Holiday rentals with a pool in Clearwater

4.89 out of 5 average rating, 133 reviews

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

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.

4.95 out of 5 average rating, 322 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!

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.

4.93 out of 5 average rating, 185 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

A covered patio area is visible, featuring comfortable wooden chairs with blue cushions and a wooden table. The scene is framed by a screened enclosure, providing an unobstructed view of a private pool surrounded by lush tropical plants.

4.88 out of 5 average rating, 288 reviews

Quiet 3 BD Large Heated Pool & Terrasse-5 mn Beach

Unwind and relax while staying at our freshly renovated Floridian nest! Pretend you are lost in our tropical garden while diving in the pool, take some time for yourself on the covered patio directly facing the blue water and the vivid green of the palm trees. Just breathe, your favorite meal smells good on the grill and your family is enjoying the large TV in the comfortable open space with high ceilings! Enjoy the sea, you are a 5 min drive from the beach and close to everything. Feels good!

4.97 out of 5 average rating, 141 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.

Home in Indian Rocks Beach

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.

4.83 out of 5 average rating, 362 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!

A scenic view of a fishing pier extends into the water, framed by gentle waves and a sandy beach. The sky is filled with colorful clouds, reflecting hues of orange and blue as the sun sets on the horizon.

4.98 out of 5 average rating, 165 reviews

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.

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.

4.9 out of 5 average rating, 443 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.

4.98 out of 5 average rating, 211 reviews

Specious home W/ Heated Pool ! ! ! Great Location.

Cozy, spacious home 🏡 w/ heated swimming 🏊‍♀️ pool, next to a golf ⛳️ course. Close to the famous beaches ⛱️, St.Pete and Tampa. This cozy open home has a large living room, big kitchen and pool deck patio. All 3 bedrooms have large TV's. The big back patio has a swimming 🏊‍♀️ pool, TV, fridge and BBQ for cook outs & R&R. Located in a quiet family-friendly neighborhood. Location! 15 min - Clearwater Beach, Dunedin, Safety Harbor 30 min from - St.Pete, TPA Airport, Tampa

Townhouse in Clearwater Beach

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.

4.99 out of 5 average rating, 133 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.

4.93 out of 5 average rating, 276 reviews

Family/Group Getaway w/ Pool Near Clearwater Beach

🏖️ Private pool + 4BR | 9 mins to Clearwater Beach Bring the whole group to this spacious 4-bedroom home designed for relaxing and entertaining. Enjoy a private pool, oversized backyard, and plenty of room for families and friends to spread out. ✔ Sleeps large groups comfortably ✔ Private pool + outdoor space ✔ Fully equipped kitchen + fast WiFi Just minutes from Clearwater Beach, dining, and attractions—your ideal home base for a fun, easy Gulf Coast getaway.

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.

4.98 out of 5 average rating, 154 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

Popular amenities for Clearwater rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.75 out of 5 average rating, 63 reviews

Paradise Vacation 10 Minute to Beach and Downtown!

A charming blue bungalow is surrounded by lush greenery, featuring a welcoming entryway. The pathway leads to a covered porch adorned with plants, inviting relaxation. A fenced backyard is visible in the background, ensuring privacy.

4.8 out of 5 average rating, 168 reviews

Backyard Paradise- Cozy Bungalow 4 Mi to Beach

5 out of 5 average rating, 4 reviews

Heated Pool + Outdoor Kitchen | Private Backyard

An outdoor seating area is illuminated by string lights, featuring a table with a fire pit at its center. Two wine glasses filled with red wine are positioned next to a bottle of wine. Nearby, two red cups and several beer bottles add to the relaxed atmosphere.

4.95 out of 5 average rating, 175 reviews

Cozy Stylish Home w/ Heated Pool & Big Parking

4.78 out of 5 average rating, 9 reviews

Balay Clearwater: Heated Pool, Grill, 15 min Beach

5 out of 5 average rating, 104 reviews

Home in Palm Harbor

The Palm Haus • Heated Pool • Near Beach • Games

5 out of 5 average rating, 4 reviews

Largo Pool Home with Grill & Private Yard

4.98 out of 5 average rating, 169 reviews

Home in St. Petersburg

The Blue Fin, 3 Bed/ Heated Pool/ XBOX

Apartment rentals with a pool

Apartment in Indian Shores

A balcony space is shown with two white lounge chairs positioned facing the ocean. The beach and turquoise waters are visible in the background, complemented by a clear blue sky. The glass door provides seamless access to the indoor area.

4.97 out of 5 average rating, 119 reviews

Relax in a Newly Renovated Beach Front Paradise

A balcony view features two cushioned chairs adorned with pink pillows, overlooking a quiet street leading to the beach. Palm trees and lush greenery frame the scene, while the ocean is visible in the distance. Bright blue skies enhance the coastal atmosphere.

4.99 out of 5 average rating, 183 reviews

Newly Reno Luxury Condo 30 Steps to Paradise

A serene waterfront view is captured from a balcony, showcasing calm bay waters reflecting the sky. A round table with chairs is positioned on the tiled floor, inviting relaxation while enjoying the scenery of nearby buildings and lush greenery across the water.

4.82 out of 5 average rating, 147 reviews

Clearwater Beach condo

4.9 out of 5 average rating, 225 reviews

A bright living room features a gray couch with colorful accent pillows, positioned next to a coffee table. Large sliding glass doors open to a view of the patio. A rug with intricate designs lies on the floor, complemented by a cozy accent chair.

Apartment in Largo

Modern and Cozy Condo 6 Minutes from the Beach !

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.

4.95 out of 5 average rating, 140 reviews

Bright and Spacious 1Bed/1Bath condo.

Apartment in Belleair Beach

A balcony view that captures the tranquil beach scene, featuring soft pastel hues in the sky. A round table with intricate design sits next to two woven chairs. Below, umbrellas dot the sandy beach, while gentle waves touch the shore.

4.71 out of 5 average rating, 516 reviews

BEACHFRONT Condo - Belleair Beach Club - RENOVATED

A modern living area features a large television mounted on the wall, framed by a stylish red console. Two comfortable chairs and a table are arranged in front of a sliding glass door, which opens to a private balcony with tropical greenery visible outside.

4.95 out of 5 average rating, 149 reviews

The Avalon - 1/1 LUXE CORNER CONDO/King size bed/

Apartment in St. Petersburg

A serene balcony offers a view of the waterfront, with two green chairs and a glass table positioned to enjoy the scenery. Palm trees are visible in the foreground, and the calm water reflects the bright blue sky, creating a tranquil outdoor space.

4.98 out of 5 average rating, 284 reviews

PRICELESS VIEW Boca Ciega Bay Condo 1/1 #209

Other holiday rentals with a pool

A shaded outdoor dining area is complemented by a circular glass table surrounded by six chairs. The pool can be seen in the background, with lounge chairs positioned nearby. Lush green grass and palm trees add to the inviting atmosphere of the backyard.

4.93 out of 5 average rating, 46 reviews

Clearwater Vacation Home!

A cozy living room corner is designed with a comfortable sectional sofa adorned with cushions in shades of yellow and black. Artwork featuring abstract designs is displayed on the walls. A round coffee table sits in front, complemented by a small yellow ottoman.

4.97 out of 5 average rating, 91 reviews

Welcome to your vacation home

A spacious pool area is surrounded by palm trees and lounge chairs, offering a vibrant atmosphere. Umbrellas are positioned for shade, and a view of the beach is visible in the background, enhancing the relaxing setting.

4.89 out of 5 average rating, 9 reviews

Two Bedroom Deluxe, Clearwater A400

5 out of 5 average rating, 8 reviews

A spacious bedroom features a four-poster bed layered with white bedding and decorative blue pillows. Natural light fills the room through a sliding glass door that leads to a private balcony with ocean views. A dresser and a television are also visible in the room.

Apartment in Sand Key

CBC 1-7C- Beautiful Gulf Front Condo with Pool!

4.89 out of 5 average rating, 19 reviews

Stylish NEW one bedroom condo Clearwater beach!

4.85 out of 5 average rating, 13 reviews

Antz Paradise

Guest house in Crescent Lake

A serene outdoor space features a saltwater pool surrounded by lush greenery. Two lounge chairs are positioned under a striped umbrella, providing shade on the pool deck. The light-colored stone tiles enhance the calming atmosphere of this private retreat.

5 out of 5 average rating, 26 reviews

Luxury Pool House