Luxury Vacation Rentals with a Private Pool in Clearwater

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

Top-rated private pool vacation rentals in Clearwater

Home in Largo

4 bedrooms•2 baths

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New

~$70 less than other sites

Home in Clearwater

12 bedrooms•11 baths

•

~$200 less than other sites

Home in Largo

3 bedrooms•2 baths

•

New

~$85 less than other sites

Home in Largo

4 bedrooms•3.5 baths

•

New

~$70 less than other sites

Home in Largo

6 bedrooms•3 baths

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New

~$100 less than other sites

Home in Largo

4 bedrooms•2 baths

•

New

~$75 less than other sites

Home in Largo

4 bedrooms•2 baths

•

New

~$70 less than other sites

Home in Largo

4 bedrooms•2 baths

•

New

~$80 less than other sites

Welcome to private poolside luxury in Clearwater

Make your Clearwater escape effortless with Wander. Our collection of luxury private-pool vacation rentals in Clearwater pairs hotel-level consistency with the privacy of a coastal home. Each stay looks exactly like the photos and is run by our in-house team.

Expect heated pools framed by palm trees, screened lanais for all-day lounging, outdoor kitchens, and plush bedrooms ready for late checkouts. Hotel-grade amenities like ultra fast WiFi, smart TVs, and crisp, professionally laundered linens come standard, along with pristine cleaning and 24/7 concierge support. When you want space to unwind or work in the sun, Wander makes it simple.

Available soon in Clearwater

Home in Largo

4 bedrooms•2 baths

•

New

~$70 less than other sites

Home in Clearwater

12 bedrooms•11 baths

•

~$200 less than other sites

Home in Largo

3 bedrooms•2 baths

•

New

~$85 less than other sites

Home in Largo

4 bedrooms•3.5 baths

•

New

~$70 less than other sites

Home in Largo

6 bedrooms•3 baths

•

New

~$100 less than other sites

Home in Largo

4 bedrooms•2 baths

•

New

~$75 less than other sites

Home in Largo

4 bedrooms•2 baths

•

New

~$70 less than other sites

Home in Largo

4 bedrooms•2 baths

•

New

~$80 less than other sites

Featured private pool vacation rentals in Clearwater

Home in Clearwater

12 bedrooms•11 baths

•

~$200 less than other sites

Highlights in Clearwater

Experience pristine white-sand beaches, vibrant marine life encounters, and unforgettable Gulf Coast sunsets in the sun-drenched paradise of Clearwater.

Clearwater Beach

Pier 60

Clearwater Marine Aquarium

Sand Key Park

Caladesi Island State Park

Coachman 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 Clearwater

Home in Largo

4 bedrooms•2 baths

•

New

~$70 less than other sites

Home in Clearwater

12 bedrooms•11 baths

•

~$200 less than other sites

Home in Largo

3 bedrooms•2 baths

•

New

~$85 less than other sites

Home in Largo

4 bedrooms•3.5 baths

•

New

~$70 less than other sites

Home in Largo

6 bedrooms•3 baths

•

New

~$100 less than other sites

Home in Largo

4 bedrooms•2 baths

•

New

~$75 less than other sites

Home in Largo

4 bedrooms•2 baths

•

New

~$70 less than other sites

Home in Largo

4 bedrooms•2 baths

•

New

~$80 less than other sites

View all homes

Most popular amenities for private pool vacation rentals in Clearwater

Outdoor dining area (1)

Microwave (10)

Dishwasher (10)

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Other popular amenities & vacation types in Clearwater

Family vacation rentals in Clearwater

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Discover more beyond the pool in Clearwater

On Florida’s sunlit Gulf, Clearwater balances postcard beaches with an inviting pace. Clearwater Beach’s sugar-white shoreline and glassy, emerald water set the mood for sunrise walks and unhurried afternoons. Evenings often center on Pier 60, where street performers and glowing sunsets feel like a standing ovation.

Venture to Caladesi Island State Park by kayak or ferry for quiet trails and shelling, or follow the Intracoastal by boat in search of dolphins. Cyclists love the Pinellas Trail, while anglers and paddleboarders find calm, protected waters year-round. With this blend of nature, gentle adventure, and coastal charm, Wander’s luxury vacation rentals in Clearwater are the perfect choice, whether you’re traveling for work or leisure.

FAQs: Vacation Rentals in Clearwater

Why should I book a Wander in Clearwater 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 Clearwater 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 Clearwater?

Some of our most popular private pool vacation rentals in Clearwater include Tropical Tee - Putt Putt - Pool - Hot Tub - Bikes, 2 Massive Homes Heated Pool Spa Pickleball GameRm, and Resort Backyard Tiki Bar Fully Renovated Pool. 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 Clearwater?

Wander offers 10 private pool vacation rentals in Clearwater, 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 Clearwater?

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

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

Yes. Every Wander home in Clearwater 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.