
Holiday rentals with a pool in Clearwater
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Clearwater
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

3 BR/2B pool home WiFI and Brand new furnishings
Lots to Love about this centrally located Clearwater beauty. This pool home is 25 minutes from the Tampa airport and 15 minutes to famous Clearwater Beach and less than a half hour to downtown St. Pete, not to mention a 10 minute walk to Phillies spring training stadium and minutes by car to hundreds of Shoppes and Restaurants. Enjoy this spacious home with split bedroom plan and brand new furnishings. Sweet dreams on the Casper mattresses. Relax Poolside in the screened lania or by the firepit

Clearwater Gameroom- Pool/Mini golf/Home Theatre
Welcome to Clearwater Hangout- This super unique house was designed to be packed with many amenities. Just 4mi to famous Clearwater Beach! Newly renovated with fresh tiles and quartz counters for a high end trendy design. Inside amenities include- LED vanity, pool tbl/ping pong, wine fridge, dining for 14, and a full transformed game room with a basketball court, Pac-man machine, and a home theatre! Outside is a very private clean space with mini golf, a salt water pool, seating area and firepit

Steps 2 beach! Beachy and Luxurious! Easy Living!
Easy Living is a beachy newly renovated condo with 2 bedrooms & 2 full bathrooms, nestled between the intercoastal water and the magnificent Clearwater beach! Located a very short walk to the beach (less than 2 blocks) and across the street from a park. The Clearwater Beach Rec Pool is another short two minute walk from the condo! The condominium is quiet area yet, it is within walking distance to practically everything in town, including the beach, many restaurants, bars, Pier 60, & the marina!

2 BR/2 BA Key West Retreat, A+Pool, 3mi to Beach
🌴 😎 Stunning Key West Style Retreat featuring: - Memory foam Queen bed - Covered porch for unwinding - Hotel linens, towels and many creature comforts Enjoy the beach 🏄♂️ vibes decor & accents in this spacious two bed two bath property. Located less than three miles from the white, sugar sand of Clearwater Beach 😎 (rated #1 beach in the US by Trip Advisor). Relax by the oversized resort style pool and clubhouse. Convenient walking distance to nearby restaurants and grocery stores.

Beachfront in exclusive resort
This upper floor, 3-bedroom modern chic condo hotel suite offers sweeping views of the Gulf of Mexico from private balconies. While preparing your morning coffee on the spacious kitchen island, you can see the shrimp trawlers making their way out to sea. Enjoy a cocktail while watching the sunset over the open water of the Gulf of Mexico. This suite can sleep 8, with King or Queen-size beds in each of the three bedrooms, a comfortable full-sized sofa bed in the living room & 3-1/2 bathrooms.

Upgraded 3 Bed, 3 Bath Corner Water Front Condo!
Stylish & Sunny Corner Unit On Dolphin Faved Inlet Across The Street From Florida's #1 Beach. This all-inclusive unit allows you to walk everywhere and enjoy all Clearwater Beach has to offer from sand & sun to restaurants & shopping. Updated & upgraded 3 bedroom, all with connected bathrooms offers amazing space, a chef's kitchen as well as bright & beautiful dining & living rooms. Private balcony to relax & watch the sunset. Beach concessions include sea kayaks, jet ski's, boating & more.

Waterfront Beach House Steps Away from #1 Beach!
Welcome to The Bombshell Beach House! This 3 story, 3 bedroom luxury water-front townhouse located in Clearwater Beach, FL has been a childhood dream come true for me as a Clearwater native! As avid travelers, my husband and I wanted to create a STAY-CATION spot that mixed in all of the comforts of HOME with all of the luxuries of a 5 star vacation & this beach house is JUST THAT! This listing is brand new and we are expecting dates to book extremely fast! Book now to secure your GETAWAY!

Luxury Oasis • Heated Salt Pool • Near Beaches
Welcome to Paradise Palms 🌴☀️- your tropical, family-friendly getaway w/ a private heated saltwater pool! Newly renovated & cleaner than a hotel, the home is filled w/ luxury amenities to create a truly unforgettable family vacation. With 7 comfy beds, there's plenty of room for everyone. Just 14 min to the famous Clearwater Beach & other beautiful white sand beaches! It's finally time to relax & soak up some Florida sun! Come experience all that Paradise Palms & Clearwater have to offer.

Beautiful Tampa Bay Pool Home Near Gulf Beaches
A beautiful Gulf Coast residence with many amenities to offer. Bright and open furnished spaces, for relaxing and entertaining up to 10 guests. A quiet, upscale neighborhood , your just 6 minutes from Madeira Beach and many other Gulf of Mexico beaches. Or, fun & sun in the private pool outback. 20 minutes from Downtown St Pete, which offers restaurants, museums, the new Pier, and excellent night life. Very close to countless restaurants, shopping, coffee shops, and grocery stores.

Watch the Sunrise at Sunrise! @ Clearwater home.
Welcome to your perfect vacation getaway! Our beautiful home offers a heated pool, perfect for relaxing any time of year—whether you’re enjoying a sunny afternoon swim or a peaceful evening under the stars. The property features plenty of space for everyone to feel comfortable, both indoors and outdoors. With open living areas, comfortable furnishings, and a spacious layout, it’s ideal for families, friends, or groups looking to unwind and create unforgettable memories.

3 Bedroom Waterfront Paradise Sleeps 8
Welcome to Brightwater Blue, our newer vacation Town Home in Clearwater Beach on the intercostal! The 3 floors of custom interior decoration and high end furnishings await you. Located on Clearwater Bay with an easy stroll (5-10 min) to Clearwater Beach, Beach Walk, Pier 60, restaurants, and shopping. You are centrally located to everything in Clearwater with luxury accommodations ! !! You have a 2 car garage, community pool, hot tub, grill steps from your back door.

Ocean Breeze • Easy - Heated Pool Access
The Avalon at Clearwater is a gated community with a nice size heated pool and community gym. Parking space is not assigned and it’s free of charge. Location is central with short distance to nearby beaches, attractions and other nearby towns. Unit is approximately 500 square feet with a living room-kitchen open concept and One bedroom - bathroom open concept. Great access from Tampa Airport 20 minutes and 1.5/hours drive from Orlando airport
Popular amenities for Clearwater rentals with a pool
House rentals with a pool

Pool |BBQ| 10 min Drive to Clearwater Beach| 6PPL

Tropical Lagoon w/ Private Pool & Game Room!

This IS IT! FREE Heated Pool 4BD/2BA 3 King beds

Paradise palms oasis Clearwater

WOW! Dunedin Coastal POOL Home-beaches-eateries

Tropical Oasis Retreat w/ Heated Pool

Walk to BayCare Ballpark! Pool, Hot Tub, Pets OK

FL Gem! XL-Pool | Pickleball | B-Ball & More!
Apartment rentals with a pool

Relax in a Newly Renovated Beach Front Paradise

Waterfront Condo | Steps to Clearwater Beach 2King

Amazing main floor condo at Avalon

Tiki Themed Waterfront Condo on Tampa Bay

Modern and Cozy Condo 6 Minutes from the Beach !

Lovely Condo minutes from beach & King bed

Bright and Spacious 1Bed/1Bath condo.

RARE April Openings: Beach & Pool | SALE
Other holiday rentals with a pool

Amenity Overload! Pool*Putt Putt*Game Room & more!

Beachfront Oasis / Pool, Beach Access & Ocean View

Clearwater Lake House

NEW! LaPlage - Centrally Located - Family Friendly

Manatee Cove Waterfront • Heated Pool, Dock, Kayak

1 Bedroom Clearwater Condo near it all

Clearwater w Pickleball Court, Cinema, Heated Pool

Heated Pool + Fire Pit | Mini Golf & Luxury Vibes
When is the best time to visit Clearwater?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £144 | £174 | £195 | £161 | £135 | £138 | £143 | £124 | £117 | £116 | £129 | £134 |
| Avg. temp | 17°C | 18°C | 20°C | 23°C | 26°C | 28°C | 29°C | 29°C | 28°C | 25°C | 21°C | 18°C |
Quick stats about holiday rentals with a pool in Clearwater

Total holiday rentals
Explore 1,980 holiday rentals in Clearwater

Nightly prices starting at
Clearwater holiday rentals start at £8 per night before taxes and fees

Verified guest reviews
Over 70,150 verified reviews to help you choose

Family-friendly holiday rentals
1,100 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 540 rentals that welcome pets

Rentals with dedicated workspaces
1,110 properties have a dedicated workspace

Wifi availability
1,960 of Clearwater holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Clearwater rentals

4.8 Average rating
Clearwater stays are highly rated by guests – averaging 4.8 out of 5!

Nearby attractions
Clearwater’s top spots include Clearwater Marine Aquarium, Pier 60 and Countryside 12
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- Anna Maria Island
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