Luxury Vacation Rentals with a Private Pool in Sarasota
Never book a bad vacation home again. Every Wander comes with hotel-grade amenities, inspiring views, pristine cleaning and 24/7 concierge service.
We found 28 private pool vacation rentals – enter your dates for availability.
Sweet deal
Sarasota, Florida
Wander Sarasota Paradise
Next avail.
Nov 29 - Dec 1
36
Sarasota, FL, US
Wander Sarasota Modern
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Nov 22 - Nov 28
610
Sarasota, FL, US
Wander Sarasota Bay Breeze
Next avail.
Dec 5 - Dec 7
610
Sarasota, Florida
Wander Sarasota Springs
Next avail.
Dec 1 - Dec 3
48
Siesta Key, Florida
Wander Siesta Key Tides
Next avail.
Dec 2 - Dec 4
312
Siesta Key, Florida
Wander Siesta Key Sands
Next avail.
Dec 2 - Dec 4
716
Sarasota, Florida
Wander Sarasota Serenity
Next avail.
Dec 2 - Dec 4
511
Sarasota, Florida
Wander Sarasota Waves
Next avail.
Dec 14 - Dec 16
912
Welcome to private poolside luxury in Sarasota
Trade ordinary for extraordinary with Wander in Sarasota. Our luxury private-pool vacation rentals in Sarasota, Florida pair the polish of a five-star stay with the privacy of a modern coastal home. Every residence is beautifully designed, professionally cleaned, and supported by 24/7 concierge, so you can arrive to a flawless poolside setting and settle in without a worry.
Think temperature-controlled pools, spacious sun terraces, and lounge-ready lanais framed by swaying palms. Inside, expect hotel-grade linens, ultra fast WiFi, smart workstations, and thoughtful touches that make blending work and relaxation effortless. If pool time is nonnegotiable, these homes make every hour golden.
Sarasota, Florida
Wander Sarasota Breeze
Next avail.
Dec 8 - Dec 10
812
Siesta Key, Florida
Wander Siesta Key Sunset
Next avail.
Dec 8 - Dec 10
310
Siesta Key, Florida
Wander Siesta Key Haze
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Dec 3 - Dec 9
511
Sarasota, Florida
Wander Sarasota Haze
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Dec 18 - Dec 20
1012
Sarasota, Florida
Wander Sarasota Sky
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Mar 28 - Apr 3
49
Sarasota, FL, US
Wander Sarasota Dunes
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Apr 15 - Apr 21
610
Sarasota, Florida
Wander Sarasota Luxury
Next avail.
Feb 1 - Feb 3
818
Siesta Key, FL, US
Wander Siesta Key Bayfront
Next avail.
Nov 17 - Nov 23
47
Sweet deal
Sarasota, Florida
Wander Sarasota Paradise
Next avail.
Dec 12 - Dec 15
36
Sarasota, FL, US
Wander Sarasota Bay Breeze
Next avail.
Dec 5 - Dec 8
610
Siesta Key, Florida
Wander Siesta Key Tides
Next avail.
Dec 5 - Dec 7
312
Siesta Key, Florida
Wander Siesta Key Sands
Next avail.
Dec 5 - Dec 7
716
Sarasota, Florida
Wander Sarasota Serenity
Next avail.
Dec 12 - Dec 14
511
Sarasota, Florida
Wander Sarasota Cottage
Next avail.
Dec 5 - Dec 7
412
Sarasota, Florida
Wander Sarasota Gulf
Next avail.
Dec 19 - Dec 21
824
Sarasota, Florida
Wander Sarasota Key
Next avail.
Dec 12 - Dec 14
412
IT'S A VACATION HOME, BUT BETTER
The Wander difference
Wander is different because we combine the quality of a luxury hotel with the comfort of a private vacation home. Your best trip ever is just a few clicks away.
All homes in Sarasota
Sweet deal
Sarasota, Florida
Wander Sarasota Paradise
Next avail.
Nov 29 - Dec 1
36
Sarasota, FL, US
Wander Sarasota Modern
Next avail.
Nov 22 - Nov 28
610
Sarasota, FL, US
Wander Sarasota Bay Breeze
Next avail.
Dec 5 - Dec 7
610
Sarasota, Florida
Wander Sarasota Springs
Next avail.
Dec 1 - Dec 3
48
Siesta Key, Florida
Wander Siesta Key Tides
Next avail.
Dec 2 - Dec 4
312
Siesta Key, Florida
Wander Siesta Key Sands
Next avail.
Dec 2 - Dec 4
716
Sarasota, Florida
Wander Sarasota Serenity
Next avail.
Dec 2 - Dec 4
511
Sarasota, Florida
Wander Sarasota Waves
Next avail.
Dec 14 - Dec 16
912
Discover more beyond the pool in Sarasota
Sarasota brings Gulf Coast beauty into sharp focus. Powder-soft sands on Siesta Key and Lido Key meet calm, teal water that invites long, sunlit days. Beyond the shoreline, mangrove tunnels, dolphin-filled bays, and spectacular sunsets keep the camera out, while the city’s creative pulse beats through The Ringling, the opera, and a full calendar of performances.
From boutique shopping on St. Armands Circle to boat days and championship golf, the pace is easy yet elevated. With mild winters and vibrant summers, it is a year-round escape that balances coastal calm with cultural depth. This is why Wander’s luxury private-pool vacation rentals in Sarasota, Florida are the perfect choice, whether you are traveling for work or leisure.