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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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Imagine enjoying a glass of fine wine on a private balcony, marveling at the spectacular views of a championship golf course! Well, this stylish 3BR, 2BA gem overlooks the 5th hole of the Wellen Park Golf & Country Club, offering unparalleled comforts and conveniences in a prime, well-connected location....
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: 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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Property OverviewAzure Isle FUSION is a listing property with two separate houses right next to each other: Azure Haven (blue house) and Isle of Green (green house). This setup provides plenty of space and privacy for everyone in your group.Sleeping Arrangements The property sleeps up to 8 guests...
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One of the BEST locations in the community! Very close to all amenities on site to ensure you have a wonderful vacation. Spotlessly clean well appointed 2 bed 2 bath villa includes Free WIFI, cable and smart TVs as well as dishwasher, washer and dryer. Conveniently located - the famous Siesta Key...
Featured review
Tropical Storm Debby tried to rain on our parade. After dumping much rain and a downed tree. Myself and a couple others cleared the tree so we could exit the premises. The weather turned gorgeous and...
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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: 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: 5 miles to Siesta Key Beach
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Welcome to your luxury Sarasota escape, a stunning newly built two-story home designed for comfort, style, and unforgettable stays. Perfect for families, multiple couples, or group getaways, this spacious 4-bedroom, 3-bath residence comfortably sleeps up to 12 guests and offers a refined blend of modern...
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Welcome to Ponderosa Pine, a charming and peaceful single-family home offering a quiet retreat just 10 minutes from the Sarasota airport. With three comfortable bedrooms and a perfectly laid-out floor plan, this home is the ideal basecamp for families or small groups looking for a relaxing Florida getaway....
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: 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...
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: 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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Steps to everything pet-friendly downtown Sarasota has to offer!Walk or bike to restaurants, shops, marina, Bayfront, Whole Foods, Coffee Shops, Opera or Symphony7 minutes to Lido Key Beach and St. Armands Circle 6 minutes to Ed Smith Stadium Oriole's Baseball, Ringling College, Opera, Symphony 5...
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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.
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...
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Sea La Vie | Heated Saltwater Pool & Hot Tub | EV Charger | Sarasota Beach House ​Escape to Sea La Vie, your ultimate 4-bedroom, 2-bathroom Sarasota vacation rental with a private heated saltwater pool, soothing hot tub, and modern amenities—including a Tesla Universal EV Charger! Designed...
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 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...
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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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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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Relax and Transcend is a 969 sq. ft. ground-floor beachfront condo with 2 bedrooms, 2 bathrooms, and accommodations for up to 5 guests.The primary bedroom has a king bed and an ocean and beach view. The second bedroom has one queen bed and one twin bed, with a view toward the bay and parking area....
Distance to beach: 14 miles to Siesta Key
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2-MONTH MINIMUM--available this coming November, December, and January. Experience elevated Sarasota living in this beautifully furnished home, ideally located within the highly sought-after Esplanade at Skye Ranch. Just two years old and meticulously maintained, this exceptional home shows like a model...
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Steps to everything pet-friendly downtown Sarasota has to offer!Walk or bike to restaurants, shops, marina, Bayfront, Whole Foods, Coffee Shops, Opera or Symphony7 minutes to Lido Key Beach and St. Armands Circle 6 minutes to Ed Smith Stadium Oriole's Baseball, Ringling College, Opera, Symphony 5...
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Discover the enchanting Siesta Key experience by staying in this stylish 2BR 2Bath condo whose relaxing design enhances your vacation. The search for a perfect getaway with an abundance of amenities, all conveniently located near fantastic dining, entertainment, beautiful beaches, and more, ends here.The...
Featured review
My husband and I rented in Siesta Key for the first time this year. We were pleasantly surprised by the beautiful beach and the area. We rented at Bay Oaks along Midnight Pass Road. The location was perfect...
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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Key Differentiators & Amenities∆ Central downtown Sarasota—walk to shops, restaurants, arts venues, and marina ∆ 1 spacious bedroom, 1 updated bathroom (perfect for couples, solo travelers, or business guests) ∆ Pet-friendly: beds, bowls, blankets, waste bags, and secure fenced dog...
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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: 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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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: 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 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...
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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...
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.
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Charming Coastal Retreat Near Siesta Key Welcome to your Sarasota getaway! This bright and airy 3-bedroom, 2-bath home is perfectly located near the south bridge to Siesta Key, offering easy access to one of Florida’s most beautiful beaches.Property Highlights - Open-Concept Living: Sun-filled...
Featured review
Very well maintained house with a great loaction near the south bridge to Siesta Key. Large screened in porch. Ride a bike to Siesta Key or Turtle Beach. The owner's are great to work with. Highly recommend.
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Key Differentiators & Amenities∆ Central downtown Sarasota—walk to shops, restaurants, arts venues, and marina ∆ 1 spacious bedroom, 1 updated bathroom (perfect for couples, solo travelers, or business guests) ∆ Pet-friendly: beds, bowls, blankets, waste bags, and secure fenced dog...
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Welcome to The Prescott Pearl, an inviting and spacious retreat nestled in the heart of Sarasota, Florida. Boasting an incredibly rare and highly sought-after layout featuring three private bedroom suites, this home offers the perfect blend of luxury, comfort, and ultimate privacy. It is the ideal getaway...
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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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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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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: 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: 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....
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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,...
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...
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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: 200 feet to Lido Beach
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This quaint downstairs condo is set up for 2 people wanting to be on this beautiful beach! A huge beach and this condo is only 1 mile from famous St. Armands Circle for all of your shopping and dining fun. This unit has 2 beds featuring a queen bed and a full size bed in the only bedroom.
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...
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Adorable upstairs unit at the Mark Twain Condos, unit D-2, on Lido Beach! This quaint upstairs condo is set up for 2 people wanting to be on this beautiful beach! A huge beach and this condo is only 1 mile from famous St. Armands Circle for all of your shopping and dining fun. This unit has a king size...
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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...
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