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Discover this amazing 2-bedroom gem in Siesta Key Jamaica Royale is a gulf side paradise. Jamaica Royale offers 300 feet of private white sandy beach on Siesta Key Beach with lush tropical grounds. There are 3 large pools for your enjoyment. One pool is right by the beach. This tranquil villa boasts 1...
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Beautifully renovated and immaculate home with pool and dock Near St Armand's and Lido BeachNEW PROPERTYWelcome to 440 Cleveland Drive, a stunning, fully renovated rental property on Lido Key where luxury meets coastal charm. Completed in March 2025, everything inside and outside this home...
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Experience Sarasota's most walkable neighborhood from this stunning 3BR/3BA modern coastal haven with private pool. Discover the perfect blend of luxury and convenience at The Palmetto House. This completely renovated modern coastal cottage puts you in the heart of Arlington Park, Sarasota's...
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The location was excellent and central to what our needs were. Plenty of nice restaurants within a couple of miles. The unit had everything that you could possibly need and would work for several couples....
Distance to beach: 2 miles to Lido
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Relax at this lovely comfortable and spacious one bedroom or studio apartments with gorgeous new inground swimming pool at the Southside Village Resort. Check out our website for all the various options that are available. We are located in the wonderful Southside Village, also known as the Hillview...
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Fantastic. Like home away from home. great Hosts and beautifully located. Flat was sparkling clean and jason and Dee and their son Storm always on hand for any help required. We can only highly reccomend...
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Experience our newly renovated private villa, designed for comfort, style, and unforgettable stays This spacious retreat features 3 beautifully appointed bedrooms and 6 beds, comfortably accommodating up to 10 guests.Step outside into your own resort-style backyard Enjoy the heated pool and hot tub,...
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Siesta Key Family Getaway – Renovated Pool Home w/ Mini Putt & Outdoor Games! Bring the whole family to this beautifully renovated Sarasota pool home, located just 15 minutes from the world-famous Siesta Key Beach! This bright and stylish 3-bedroom, 2-bath retreat comfortably sleeps up to 10...
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A Great Home Away from Home Boatyard Gated Community Comfy Lanai for relaxing and entertaining Bamboo Wood Floors 2 bedrooms (one king and one queen bed) and 2 bathrooms Main bedroom new comfy king mattress Nice kitchen amenities like air fryer Extra capacity water heater Heated Pool Upgraded...
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Located in a quiet cul-de-sac, this property offers a peaceful and tranquil setting. Away from the hustle and bustle of the city, you can enjoy a serene and calm environment in your own home.The private lanai with a heated pool provides a secluded outdoor space where you can relax and unwind. Whether...
Featured review
Very spacious updated home. Beautiful kitchen with all new appliances. Lovely lanai with pool. Very private. Owners were very responsive with questions. They provided written information about the home,...
Distance to beach: 50 yards to Lido Beach
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Welcome to our stunning ground floor condo, nestled directly on the pristine Gulf of America along a tranquil stretch of Lido Beach. Say goodbye to stairs and elevators – step right into your paradise!Completely renovated in 2025, this condo offers a fresh and modern retreat, designed with...
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We rented this gorgeous Condo for the month of March, 2024. First of all, the location is perfect, right on Lido Beach with a pool onsite and right down the street from St. Armand's Circle in Sarasota....
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Spring comes alive at this creekside retreat, where gentle breezes and the songs of local birds fill your mornings. Spend your days paddling along the winding creek, explore nearby sandy beaches, or cast a line for fishing. Discover local culture at nearby museums & art galleries; return to unwind...
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We were located near the airport and the beaches. We would drive to the beach areas and get on the free trolleys to explore the various parts of the city and islands, or enjoy the sunny weather on the...
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A Florida style charming paradise cottage featuring a tropical oasis backyard with large in-ground pool and bar area. This home is fully furnished and conveniently located. Enjoy a newly renovated home that includes an updated kitchen, living room, bathroom and bedrooms, and new central air and roof....
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We just ended our stay at this charming Florida cottage and can’t wait to return next year. This two/three bedroom house is clean and comfortable and is located in an older quiet and friendly neighborhood...
Distance to beach: 1 miles to Siesta Key
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OUR RATES:April 2026 $3000 May-November 2026 2025 $2250 December 2026 $3000 January 2027 $4500 February 2027 $5000 March 2027 $5500*Calendar months only. *Ask for our 6-month plus special rate *Pet Friendly, Community pool and gym boutique-style condominium community that offers:WELCOME...
Featured review
It was a pleasure working with Ana (and her husband). The unit was clean, modernized, and comfortable. The area was very nice, quiet, friendly neighbors and kept clean. Location was good, plenty of restaurants...
Distance to beach: 2 miles to Siesta Key beach
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OUR RATES:May -November $1999 December $3000 January $4200 February-March $4500 April $2500*Calendar months only. *Pet Friendly, Private Yard, First Floor Unit. *Community pool and gym in Complex. *Ask for our 6-month plus special rate *Boutique-style condominium community that offers:WELCOME...
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We stayed here for a clinical rotation from July - October at the Oasis on Osprey. It was truly a wonderful experience. Ana was always so helpful and attentive whenever we needed something. The area surrounding...
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Escape to your own slice of paradise in the heart of Sarasota's coveted Gulf Gate community with this beautifully updated 2-bedroom, 2-bathroom retreat, designed with a relaxing stay in mind. Featuring a heated, caged pool, and just moments away from the world-renowned Siesta Key Beach, this gem...
Distance to beach: 2 miles to Siesta Key Beach / Cresant Beach
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Quiet, private and pet friendly 2 bedroom, 2 bath, swimming pool home in Gulf Gate just 5 minutes to Siesta Key and her Beaches! Your Rental Fee includes the following (Rent, Cleaning Fee, Florida 12% taxes, Cable, Water & Utilities). Pet Fee additional to rental fee. NO Owners or Service Fees, ever.Be...
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Amazing home, awesome location just outside of Siesta Keys yet in a quiet and quaint subdivision in Gulf Gate.We stayed all of Feb 2026 and enjoyed every day there – wished we could’ve stayed longer. The...
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Seascape on Clarinda | Spacious 4BR/4BA Private Pool Home with Outdoor Kitchen & Beach GearWelcome to Seascape on Clarinda, a stunning full-house rental nestled in Sarasota, Florida, just 20 minutes from the world-famous Siesta Key Beach. This beautifully appointed 4-bedroom, 4-bathroom home comfortably...
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Fantastic totally remodeled vacation spot with a luxurious screened in private heated pool - this spacious house has all the amenities of home so you'll never want to leave! Just a quick 7-10 minute drive to the beautiful free public beach, 12 minutes to fun Siesta Village, and 20 minutes to St...
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Minutes to Siesta Key, downtown Sarasota, hospital, restaurants, shopping, fitness and schools. Entertaining and seamless indoor/outdoor living from a large 17-by-37 resort-style pool with fountains, an alcove with a built-in table and seating is incredible, tranquil and relaxing. There is a hard-to-find...
Featured review
Owners Rachael & Sarab were wonderful during our stay and great to work with. The pool was as advertised, very large, great for a good sized family with kids. The home layout was great for our family as...
Distance to beach: 0.1 miles to Lido
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Lovely remodeled and refurbished 5 bedroom 5.5 bath pool home on desirable St. Armand's Circle! This 3,000 s.f. home comfortably sleeps (8) in beds, and has T.V.'s in the family room and living room for when the family is not enjoying the caged pool and spa. Professionally decorated, quality...
Distance to beach: 1 miles to Longboat Key
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Charming, waterfront Longboat Key surprise! This 2 bedroom 2 bath house is sure to impress. Total renovation will bring you delight upon entering. Fun, chic, beach inspired decorating with the fun, splattered octopus theme to bring a smile to anyone. Plenty of dishware, gadgets, cooking equipment for...
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Very inviting home with pool, fenced yard and simple walk to St Armand's Circle.A Jewel on St. Armands Circle! The location makes this spacious 3BR+Casita/3BA with a private pool in a botanical setting a perfect month long vacation spot. This residence has it all for those who want to be right...
Distance to beach: 0.1 miles to Lido
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St. Armand's Canal-Front Pool Home steps to the beach!This gem, ranch style home estate has been completely rebuilt and remodeled in 2015 from the frame including all new finishes inside and out. With fresh, coastal Old-Florida decor, it is in one of the most desirable locations on the west...
Distance to beach: 3 miles to Siesta Key
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My wife and I are recently retired educators. We ARE NOT multiple rental property owners. We own this one condo and are snowbirds from Pennsylvania. Our place is newly remodeled floor to ceiling! The Oasis complex is a prime location in close proximity to downtown Sarasota, Siesta Village, & nationally...
Featured review
We enjoyed a 3-month stay in Bellamar at Beachwalk. It’s close to everything - restaurants, grocery store within walking distance and Fort Myers Beach, Sanibel, Captiva, MN Twins/Boston Red Sox spring...
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Welcome to Glamor Manor, your luxurious retreat in the heart of Sarasota, Florida! This exquisite vacation rental offers an unparalleled experience of comfort, style, and relaxation.Property Highlights: Pet friendly : $200 non-refundable pet fee Heated Swimming Pool: Dive into luxury with our private...
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Direct beachfront condo located on the desirable Crescent Beach at the southern end of Siesta Key. Views for miles of the sparkling gulf waters, white sand and Point of Rocks from all rooms. An open and spacious floor plan, generous balconies, washer/dryer in the condo. Covered parking and elevators all...
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Contact: Erana Pulli or Joesgirl16@ Newly renovated condo. First-floor end unit with a beautiful, private courtyard. Large, light, bright, and airy best describes our home! Granite countertops and stainless steel appliances are found in our eat-in kitchen. Another large dining table off the living area....
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a small studio condo: a fairly private bedroom (no door) and a sleeper sofa in the living room; best for 2, but sleeps 4. There is a very small screened balcony. The one bath has a shower. The guest section of the closet has hanging space, several shelves and drawers; the bedside tables have 4 compartments...
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Bring the whole family as this home features 3 bedrooms and 2 1/2 baths. This very spacious home is almost 2,600 square feet with plenty of room to relax. Huge open living area. You will love the fenced backyard featuring multiple seating areas and a pool to relax in. Portable putting green and safe ax...
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Welcome to your dream vacation home in Sarasota! This exceptional 3-bedroom, 2.5-bath house in the peaceful Coral Cove neighborhood offers a perfect blend of comfort and convenience. Relax by the private pool, enjoy the open floor plan with granite countertops, stainless steel appliances, and new furnishings....
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Brought to you by Pier Property Management. Get ready to immerse yourself in the coastal vibe and everything the gulf beaches have to offer. This charming 1/2-acre home located in one of Sarasota's most desirable communities features 4 bedrooms, 3 full baths and an enclosed caged pool with a white...
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Wood-Burning Fire Pit | Cable TVs With at-home conveniences and sought-after amenities at your fingertips, this well-appointed home is perfect for families looking to explore Sarasota! Bedroom: Queen Bed | Living Room: Queen Sleeper Sofa | Screened-In Porch: Queen Sleeper Sofa RESORT AMENITIES: Hot tub,...
Distance to beach: 7 miles to Siesta Key Beach
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Luxury lakefront home on a quiet cul de sac located in pristine Palmer Ranch. Kick back on the covered front porch and relax in the glider and rocking chairs. Soak up some sun in the screened in lanai with heated saltwater pool overlooking the lake. Enjoy community amenities such as the clubhouse, community...
Distance to beach: 8 miles to Lido Key
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* New Resort Style Backyard!Welcome to Saltwater Siesta — a family favorite near IMG Academy and the Gulf’s top white-sand beaches! Enjoy the new resort style outdoor space! Lounge by the heated (no heating fee!) saltwater pool, play mini putt, bocce, frisbee golf, yard and pool games....
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This beautiful home is brand new inside! It features 2 family rooms and a split floor plan that makes it perfect for families or 2 couples. Enjoy the morning breeze by the screened -in pool. The family room and Master Suite have French doors that open to the pool. 4 miles to siesta key, 3 miles...
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OPEN FOR RENT AFTER HURRICANE You'll really enjoy this vacation home. This very spacious 3 bedroom, 2 bath home has plenty of room in the living, dining, and pool deck . This recently renovated ranch style is in one of the most desirable locations in Sarasota! Nestled in the quaint area of Gulf Gate....
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Located in the heart of Sarasota, less than ten minutes to Siesta Key Beach and Downtown Sarasota, completely renovated home has it all. Ranch style has tall ceilings, modern kitchen, open layout. Four bedrooms to choose from . A spacious master bedroom and a spa like bathroom that has a soaking tub and...
Distance to beach: 4 miles to Siesta Key/Crescent Beach
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This exquisite Coastal House with all brand NEW furnishings has a beachy style with King size beds in ALL 3 bedrooms! It’s conveniently located just 3.8 miles from #1 Siesta Key Beach, only 5 miles to downtown Sarasota, just 7.5 miles to Lido Key Beach/St. Armand's Circle, 2 houses down from...
Featured review
We had a lovely stay at this newly remodeled home in Sarasota. We enjoyed morning coffee on the back patio after a great night's rest in the king size beds (three KING beds--what a bonus!), and we definitely...
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Fabulous 4 bedroom 3 bath home with a light and bright open floor plan. You will enjoy the new kitchen with granite, stainless steel appliances and breakfast bar. The dining table overlooks the pool area and seats 8. The primary bedroom en suite bathroom is spacious and luxurious with a tub and shower....
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Stunning waterfront home located on popular Lido Key. Situated directly on the picturesque canal, this home is perfect for boating enthusiasts or anyone who appreciates the beauty and serenity of waterfront living. Get ready to enjoy your days lounging by the pool, sitting around the outdoor fire pit,...
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