Holiday rentals with a pool in Clearwater Beach

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Top-rated rentals with a pool in Clearwater Beach

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Top guest favourite
Home in Clearwater Beach
4.97 out of 5 average rating, 250 reviews

Waterfront Townhome w/Game Room & Boat Slip! Walk

PLEASE ASK ABOUT OUR OTHER 2 WATERFRONT PROPERTIES ON CLEARWATER BEACH IF YOUR DATES ARE NOT AVIALABLE!! Welcome to Brightwater Blue, our newer vacation Town Home in Clearwater Beach! 3 floors of fun, elegance & relaxation await you. Custom interior decorated with Restoration Hardware & other high end furnishings. Located on Clearwater Bay & within easy walking distance to Clearwater Beach, Beach Walk, restaurants, shopping & everything Clearwater Beach has to offer! Why book 3 hotel rooms when

Top guest favourite
Apartment in Madeira Beach
4.98 out of 5 average rating, 105 reviews

Beach Front at “The Shore”

Welcome to The Shore —a beautifully renovated beachfront retreat in the heart of Madeira Beach. This second-floor 2-bedroom, 2-bath condo offers completely unobstructed Gulf views and the rare feeling of being almost directly on the water. Relax with your morning coffee in the signature blue chairs, watch breathtaking sunsets from the living room, and enjoy easy access to John’s Pass, waterfront dining, shopping, and the best of Gulf Coast beach living, where the shoreline feels just feet away.

Top guest favourite
A pool area is surrounded by vibrant tropical landscaping, featuring lounge chairs arranged around a circular pool. Soft lighting illuminates the scene, enhancing the greenery. In the background, a pink float adds a playful touch to the inviting ambiance of the outdoor space.
Bungalow in Indian Rocks Beach
4.93 out of 5 average rating, 167 reviews

Neptune's Nest | Amazing Htd Pool | Steps to Beach

An original early 1900 Indian Rocks Beach bungalow, updated with all the comforts of home. Grill on your private patio or relax in the pool area in our tropically landscaped grounds. Cross Gulf Boulevard to 8th Ave beach access to the beautiful turquoise waters and white sandy beaches of the Gulf of Mexico. Enjoy swimming, shelling and fishing as you live the island life. Splash Harbour water park, shops and restaurants are within walking distance. Come for an unforgettable stay! City tax#1479

Guest favourite
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, 197 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 favourite
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.
Apartment in Clearwater Beach
4.95 out of 5 average rating, 333 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 favourite
Bungalow in Indian Shores
4.96 out of 5 average rating, 188 reviews

Private Beachfront 2BR BUNGALOW*POOL*PETS ok

DIRECT BEACHFRONT BUNGALOW "MARLIN'S HIDEAWAY." Rare free standing direct beach front house! with private sandy beach backyard! NOT a condo - No crowded elevators, hallways, lobby area, NO faraway parking spaces FEATURES: Great room plan, Sleeps 6, 2 BR + sleeper sofa, all SMART TVs, high speed Wi-Fi. Kitchen is fully equipped. Bathroom is tub/shower with seat. Approx 850 sq ft. Private, fenced deck - PETS ok. BARRETT BEACH BUNGALOWS is a boutique resort ONLY 4 bungalows share heated pool

Top guest favourite
A beachfront balcony features a round table with four striped chairs, inviting outdoor relaxation. The expansive view showcases sandy shores meeting the calm turquoise waters under a clear blue sky. Sliding glass doors provide easy access to the living space.
Apartment in Indian Shores
4.99 out of 5 average rating, 129 reviews

Five Star Beachfront Condo Newly Renovated

A newly transformed beachfront Condo offers five-star accommodations in sleepy Indian Shores, Florida. This is the second renovated unit by a Superhost/owner. This unit is only feet from the beautiful white sand & crystal clear water. The sunsets are epic from the balcony. Several great restaurants & bars are within walking distance of your front door. Amenities include a fully stocked kitchen, heated pool, SmartTV's, high speed Wi-Fi, reserved parking and only minutes from the Tampa airport.

Superhost
The outdoor pool, surrounded by palm trees, reflects the clear blue sky. Comfortable loungers are placed nearby, offering ample space for relaxation. The glistening water leads to views of the waterfront, enhancing the serene atmosphere of the outdoor environment.
Home in Indian Rocks Beach
4.83 out of 5 average rating, 367 reviews

Stunning views! Spot dolphins from the pool!

BTR#2114 This home has it ALL including incredible open water sunsets! Every detail has been carefully thought out and updated. This is a VERY upscale, coastal, single story waterfront home. A complete waterfront remodel w/ dock & pool that looks and feels like a new home w/ stunning water views from your own back patio! The water glistens and sparkles from 3 pm thru sunset and after, the sky is set on fire for 40 minutes. White sandy beach is only few blocks away! Amazing home inside & out!

Guest favourite
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.
Flat in Clearwater Beach
4.89 out of 5 average rating, 259 reviews

Waterfront 2BR Escape Walk to Beach Pool Sleeps 6

🌴 Your Clearwater Beach Escape Starts Here Wake up to peaceful water views, sip coffee on your private patio, and end your day watching the sunset just minutes away on the beach. This spacious 2BR/2BA condo perfect for families, couples, or small groups looking for a relaxing getaway.Quiet location while still being close to everything Waterfront patio with serene views (yes, dolphins are often spotted 🐬) Walk to Clearwater Beach, restaurants, and shops Pool for relaxing after the beach

Top guest favourite
An open-concept living area features a light-colored, patterned sofa paired with a wooden coffee table. A large flat-screen TV is mounted on the wall, and a serene window nook offers natural light, enhancing the coastal charm of the space.
Apartment in Treasure Island
4.97 out of 5 average rating, 214 reviews

*Shore Thing* Walk to Beach | Intercoastal Views

🏖️ Shore Thing Condo 🏖️ Escape to pure coastal paradise at this chic Treasure Island condo. You are mere footsteps away from sugar-sand beaches, refreshing salt air, and unmatched sunsets. Don't forget to watch the water as dolphins and manatees drift along the shore. Indoors, unwind surrounded by elevated, modern coastal design. From cooking dishes in the upscale kitchen to swimming in the heated intercoastal pool, my signature service guarantees your peace of mind is the top priority.

Guest favourite
A set of two white wicker chairs and a small table are positioned on a balcony, providing views of the Gulf of Mexico. The ocean and sandy beach stretch into the distance, with clear blue skies overhead.
Apartment in Clearwater Beach
4.9 out of 5 average rating, 455 reviews

Amazing views on beachfront

This spacious upper-floor, 3-bedroom condo hotel suite offers views of the Gulf of Mexico from your private balconies. While preparing your morning coffee on the spacious kitchen island, you can see the water of the Gulf of Mexico. Each suite can accommodate 10 people, with 3 bedrooms, 2 of them with a King bed in each bedroom and the third with 2 Queen beds, each of them with their own ensuite bathroom, in total 3 1/2 bathrooms, also a comfortable full-sized sofa bed in the living room.

Top guest favourite
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, 136 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.

Popular amenities for Clearwater Beach rentals with a pool

When is the best time to visit Clearwater Beach?

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Quick stats about holiday rentals with a pool in Clearwater Beach

  • Total holiday rentals

    Explore 1,100 holiday rentals in Clearwater Beach

  • Nightly prices starting at

    Clearwater Beach holiday rentals start at £37 per night before taxes and fees

  • Verified guest reviews

    Over 42,630 verified reviews to help you choose

  • Family-friendly holiday rentals

    550 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 260 rentals that welcome pets

  • Rentals with dedicated workspaces

    590 properties have a dedicated workspace

  • Wifi availability

    1,080 of Clearwater Beach holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Clearwater Beach rentals

  • 4.8 Average rating

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

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