Best Clearwater rentals with pool - St. Petersburg - Clearwater for 2025

Explore Clearwater rentals with pools

☀Shelley Casa, 3BR/2BA,Stunning- ✔Pool✔WHOLE HOUSE

Sleeps 10 · 3 bedrooms · 2 bathrooms

Open flor plan tastefully accented with beach decor.⚓️

AVALON RESORT, LUXURY CUSTOM 2/2 BEACH THEMED CONDO, HEATED POOL, CLOSE TO BEACH

Sleeps 6 · 2 bedrooms · 2 bathrooms

Top rated rentals with pools - Clearwater

Premier Host

Week at The Cove

Had an amazing time at The Cove. Lovely property with all you need for a relaxing holiday, either lounging around the pool or at the beach. The bikes made exploring the local area super easy. Would definitely highly recommend and stay again.

Niall M.

Stayed Jul 2025

Watch for dolphins as you relax poolside in our heated pool!

Premier Host

The perfect VRBO Condo

This is definitely the best Condo to stay at in Clearwater The unit was immaculate Anything we could think of needing was already there The owner, Bryan, was totally available for any questions and stopped by shortly after we arrived to make sure all was ok The view was great and location perfect The unit unquestionably deserves a "10" TMC Utica, NY.

Theodore C.

Stayed Nov 2024

Just relax and have fun in a beautiful heated pool - AVALON at CLEARWATER

Premier Host

Excellent holiday location

We enjoyed an excellent two weeks in the Royal Marina condo. The apartment is extremely comfortable very well equipped with all the day-to-day necessities. We particularly liked the nautical theme in the lounge area and the convenience of the balcony facility off the lounge/master bedroom. The condo hosts did an excellent job in preparing the place for our arrival and keeping us informed throughout our stay. Would definitely recommend. One of the best locations we have stayed at.

Phil W.

Stayed Sept 2024

Premier Host

Fantastic location & Property

Spacious property, well provisioned, clean & fantastic location with a lovely host. Only negative feedback ; original check in a little confusing at 11pm in the dark as wasn’t sure whereabouts the property was, a map would be super helpful. A clothes airer or line to dry any washing would again be helpful. Neither were an issue or detracted from our stay.

nikki b.

Stayed May 2023

Premier Host

Very nice stay, extremely clean,

Needed a dishwasher for perfect stay. Couldn't find iron or ironing board. Perfect space for 2 couples. Nice clean pool.

Susan D.

Stayed Nov 2022

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Frequently asked questions

Are there any holiday rentals with a pool in Clearwater?

You can choose from 5,871 holiday rentals with a pool in Clearwater that have all the privacy, space and amenities you need for a splashing good time. Browse houses in sought-after neighbourhoods such as Clearwater Point, Island Estate and Old Clearwater Bay.

How much does it cost to stay in a holiday rental with a pool in Clearwater?

Exactly where you stay, what time of year you travel and the length of your escape will determine the price of a holiday rental with a pool in Clearwater. Key in your travel dates on Vrbo, then pick the ideal one for you and prepare to make a splash.

When is the best time to book a holiday rental with a pool in Clearwater?

If you want to enjoy Clearwater at a busy time, consider going in March. That's when temperatures range from around 17ºC (63ºF) to 23ºC (73ºF), and when many guests secure their holiday rental with a pool in this destination. Of course, there are other great times to travel to this corner of St. Petersburg - Clearwater, so do some research into which month or season best suits your plans.

What holiday rentals with a pool in Clearwater have nice views?

If your idea of the ideal escape involves poolside fun and picturesque scenery, you'll find Clearwater holiday rentals with a pool that deliver just that. Book one with beach views and dive into a blissful holiday experience.

Are there holiday rentals with a private pool in Clearwater?

Select a holiday rental with a private pool in Clearwater and enjoy a morning swim or midnight soak — or whenever you're in the mood! You can keep your kids entertained, and you won't have to worry about sharing with other guests. Use our "Private pool" filter to discover your perfect holiday home.

What are the top things to do in Clearwater?

Fun times in Clearwater await for the family when you book a holiday home rental with a pool. On top of exploring leading attractions like Clearwater Marine Aquarium, Pier 60 Park and Sand Key Park, you'll be able to spend your downtime practicing cannonballs.

Why should I book my holiday rental with a pool with Vrbo?

When you stay in a Vrbo holiday rental with a pool, the only people you'll share your space with are whoever you bring along. It will just be you and your family with the whole property to yourselves having a splashing good time. Also, with our free rewards programme, One Key™, you can collect and spend OneKeyCash™* on eligible bookings made through Vrbo. Plus, our flexible cancellation policies also mean you can book your rental house with peace of mind if your plans change. *OneKeyCash disclaimer - OneKeyCash is not redeemable for cash and can only be used on Vrbo.