Luxury Vacation Rentals with a Private Pool in Sarasota

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 30 private pool vacation rentals – enter your dates for availability.

Top-rated private pool vacation rentals in Sarasota

Charlotte Ave Coastal Retreat Private Pool Fire Pit & Backyard Lounge property photo 1

Charlotte Ave Coastal Retreat Private Pool Fire Pit & Backyard Lounge

3 bedrooms•2 baths
779 US dollars for 4 nights•
New

~$60 less than other sites

Legacy's Palm of Paradise property photo 1

Legacy's Palm of Paradise

3 bedrooms•2 baths
1,673 US dollars for 3 nights•

~$130 less than other sites

Knot A Basic Beach House property photo 1
Luxury

Knot A Basic Beach House

6 bedrooms•7 baths
8,658 US dollars for 8 nights•
New

~$675 less than other sites

Waterfront Siesta Key Home l w/ pool, hot tub, mini putt, bikes & mins to beach property photo 1

Waterfront Siesta Key Home l w/ pool, hot tub, mini putt, bikes & mins to beach

5 bedrooms•3 baths
2,480 US dollars for 3 nights•

~$195 less than other sites

Siesta Sunset Sanctuary property photo 1
Luxury

Siesta Sunset Sanctuary

4 bedrooms•5.5 baths
2,982 US dollars for 3 nights•
New

~$230 less than other sites

Private Pool, Fire Pit, Game House property photo 1

Private Pool, Fire Pit, Game House

3 bedrooms•2 baths
1,070 US dollars for 3 nights•
New

~$80 less than other sites

Charming Condo with Gulf Views property photo 1

Charming Condo with Gulf Views

2 bedrooms•2 baths
5,432 US dollars for 30 nights•
New

~$425 less than other sites

Lido Luxe Estate property photo 1
Luxury

Lido Luxe Estate

6 bedrooms•6.5 baths
8,094 US dollars for 7 nights•
New

~$635 less than other sites

Welcome to private poolside luxury in Sarasota

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.

Available soon in Sarasota

Legacy's Palm of Paradise property photo 1

Legacy's Palm of Paradise

3 bedrooms•2 baths
1,673 US dollars for 3 nights•

~$130 less than other sites

Waterfront Siesta Key Home l w/ pool, hot tub, mini putt, bikes & mins to beach property photo 1

Waterfront Siesta Key Home l w/ pool, hot tub, mini putt, bikes & mins to beach

5 bedrooms•3 baths
2,480 US dollars for 3 nights•

~$195 less than other sites

Siesta Sunset Sanctuary property photo 1
Luxury

Siesta Sunset Sanctuary

4 bedrooms•5.5 baths
2,982 US dollars for 3 nights•
New

~$230 less than other sites

Private Pool, Fire Pit, Game House property photo 1

Private Pool, Fire Pit, Game House

3 bedrooms•2 baths
1,070 US dollars for 3 nights•
New

~$80 less than other sites

High Tide (SKLRP) property photo 1

High Tide (SKLRP)

6 bedrooms•6.5 baths
4,439 US dollars for 3 nights•
New

~$345 less than other sites

Sunset Splash property photo 1

Sunset Splash

8 bedrooms•7.5 baths
4,272 US dollars for 3 nights•
New

~$330 less than other sites

Sunset View property photo 1

Sunset View

8 bedrooms•5.5 baths
4,108 US dollars for 3 nights•
New

~$320 less than other sites

Private Heated Pool Yacht Rental BBQ Firepit Near Water property photo 1

Private Heated Pool Yacht Rental BBQ Firepit Near Water

3 bedrooms•2 baths
489 US dollars for 1 night•

~$35 less than other sites

Featured private pool vacation rentals in Sarasota

Knot A Basic Beach House property photo 1
Luxury

Knot A Basic Beach House

6 bedrooms•7 baths
8,658 US dollars for 8 nights•
New

~$675 less than other sites

Lido Luxe Estate property photo 1
Luxury

Lido Luxe Estate

6 bedrooms•6.5 baths
8,094 US dollars for 7 nights•
New

~$635 less than other sites

High Tide (SKLRP) property photo 1

High Tide (SKLRP)

6 bedrooms•6.5 baths
4,439 US dollars for 3 nights•
New

~$345 less than other sites

Sunset Splash property photo 1

Sunset Splash

8 bedrooms•7.5 baths
4,272 US dollars for 3 nights•
New

~$330 less than other sites

Ocean Overlook property photo 1
Luxury

Ocean Overlook

8 bedrooms•9 baths
4,434 US dollars for 3 nights•
New

~$345 less than other sites

Sunset View property photo 1

Sunset View

8 bedrooms•5.5 baths
4,108 US dollars for 3 nights•
New

~$320 less than other sites

Beach Views property photo 1

Beach Views

7 bedrooms•7.5 baths
10,117 US dollars for 9 nights•
New

~$795 less than other sites

Seascape property photo 1

Seascape

8 bedrooms•8.5 baths
8,783 US dollars for 8 nights•
New

~$690 less than other sites

Highlights in Sarasota

Discover a vibrant coastal city where stunning white-sand beaches meet a rich cultural scene, from world-class art museums to circus history.
The Ringling
Siesta Key Beach
Marie Selby Botanical Gardens
St. Armands Circle
Mote Marine Laboratory & Aquarium
Lido Key Beach
Myakka River State Park

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.

Only the best homes

We’ll never not look like the pictures. Every Wander is beautiful and expertly operated, so you can leave any stress at the door.

Hotel-grade amenities

We’ll never leave you with nothing to do. From ultra fast WiFi to gyms and pools, our homes make it easy to blend work and play.

24/7 concierge service

We’ll never leave you hanging. Our chat-based Concierge is always available to help – from trip questions to special requests.

Inspiring and stunning views

We’ll never leave you uninspired. Every Wander has stunning views to refresh and inspire your soul. Adventure awaits.

Meticulous cleaning

We’ll never have you check in to a dirty house. Our cleaning teams are meticulous, and there are no chores at checkout.

Safety and security

We’ll never pass you off to a stranger. Every Wander location meets our industry-leading safety standards to give you peace of mind.

All homes in Sarasota

Charlotte Ave Coastal Retreat Private Pool Fire Pit & Backyard Lounge property photo 1

Charlotte Ave Coastal Retreat Private Pool Fire Pit & Backyard Lounge

3 bedrooms•2 baths
779 US dollars for 4 nights•
New

~$60 less than other sites

Legacy's Palm of Paradise property photo 1

Legacy's Palm of Paradise

3 bedrooms•2 baths
1,673 US dollars for 3 nights•

~$130 less than other sites

Knot A Basic Beach House property photo 1
Luxury

Knot A Basic Beach House

6 bedrooms•7 baths
8,658 US dollars for 8 nights•
New

~$675 less than other sites

Waterfront Siesta Key Home l w/ pool, hot tub, mini putt, bikes & mins to beach property photo 1

Waterfront Siesta Key Home l w/ pool, hot tub, mini putt, bikes & mins to beach

5 bedrooms•3 baths
2,480 US dollars for 3 nights•

~$195 less than other sites

Siesta Sunset Sanctuary property photo 1
Luxury

Siesta Sunset Sanctuary

4 bedrooms•5.5 baths
2,982 US dollars for 3 nights•
New

~$230 less than other sites

Private Pool, Fire Pit, Game House property photo 1

Private Pool, Fire Pit, Game House

3 bedrooms•2 baths
1,070 US dollars for 3 nights•
New

~$80 less than other sites

Charming Condo with Gulf Views property photo 1

Charming Condo with Gulf Views

2 bedrooms•2 baths
5,432 US dollars for 30 nights•
New

~$425 less than other sites

Lido Luxe Estate property photo 1
Luxury

Lido Luxe Estate

6 bedrooms•6.5 baths
8,094 US dollars for 7 nights•
New

~$635 less than other sites

View all homes

Most popular amenities for private pool vacation rentals in Sarasota

Outdoor pool (29)
Heated pool (18)
Ocean view (12)
Jacuzzi (15)
Hot tub (15)
Private chef (1)
Putting green (5)
Beachfront (1)
Kayaks (2)
Waterfront (2)
Beach access (5)
Bbq area (24)
Gym (1)
Bicycle (2)
Beach essentials (3)
Garden (24)

More popular private pool destinations near Sarasota

Private pool vacation rentals in Siesta Key
Private pool vacation rentals in Bradenton Beach
Private pool vacation rentals in Anna Maria
Private pool vacation rentals in Captiva
Private pool vacation rentals in Fort Myers Beach
Private pool vacation rentals in Kissimmee
Private pool vacation rentals in Marco Island
Private pool vacation rentals in Melbourne Beach

Other popular amenities & vacation types in Sarasota

Family vacation rentals in Sarasota
Large group vacation rentals in Sarasota
Hot tub vacation rentals in Sarasota
Discover more beyond the pool in Sarasota

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.

FAQs: Vacation Rentals in Sarasota

Why should I book a Wander in Sarasota over other private pool vacation rentals?

Wander offers a level of consistency and quality you won’t find with most private pool vacation rentals.
Every home in Sarasota delivers the quality of a luxury hotel, paired with the comfort and space of a private vacation home. You get hotel-grade amenities, meticulous cleaning, stunning views, and 24/7 concierge support in every stay. Why would you want to stay anywhere else?

Which are Wander’s most popular private pool vacation rentals in Sarasota?

Some of our most popular private pool vacation rentals in Sarasota include Charlotte Ave Coastal Retreat Private Pool Fire Pit & Backyard Lounge, Legacy's Palm of Paradise, and Knot A Basic Beach House. Guests love the quality of a luxury hotel, the comfort of a private vacation home, and the consistently exceptional experience Wander is known for. Explore the full collection to find the perfect home for your next stay.

How many different private pool vacation rentals does Wander have available in Sarasota?

Wander offers 30 private pool vacation rentals in Sarasota, each carefully designed and expertly operated. Browse the full collection to see what’s available for your trip.

What time is check-in and check-out at Wander’s private pool vacation rentals in Sarasota?

You can check-in to Wander private pool vacation rentals in Sarasota after 4.00pm and check-out before 10.00am.

Do Wander’s private pool vacation rentals in Sarasota have WiFi access?

Yes. Every Wander home in Sarasota has ultra fast, reliable WiFi so you can stay connected throughout your stay.

What is Wander’s cancellation policy?

You can cancel your reservation within 24 hours of booking for a full refund.
For stays of less than 15 nights, you can cancel or reschedule up to 14 days before check-in for a full refund. For stays of 15 nights or longer, the cancellation window is 60 days.
For some homes, a 30-day deadline applies; this will be clearly shown before you book.