
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.

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

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

[Kids Favourite] Family Fun Getaway | Heated Pool
Discover your ideal getaway, complete with all your dreams come true! Located just minutes from stunning beaches & conveniences, this fantastic home offers endless fun! From a heated pool, hot tub, and 2 person hammock, to a fire pit, BBQ, and a fully-equipped kitchen for your delight! Your family will be close to everything when you stay at this centrally-located home. 1 min to Largo Tennis Courts, Olympic size pool, baseball 8 min to Independence Square 5 min to beach 4 min to laundromat

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.

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!

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.

Relax in a Newly Renovated Beach Front Paradise
Immerse yourself in the stunning beauty of the Gulf Coast at this hidden gem, perfectly nestled in the charming Indian Shores. This property exudes a coastal ambiance, providing a tranquil sanctuary to bask in the sugar-white sands and sparkling turquoise waters. Beach chairs & towels are thoughtfully provided. All you need to bring is a swimsuit & toothbrush. Exciting updates include new furniture & bedding added in '25 as well as a beautifully renovated walk-in shower in '24.

Beach 1BR Suite w/full kitchen on Clearwater Beach
š¬ The Porpoise Inn & Suites is a charming boutique motel located right on world-famous Clearwater Beach. Just steps from the sand, shops, restaurants, attractions, and even a recreation pool, itās the perfect spot for your next Florida getaway. Newly renovated suites feature the stylish touches of coastal living youāll love, creating a cozy and welcoming space. Come for the location, stay for the charm šļøāØ (4 Max. Guest/Strictly Enforced & No Pets Strictly Enforced!)

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.

Newly Reno Luxury Condo 30 Steps to Paradise
Welcome to our serene top-floor beach condo. This is a two-bedroom, two-bathroom condo in the heart of Clearwater Beach. This ocean-side condo is steps from the country's #1-rated beach and less than a five-minute walk from top restaurants and shopping. Clearwater Beach is renowned for its award-winning beaches, incredible restaurants, and lively nightlife. We have made every effort to make this condo a home away from home! We hope you enjoy our piece of paradise.

Family/Group Getaway w/ Pool Near Clearwater Beach
šļø 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. ā Sleeps large groups comfortably ā Private pool + outdoor space ā Fully equipped kitchen + fast WiFi Just minutes from Clearwater Beach, dining, and attractionsāyour ideal home base for a fun, easy Gulf Coast getaway.

Tiki Bungalow | Gorgeous Htd Pool | Steps to Beach
An original early 1900 Indian Rocks Beach bungalow, beautiful and bright with pool! Across Gulf Boulevard from 8th Ave beach access with all the comforts of home. Rest in the tropical garden pool, hang out in the private tiki hut out back , hop on the trolley to explore the area. Many shops and restaurants are within walking distance. Splash Harbour water park at the Holiday Inn is walking distance for a day of fun! Have an unforgettable stay! City tax#1479
Popular amenities for Clearwater Beach rentals with a pool
House rentals with a pool

TIKI Bar+SAUNA+HOT Tub+Heated POOL! 2 KING beds!

Backyard Paradise- Cozy Bungalow 4 Mi to Beach

Sunrise Harbor in Indian Rocks Beach

Sea Breeze - Pool and Spa - 2 Houses to Beach

Modern Pet-Friendly Beach House w/ Heated Pool & S

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

Mac Crillus Beach House Pet friendly

Hannahās beachside resort Saltwater Heated Pool
Apartment rentals with a pool

2 BR/2 BA Key West Retreat, A+Pool, 3mi to Beach

Clearwater Beach condo

Lux Condo w/ 2 balconies, Ocean & Marina views

Beach Across the St | No Stairs |Parking in Front!

Tiki Themed Waterfront Condo on Tampa Bay

Modern and Cozy Condo 6 Minutes from the Beach !

BEACHFRONT Condo - Belleair Beach Club - RENOVATED

Beachfront Condo with Centerline Sunsets
Other holiday rentals with a pool

Clearwater Vacation Home!

Fantastic Condo at Avalon - Fully Renovated!

Gorgeous Villa with Heated Pool & Beach Views!

Spacious Family Waterfront Beach Home with Pool

Tropical Paradise - Private Pool, Spa & BBQ !

Waterfront Luxury Estate | Heated Pool! Dock

Luxury Pool House

Luxury Ocean Front Duplex
When is the best time to visit Clearwater Beach?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £158 | £196 | £237 | £183 | £147 | £155 | £157 | £131 | £125 | £123 | £136 | £147 |
| 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 Beach

Total holiday rentals
Explore 1,070 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 40,930 verified reviews to help you choose

Family-friendly holiday rentals
560 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 250 rentals that welcome pets

Rentals with dedicated workspaces
580 properties have a dedicated workspace

Wifi availability
1,070 of Clearwater Beach holiday rentals include wifi access

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

4.7 Average rating
Clearwater Beach stays receive an average rating of 4.7 out of 5 from guests
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- Anna Maria Island
- Raymond James Stadium
- Busch Gardens Tampa Bay
- John's Pass
- Weeki Wachee Springs
- Coquina Beach
- Vinoy Park
- Lido Key Beach
- Amalie Arena
- Dunedin Beach
- Bean Point Beach
- Cortez Beach
- Jannus Live
- Anna Maria Public Beach
- ZooTampa at Lowry Park
- Hard Rock Casino
- Tampa Palms Golf & Country Club
- River Strand Golf and Country Club
- Tampa Convention Center
- North Beach At Fort DeSoto Park
- Splash Harbour Water Park
- Busch Gardens
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