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Experience luxury downtown Sarasota living in this impeccably upgraded 15th-floor residence at Bayso. Perfectly positioned with coveted southern exposure, this 1,578-square-foot home offers panoramic views of Sarasota Bay, the Gulf, the marina, and the city skyline from its expansive 222-square-foot private...
Distance to beach: 24 miles to Lido Key Beach
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A Horse‑Owner’s Dream Rental — Space, Privacy & Everything You Need for Happy, Healthy HorsesWelcome to 3717 Downer Ave, a rare Sarasota rental that truly caters to equestrians. Set on more than 5 peaceful acres in the Old Myakka area, this property offers the ideal environment for...
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Apr-Dec: $990/week, $2990/month Dec-Mar: $3500/week, $12,990/monthSPRING SPECIAL!!! 2/2 BEAUTIFUL VILLA! 2 BR, 2 BA, Heated pool and Jacuzzi! WiFi POOL AREA with LAKE-VIEW, KING BED, WOOD/Ceramic FLOOR (no carpets!) and FREE WIRELESS HIGH-SPEED INTERNET all for the LOWEST PRICE in the area !!! -...
Distance to beach: 4 miles to Siesta Key Beach
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Settle into coastal living in this beautifully renovated Sarasota retreat just minutes from Siesta Key’s world-famous white sand beaches. With a full kitchen, large fenced yard, and space to sleep 8, this home is perfect for both relaxing getaways and longer stays in the sun.The Space This...
Distance to beach: 4 miles to Siesta Beach
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Welcome to Sea Glass Cottage, a peaceful coastal retreat just minutes from Siesta Key Beach. This private guest cottage offers the perfect blend of comfort, charm, and convenience, with everything you need for a relaxing Sarasota stay. Whether you're chasing sunsets, beach days, or a quiet getaway,...
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Distance to beach: 7 miles to Siesta beach
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Your Sarasota adventure begins at this completely remodeled 2 bedroom / 2 bathroom FULLY FURNISHED condo. Spacious and serene in a park like setting. Centrally located only 6.5 miles from world famous Siesta Key beach. With a king bed and a twin trundle day bed guest will find comfort and relaxation in...
Distance to beach: 0.5 miles to Siesta Key Crescent Beach
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Recently Remodeled Luxury Waterfront Condo – Perfect Couples’ GetawayEnjoy the ultimate Siesta Key escape in this beautifully remodeled waterfront condo, complete with a private boat dock and slip for boats or jet skis. Ideally located, you can walk to the beach, village shops, top-rated...
Featured review
Beautifully decorated condo in prime location. Extra clean and upscale. Best location on the harbor with water views and walking distance across the bridge onto Siesta Key's Tiki Bar. Owner is a pleasure...
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Beautifully maintained home with tasteful furnishings and a heated swimming pool, located on a 27-hole golf course in a very quiet, 24/7 gated and guarded community. 12 lighted tennis courts, 2 pickleball courts, croquet and a fitness center. The Park Grille & Café featuring live music every...
Distance to beach: 3 miles to Siesta Key
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Newly renovated 1br/1ba, 2nd floor condo in the Sienna Park, Sarasota, Fl. A community pool and a tennis court are provided at 1+1 condo, which is set in Sarasota, 5 min drive from Siesta Key Public Beach. This apartment offers air-conditioned accommodation with a balcony. The apartment features 1 separate...
Featured review
We were in unit 146 and totally loved it. So clean and welcoming. Would definately rent again. Thank you!
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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...
Distance to beach: 14 miles to Siesta Key Beach
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Our penthouse condo is located in Sarasota (Manatee County), Florida within the Palm Aire residential condominium community at Palm Aire at DeSoto Lakes, Inc., Golf Side. It is uniquely situated on the top floor of the only 4-story building erected within the Golf Side community. Directly across from...
Featured review
Condo was very comfortable for 2 people. If you don’t mind a queen size bed. Great view of golf course off back glassed in sitting area. Though this unit doesn't come with golf privileges. It is very...
Distance to beach: 0.5 miles to Siesta Key Crescent Beach Access 12
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This newly decorated luxury condominium is located in The Boatyard, a highly sought after, gated community on the intracoastal. It is within walking distance to gorgeous Siesta Key Crescent Beach, many water sport activities, shopping, restaurants and more. Private boat slips are also available, right...
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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....
Featured review
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: 11 miles to Siesta Key Beach
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Step into your relaxing getaway in beautiful Sarasota, Florida! This thoughtfully designed townhome offers the perfect blend of modern comfort, convenience, and charm—just a 20-minute drive to Siesta Key Beach, ranked the #1 beach in the U.S.With sleek fixtures, updated appliances, and warm...
Featured review
This was our first time booking with Florida rentals. This property was just what it showed. Clean, heated pool just a short walk . Host was good at communicating. Would go back again.
Distance to beach: 2 miles to Siesta Key Beach
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Newly renovated water view home - Walk to the beach, boat rentals, town, shopping, top restaurants, live music, and entertainment.Walk out of the front door of this fantastic home, grab your beach gear and take a short walk or bicycle ride and you'll hit the beach. This rental is close to everything....
Featured review
Great nice house close to the beach , totally recommended. Will rent again. It was pleasure to stay in this beautiful house.
Distance to beach: 7 miles to Siesta Key
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Located in Orange Acres Estates at Clark Rd and I 75. $1400 monthly 30 day minimum *** Pet free community ***Cozy home in a clean family run community. 765 sq ft with additional living space in attached screened in lanai.Carport and shed with washer/dryerBeautiful, deep pool with newer...
Distance to beach: 0.5 miles to Siesta Key
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Recently Redecorated Luxury Waterfront Condo – Perfect Couples’ GetawayEnjoy the ultimate Siesta Key escape in this beautifully decorated waterfront condo, complete with a private boat dock and slip for boats or jet skis. Ideally located, you can walk to the beach, village shops, top-rated...
Featured review
This is such a comfortable, well decorated and fully equipped condo. The location was very quiet with nice views and in a great location for accessing the beach and siesta key. You can easily bike to siesta...
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Your own private Sarasota retreat — just minutes from Siesta Key!Dreaming of leaving the cold behind and spending the fall and winter months in beautiful Sarasota? A fully furnished 3-bedroom, 2-full-bath ranch home with a private heated, screened-in pool will be available beginning November...
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Newly renovated 1 bedroom 1 bath condo. West of the trail just north of stickney point. 3/4 of a mile from the south bridge to siesta key. New bathroom and walk in shower. Brand new kitchen and appliances. Laundry facilities on property. Second floor unit. Small storage closet
Distance to beach: 6 miles to Siesta Key
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The house has two bedrooms and two bathrooms, a full kitchen, living room and study space, inside it has washers and dryers, a large patio for relaxation, fenced all around, air conditioning and heating, hot water.Excellent property very close to Siesta Key Beach, known as the number one beach in the...
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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,...
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Beautiful townhome condominium. Large courtyard with private pool. Small association, only 12 units. Very private. Off Sarasea Circle. 2 minute walk to beach, restaurants and stores. Private off-street parking for 2 cars. 2 outside decks overlooking courtyard.
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$3500 off season (May-October) - $4000 in season (November-April) 2/2 + Den/Office Fully Furnished in quiet established Beekman Place Community. Recently completely renovated. All new appliances including washer/dryer. 2 car garage. Private corner lot with mature trees, beautiful patio and fenced...
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Distance to beach: 4 miles to Siesta Key Beach
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Siesta Key sand. Mainland ease. And yes, your dog is invited.Here's the problem with staying on Siesta Key itself: bridge traffic, circling for parking, paying $300 to $600 a night, and most condo associations won't let your dog through the door.Here's the smarter play. This freshly...
Featured review
My husband and I stayed here with our dog.. overall we where pleased . Clean and comfortable nicely decorated but could use a new mattress in the master....also the shower curtain rod is rusted and needs...
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...
Featured review
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...
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. Just step right into your paradise!Completely renovated in 2026, this condo offers a fresh, modern retreat designed with your comfort...
Featured review
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....
Distance to beach: 100 yards to Lido Beach
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Quaint Studio on gorgeous Lido Key Beach in Sarasota.Heated pool right out the front door. Parking in front of the unit. Queen size bed with fully stocked kitchenette and open patio. Beach chairs, beach bag, cooler, and beach towels provided!
Featured review
Very accommodating,hostess could not have been more pleasant.Relaxing at its best.Excellent proximity to restaurants and shopping and entertainment.
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...
Featured review
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...
Distance to beach: 3 miles to Lido Beach
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Your home away should feel like home. This 2 bedroom 2 bath villa is smartly decorated and equipped with all the things necessary for comfort and practical living. Fully furnished with comfort in mind. The primary bedroom has a queen-sized bed, an en-suite bath, walk-in closet and sliders to the screened...
Featured review
We loved our stay at the hidden gem! The kitchen is stocked with everything you need. Lots of towels, beach towels, and sheets. Supplies for a beach day are also provided. The location is great-very close...
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To view complete details callThis home is a beautiful waterfront beach bungalow located on Little Sarasota Bay on the desirable and less congested location of South Siesta Key, Sarasota FL. This sanctuary is within walking distance of the public amenities of Turtle Beach, the Tiki Hut Pub, Bayfront...
Featured review
This house and grounds were AMAZING! The decks, dock, and gliders were relaxing and quiet-we enjoyed the bird watching and saw dolphins on our last day! Turtle Beach is nice-not quite Siesta Key sand,...
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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...
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Welcome to your Sarasota home away from home!Nestled in the highly desirable Coral Cove neighborhood, this beautifully remodeled apartment offers the perfect blend of comfort, convenience, and coastal living. Located just a few blocks from the South Bridge to Siesta Key and less than one mile from...
Featured review
I teach high school and decided to do something fun this summer during my break, so I stayed on Starfish Dr. in Ana's rental for 5 weeks (only 10 minutes away from my new granddaughter.) Everything about...
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...
Featured review
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...
Distance to beach: 1 miles to Siesta Key
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OUR RATES:May-November 2026 2025 $2000 December 2026 $3000 January 2027 $4500 February 2027 $5000 March 2027 $5500 April 2026 $3000*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: 4 miles to Siesta Key Beach
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Newly renovated 2br /1 ba, shower cubicle, 980sqft, ground floor, private backyard, condo in the Sienna Park, Sarasota Fl.
Featured review
I very much enjoyed staying here for two months. Everything in the condo worked well, the location was great for me and my cat. Easy to get downtown or to the beaches and many golf courses.The complex is...
Distance to beach: 4 miles to Lido Key
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Enjoy this delightful and brand new home located in Gillespie park. The layout of the house is very comfortable with a delightful front porch and a lanai for morning coffee in the private back yard. The kitchen is well stocked with dishes and cookware, with the newest appliances. It is fully furnished...
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For less than you would pay for a small 3 star hotel room, you can rent our turn-key furnished condo overlooking Bobby Jones golf course. NO hurricane damage. Up 5 steps from your enclosed stone lanai to your wood deck. Available at off season rates. One month minimum.Tucked behind Bobby Jones Golf...
Featured review
We actually stayed at a different one from what was listed owner has 9 rental properties. Overall was fine. Outside could use updates.
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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: 4 miles to Lido Key
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This brand new comfortable apartment is full of light and fully furnished. The living area is sunny and is a great room design with an open kitchen. The bedroom is large and the bathroom is well designed with a walk in tiled shower. The location is sweet! Walkable to restaurants, and one block from...
Distance to beach: 5 miles to Siesta Key Public Beach Access
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Come and unwind in this quiet and cozy 2 br/1.5 ba, first floor end unit condo, situated just a short 10 minute drive to the cool emerald waters of Siesta Key, named the nation's best beach - twice! Relax in this tastefully furnished condo located in a small, quiet community, surrounded by grocery...
Featured review
We had a wonderful stay in this beautifully decorated and updated condo. Enjoyed the pool. The place was quiet and close to the beach. The owner was very friendly and accommodating. We loved it so much...
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2br/2ba first floor condo, Situated a short 5-minute drive from the cool emerald waters of Siesta Key Beach, on the North edge of Palmer Ranch. This tropical resort community is a relaxing oasis under the warm skies of the Gulf Coast. With its swaying palms, shimmering lake views and world-class resort...
Featured review
Excellent location close to everything. Clean, private patio. Eva was an excellent host, quick to respond to any questions. I would stay here again
Distance to beach: 10 miles to Lido Key
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Welcome to PAR-TEE, your private tropical oasis perfect for large families or groups! Close to ALL of Florida's top rated beaches - Siesta Key, Lido Key & Anna Maria Island - Ringling Museum, IMG, downtown Sarasota and Sarasota-Bradenton airport, this property is situated on almost a half an...
Distance to beach: 5 miles to Lido Key
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VISIT OUR LISTING ON VRBO (#2568344) TO SEE ALL 5 STAR REVIEWS! SIGNIFICANT SAVINGS BOOKING HERENEW IN 2024: Outdoor spa shower and propane firepit areaPET-FREE HOME Updated, bright and airy bungalow at the edge of downtown Sarasota, where you're just minutes from everything a vacation in...
Featured review
Met our needs perfectly and provided easy access to the fun around Sarasota. Nicely decorated, very clean and comfortable.
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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...
Distance to beach: 4 miles to Crescent Beach/Siesta Key
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Freshly renovated and just 4 miles from world-famous Siesta Key Beach, this comfortable 3-bedroom Sarasota cottage is the perfect home base for a Florida getaway. Enjoy an updated kitchen, newly renovated bathroom, fresh living-room furnishings, and a large private fenced yard — especially convenient...
Distance to beach: 2 miles to Siesta Key
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AVAILABLE October 1, 2026 TO DECEMBER 18, 2026 Welcome to this beautifully updated 2-bedroom, 2-bathroom first-floor condo located in the desirable Ashton Lakes community. Enjoy the convenience of step-free living with an assigned carport just steps from your front door—no stairs to climb.This...
Featured review
We very much enjoyed our winter vacation at Jeff & Jennifer’s Ashton Lake unit. The condo was very clean, updated and renter friendly. It has one of the best community pools that I have seen. Detwiler...
Distance to beach: 4 miles to Lido Key
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Experience elevated city living in this stunning residence nestled in Sarasota’s vibrant Rosemary District. Designed for those who appreciate style, comfort, and walkability, this home offers a perfect blend of urban sophistication and private tranquility.Step inside to soaring 11-foot ceilings...
Featured review
We had an amazing stay at the property, location is super, just 5 minutes walk to restaurants, downtown and to rosemary district, also, the apartment has meticulous furnishing, very artsy, bright and...
Distance to beach: 13 miles to Siesta Key Beach
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Enjoy a 5-star experience at this centrally-located home. Great location, close to shopping, Downtown Sarasota, a quick drive to Siesta Key Beach! Please note this property is not suitable for children under 12 years old. This property has 3 comfortable, stylish bedrooms, the primary is en suite, 2 guest...
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...
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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 : $250 non-refundable pet fee. However, we are unable to accept agressive breeds....
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