
Vacation 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.

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.

Palms and Dreams Villa 3/2 Heated Pool•BEACH 5 mi
Book your dream getaway in this bright, spacious, updated 3bd 2ba home for up to 10 guests. Nestled in a safe, quiet neighborhood, minutes from beaches, dining, and shopping. Relax in your private backyard oasis with cozy seating, a gorgeous seasonally heated pool, an outdoor dining area, a gentle flow spa (not a hot tub), a BBQ grill, and lush greenery. Every detail has been designed to make your stay unforgettable. Reserve our home today and start making memories with family and friends!

Casa Palmera! *Heated Pool!
Step into relaxation as you enter this tropical pool home, centrally located to everything one would need staying in Clearwater! This 4 bedroom, 2 bath home has been meticulously curated to give our guests the best experience imaginable during their stay on the west coast of Florida. Only 5 miles from world renown Clearwater Beach, 1 mile from the Phillies spring training site, less than 2 miles from some of the best local eateries in Safety Harbor and Dunedin. Come stay at Casa Palmera!

Waterfront Modern Chic #1 Clearwater Beach
This prime location is on the bay just steps away from the beach and the main strip offering a complete home experience. This spacious apartment is equipped with a full kitchen, washer/dryer, two full bathrooms, a large family room, dining area, access to the pool and two assigned parking spaces. A split floor plan ensures privacy, accommodating guests on either side of the apartment. The private patio overlooks the bay, offering stunning views of the sunrise and the occasional dolphin.

Tootsie’s Beachside Retreat-New Heated Pool
LUXURY SALTWATER HEATED POOL HOME! JUST 1.5 MILES TO BEAUTIFUL REDINGTON BEACH. AMAZING REMODELED HOME WITH HIGH END FINISHES LOCATED ON 1/2 ACRE LOT. BRAND NEW CUSTOM POOL WITH PEBBLETECH FINISH AND BAJA SHELF. BEAUTIFUL WHITE SAND BEACHES ONLY 1.5 MILE RIDE! 5 MIN. FROM: 3 COFFEE SHOPS,OUTSIDE MALL WITH SHOPPING, RESTAURANTS AND MOVIES. HOUSE IS ON RARE 1/2 ACRE PROPERTY IN UPSCALE NEIGHBORHOOD. RENOVATED WITH HIGH END FURNITURE AND FIXTURES, SAMSUNG 4K LED T.V.’S IN EVERY ROOM.

Luxury Beach Cottage | Walk to Dining & Sunset
Escape to paradise at Sunshine Escapes IRB! Welcome to Coco, nestled in the heart of Indian Rocks Beach. IRB is a hidden gem that radiates a whimsical, small-town charm, evoking nostalgic memories of carefree childhood summers by the shore—the Gulf of Mexico beckons just two blocks away, offering pristine, fluffy sands and unforgettable sunsets. As the sister cottage of Mango, Coco invites you to immerse yourself in the laid-back beachy vibes of IRB. Your perfect getaway awaits!

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

Bright and Spacious 1Bed/1Bath condo.
Enjoy your getaway in this relaxing, clean, bright, and cozy 1 bedroom/1 bath condo on the 1st floor of a gated community, fully equipped for your stay including beach chairs, umbrella and a cooler. You will have a private entrance to the condo, free parking, a heated pool open all year, a clubhouse with a basic gym. We are conveniently located 15 minutes away from Clearwater Beach and an easy 30-minute drive to Tampa International Airport.

Bayside Retreat your tropical oasis
"Bayside Retreat" is a Charming Private 1~bedroom/1 bath with full living room suite, located right on the water of upper Tampa Bay. Spend a quiet day lounging in the grotto pool, kayaking the bay, or a lazy day reading in the hammock. Enjoy breath taking sunrise and sunsets from the dock. Your own Tropical Paradise away from the rest of the world....... Just 15min to Raymond James Stadium. Centrally located 15 miles from TPA Airport
Popular amenities for Clearwater rentals with a pool
House rentals with a pool

Beach or Relax | Heated Pool home/Spa | Pets OK

Modern Cozy 3BR | Walk to IRB Beach + Heated Pool

Pool•Hot Tub•Free EV Charger•5 Mins to Beaches

Endless Summer in Clearwater-HeatedPool-Golf-Beach

Tropical Oasis Retreat w/ Heated Pool

3 BR/2B pool home WiFI and Brand new furnishings

Heated Pool | 2BD 2BA | Home near Beaches

4BD/3BA + Pool + Hot Tub + Game Rm—5 mi to Beach!
Condo rentals with a pool

Gulf-View 2BR/2BA Beach Condo!

Beach Haven in South Clearwater Beach

Amazing main floor condo at Avalon

Tropical Beachfront Penthouse-Beach Cottages

2 King Suites • Waterfront • Walk to Beach

POOL VIEW IN A MODERN CONDO - Feel at Home

Spectacular beach to bay views from this resort.

Royal Orleans and Redington Beach ( Studio 203 )
Other vacation rentals with a pool

Luxury Tiny Home 1 Bed - 1 Bath Unit B "Sandy"

Backyard Paradise- Cozy Bungalow 4 Mi to Beach

Avalon. Clearwater. Cozy condo. Pool view.

Waterfront Clearwater Beach #16| Pool | Parking

Avalon Sunshine: Relax, Recharge+ Free Parking

1 Bedroom Clearwater Condo near it all

Sea Side Sunsets Unit C

Paradise Point Home in Clearwater-5 miles to beach
When is the best time to visit Clearwater?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$39,571 GYD | G$47,902 GYD | G$53,733 GYD | G$44,361 GYD | G$37,280 GYD | G$37,905 GYD | G$39,363 GYD | G$34,156 GYD | G$32,073 GYD | G$31,865 GYD | G$35,614 GYD | G$36,863 GYD |
| 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 vacation rentals with a pool in Clearwater

Total vacation rentals
Explore 1,980 vacation rentals in Clearwater

Nightly prices starting at
Clearwater vacation rentals start at G$2,083 GYD per night before taxes and fees

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

Family-friendly vacation rentals
1,100 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 540 rentals that welcome pets

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

Wi-Fi availability
1,960 of Clearwater vacation rentals include wi-fi 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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