    5.0 kilometres from Legacy Trail
    3 Bedrooms, 2 Bathrooms, Sleeps 15 Quick View
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    • Air Conditioning
    • Wi-Fi
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    • Hot Tub
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Elevated & spacious conveniently located home is nestled above 2 acres of Old Florida. The forest view home is 1400 ft.², 3Br/2Ba, LR, DR, Kit. For current and extensive reviews, visit the Tropical Escape in Sarasota, FL on Airbnb. A place worth reading about :) Early bookings may receive special...
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    Location Information
    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 15
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    1.2 kilometres from Legacy Trail
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a spacious house, located in Winchester Drive, close to downtown and beaches. With 2 bedrooms, 2 bathrooms, equipped kitchen and TV equipped living room, it can perfectly accommodate a family or group of friends of 4 guests. The house is located in Bayshore residential area, really close to...
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    Location Information
    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    5.3 kilometres from Legacy Trail
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Ocean Views
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located directly on the healing waters of Sarasota Bay, this home starts each day with glorious sunrises and ends with joyful dolphins swimming right up to the sea wall. Located at the end of a quiet street on Longboat Key’s exclusive Country Club Shores, this grand home was fully renovated only a...
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    Longboat Key, Florida
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    Location Location Location,The 'NEST' west of Tamiami Trl close to everything.1 / 14
    (1)Excellent
    5.2 kilometres from Legacy Trail
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Sarasota, Southwest Gulf Coast
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    5.1 kilometres from Legacy Trail
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a charming house, located on the quiet Sydelle Street in central Sarasota. With 3 bedrooms, 2 bathrooms, a veranda, garden, equipped kitchen and cosy living room, it can perfectly accommodate a family or group of friends. All commodities downtown Sarasota are a short drive away with Payne...
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    Location Information
    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Vacation Sarasota in great location to all venues....1 / 19
    (1)Excellent
    5.9 kilometres from Legacy Trail
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 March 2018
    This one level house as it all! Great location-close to beaches and just a short walk down the street to a community pool, three excellent sized bedrooms with band new bedding...
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    About this property
    This home has a living room, den, high top table that seat 6 for dining, small table in kitchen for 4, dishwasher, all utensils, and amenities. Conveniently located 4.2 miles from Siesta key or 3.5 miles from Lido beach and St.Armands circle. You can walk to Hillview st full of restaurants, bars...
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    Location Information
    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3.9 kilometres from Legacy Trail
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Cable/satellite TV
    • Housekeeping Included
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    Pet friendly
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    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
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    3 Bedroom House1 / 38
    (4)Very good
    2.6 kilometres from Legacy Trail
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Washer
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    • Private Garden
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    • Outdoor Dining Area
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 February 2018
    Bright and clean, lots of space, easy to get to and Darius was very helpful. This was the first time I've rented a home and it was a pleasure all round.
    Reviewed 22 November 2016
    The house was in a lovely neighborhood, convenient to family and to the beach. It was extremely clean and with much natural light. The kitchen and front bathroom were beautiful...
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    About this property
    This 3 bedroom 2 bath house is in immaculate conditions, ready to move in. This is a 2175 square foot newly renovated house. It offers a king size bed in two bedrooms, queen size bed in one bedroom, extra Pull-out Sofa Bed queen size in living room. The kitchen area has everything you would need to...
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    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    3.6 kilometres from Legacy Trail
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Big house is located in Sarasota-Downtown Area, just 2 minutes walking, 3 bedrooms(1 King, 2 queens), 1 sofa-bed, 1 bathroom, fully equipped kitchen, stove, living room, WiFi, Cable TV, washer-dryer, all linens and towels. Home is centrally located near restaurants, bars, beaches, can host up...
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    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 7
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    Sarasota Florida Paradise!1 / 19
    (15)Excellent
    3.3 kilometres from Legacy Trail
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Private Outdoor Pool (Unheated)
    • Internet Access
    • Patio
    • Cable/satellite TV
    • DVD Player
    • Grill
    • Air Conditioning
    • Washer
    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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    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    0.1 kilometres from Legacy Trail
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
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    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    1950's bungalow completely redone inside and out! Beautifully decorated in a French Country/Florida style with pops of color throughout! Enjoy a cup of morning Joe while relaxing in the breakfast nook as the Gulf breezes wash over you. The breakfast nook opens into the newly remodeled kitchen with...
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    Location Information
    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4.0 kilometres from Legacy Trail
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2/2 Turn key fully furnished and ready to be your home away from home! This place has all the comforts of home and then some. Master bedroom features a King Sized bed, built in dresser, 3 closets and a en suite with large shower. Hall bath features full tub/shower combo with extra linen storage....
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    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Sarasota Waterfront Suite1 / 8
    (1)Very good
    5.6 kilometres from Legacy Trail
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    King Size Bed, condo room - 350 sq ft, 1 bath PRIVATELY OWNED - INDEPENDENTLY OPERATED CONDOMINIUM LOCATED in a hotel at 7150 N Tamiami Trail, SARASOTA...WITH: Direct water views of the Sara Bay Marina. 1 bedroom Studio Suite. King size bed, small fridge with ice maker, full size microwave,...
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    Location Information
    Sarasota, Southwest Gulf Coast
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Downtown Apartment in Historic Burns Square downtown Sarasota1 / 21
    (1)Excellent
    4.0 kilometres from Legacy Trail
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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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
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    3.3 kilometres from Legacy Trail
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Internet Access
    • Balcony
    • Private Outdoor Pool (Unheated)
    • Terrace
    • Parking
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    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
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    4.2 kilometres from Legacy Trail
    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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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
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 7
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    5.6 kilometres from Legacy Trail
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    New king size bed with new 47 inch led flat screen television with full cable and HBO. Full bathroom with bath/shower. Microwave and small refrigerator. Beds: 1 King Bed. Beautiful hotel room located at the Ramada Inn Sarasota, operated independently from the hotel, but serviced by the hotel!...
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    Location Information
    Sarasota, Southwest Gulf Coast
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1.8 kilometres from Legacy Trail
    4 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Pet friendly
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    About this property
    This home has just been listed on Trip Advisor but has been on VRBO and Homeaway for over a year with all 5 star reviews. This beautiful Italianate-style 2-story home was built in 1925 during the John Ringling era. It is a rare find, nestled in a quiet, peaceful neighborhood and listed on the...
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    Location Information
    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 7
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    Cozy 2 Bedroom with Pool - Convenient Location - Walk to the Bay1 / 7
    (1)Very good
    3.9 kilometres from Legacy Trail
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    • Private Garden
    • Patio
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    • Private Outdoor Pool (Unheated)
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    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We also have two main rooms with 2 couches. A pool/ping pong table waiting to be used! Wi-fii is available. Washer/dryer access is flexible -- please ask. Screened-in lanai and swimming pool are ready to be used. If you forgot an amenity, please feel free to use those that we provide for...
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    Location Information
    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 5
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    5.6 kilometres from Legacy Trail
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Our place is right at the beach (very first row, no streets to cross, direct view onto the beach, dolphins, and sunset). You’ll love the place because of the , down-to-earth Longboat Key island atmosphere, the sunsets, a great kitchen, and the comfy bed. The place is good for couples, solo...
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    Location Information
    Sarasota, Southwest Gulf Coast
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    5.9 kilometres from Legacy Trail
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This spacious and bright 3BR/2BA Sarasota house is less than 5 mi away from Siesta Key Beach, one of America's Best Beaches as well as Lido Key home of St. Armand's Circle and the Lido Beaches and Parks. Both offer multiple options for lounging or water sports including boating, jet skiing,...
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    Location Information
    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4.0 kilometres from Legacy Trail
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Location Information
    Sarasota, Southwest Gulf Coast
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    4.2 kilometres from Legacy Trail
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    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
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    0.3 kilometres from Legacy Trail
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Patio
    • Air Conditioning
    • Wi-Fi
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the year-round warmth of Florida at this 3BR/3BA Sarasota home with outdoor amenities galore—all just one block from the stunning Sarasota Bay. Spend leisurely afternoons splashing in your private pool, surrounded by tropical landscaping and privacy fencing. The kids (and the family dog)...
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    Location Information
    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    5.6 kilometres from Legacy Trail
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Unheated)
    • Washer
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • Grill
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The star attraction of this 3BR/2BA Sarasota home is undoubtedly the screened pool — complete with an outdoor living area and a dining table for al fresco meals prepared on the gas grill. Spend lazy days swimming, sprawled out on a sun lounger, or reading on the outdoor sectional under the cooling...
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    Location Information
    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3.0 kilometres from Legacy Trail
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Wi-Fi
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Entertain your family or small group after a day of golfing or a day on the beaches. This newly built, town home in South Sarasota, is ideally located with easy access to Siesta Key beaches, and only minutes from large shopping malls, restaurants and Florida fun. Sarasota is the cultural center of...
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    Location Information
    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4.0 kilometres from Legacy Trail
    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
    Condo/Apartment - 1 Bathroom, Sleeps 3
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    3.3 kilometres from Legacy Trail
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    The Siesta Studio is a private entrance unit that is attached to my home. A comfortable queen bed with a private master bath, large walk in closet with plenty of hangers, iron and ironing board, hair dryer, stocked K-Cup coffee station, kitchenette for your continental needs, and a large outdoor...
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    Location Information
    Sarasota, Southwest Gulf Coast
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    An Upscale Romantic Getaway in Historic Laurel Park, Sarasota1 / 15
    (1)Excellent
    4.1 kilometres from Legacy Trail
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Balcony
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 February 2017
    This apartment is in a unique and beautiful neighborhood of Sarasota and about a 5 minute walk to the heart of downtown Sarasota. There are countless restaurants and bars on...
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    About this property
    Who ever knew you could fit so much convenience and luxury into 500 square feet? Our brand-new one bedroom apartment features a gourmet kitchen, a luxurious cathedral-ceilinged living room, a bedroom and a deck that faces the sunset. The front deck is a great place to have your morning...
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    Location Information
    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Experience Old Florida ~ Historic Downtown Laurel Park - Updated Cottage1 / 11
    (1)Excellent
    4.0 kilometres from Legacy Trail
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 April 2018
    Joseph and Leslie were very friendly, helpful and responsive to our requests. They have lovingly restored these delightful cottages, and the furnishings and accessories were...
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    About this property
    STRICT EIGHT NIGHT MINIMUM IMPOSED BY SARASOTA ZONING REGULATIONS. Due to limitations on Tripadvisor site, the quoted 7 day rate is for EIGHT NIGHTS. Five adjacent Cottages 1, 2 & 3 Br's all updated and ideal for families. Historical Sarasota Cottages Meets Key West Cool ~ Meets Shabby Chic....
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    Location Information
    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    5.7 kilometres from Legacy Trail
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    5.6 kilometres from Legacy Trail
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    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
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    2.5 kilometres from Legacy Trail
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A 3 bedroom/2 bathroom villa situated in a quiet residential location only minutes from downtown Sarasota.It has a private and secluded south facing garden with its own caged, solar heated private pool which catches the sun throughout the day.(electric pool heater is available for the cooler winter...
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    Location Information
    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.5 kilometres from Legacy Trail
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    This is a freshly remodeled 600 square foot one bedroom apartment in a historic home located in the coveted safe Northwest Sarasota neighborhood. Outside is your small but quaint front porch. Your front door leads directly into a funky well equipped ovenless galley kitchen. Beyond there you will...
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    Location Information
    Sarasota, Southwest Gulf Coast
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    0.3 kilometres from Legacy Trail
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in the Ringling Museum area. Very quiet and friendly neighborhood. Close to grocery store, pharmacy, liquor. 1 block to the bay - 6 miles from the Gulf of Mexico. Full kitchen, screened in porch, full yard completely fenced in. Great for a family getaway or large group. Sleeps 6...
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    Location Information
    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1.0 kilometres from Legacy Trail
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Private Outdoor Pool (Heated)
    • Parking
    • Washer
    • Cable/satellite TV
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    • Hot Tub
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    La Casita This totally remodeled new 2 bedroom, 2 bathroom cottage has everything. A wood burning fireplace, salt water heated swimming pool and spa, brand new kitchen, all new upscale stainless steel appliances with an induction stove. This quite cottage features an outdoor eating area and a...
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    Location Information
    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    0.6 kilometres from Legacy Trail
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Smoking allowed
    About this property
    You'll love the stunning brand new interior and excellent location of this house. Excellent location near Ringling Museum, Selby Gardens, Van Weazal, Downtown Sarasota, Ringling College of Art. This house is great for couples, family, or solo travelers. You'll enjoy a full kitchen, rain shower,...
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    Location Information
    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    4.7 kilometres from Legacy Trail
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    4/5 Bed Rooms, 3 Baths, Sleeps 8 to 12 Very elegant, updated, 4br, 3 ba, heated pool home, in the heart of Sarasota, close to every thing, down town, beaches, lido key, St Armand cir, marina jacks, gulf courses, museums . The house is fully renovated and updated, elegantly furnished and very...
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    Location Information
    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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