
Holiday rentals with a pool in Clearwater Beach
Find and book unique homes with a pool on Airbnb
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

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.

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.

Poolside • Zero Stairs • King Bed • Near Beaches
📍 Prime Clearwater Location — Minutes to the Beaches & Major Airports Stay in the heart of Clearwater, just minutes from the award-winning Clearwater Beach. This central, easy-to-navigate location puts you close to everything you need-grocery stores, restaurants, coffee shops, parks, and top local attractions. Whether you’re planning a beach getaway, family vacation, or remote work stay, this convenient home makes arrival, travel, and exploring the area simple, quick, and stress-free.

Beachfront Condo Resort on Treasure Island
Be among the first to experience this new condo resort. 992 sq ft of beachfront luxury with full resort amenities. These upper-floor corner units have gorgeous views of the ocean, and each room has a window with beach views. With 2 bedrooms and 2 bathrooms and a pullout couch in the living room, these units can comfortably house 6 people. After arriving in your open concept living area, you will access your private balcony through retractable sliding doors that let the ocean air in.

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!

Beach Front Madeira Beach
PLEASE NOTE: SEVERAL UNITS UNDER CONSTRUCTION in the building. And our swimming pool is currently closed for renovations as well. Expected completion by May 31. Amazing beachfront condo, newly remodeled on the second floor. Vinyl plank flooring throughout, No CARPET. 2 Bedroom, 2 Bath. Completely unobstructed views of the beach. It is centrally located less than 1 mile from World Famous Johns Pass. Enjoy breathtaking sunsets from your living room with the water just feet away.

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.

*Shore Thing* Walk to Beach | Intercoastal Views
🏖️ Shore Thing Condo 🏖️ Experience the ultimate blend of Sunset Bliss at this stylish Treasure Island retreat. Just steps from powdery sands, ocean breezes and breathtaking sunsets. Keep an eye out for local wildlife as dolphins and manatees glide by. Inside, enjoy coastal vibes featuring modern beachy interiors. Whether you are preparing a meal in the luxury kitchen or diving into the intercoastal heated pool, my service ensures your comfort always comes first.

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.
Popular amenities for Clearwater Beach rentals with a pool
House rentals with a pool

Sunrise Harbor in Indian Rocks Beach

Tropical Paradise - Private Pool, Spa & BBQ !

Paradise palms oasis Clearwater

Private pool, Golf Cart, Completely Renovated!

Ocean Dreaming: Waterfront Home with Heated Pool,

Heated Pool•Gym•Sauna•Hot Tub•Fire Pit & 7 Beds!

Piece of paradise in Indian Rocks Beach.

🍍Beautiful Home Heated POOL 5min to BEACH. 8 ppl🍍
Apartment rentals with a pool

Oceanfront View, Spacious Townhouse, Heated Pool

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

Clearwater Beach condo

Modern and Cozy Condo 6 Minutes from the Beach !

BEACHFRONT Condo - Belleair Beach Club - RENOVATED

Modern Waterfront Condo - Captivating Sunset Views

Sandy Feet Retreat

Stunning BEACH FRONT Condo, KING Size Bed, Balcony
Other holiday rentals with a pool

Upscale Oceanfront Paradise 202

Beachfront Oasis / Pool, Beach Access & Ocean View

Gulf View Penthouse | Steps to Beach + Johns Pass

The Harbor Condo Beach Escape!

Luxury Pool House

Beachfront, Top Floor Stunning Views & Interior.

Walk to Beach (4 min), Pool, Private Roof Deck

Mel's Beach Retreat with Private Dock
When is the best time to visit Clearwater Beach?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $257 SGD | $332 SGD | $393 SGD | $312 SGD | $251 SGD | $263 SGD | $267 SGD | $224 SGD | $212 SGD | $210 SGD | $231 SGD | $251 SGD |
| 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 1,100 holiday rentals in Clearwater Beach

Nightly prices starting at
Clearwater Beach holiday rentals start at $64 SGD 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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- Anna Maria Island
- Raymond James Stadium
- Busch Gardens Tampa Bay
- John's Pass
- Anna Maria Island Beach
- Bean Point Beach
- Weeki Wachee Springs
- Coquina Beach
- Lido Key Beach
- Vinoy Park
- Amalie Arena
- Tampa Convention Center
- Dunedin Beach
- Sand Key Beach
- Cortez Beach
- St Pete Beach
- Hard Rock Casino
- Jannus Live
- Anna Maria Public Beach
- Tampa Palms Golf & Country Club
- ZooTampa at Lowry Park
- River Strand Golf and Country Club
- Tropicana Field
- University of South Florida





