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Holiday Rentals in Sarasota, FL

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    Travellers to Sarasota are booking April dates now. Secure your holiday home today, and have the perfect trip.
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    5 of 5 bubbles (5) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Are you a Professional who is relocating to Sarasota or a vacationer who is looking to enjoy a first class accommodations? $ 2,000 per month from April through December. You will pay only $67.00 Per night for a minimum of one month. (IF YOU ARE LOOKING TO STAY FOR SIX TO NINE MONTHS, THE RENT... View all property information
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    Sarasota, Southwest Gulf Coast 34235
    1 / 23
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Outstanding views of the Palm Aire Championship Golf Course and Waterway from this second floor Condo. 2 King Size Bedrooms , 2 Full Bathrooms plus a Den w/ sleeper sofa and 40 in. flat screen cable TV. Free high speed internet & Free calling in North America. The condo is clean, comfy and... View all property information
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    Sarasota, Southwest Gulf Coast 34243
    1 / 26
    5 of 5 bubbles (76) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Very convenient, comfortable, tranquil Sarasota Vacation House. 5 minutes to Siesta Key.& Beaches. (2.8 miles to closest beach, Crescent Beach access, Siesta Public Beach about 4.5miles, Turtle Beach about 5miles). Features fully equipped kitchen, laundry with washer & dryer. Fireplace, tile floors... View all property information
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    Sarasota, Southwest Gulf Coast FL34231
    1 / 53
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Recently updated 2 bdr 2 bth 1,350 sq ft Gulf side condominium on Siesta Key. Located on ground floor overlooking a private landscaped pond with a full glass enclosed lanai, 3 minute walk to beach side pool and private white sands of beautiful Crescent Beach (designated #1 beach in the US.) Newly... View all property information
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    Sarasota, Southwest Gulf Coast 34242
    1 / 24
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    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... View all property information
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    Sarasota, Southwest Gulf Coast 34231
    1 / 18
    5 of 5 bubbles (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    This is a no smoking newly decorated (2008) second floor Condo. The entire complex of Sunset Royale has been renovated at a cost of 3 million dollars. The Floridian Room and Bedroom have a perfect view of the Siesta Beach and the Gulf of Mexico. We are only fifty steps from the white cool powdery... View all property information
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    Sarasota, Southwest Gulf Coast 34242
    1 / 24
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    2505 Mooring Lane has been completely updated inside and out with new Hardi-Plank exterior, new paint inside and out, new furniture and furnishings, renovated tile bathrooms, countless updates. Located adjacent to the retired executive par 3 golf course (now a pasture), quiet yet convenient to... View all property information
    Location Information
    Sarasota, Southwest Gulf Coast 34231
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    1 / 9
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    Moomist Villa is an idyllic setting to relax and rewind. It is located within Polynesian Gardens across the street from beautiful Siesta Key beach (Number 1 on the list of Top 10 most beautiful beaches in the USA). Out the front door you have a “peek-a-boo” view of the bay with boats cruising by.... View all property information
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    Sarasota, Southwest Gulf Coast 34242
    1 / 24
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    GOLF COURSE CONDO in gated community with wonderful amenities. <BR><BR>Our private, gated community in sunny Sarasota pairs amazing amenities with decidedly friendly residents, making Heritage Oaks a wonderful respite to call home- even if you're only renting for a month.<BR> <BR>Renting a condo... View all property information
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    Sarasota, Southwest Gulf Coast 34241
    1 / 24
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Beautifully and uniquely renovated home 1.25 miles from the # 1 Beach in the USA (Siesta Key Beach). (Ask Owner about closest beach access!) HOUSE HUNTERS AND RE-LOCATORS TO SARASOTA TAKE NOTICE SPECIAL DEALS NOW AVAILABLE for SEPTEMBER, OCTOBER & NOVEMBER; THAT'S PLENTY OF TIME TO FIND YOUR... View all property information
    Location Information
    Sarasota, Southwest Gulf Coast 34231
    1 / 11
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    A beautiful and spacious, 3-bedroom, 2-bath villa with a 2-car garage, your seasonal home away from home is extra comfortable with brand new furniture and linens and a flat-screen TVs in each bedroom. The living room also boasts a huge flat-screen TV. The lanai is glass-enclosed for use, no matter... View all property information
    Location Information
    Sarasota, Southwest Gulf Coast 34235
    1 / 12
    2 Bedrooms, 2 Bathrooms, Sleeps 1 | Quick View
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    Updated upstairs 2 bedroom 2 bath garden apartment. Very tastefully decorated with glass sliders enclosing the lanai and a beautiful lake view. Enjoy the heated community pool, 20 miles of walking trails, or a round of golf at the Meadows Country Club. There is one public golf course and seasonal... View all property information
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    Sarasota, Southwest Gulf Coast 34235
    1 / 9
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    Beautifully newly decorated in law suite off ,ain house. 1 bedroom, 1 full bath, kitchennett, & living room. Bedroom is 141sqft, living room is 218sqft, & a 30sqft kitchennett area. Includes queen bed,washer dryer. Spacious patio, firer pit, gas grill. SEASONAL OR ANNUAL RENTAL $125 dog fee... View all property information
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    Sarasota, Southwest Gulf Coast 34224
    1 / 34
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Our home is located in San Michele, a luxury townhome community featuring a beautiful lakefront. It is newly and fully furnished, comfortable, spacious and perfect for extended stays. It is minutes away from downtown Sarasota, the beaches, UTC Mall, IMG Academy, Ringling Museum of Art, baseball... View all property information
    Location Information
    Sarasota, Southwest Gulf Coast 34243
    1 / 24
    5 of 5 bubbles (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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.... View all property information
    Location Information
    Sarasota, Southwest Gulf Coast 34233
    1 / 13
    2 Bedrooms, 2 Bathrooms, Sleeps 1 | Quick View
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    This beautiful 2-bedroom 2-bathroom condo features not 1, but 2, screened-in lanais. 2nd floor allows you to view all the activity into the canal below. 1-car attached garage. Beautifully decorated and well maintained. Enjoy the heated community pool, 20 miles of walking trails, or a round of golf... View all property information
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    Sarasota, Southwest Gulf Coast 34235
    1 / 32
    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    This exquisite 4 Bedroom, 2.5 Bath expansive home, “The Riverfront Cottage” may well have the most fabulous waterfront vista of all off-island homes on Phillippi Creek, here in Sarasota. In an excellent location, only 2 miles or 7 minutes from the actual beach at Siesta Key’s south bridge, this... View all property information
    Location Information
    Sarasota, Southwest Gulf Coast 34231
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    1 / 9
    5 of 5 bubbles (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    Delightful one bedroom, one bath, 1925 bungalow. This immaculately clean, charming home has been lovingly renovated and features a fully stocked eat-in kitchen, a living room decorated in a comfortable cottage/coastal style and a large laundry room with a washer and dryer. Relax on the breezy,... View all property information
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    Sarasota, Southwest Gulf Coast 34236
    1 / 25
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    This newly renovated pet friendly mediterranean home features a large fenced in back yard with patio area. The large open concept kitchen features all stainless steel appliances and quartz counter tops. Oversized washer and dryer make it convenient to do laundry quickly! Master suit features a... View all property information
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    Sarasota, Southwest Gulf Coast 34239
    1 / 11
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    7N/8D Minimum Location, Location, Location! We have 7 cottages, all located in a very special residential community right downtown within easy walking distance to everything: restaurants, cafe's, shopping, theater's, the marina, etc. Laurel Park was voted the #1 neighborhood in Sarasota by "The... View all property information
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    Sarasota, Southwest Gulf Coast 34236
    1 / 22
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Private elevator into the home. Third bedroom is an office with two work areas and built ins. High end Exercise room. Pool and Hot Tub. Private access from our Lanai to the pool and Hot tub.Very exclusive only 16 owners in building. On the water with views of the gulf. Walk across the street to... View all property information
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    Sarasota, Southwest Gulf Coast 34242
    1 / 13
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    7N/8D Minimum We have 7 cottages for you to choose from. You can see all of them on our website ww w. sarasota cottage. com (type with no spaces) All of the cottages are located within walking distance to the most sought-after areas of Downtown and The Harbor. This one bedroom Coral Cottage Rear... View all property information
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    Sarasota, Southwest Gulf Coast 34236
    1 / 48
    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    Casa Antigua Welcome to Casa Antigua! Please Note: Sleeps 8: K, 2Q, 2T There is a 14 night minimum stay or 1 rental per 30 day period, per Sarasota, FL ordinance If this unit is not available, please contact us for the availability of another comparable one! Casa Antigua is a four (4) bedroom, two... View all property information
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    Sarasota, Southwest Gulf Coast
    1 / 31
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    Private updated modern 2 bedroom guest apartment with shared yard. Ride bikes to the beach only 3 1/2 miles, walk to shops and be in the middle of the action. Near Proctor and 41 just minutes from Siesta Key. Quiet residential home with friendly hosts. RV parking too. The Space Discover Siesta... View all property information
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    Sarasota, Southwest Gulf Coast 34231
    1 / 4
    5 of 5 bubbles (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 5 | Quick View
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    This one bedroom apartment combines the charm of old Florida and the perfect location. Only a 5 minute walk to the beautiful sugar sands of Lido Beach and only 10 to the shops and restaurants on St. Armands Circle. Enjoy your stay in this 1 bedroom / 1 bath apartment. Recently renovated kitchen... View all property information
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    Sarasota, Southwest Gulf Coast 34236
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Beautiful contemporary 2/2 with attached garage, caged private pool, hot tub, large entertainment bridge over part of pool (all pool is swimmable, just swim under the bridge) twin beds in guest room, king in master, both with bathrooms. Master is very large and will also accommodate two rollaway... View all property information
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    Sarasota, Southwest Gulf Coast 34232
    1 / 24
    5 of 5 bubbles (3) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Newly renovated 1/1 large (780 Sq.Ft.) 2nd floor condo 5 Minutes drive from #1 Siesta Key Beach. - Community pool - King size bed - Flat screen TVs - High-Speed WIFI internet Beds: 1 King Bed, 1 Sofa Bed View all property information
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    Sarasota, Southwest Gulf Coast
    1 / 7
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    Charming condo on second/top floor overlooking pool and ocean. Beautifully furnished, 5 minute bike ride (bikes included) to beach and 5 minute walk to famous Siesta Key Village. UNOBSTRUCTED water view from comfortable patio with chairs and dining table. Discount for 60 or 90 day rentals... View all property information
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    Sarasota, Southwest Gulf Coast 34242
    1 / 19
    4 of 5 bubbles (2) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    Great private cozy home with a nice outdoor terrace, bbq area, and tropical garden to enjoy!<BR>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,... View all property information
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    Sarasota, Southwest Gulf Coast 34231
    1 / 18
    5 of 5 bubbles (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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,... View all property information
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    Sarasota, Southwest Gulf Coast 34238
    1 / 15
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Condo Description<BR><BR>This Siesta Harbor Condo is a larger end-unit on the first floor of the Siesta Harbor Dolphin building with additional windows facing East and a hurricane proof lanai enclosure with screens overlooking the Yacht-Harbor turning basin. Covered parking for your car is... View all property information
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    Sarasota, Southwest Gulf Coast 43232
    1 / 12
    2 Bedrooms, 2 Bathrooms, Sleeps 1 | Quick View
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    Downstairs garden apartment with large eat-in kitchen, glass enclosed lanai, and view of the pool. Enjoy the heated community pool, 20 miles of walking trails, or a round of golf at the Meadows Country Club. There is one public golf course and seasonal golf, tennis, and social memberships are... View all property information
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    Sarasota, Southwest Gulf Coast 34235
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    This Beach Cottage has it all! Plenty of space for your friends and family and is located just steps from the World Famous Siesta Key Public Beach. This spacious Cottage has 4-5 available bedrooms and a fenced in backyard with propane grill. This house is ready for your next Siesta Key get... View all property information
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    Sarasota, Southwest Gulf Coast 34242
    1 / 29
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    2 BR. - 2 BA -- 6 Person Max. -- High Rise -- Beach View 1055 - 703 is a Gulfside Highrise unit, located approximately 75 yards away from Crescent Beach 2 Bedroom / 2 Bath unit. Approx. 1250 Sq. Ft. (1375 including the lanai) Bedding: Master Bedroom: King Guest Bedroom: 2 Twins... View all property information
    Location Information
    Sarasota, Southwest Gulf Coast 34242
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    This duplex normally houses actors from all over the country who come to Sarasota to perform at a live, professional theatre, but it's available now! Not only will you have a clean, comfortable place to rest in between adventures, but guests who stay at least a week will also receive, based on... View all property information
    Location Information
    Sarasota, Southwest Gulf Coast 34236
    1 / 24
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Wi-Fi
    • Hot Tub
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    ANNUAL RENTAL - BRING YOUR BOAT with deep water access and 14,000 pound boat lift just a few minutes from the Sarasota Bay Intracoastal Waterway. The home has been completely renovated and professionally decorated. Offering 3 bedrooms with master overlooking the pool, hot tub and waterway. Pool,... View all property information
    Location Information
    Sarasota, Southwest Gulf Coast 34231
    1 / 10
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
    • Private Indoor Pool
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    • x
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    • x
    About this property
    Luxury house with private pool situated on Tara golf and country club in Sarasota, Florida. <BR><BR>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. <BR>There is a large bright fully equipped kitchen... View all property information
    Location Information
    Sarasota, Southwest Gulf Coast 34203
    1 / 11
    Lido Key
    1 Bedroom, 5 Bathrooms, Sleeps 4 | Quick View
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    • Satellite TV
    • Waterfront
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    • Pet-friendly
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    • x
    • ?
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    • x
    About this property
    Large 1 bedroom fully furnished condo (981 square feet) includes 1 bedroom, 1.5 baths, featuring an open kitchen with island, dining room, living room and an office. 10th floor.<BR><BR>Fully equipped, brand new kitchen with granite countertops, sofa sleeper, cable TV, telephone, and WiFi. Laundry... View all property information
    Location Information
    Lido Key, Sarasota 34236
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    5 of 5 bubbles (1) Excellent
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Get into a tropical state of mind with a vacation in this refreshing Sarasota cottage. It features a private hot tub, ocean access for fishing and kayaking, and plenty of modern conveniences for a comfortable stay with up to six guests and two dogs. This home resides in Indian Beach/Sapphire... View all property information
    Location Information
    Sarasota, Southwest Gulf Coast 34234
    1 / 22
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    Welcome to your 3-bedroom pool home located in Sarasota Florida. If you’re looking for a place near local shops, restaurants and local beaches this is the home for you. Being close to I75 will also make traveling to nearby areas a breeze. This home features all the latest upgrades and is situated... View all property information
    Location Information
    Sarasota, Southwest Gulf Coast 34243
    1 / 13
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Washer
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    • Shared Outdoor Pool...
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    • ?
    • ?
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    • x
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    Available for Season 2017! Beautifully updated 2nd-floor 2/2 condo in Willow Links. This unit has a brand new kitchen with solid-wood cabinetry and beautiful marble counters. Wood laminate and ceramic tile flooring throughout. Tasteful, updated decor. King sized bed in master and twins in guest... View all property information
    Location Information
    Sarasota, Southwest Gulf Coast 34235
    1 / 29
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    • Wi-Fi
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    • Balcony
    • Shared Outdoor Pool...
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    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Step out onto your private balcony and watch the boats docked in a small cove just off the intercostal. - Completely redone 2 bedrooms, kitchen, baths, living room in a beautiful beach theme with predominantly white colors with pops of turquoise, teal and calming sea blue. - Enjoy the king bed in... View all property information
    Location Information
    Sarasota, Southwest Gulf Coast 34242
    1 / 9
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    This home normally houses actors from all over the country who come to Sarasota to perform at a live, professional theatre, but it's available now! Not only will you have a clean, comfortable place to rest in between adventures, but guests who stay at least a week will also receive, based on... View all property information
    Location Information
    Sarasota, Southwest Gulf Coast 34236
    1 / 10
    Lido Key
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Parking
    • Private Garden
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    • x
    About this property
    Wonderful cottage - the first house across the street from the beautiful white sand of Lido Key! Short walk (less than half a mile) to the famous St. Armand's Circle and it's quaint Restaurants, Shopping and Entertainment. This is the rear of a duplex house which has 1 bedrooms (queen bed) and one... View all property information
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    Lido Key, Sarasota 34236
    1 / 12
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    2 Bedroom Apartment, $1050 a week or $1895 Mo.for April , $ 1695 May - December 2017 & $4300 Mo. January, February & March 2018 must rent Jan.- March. Cable included , Sleeps 6 , VOTED # 1 BEACH IN THE US ' Walk to beach, 1 1/2 blocks to beach very tropical right on bay near Stickney Point... View all property information
    Location Information
    Sarasota, Southwest Gulf Coast 34231
    1 / 15
    2 Bedrooms, 2 Bathrooms, Sleeps 3 | Quick View
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    • Internet Access
    • Satellite TV
    • Shared Garden
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    • Grill
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Furnished home rental RATE available for ANNUAL / NOT MONTHLY rental contract with RoseBay rental program. House rental is for ANNUAL rental due to insurance and community tax regulations. If you want a monthly period, I suggest you try the monthly rentals at condos on siesta Key. If I rent for... View all property information
    Location Information
    Sarasota, Southwest Gulf Coast 34242
    1 / 24
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Parking
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    • Outdoor Dining Area
    • Porch
    • Internet Access
    • Patio
    • Washer
    • Grill
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Your upcoming Florida vacation will be everything you imagined and more when you book a stay at this Sarasota house! This quaint 3-bedroom, 2-bathroom abode comfortably sleeps 6 and provides all the amenities of home, providing a comfortable stay.   The ultimate Florida vacation awaits at this... View all property information
    Location Information
    Sarasota, Southwest Gulf Coast 34242