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From $456 per night (USD)
VRBO
The Wisteria Oasis with heated pool and hot tub
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Come Relax with your family at this peaceful 3 bedroom cottage, It has a private fenced in backyard w/ new heated saltw ...
From $456 per night (USD)
VRBO
From $331 per night (USD)
Expedia
Welcome to Off Tropic!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Highlights • Private pool • Less than 5-miles to the beach • Outdoor living space • Washer and dryer • Near restau ...
From $331 per night (USD)
Expedia
From $214 per night (USD)
VRBO
Sarasota Duplex in Gillespie Park: 1 Mi to Dtwn!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Embark on your next adventure in Florida with a stay at this vacation rental in sunny Sarasota! Complete with practical ...
From $214 per night (USD)
VRBO
From $407 per night (USD)
Expedia
The Palmy Pickle w/ Pickleball Court + Fire Pit!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
BNB Breeze Presents: The Palmy Pickle Newly renovated space in Sarasota, FL with private pickleball court, fire pit, la ...
From $407 per night (USD)
Expedia
From $280 per night (USD)
VRBO
Luxurious 2/2 Water View Corner Unit The Strand w/ 2 balconies
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Enjoy your Sarasota stay in this newly furnished waterfront corner unit on the 4th floor of The Strand, heated communal ...
From $280 per night (USD)
VRBO
From $214 per night (USD)
Expedia
10 min Lido Key Beach~St. Armand Circle~ Short drive to Siesta Key Beach
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Coastal Cabana Hideout is a single-family home six minutes from beautiful downtown Sarasota, Florida. A 10-minute car ...
From $214 per night (USD)
Expedia
From $342 per night (USD)
VRBO
Luxury Family size house, 9 miles away from siesta key, with pool
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Step into the heart of Florida's allure as you discover one of the Sunshine State's most sought-after and secure destina ...
From $342 per night (USD)
VRBO
From $299 per night (USD)
VRBO
Stylish Pool Villa 3BR/2BA close to the Beaches
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The "Serenity Retreat" with 3 BR, 2 BA is located close to Downtown Sarasota, beaches, grocery stores, restaurants, muse ...
From $299 per night (USD)
VRBO
From $657 per night (USD)
VRBO
Luxurious Dual-Home Retreat in Prime Sarasota Location
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Experience the ultimate botanical garden retreat in the exclusive Sapphire Shores / Indian Beach neighborhood of Sarasot ...
From $657 per night (USD)
VRBO
From $318 per night (USD)
Expedia
5 Star! Spacious Home Near Downtown, Restaurants, Shopping & Beaches
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Completely private beach cottage with 3 Bedrooms and 2 Bathrooms. Centrally located 6 mins from Main Street + restaurant ...
From $318 per night (USD)
Expedia
From $658 per night (USD)
VRBO
Luxe Oasis | Private Pool, In St Armands Circle, Near Lido Key Beach!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
🌴 Luxe Oasis | Private Pool, Walk to Lido Beach & St. Armands 💖 Why You'll Love This Home Tucked into a lush, walkabl ...
From $658 per night (USD)
VRBO
From $347 per night (USD)
VRBO
Villa Sunrise, 3BR/3.5BA, private pool, Bird Key, close to Siesta Key
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This beautiful house is located on Bird Key, a small island offshore to Downtown, St. Armands Circle and Lido Key. Bird ...
From $347 per night (USD)
VRBO
From $279 per night (USD)
VRBO
Waterfront, Pet-Friendly Condo with Pool, Spa, and Fitness Center near Downtown Sarasota
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to your dream Sarasota escape—where luxury meets lifestyle just minutes from sun-drenched beaches, vibrant arts, ...
From $279 per night (USD)
VRBO
From $934 per night (USD)
Expedia
Quiet peaceful home on the canal with a dock; 2 minute walk to St Armands Circle
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Relax at Edgewater Escape, the ultimate waterfront home on Lido Key. This magnificent 3-bedroom, 3-bathroom home offers ...
From $934 per night (USD)
Expedia
From $2530 per night (USD)
VRBO
Downtown Sarasota Compound |Pet Friendly | Extended Stays |Large Groups | Beach
Bedrooms:
9
Bathrooms:
8
Sleeps:
20
Gillespie Park includes 10 acres of trails, playground, basketball, pickleball courts, tennis courts, pond & 2 public do ...
From $2530 per night (USD)
VRBO
From $1718 per night (USD)
Expedia
Waterfront Luxury - Direct Gulf Views - Resort Pool/Spa - Siesta Key Village
Bedrooms:
6
Bathrooms:
5
Sleeps:
12
Vunique Vacations - Distinct vacation homes for the discerning traveler who is seeking a truly unforgettable vacation ex ...
From $1718 per night (USD)
Expedia
From $239 per night (USD)
VRBO
Luxury Condo Living on Sarasota Bay, Minutes From Downtown - Admirals Watch
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Welcome to Admirals Watch, a sophisticated sanctuary on the 5th floor of The Strand, Professionally managed by Gulf Coas ...
From $239 per night (USD)
VRBO
From $814 per night (USD)
Expedia
Perfect for Large Families - Sleeps 14 | Walk to Lido Beach & St. Armands | Downstairs Game Room!
Bedrooms:
4
Bathrooms:
4
Sleeps:
14
Enjoy automatic discounts based on your stay length, no codes needed, and the price you see already includes your saving ...
From $814 per night (USD)
Expedia
From $295 per night (USD)
VRBO
1/1.5 Modern Waterfront Condo with Pool and Fitness Room
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This fully furnished third-floor waterfront condo is centrally located on the West side of “The Strand” and spreads over ...
From $295 per night (USD)
VRBO
From $575 per night (USD)
Expedia
Tiki Tide Villa | Private POOL + Tiki Hut!
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
BNBBreeze Presents Tiki Tide Villa! Experience the essence of coastal living at Tiki Tide Villa. Just 25 minutes from Si ...
From $575 per night (USD)
Expedia
From $1140 per night (USD)
VRBO
Serenity Springs | Private Heated Pool + Waterfall
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
BNBBreeze presents Serenity Springs! Experience this stunning, peaceful oasis in the heart of Sarasota, located moments ...
From $1140 per night (USD)
VRBO
From $805 per night (USD)
Expedia
Modern New Home - Private Pool, Spa, Rooftop Deck, Game Room, & More!
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Waldemere's Wonderland: A Luxurious Retreat in Sarasota Welcome to Waldemere's Wonderland, a stunning luxury home nestle ...
From $805 per night (USD)
Expedia
From $730 per night (USD)
VRBO
Arlington Ocean Oasis 5br 5ba Htd Saltwater Pool
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Summary: Welcome to the Arlington Ocean Oasis, a modern and luxurious rental property offering an unparalleled coastal e ...
From $730 per night (USD)
VRBO
Click For Pricing
Expedia
Seaside Haven 10min to Siesta Keys - 4BR / 2.5BA House
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Escape to this stunning NEW (2024 built) villa in Arlington Park, Sarasota! Featuring 4 BD, 2.5 BA, and just 10 min fr ...
Click For Pricing
Expedia
From $1121 per night (USD)
VRBO
Five Palms-Indulge in a Stunning Lido Key Retreat with Private Pool, Firepit, and Steps to the Beach
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
"🌴 Five Palms | Luxury Tropical Oasis, Private Pool + Prime St. Armands / Lido Location 💖 Why You'll Love This Home ...
From $1121 per night (USD)
VRBO
From $464 per night (USD)
Expedia
Luxury Home, Pool, Mins to Beach and Downtown Sarasota
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to your modern oasis in the heart of Sarasota, where chic design meets luxurious comfort. This stunning two-stor ...
From $464 per night (USD)
Expedia
From $282 per night (USD)
VRBO
Dog-Friendly, Cozy Cottage, Private Patio, Walk to Bay, Near Downtown
Bedrooms:
2
Bathrooms:
2
Sleeps:
100
Welcome to your serene escape in the heart of Sapphire Shores, a picturesque neighborhood in Sarasota just blocks from t ...
From $282 per night (USD)
VRBO
From $192 per night (USD)
Expedia
Charming Artist 2-bedroom bungalow in Historic Gillespie Park
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Stay comfortably in Sarasota at this 2-bedroom bungalow. Experience the cool vibe of this wonderful property with a gour ...
From $192 per night (USD)
Expedia
From $230 per night (USD)
VRBO
Resort Pool & Spa, Fitness Center, Pet Friendly, Waterfront Condo in Downtown!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Escape to The Strand, a luxurious waterfront condominium offering stunning views of Sarasota Bay and the surrounding are ...
From $230 per night (USD)
VRBO
From $163 per night (USD)
Expedia
Hidden Oasis Newly Updated Beautiful Condo & Private Courtyard to Wine & Dine!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Oasis on Osprey in charming Sarasota is only minutes away from the white sand beaches of Siesta Key, Marina Jack, Downt ...
From $163 per night (USD)
Expedia
From $165 per night (USD)
VRBO
Peaceful Beach Home Fully Equipped!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Fully equipped cozy beach home warmly decorated! Just steps away from Publix, Payne Park and Legacy Trail. Short drive t ...
From $165 per night (USD)
VRBO
From $1402 per night (USD)
Expedia
New-Luxurious St. Armands Vacation Home, Walk to Beach, Gulf Views, Resort Pool
Bedrooms:
6
Bathrooms:
5
Sleeps:
16
Vunique Vacations - Distinct vacation homes for the discerning traveler who is seeking a truly unforgettable vacation ex ...
From $1402 per night (USD)
Expedia
From $145 per night (USD)
VRBO
Sunny Central Sarasota Retreat
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
Welcome home to your sunny Sarasota oasis! This newly remodeled 2BR, 2BA condo is perfectly located just 1 mile from the ...
From $145 per night (USD)
VRBO
From $422 per night (USD)
Expedia
Walk to Downtown, Rooftop Jacuzzi, Contemporary Decor
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Welcome to Cityscape Retreat, an exquisite 4-story modern townhome nestled in the vibrant uptown district of Sarasota. P ...
From $422 per night (USD)
Expedia
From $399 per night (USD)
VRBO
Historic Downtown Sarasota - Gem I
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Beautifully restored home in the Historic downtown of Sarasota. We have a cluster of 3 neighboring homes fresh off a $2. ...
From $399 per night (USD)
VRBO
From $407 per night (USD)
Expedia
Stylish Newly Remodeled Condo, Walk to Beach & St. Armands, Heated Pool/Spa, Free Activities Daily
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Enjoy automatic discounts based on your stay length, no codes needed, and the price you see already includes your saving ...
From $407 per night (USD)
Expedia
From $343 per night (USD)
VRBO
Penthouse #1 Oceanfront on Lido Beach! Sunrise & Sunset Views - 2 Bed 2 Bath
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
This special 2 bedroom/2 bathroom Penthouse has been recently renovated with luxury in mind! Located in The Lido Beach C ...
From $343 per night (USD)
VRBO
From $406 per night (USD)
Expedia
Historic Downtown Sarasota - Gem II
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Beautifully restored home in the Historic downtown of Sarasota. We have a cluster of 3 neighboring homes fresh off a $2. ...
From $406 per night (USD)
Expedia
From $325 per night (USD)
VRBO
Beautiful 3-bedroom house with heated pool and e-bikes near Siesta Key beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Discover this charming Sarasota Sunshine Pool House, 10 min from Siesta Key Beach and 5 min from downtown Sarasota’s res ...
From $325 per night (USD)
VRBO
$Luxury Apartment - Downtown Sarasota\n\n$
Click For Pricing
Expedia
Luxury Apartment - Downtown Sarasota\n\n
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Enjoy a stylish experience at this centrally-located apartment close to everything! Apartment is located 5 minutes to d ...
Click For Pricing
Expedia
From $322 per night (USD)
VRBO
Historic Downtown Sarasota - Gem III
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This home is nestled in a quaint historic district of Sarasota close to the vibrant action of downtown yet offers serene ...
From $322 per night (USD)
VRBO
From $191 per night (USD)
Expedia
Surfside Villa | Private POOL + Sunroom!
Bedrooms:
3
Bathrooms:
3
Sleeps:
9
BNB Breeze Presents: Surfside Villa! Experience this stunning, newly-renovated home in the heart of Sarasota, located ju ...
From $191 per night (USD)
Expedia
From $1257 per night (USD)
VRBO
New-Luxurious St. Armands Vacation Home, Walk to Beach, Gulf Views, Resort Pool
Bedrooms:
6
Bathrooms:
5
Sleeps:
16
Vunique Vacations - Distinct vacation homes for the discerning traveler who is seeking a truly unforgettable vacation ex ...
From $1257 per night (USD)
VRBO
From $264 per night (USD)
VRBO
Pineapple House 15min to Siesta & Lido Key Beaches
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
This 3-bedroom house in Sarasota is perfect for your escape to relaxation. With a plush king bed, a comfortable queen be ...
From $264 per night (USD)
VRBO
From $675 per night (USD)
VRBO
Sarasota Memories For a Lifetime, 3 Bedroom, 3 Bathroom With Large Heated Pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
9
Experience the allure of Sarasota Memories for a Lifetime, a beautiful rental with a Mid Century Modern Feel. This 3-bed ...
From $675 per night (USD)
VRBO
From $94 per night (USD)
VRBO
Beautiful 1-bedroom condo in The Meadows, minutes from the beach, golf, shopping
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Located in Sarasota, enjoy what this 1-bedroom condo has to offer. This welcoming property is a 2nd floor condo unit in ...
From $94 per night (USD)
VRBO
From $186 per night (USD)
VRBO
Robinhood Beach Villa
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
You will feel right at home in this cozy beach villa which gives you a natural beach feeling AND adds a modern feel with ...
From $186 per night (USD)
VRBO
From $204 per night (USD)
Expedia
2 Bedroom Lido Key Condo by FVC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Professionally managed and offered by FL Vacation Connection. This is a spacious two bedroom condo perfectly situated t ...
From $204 per night (USD)
Expedia
From $558 per night (USD)
VRBO
Inn on the Beach 7304 by FVC
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Your Longboat Key Retreat with Sleepy Lagoon Views by FVC Experience the pinnacle of coastal living in this beautifully ...
From $558 per night (USD)
VRBO
From $530 per night (USD)
Expedia
Bayview Paradise by FVC
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to Bayview Paradise managed by Florida Vacation Connection. This spacious 4 bedroom/ 3 full baths private pool ...
From $530 per night (USD)
Expedia
From $416 per night (USD)
VRBO
Stylish Coastal 3BR • Pool • Near Downtown & Sand
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to Casa Azul! This fully renovated 3BR/2BA coastal retreat (2024) offers a bright, open floor plan, chef’s kitch ...
From $416 per night (USD)
VRBO
From $865 per night (USD)
Expedia
Sarasota House, A Perfect Beach Getaway!!! Spacious 4-bedroom house & Pool !!!
Bedrooms:
2
Bathrooms:
4
Sleeps:
14
Sarasota Seascape House: A Perfect Beach Vacation Getaway Welcome to Sarasota Seascape House, your ultimate retreat for ...
From $865 per night (USD)
Expedia
From $333 per night (USD)
VRBO
Family Friendly House with Private Pool near Downtown Sarasota
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Escape to this beautiful 3-bedroom, 3-bathroom fully furnished home, perfectly located just minutes from downtown Saraso ...
From $333 per night (USD)
VRBO
From $300 per night (USD)
Expedia
1-403 in Sarasota, FL
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to your Siesta Key retreat! This stylish condo is the perfect blend of comfort and convenience for your beach va ...
From $300 per night (USD)
Expedia
Click For Pricing
VRBO
Premier Access to Downtown Sarasota! Private Pool, Game Room, & More!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to The Ringling House, a historic home located west of the trail in downtown Sarasota, near Southside Village, S ...
Click For Pricing
VRBO
From $348 per night (USD)
Expedia
Sarasota Prime. 4-bedroom house in phenomenal Sarasota
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Welcome to your ultimate vacation haven in sunny Sarasota, Florida! This spacious 4-bedroom, 3-bathroom home is just a s ...
From $348 per night (USD)
Expedia
From $569 per night (USD)
VRBO
Luxury Tropical Retreat, Pool, King Beds & Game Room
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Sunset Villa – Luxury Tropical Retreat Near Siesta Key & Lido Key Spacious Sarasota vacation rental just minutes from S ...
From $569 per night (USD)
VRBO
From $419 per night (USD)
Expedia
Cozy & Charming 4/4 bungalow with pool close to the Village, Lido & Siesta Keys
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Consider this house your home away from home while you visit Sarasota. A treasure West of the Trail, boasting Mexican ti ...
From $419 per night (USD)
Expedia
From $299 per night (USD)
VRBO
Vintage Vibes - Grill, Chill & Beach Thrills
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Summary: 🌴 Vintage vibes meet modern comfort just minutes from Siesta Key's sugar-sand paradise! Chill by the fire pit ...
From $299 per night (USD)
VRBO
From $180 per night (USD)
Expedia
Artsy Getaway with Vibrant Design Flair
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Your chic color-party pad where navy, gold & peach throw the most stylish soirée in town! This spacious stunne ...
From $180 per night (USD)
Expedia
From $384 per night (USD)
VRBO
Traquil Gem
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
**Newly remodeled home with all new furniture and decor*. Peaceful home surrounded by lush palms in the heart of Saraso ...
From $384 per night (USD)
VRBO
From $241 per night (USD)
Expedia
Vibrant Modern Escape, Walk to Dining, Near Beach
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Summary: - Chic, minimalist space with eye-catching blue and gold accents - Just a short drive to the soft sands of Sies ...
From $241 per night (USD)
Expedia
From $266 per night (USD)
VRBO
Lux Siesta Key & Lido Beach - Sarasota Getaway
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to our charming 3BR Retreat – Near Beaches, Dining, Downtown & UTC Mall -15 minutes to Siesta Key & Lido -8 min ...
From $266 per night (USD)
VRBO
From $242 per night (USD)
Expedia
Orchid Oasis Retreat | Dog Friendly | Perfect Location | Large Yard
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Enjoy automatic discounts based on your stay length, no codes needed, and the price you see already includes your saving ...
From $242 per night (USD)
Expedia
From $167 per night (USD)
VRBO
Trendy Home by Jet Skis, Parks & Art Hotspots
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Summary: - Modern retreat near Rosemary District with a bold indoor grass wall - Walk to downtown, Pioneer Park, and Van ...
From $167 per night (USD)
VRBO
From $207 per night (USD)
Expedia
Retro-Inspired Stay, BBQ Patio, Close to Downtown
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Summary: - Relax in a stylish mid-century home just minutes from Siesta Key Beach - Enjoy the fenced backyard with BBQ, ...
From $207 per night (USD)
Expedia
From $271 per night (USD)
VRBO
Siesta private house is Sarasota Florida, 3 ml to Siesta Key Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Siesta Queen! This beautifully decorated 3-bedroom, 2-bathroom home offers the perfect blend of comfort, styl ...
From $271 per night (USD)
VRBO
From $339 per night (USD)
Expedia
Dog-Friendly, Private Pool Home with Golf & Cycling at Bobby Jones Golf Club
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Bobby Jones Golf Club! This dog-friendly 3-bedroom, 2-bathroom pool home is perfect for golf lovers, nature enthusiasts, ...
From $339 per night (USD)
Expedia
From $302 per night (USD)
VRBO
Retro Laurel Park Guest Cottage
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Experience luxury & comfort in this beautifully renovated guest house, featuring a stylish retro vibe, nestled in the he ...
From $302 per night (USD)
VRBO
From $862 per night (USD)
Expedia
Experience Ultimate Relaxation at The Sandcastle, a New Luxury Home in Lido Key!
Bedrooms:
7
Bathrooms:
6
Sleeps:
12
The Sandcastle by Lido Key Vacations Home in Sarasota, Florida Welcome to The Sandcastle, a stunning new constructio ...
From $862 per night (USD)
Expedia
From $298 per night (USD)
VRBO
White Ibis - Home with Heated Pool & Private Garden by Gulfcoast Holiday Homes
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
This beautifully furnished and stylish contemporary home features a pool and a spacious backyard adorned with exotic veg ...
From $298 per night (USD)
VRBO
From $92 per night (USD)
Expedia
Charming 1/1 Golf Course Front condo Bunker Oaks
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to your tranquil retreat in Bunker Oaks! This beautifully furnished 1-bedroom, 1-bathroom condo offers 428 sq. ...
From $92 per night (USD)
Expedia
Click For Pricing
VRBO
Beautiful 3 bedroom with views of the Beach of Longboat Key.
Bedrooms:
3
Bathrooms:
3
Sleeps:
4
This exquisite 3 bed, 3 bath condo, nestled in the heart of the amazing Pierre community, is an exceptional opportunity ...
Click For Pricing
VRBO
From $314 per night (USD)
Expedia
HUGE HEATED SALT POOL! NEAR DOWNTOWN! TV IN EVERY BEDROOM!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
30 FT LONG HEATED POOL. 8 minutes away from downtown Sarasota. Walking distance to a major plaza that has grocery store ...
From $314 per night (USD)
Expedia
From $157 per night (USD)
VRBO
Nottingham Beach Bungalow near Siesta Key
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
This cozy beach bungalow is in a PRIME location to enjoy the best of Sarasota! With a large fenced-in yard, and a firep ...
From $157 per night (USD)
VRBO
From $373 per night (USD)
Expedia
Sarasota escape awaits- a 4-bedroom, 2-bathroom home featuring a brand-new pool.
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Bring the whole family to this newly renovated 4 bedroom house, with lots of room for fun. Heated pool available from No ...
From $373 per night (USD)
Expedia
From $312 per night (USD)
VRBO
NEW! Waterfront Luxury in Sarasota – Near Downtown & Beaches!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to The Strand, where luxury waterfront living meets convenience and comfort. This rental unit features one bedr ...
From $312 per night (USD)
VRBO
From $522 per night (USD)
Expedia
Canal Front Home in Sarasota with Private Heated Pool & Outdoor Patio!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Bay Breeze Bungalow - Waterfront Pool, Dock & Kayaks 💖 Why You'll Love This Home Glide your kayak from a private dock ...
From $522 per night (USD)
Expedia
From $285 per night (USD)
VRBO
Step into the charm of yesteryear with the modern comforts of today at City Cottage!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Step into the charm of yesteryear with the modern comforts of today at City Cottage! Nestled in the heart of the City o ...
From $285 per night (USD)
VRBO
From $509 per night (USD)
Expedia
Charming 3BR Coastal Home Near Trails, Shops
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to your perfect Sarasota retreat! Nestled in the heart of the city, this charming 3-bedroom, 2-bathroom Florida ...
From $509 per night (USD)
Expedia
From $389 per night (USD)
VRBO
Sarasota Cottage w/ Heated Salt Water Pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: Escape to this delightful 3-bedroom, 2-bathroom cottage, complete with modern amenities and a serene outdoor oa ...
From $389 per night (USD)
VRBO
From $278 per night (USD)
Expedia
Escape to Paradise: Charming 2BR Condo, Sarasota Bay - Serenity Meets City Vibes
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Brand New Rental - Your home away from home in the Heart of Sarasota. This 890-square-foot haven is perfect for couples ...
From $278 per night (USD)
Expedia
From $192 per night (USD)
VRBO
Charming Villa 14 mins away from Siesta Key Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This villa close to Siesta Key Beach serves as the perfect escape for those looking to enjoy Sarasota. The property come ...
From $192 per night (USD)
VRBO
From $398 per night (USD)
Expedia
Brookline Retreat | Private Pool + Pickleball!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
BNB Breeze Presents: Brookline Retreat! This charming rental home in Sarasota, Florida, offers a perfect blend of comfor ...
From $398 per night (USD)
Expedia
From $1314 per night (USD)
VRBO
Coastal Retreat Near Siesta Key- 5 Bedrooms, Pool & Spa- 1 month minimum
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Discover the beauty of Sarasota from this 5-bedroom house. With 2 king beds, 2 queen beds, and 1 bunk bed, our nice prop ...
From $1314 per night (USD)
VRBO
From $256 per night (USD)
Expedia
Stylish 2-Bedroom Home in Downtown Sarasota
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Summary: Welcome to your stylish retreat in Downtown Sarasota! - 2-bedroom, 2-bathroom home with a modern open-concept ...
From $256 per night (USD)
Expedia
Click For Pricing
VRBO
9-Bedroom Waterfront Getaway, Steps from Lido Key Beach and St. Armands Circle!
Bedrooms:
9
Bathrooms:
9
Sleeps:
10
Sunset Dreams by Lido Key Vacations Home in Sarasota, Florida Experience luxury at Sunset Dreams, a stunning 9-bedroo ...
Click For Pricing
VRBO
From $1243 per night (USD)
Expedia
4 BR SIESTA KEY SPA GETAWAY WITH GOLF SIMULATOR, TURFED YARD, AND MANCAVE.
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Beautiful rental on the North end of Siesta Key! This five-bedroom, 3.5-bath fully turfed home is in the prime of all Sa ...
From $1243 per night (USD)
Expedia
From $229 per night (USD)
VRBO
Osprey Nest in Sarasota
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This brand-new custom townhome offers unparalleled luxury living with a prime location overlooking the 10-acre Gillespie ...
From $229 per night (USD)
VRBO
From $147 per night (USD)
VRBO
VILLA SIESTA IV-priv cottage Downtown Secret Community-Heated Pool!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Come to our hidden secret community, -moments to downtown- private, pristine, and very quiet! . Be our gu ...
From $147 per night (USD)
VRBO
From $236 per night (USD)
VRBO
NEW! Stunning Waterfront 1.5/2 at The Strand
Bedrooms:
2
Bathrooms:
2
Sleeps:
3
Welcome to The Strand, where luxury waterfront living meets convenience and comfort. This rental unit features one bedr ...
From $236 per night (USD)
VRBO
From $230 per night (USD)
Expedia
Entire home in Sarasota, Florida
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
MINUTES FROM BEACHES AND DOWNTOWN SARASOTA This unique coastal home was thoughtfully designed to provide you with both c ...
From $230 per night (USD)
Expedia
From $244 per night (USD)
VRBO
Spacious salt water pool home minutes from Siesta Key & downtown
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This spacious, updated 3-bedroom, 2-bathroom pool home is nestled on a quarter-acre lot in a quiet residential neighborh ...
From $244 per night (USD)
VRBO
From $513 per night (USD)
VRBO
Luxury Sports Vacation Pool House-Downtown Sarasota-Pickleball/Volley/Basketball
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to the Luxury Sports Vacation Pool House located in Downtown Sarasota, the only vacation rental in Sarasota, tha ...
From $513 per night (USD)
VRBO
From $1179 per night (USD)
VRBO
Pearl on the Bay - A breathtaking Pool & Bayfront property - an unparalleled vacation experience
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Escape to Paradise at The Pearl on the Bay Indulge in the ultimate waterfront escape at The Pearl on the Bay, a breatht ...
From $1179 per night (USD)
VRBO
From $163 per night (USD)
VRBO
Summer/Fall Special low rates! Delightful condo 6.5 miles to Siesta Key Beach.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Don't Miss this Unique Opportunity to Rent Just Minutes from the White Sandy Beaches of Sparkling Siesta Key! Freshly up ...
From $163 per night (USD)
VRBO
From $480 per night (USD)
VRBO
3-bedroom house in awesome Sarasota with WiFi, AC. Enjoy your stay
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Your cozy getaway awaits in Sarasota at this terrific house. With 3 bedrooms including 1 king, 1 queen, and 1 twin bed, ...
From $480 per night (USD)
VRBO
From $1027 per night (USD)
Expedia
Escape to The Big Dipper: Siesta Key Canal Front Home with Pool & Private Dock!
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
The Big Dipper by Siesta Key Luxury Rental Properties Home in Siesta Key, FL 34242 Experience the ultimate vacation a ...
From $1027 per night (USD)
Expedia
From $206 per night (USD)
VRBO
NEW! Charming 3/3 Home near Payne Park and Legacy Trail
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Enjoy your stay in this beautiful 3 bedroom, 3 bathroom home across 1,804 sq ft in the sought after Alta Vista neighborh ...
From $206 per night (USD)
VRBO
From $542 per night (USD)
Expedia
Breezemont Bungalow | Private pool, Hot tub + Sauna
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
BNB Breeze Presents: Breezemont Bungalow! Experience this stunning Sarasota home that perfectly blends comfort and luxur ...
From $542 per night (USD)
Expedia

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