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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.

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Guest favorite
The outdoor area showcases a saltwater pool within a screened lanai, surrounded by a patio area with seating. The pool area is illuminated by natural light, enhancing the space's openness. A game room features plush seating arranged for viewing films, with walls designed for a cinematic experience.
Home in Clearwater
4.93 out of 5 average rating, 170 reviews

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

Top guest favorite
Gentle waves lapping against a sandy shore create a serene coastal scene. The sky is filled with wispy clouds and varying shades of blue, reflecting the tranquil atmosphere of the beach. The shoreline reveals patterns in the wet sand as the water recedes.
Condo in Clearwater Beach
4.95 out of 5 average rating, 313 reviews

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!

Top guest favorite
Condo in Clearwater
4.97 out of 5 average rating, 135 reviews

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.

Guest favorite
A spacious outdoor area surrounded by lush greenery showcases a seasonally heated pool. Comfortable sectional seating is arranged around a glass table, complemented by large sun umbrellas. A BBQ grill and outdoor dining table are visible, creating an inviting space for relaxation.
Home in Clearwater
4.94 out of 5 average rating, 144 reviews

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!

Superhost
A spacious outdoor area features a dining table surrounded by chairs, with a large pool reflecting the blue sky. Tropical plants and palm trees add greenery, while a sign reading 'Clearwater' enhances the relaxed vibe. Bright umbrellas provide shade for the inviting lounging spots.
Home in Clearwater
4.9 out of 5 average rating, 136 reviews

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!

Guest favorite
A modern dining area features a round glass table set for six, surrounded by white chairs. A unique blue chandelier hangs above, while large windows offer a view of the water. The kitchen area is equipped with white cabinetry and stainless steel appliances.
Apartment in Clearwater Beach
4.88 out of 5 average rating, 245 reviews

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.

Top guest favorite
An aerial view captures a spacious patio surrounding a custom saltwater pool, where lounge chairs are arranged alongside. Lush landscaping features palm trees and flower beds, while a covered seating area, equipped with outdoor furniture, is visible behind the pool. The home showcases a modern design with a sleek metal roof.
Home in Seminole
4.99 out of 5 average rating, 152 reviews

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.

Top guest favorite
A vibrant tropical mural featuring large flowers adds a pop of color to the room, while a cozy seating area includes a sofa adorned with decorative pillows. A small dining table with tropical-patterned chairs provides a space for meals. The outdoor area showcases a lit pool, creating a serene evening ambiance.
Cottage in Indian Rocks Beach
4.99 out of 5 average rating, 204 reviews

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!

Top guest favorite
The image captures a spacious townhouse community, featuring white architectural designs. A clear view of the intercoastal waterway is presented, with boats visible in the distance. A community pool is seen among vibrant greenery, inviting leisure and relaxation.
Townhouse in Clearwater Beach
4.99 out of 5 average rating, 121 reviews

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.

Top guest favorite
A modern kitchen features white cabinetry and sleek stainless steel appliances. A central island with two wooden stools invites gatherings. Natural light spills through a nearby doorway, illuminating decorative greenery and tasteful textures along the walls.
Condo in Clearwater
4.99 out of 5 average rating, 148 reviews

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

Top guest favorite
An exterior view of a yellow condo building is depicted, featuring palm trees and shrubs. A pathway leads to a private entrance, while large windows allow ample natural light. The surrounding landscaping creates a welcoming atmosphere in the gated community.
Condo in Clearwater
4.96 out of 5 average rating, 135 reviews

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.

Top guest favorite
The grotto-style pool area features natural rock formations with cascading waterfalls and lush tropical plants. A hot tub is integrated into the design, providing a relaxing space. The serene water reflects the clear blue sky, while views of the bay are visible in the background.
Home in Oldsmar
5 out of 5 average rating, 148 reviews

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

When is the best time to visit Clearwater?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$39,571 GYDG$47,902 GYDG$53,733 GYDG$44,361 GYDG$37,280 GYDG$37,905 GYDG$39,363 GYDG$34,156 GYDG$32,073 GYDG$31,865 GYDG$35,614 GYDG$36,863 GYD
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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

Destinations to explore