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Holiday Rentals nearby Legacy Trail

Train Depot, Sarasota, Florida
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    Travellers to Sarasota are booking December dates now. Secure your holiday home today, and have the perfect trip.
    All 96 Rentals in Sarasota
    Fido Friendly w/Fenced Yard, Spa/Swimming Pool,  Wifi, Large Ranch Home, Large L1 / 35
    (1)Excellent
    4.5 kilometres from Legacy Trail
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Beautiful Main Street Loft Apartment1 / 10
    (1)Excellent
    3.4 kilometres from Legacy Trail
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Walk to Everything Downtown, Bring Fido, Wifi, Huge Screened Lanai, Extensive Ou1 / 28
    (1)Very good
    3.2 kilometres from Legacy Trail
    2 Bedrooms, 1 Bathroom, Sleeps 4 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 9 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 25 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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    3.9 kilometres from Legacy Trail
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Cable/satellite TV
    • Housekeeping Included
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We are in the heart of historic Burns Square in downtown Sarasota, nestled between high end residential neighborhoods S. Palm Avenue, Laurel Park and Hudson Bayou. The property is a mixed-use historic property with residential on the second floor with stairs. You do not need a car as we are in...
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    Sarasota, Southwest Gulf Coast
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    2.5 kilometres from Legacy Trail
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Patio
    • Washer
    • Grill
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Uplands Oasis Find your Oasis in the relaxing global stylings of this unique 2bedrooms/2 baths, single-family ranch style house. Located in the quaint northern Sarasota neighborhood of the Uplands, the Uplands Oasis home provides all the features and amenities to make Sarasota your next home...
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    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    4.2 kilometres from Legacy Trail
    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Washer
    • Central Heating
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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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    Lido Key, Sarasota
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 7
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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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    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Sarasota, Southwest Gulf Coast
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    4.2 kilometres from Legacy Trail
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Secure Parking
    • Air Conditioning
    • Washer
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in the heart of Sarasota City, just minutes to shopping, dining, golf courses and of course the #1 Beach in the USA along with multiple other beautiful beaches including Lido Key, Casey Key, Turtle Beach and more. This is a 1000 square foot two bedroom apartment with 1 car garage, offers a...
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    Lido Key, Sarasota
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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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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    Spacious Apt. #1 Historic Walkable Downtown, between Siesta & Lido Beach1 / 30
    (2)Very good
    4.0 kilometres from Legacy Trail
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
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    • Housekeeping Included
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 February 2016
    We just spent a delightful 4 days in the heart of historic Burns Court. This renovated apartment was so wonderfully located in it's proximity to historic Sarasota. Everything is...
    Reviewed 19 August 2015
    We had a great stay here, the apartment was right downtown, it was very comfortable, and we hope to return soon!Denise was very helpful.
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    About this property
    Historic 1920's Mediterranean & 1950’s Historic mixed-use building in Burns Square, downtown Sarasota, safely nestled between high-end residential neighborhoods of Palm Avenue, Laurel Park and Hudson Bayou. Apartment is private and secure, located on the second floor (stairs) with original hardwood...
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    Location Information
    Sarasota, Southwest Gulf Coast
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    4.2 kilometres from Legacy Trail
    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
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    4.0 kilometres from Legacy Trail
    Studio, 1 Bathroom, Sleeps 3 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    4.2 kilometres from Legacy Trail
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Washer
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    • Wi-Fi
    • Secure Parking
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a 1000 square foot newly renovated 2 bedroom, 1 bath, 1 car garage town-home. It offers a Queen size bed in Master bedroom, two twin size beds in second bedroom and two sofa's beds (Full size) in the Living room. The kitchen has everything you would need to cook. 32' LED TV, WiFi internet,...
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    Location Information
    Lido Key, Sarasota
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    4.0 kilometres from Legacy Trail
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    My historic building was built in the 1950's and has clean character and ambiance. Walking distance to Whole Foods/Publix, fabulous restaurants, diverse shopping options, performance theaters, movie theaters, nightlife, public transport, boat/water activity rentals, parks, spas, and a short...
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    Location Information
    Sarasota, Southwest Gulf Coast
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    3.3 kilometres from Legacy Trail
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Patio
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Waterfront
    • DVD Player
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    JUST LISTED! Newly updated, FULLY FURNISHED, 3 bedroom, 2 bath home with an office space. Located just minutes from the world-renowned SIESTA KEY BEACH, and in the highly sought-after GULF GATE EAST in the PALMER RANGE area. This home features a screened, private, solar-heated pool overlooking a...
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    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    3.8 kilometres from Legacy Trail
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Recent remodel with new everything! Close enough to walk everywhere. Three blocks to the bay, over 20 restaurants and 2.5 miles to beach. In the middle of it all. Outdoor seating at sidewalk French Cafe. The new memory foam mattress is amazing! Sleep like a baby :). A cafe' & wine bar is below...
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    Sarasota, Southwest Gulf Coast
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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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
    • Air Conditioning
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    Suitability
    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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    Boat-Shaped Home, Built by Master Shipbuilder - Local Icon!1 / 19
    (1)Excellent
    3.3 kilometres from Legacy Trail
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Washer
    • Balcony
    • Patio
    • Cable/satellite TV
    • Parking
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 September 2018
    We stayed @ The Rowe Boat for 7 glorious days. The pictures are EXACTLY as shown on their internet sites. The location is fabulous & neighborhood is historic - which I...
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    About this property
    Designed to accurately emulate ocean living, this historic home was built for John Ringling's (Ringling Bros. Circus Founder) skipper, Arthur Rowe and has affectionately been named The Rowe Boat. Part of local Sarasota lore and legend, the structure was designed and built in 1933 by famous...
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    Location Information
    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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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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    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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    0.3 kilometres from Legacy Trail
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Cable/satellite TV
    • 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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    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    A luxurious 1926  Florida bungalow, located in historic Laurel Park, Sarasota1 / 17
    (3)Excellent
    4.1 kilometres from Legacy Trail
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Balcony
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Terrace
    • Patio
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 February 2017
    I'll be the first to admit I didn't know much about Sarasota before heading to Susan and Jerry's bungalow, but I left feeling like a regular! It is the perfect location from...
    Reviewed 13 February 2017
    We stayed here because we wanted a quiet location within easy walking distance of the Marie Selby Botanical Gardens, the Marina complex and Sarasota center with its many shops...
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    About this property
    This upscale and unique 1926 Florida bungalow, with two bedrooms and two bathrooms, is located in the historic Laurel Park District of Sarasota. It features the charm of the old with the convenience of the new. The 1300 square foot home, with original old pine floors, was totally and elegantly...
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    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1.3 kilometres from Legacy Trail
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a spacious house, located in a very charming area. You are few minutes away from Sarasota Jungle Gardens, Ringling Museum and from the airport. This one of the best area in Sarasota. With 3 bedrooms, 2 bathrooms, equipped kitchen and TV equipped living room, it can perfectly accommodate a...
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    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.6 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
    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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    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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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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    3 Bedroom House1 / 76
    (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 26 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 21 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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    Location Information
    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    4.7 kilometres from Legacy Trail
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience the picturesque and beauty of waterfront downtown Sarasota by staying in this peaceful and quaint cottage on the east side of downtown Sarasota. This cottage home is centrally located and is only minutes from central downtown, Sarasota Marina, and Bayfront Park. The amenities of Payne...
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    Location Information
    Sarasota, Southwest Gulf Coast
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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
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    • Washer
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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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    The Historic 1936 Bird House Bungalow'charming'1 / 19
    (9)Excellent
    2.0 kilometres from Legacy Trail
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Parking
    • Wi-Fi
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    • DVD Player
    • Cable/satellite TV
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 October 2017
    The Bird House is a jewel, carefully decorated and furnished with unique pieces and antiques. I had the place to myself but could have shared it with 6 or 7 others comfortably...
    Reviewed 21 May 2017
    We were looking for a place convenient to downtown, to walks toward the water, and a relatively short ride to Lido beach. To find one with artistic features and nostalgic...
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    About this property
    NOTE : :PLEASE DISREGARD ANY QUOTES OR INFORMATION ON THE BOOKING POLICY PAGE.Contact us for rate quotes and possible shorter stays.The Bird House Bungalow is a 1936 home with 3 bedrooms and 3 baths. King and full downstairs with full and sitting area upstairs. Each bedroom has its own separate...
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    Location Information
    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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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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    • Parking
    • Private Garden
    • Wi-Fi
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    • Air Conditioning
    • Balcony
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 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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    3.8 kilometres from Legacy Trail
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Recent remodel with fresh new everything! You're close enough to walk everywhere. This spacious apartment is above a popular French Pastry & Coffee Shop, 3 blocks to the bay & park, main street and famous Marina Jack's. Space optimized - 550 sq ft. Includes: *Washer/dryer in unit *4K Roku TV...
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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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    • Parking
    • Patio
    • Air Conditioning
    • Private Garden
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    • Washer
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Parking
    • Air Conditioning
    • 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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    3.6 kilometres from Legacy Trail
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Secure Parking
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    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Private Back-Apartment renovated and available for your vacation, 2 rooms, 1 bathroom ,two beds( 2 queen size), kitchen fully furnished, Cable-TV, Internet Wifi. Humble place(not a five star hotel), centrally located at Sarasota Downtown Area and Marina Jack Bay. Apartment is attached to the...
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    Location Information
    Sarasota, Southwest Gulf Coast
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    1.5 kilometres from Legacy Trail
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
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    • Patio
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *Please note that the homeowner lives on site, in a completely separate unit, and may be present during your stay* Experience the best of Sarasota’s attractions and stay at this charming, private 1-bathroom vacation rental studio that sleeps 2. This quiet, newly remodeled unit, surrounded by...
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    Location Information
    Sarasota, Southwest Gulf Coast
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    4.0 kilometres from Legacy Trail
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
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    • DVD Player
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Discover your own slice of heaven with this quaint Sarasota studio, which sleeps 2. Nestled on a quiet street within walking distance of Sarasota Bay and downtown, this marvelous unit offers vintage charm and everything necessary for an unforgettable Sunshine State retreat. THE PROPERTY From the...
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    Location Information
    Sarasota, Southwest Gulf Coast
    Condo/Apartment - 1 Bathroom, Sleeps 2
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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)
    • Washer
    • Cable/satellite TV
    • Parking
    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
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Patio
    • Grill
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    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    PROPERTY OVERVIEW Whether lounging under the sun in the spacious backyard, watching a professional spring training baseball game a block away, or exercising at the Youth Athletic Complex across the street, you’ll adore this dog-friendly 3BR one-level home with a premier Sarasota location. Enjoy...
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    Location Information
    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    3.8 kilometres from Legacy Trail
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Wi-Fi
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    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Recent remodel with fresh new everything! Close enough to walk everywhere. This spacious studio apartment is above a popular French Coffee Shop & wine bar, 3 blocks to the bay & park, Main Street and famous Marina Jack's. Outdoor seating at sidewalk French Cafe. You'll love the new memory foam...
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    Location Information
    Sarasota, Southwest Gulf Coast
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    4.0 kilometres from Legacy Trail
    2 Bedrooms, 1 Bathroom, Sleeps 2 Quick View
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    • Grill
    • Air Conditioning
    • Parking
    • Patio
    • Internet Access
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful dog-friendly gold cottage offers a whimsical oasis for its guests! This home offers a one-of-a-kind glass tiled bathroom and a private garden, perfect for journaling or enjoying a cool beverage. The garden is mostly shaded by an indigenous Giant Oak Tree and provides a truly unique...
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    Location Information
    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 2
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    0.7 kilometres from Legacy Trail
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Cable/satellite TV
    • Air Conditioning
    • Parking
    • Waterfront
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Treat your family, friends, and beloved 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
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4.1 kilometres from Legacy Trail
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Patio
    • Washer
    • Grill
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    • Cable/satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy this perfect little studio nestled in Sarasota's Historic Laurel Park District. You'll be surrounded by palm trees, bamboo, and jacaranda trees. Amenities include a private washer/dryer, large walk-in closet, central A/C, and a gas grill. The Treehouse is perfect for a quiet getaway for two!...
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    Location Information
    Sarasota, Southwest Gulf Coast
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    3.8 kilometres from Legacy Trail
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Clean and crisp, remodeled 2018. Be in the center of it all! This apartment is three blocks to the bay & park, main street and famous Marina Jack's. Spacious - 750 sq ft. Sleep 6 comfortably - 2 Queen beds and a queen sleeper sofa. Parking is at a premium downtown. This unit has a FREE parking...
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    Location Information
    Sarasota, Southwest Gulf Coast
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
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    charming home near down town Sarasota1 / 24
    (1)Very good
    1.7 kilometres from Legacy Trail
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This three bedroom, two bath ranch style home has a great location, foot steps from down town Main Street and the Ringling School of Art. It is modern, updated and comfortable. Large TV with surround system in the living room. A private little back yard invites for enjoying the outdoors. Being in...
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    Location Information
    North Sarasota, Southwest Gulf Coast
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4.1 kilometres from Legacy Trail
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • Parking
    • Internet Access
    • Patio
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    • Cable/satellite TV
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience Old Florida like you never have before at this vintage 1926 cottage tucked away among the bamboo, palms, and jacaranda trees right in the Historic District. This home's outdoor tropical paradise boasts a spacious deck, outdoor seating for eight, and an outdoor grill surrounded by lush...
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    Location Information
    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    4.7 kilometres from Legacy Trail
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Washer
    • Patio
    • Hot Tub
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    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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    3.8 kilometres from Legacy Trail
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This newly remodeled window filled apartment is spacious, romantic and very comfortable. Perfect for a couple. Three blocks to the bay & park, main street and 2.5 miles to the beach. This 10 apartment building only has 3 dedicated parking spaces for tenants. Lucky you, this unit comes with a...
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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, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Parking
    • Private Garden
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful furnished condo in PalmAire Country Club close to Lido Beach and Longboat Key. First class shopping, golf courses and restaurants( you wil never have to cook!) Stainless steel kitchen, clean, wi-fi internet, cable and community pool. the location is right on University with Whole Foods,...
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    Location Information
    Sarasota, Southwest Gulf Coast
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1.0 kilometres from Legacy Trail
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Your modern 2-bedroom oasis awaits! Welcome to this stunning, spacious home with a private pool in one of Sarasota's most desirable neighborhoods, Indian Beach-Sapphire Shores, nestled between the beautiful aqua waters of Sarasota Bay and the Gulf of Mexico. This vacation home beauty is just two...
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    Location Information
    Sarasota, Southwest Gulf Coast
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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