Luxury Vacation Rentals with a Private Pool in Siesta Key

Luxury Vacation Rentals with a Private Pool in Siesta Key

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

Top-rated private pool vacation rentals in Siesta Key

Home in Siesta Key property photo 1

Home in Siesta Key

6 bedrooms•6.5 baths
4,187 US dollars for 3 nights•
New

~$370 less than other sites

Home in Siesta Key property photo 1

Home in Siesta Key

8 bedrooms•5.5 baths
3,828 US dollars for 3 nights•
New

~$335 less than other sites

Home in Siesta Key property photo 1
Luxury

Home in Siesta Key

4 bedrooms•5.5 baths
New
Home in Siesta Key property photo 1
Luxury

Home in Siesta Key

8 bedrooms•9 baths
4,273 US dollars for 3 nights•
New

~$375 less than other sites

Home in Sarasota property photo 1

Home in Sarasota

5 bedrooms•5 baths
3,147 US dollars for 3 nights•
New

~$275 less than other sites

Home in Siesta Key property photo 1

Home in Siesta Key

8 bedrooms•7.5 baths
4,030 US dollars for 3 nights•
New

~$355 less than other sites

Home in Siesta Key property photo 1

Home in Siesta Key

3 bedrooms•2.5 baths
3,723 US dollars for 7 nights•
New

~$330 less than other sites

Home in Siesta Key property photo 1

Home in Siesta Key

3 bedrooms•2 baths
2,214 US dollars for 7 nights•
New

~$195 less than other sites

Welcome to private poolside luxury in Siesta Key

Welcome to private poolside luxury in Siesta Key

Claim your own slice of island luxury with Wander’s portfolio of luxury private pool vacation rentals in Siesta Key. Each home is architecturally striking, impeccably clean, and professionally operated, so what you see is exactly what you get.
Spend unhurried mornings by your private heated pool, then step inside to hotel-grade touches like plush linens, ultra fast WiFi, and inspiring views, all backed by 24/7 concierge support.
Designed for work and play, our residences pair serene outdoor lounges with thoughtful interiors that make every stay effortless.

Available soon in Siesta Key

Home in Siesta Key property photo 1

Home in Siesta Key

6 bedrooms•6.5 baths
4,187 US dollars for 3 nights•
New

~$370 less than other sites

Home in Siesta Key property photo 1
Luxury

Home in Siesta Key

4 bedrooms•5.5 baths
2,916 US dollars for 3 nights•
New

~$255 less than other sites

Home in Siesta Key property photo 1
Luxury

Home in Siesta Key

8 bedrooms•9 baths
4,273 US dollars for 3 nights•
New

~$375 less than other sites

Home in Sarasota property photo 1

Home in Sarasota

5 bedrooms•5 baths
3,147 US dollars for 3 nights•
New

~$275 less than other sites

Home in Siesta Key property photo 1

Home in Siesta Key

4 bedrooms•2.5 baths
2,250 US dollars for 3 nights•

~$200 less than other sites

Home in Siesta Key property photo 1

Home in Siesta Key

8 bedrooms•6 baths
6,154 US dollars for 3 nights•
New

~$545 less than other sites

Home in Siesta Key property photo 1

Home in Siesta Key

3 bedrooms•2.5 baths
2,077 US dollars for 3 nights•

~$180 less than other sites

Home in Siesta Key property photo 1
Luxury

Home in Siesta Key

7 bedrooms•6.5 baths
5,817 US dollars for 3 nights•

~$515 less than other sites

Featured private pool vacation rentals in Siesta Key

Home in Siesta Key property photo 1

Home in Siesta Key

6 bedrooms•6.5 baths
4,187 US dollars for 3 nights•
New

~$370 less than other sites

Home in Siesta Key property photo 1

Home in Siesta Key

8 bedrooms•5.5 baths
3,828 US dollars for 3 nights•
New

~$335 less than other sites

Home in Siesta Key property photo 1
Luxury

Home in Siesta Key

8 bedrooms•9 baths
4,273 US dollars for 3 nights•
New

~$375 less than other sites

Home in Sarasota property photo 1

Home in Sarasota

5 bedrooms•5 baths
3,147 US dollars for 3 nights•
New

~$275 less than other sites

Home in Siesta Key property photo 1

Home in Siesta Key

8 bedrooms•7.5 baths
4,030 US dollars for 3 nights•
New

~$355 less than other sites

Home in Siesta Key property photo 1

Home in Siesta Key

6 bedrooms•5 baths
4,941 US dollars for 3 nights•

~$435 less than other sites

Home in Siesta Key property photo 1

Home in Siesta Key

4 bedrooms•2.5 baths
2,250 US dollars for 3 nights•

~$200 less than other sites

Home in Siesta Key property photo 1

Home in Siesta Key

8 bedrooms•6 baths
6,154 US dollars for 3 nights•
New

~$545 less than other sites

Highlights in Siesta Key

Discover the award-winning white-sand beaches, vibrant village life, and stunning Gulf sunsets that make this barrier island a paradise.
Siesta Beach
Siesta Key Village
Crescent Beach
Point of Rocks
Turtle Beach
Siesta Key Drum Circle

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 Siesta Key

Home in Siesta Key property photo 1

Home in Siesta Key

6 bedrooms•6.5 baths
4,187 US dollars for 3 nights•
New

~$370 less than other sites

Home in Siesta Key property photo 1

Home in Siesta Key

8 bedrooms•5.5 baths
3,828 US dollars for 3 nights•
New

~$335 less than other sites

Home in Siesta Key property photo 1
Luxury

Home in Siesta Key

4 bedrooms•5.5 baths
New
Home in Siesta Key property photo 1
Luxury

Home in Siesta Key

8 bedrooms•9 baths
4,273 US dollars for 3 nights•
New

~$375 less than other sites

Home in Sarasota property photo 1

Home in Sarasota

5 bedrooms•5 baths
3,147 US dollars for 3 nights•
New

~$275 less than other sites

Home in Siesta Key property photo 1

Home in Siesta Key

8 bedrooms•7.5 baths
4,030 US dollars for 3 nights•
New

~$355 less than other sites

Home in Siesta Key property photo 1

Home in Siesta Key

3 bedrooms•2.5 baths
3,723 US dollars for 7 nights•
New

~$330 less than other sites

Home in Siesta Key property photo 1

Home in Siesta Key

3 bedrooms•2 baths
2,214 US dollars for 7 nights•
New

~$195 less than other sites

View all homes

Most popular amenities for private pool vacation rentals in Siesta Key

Outdoor pool (18)
Heated pool (16)
Jacuzzi (11)
Hot tub (11)
Private chef (1)
Ocean view (5)
Beachfront (1)
Waterfront (3)
Putting green (1)
Beach access (11)
Bbq area (18)
Sound system (1)
Game console (2)
Ping pong table (3)
Foosball table (2)
Kitchen (19)

More popular private pool destinations near Siesta Key

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Other popular amenities & vacation types in Siesta Key

Family vacation rentals in Siesta Key
Large group vacation rentals in Siesta Key
Beachfront vacation rentals in Siesta Key
Hot tub vacation rentals in Siesta Key
Discover more beyond the pool in Siesta Key

Discover more beyond the pool in Siesta Key

Sugar-soft quartz sand, turquoise Gulf water, and sunsets that feel cinematic define Siesta Key. The beaches stay cool underfoot and the surf is gentle, making long shoreline walks and easy swims a daily ritual.
Paddle mangrove tunnels on calm bays, snorkel the limestone at Point of Rocks, or drift between laid-back cafés and live music in the Village. Sarasota’s galleries and theaters sit just over the bridge, yet the Key keeps its breezy rhythm.
All of this is why Wander's luxury private pool vacation rentals in Siesta Key are the perfect choice, whether you're traveling for work or leisure.

FAQs: Vacation Rentals in Siesta Key

Why should I book a Wander in Siesta Key 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 Siesta Key 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 Siesta Key?

Some of our most popular private pool vacation rentals in Siesta Key include High Tide (SKLRP), Sunset View, and Siesta Sunset Sanctuary. 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 Siesta Key?

Wander offers 19 private pool vacation rentals in Siesta Key, 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 Siesta Key?

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

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

Yes. Every Wander home in Siesta Key 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.