
Vacation rentals with a pool in Clearwater Beach
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in Clearwater Beach

Total vacation rentals
Explore 1,100 vacation rentals in Clearwater Beach

Nightly prices starting at
Clearwater Beach vacation rentals start at G$10,449 GYD per night before taxes and fees

Verified guest reviews
Over 42,630 verified reviews to help you choose

Family-friendly vacation rentals
550 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 260 rentals that welcome pets

Rentals with dedicated workspaces
590 properties have a dedicated workspace

Wi-Fi availability
1,080 of Clearwater Beach vacation rentals include wi-fi 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!
Top-rated rentals with a pool in Clearwater Beach
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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

Relax in private Heated pool Family-Friendly comfo
🌴 Outdoor Paradise Your private backyard is the star of the show. A 10,000-gallon PebbleTec heated pool (up to 8 ft deep) anchors a resort-style outdoor space designed for pure Florida living — complete with a cantina bar for poolside drinks, teak lounge seating, chaise chairs, resort umbrellas, and lush landscaping that gives you the perfect balance of sun and shade. Fire up the Weber propane grill and let the evening take care of itself. 🍳 Fully Equipped Kitchen Cook like you mean it or kee

Spectacular beach to bay views from this resort.
Our condo has spectacular water views from the Bay to the Beach. We have a large one of a kind kitchen that is unique to our resort, with granite counter tops, hardwood cabinets, and all stainless steel appliances. Everything you need to prepare a meal is provided along with basic spices and condiments, Coffee, creamer, and sugar. The master bedroom has a new king size bed and walk in closet with all beach gear also available for your use. We have 2 - 50" flat screen TV's with cable as well.

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

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!

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

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.

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

Ocean Dreaming: Waterfront Home with Heated Pool,
Waterfront home: pool, dock, golf cart, kayaks, paddle board. This home has a private, zero-entry heated pool and dock (tie up your own boat or daily/weekly rental). 6-seat golf cart, 2-paddle boards, 2-sea kayaks, 6-bicycles and more are included. Two master bedroom suites with water views and soaking tubs plus a third bedroom with custom King Bed and Twin bunk beds. Two living areas are also each furnished with a queen sofa sleeper to accommodate a total of 12 people.

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.

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 Beach rentals with a pool
House rentals with a pool

Heated Pool and Spa | 5 min to beach

Casa Flamingo - Private - Outdoor Bar+TV - Games

Private pool, Golf Cart, Completely Renovated!

Marie's Oasis‐4 min walk to sandy white beaches!

Sandy Morning Restored | Pool Spa

Best Celebration - Heated Pool - Hot Tub - Arcade

Lux Spa Retreat•Pool•Hot Tub•Sauna•10 min to Beach

The Oasis - Arcades - Golf & Games - Firepit
Condo rentals with a pool

Waterfront Condo - Sunset View of Tampa Bay

Newly Reno Luxury Condo 30 Steps to Paradise

BEACHFRONT Condo - Belleair Beach Club - RENOVATED

Beachfront Condo with Centerline Sunsets

Beach Front at “The Shore”

Five Star Beachfront Condo Newly Renovated

Sandy Feet Retreat

Luxury Seashell Oceanfront Condo with Pool
Other vacation rentals with a pool

Wonderful Condo at Avalon - Fully Renovated!

CBC 2-17A –Newly Updated Beach Front Condo!

Fun, Funky, Fire Pit, Pool! 4 miles to Beach

Tiki Bungalow | Gorgeous Htd Pool | Steps to Beach

Luxury Pool House

CWB Retreats at Baymont Lofts - Loft A

Four Bedroom Presidential, Clearwater A820

Waterfront with Dock, Heated Pool, Kayaks, Games
When is the best time to visit Clearwater Beach?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$42,215 GYD | G$54,545 GYD | G$64,577 GYD | G$51,202 GYD | G$41,170 GYD | G$43,260 GYD | G$43,887 GYD | G$36,782 GYD | G$34,901 GYD | G$34,483 GYD | G$38,035 GYD | G$41,170 GYD |
| 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 |
Destinations to explore
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- Rentals with pools United States
- Anna Maria Island
- Weeki Wachee Springs
- Raymond James Stadium
- Anna Maria Island Beach
- Busch Gardens Tampa Bay
- Coquina Beach
- Lido Key Beach
- Bean Point Beach
- Amalie Arena
- Dunedin Beach
- Vinoy Park
- Tampa Convention Center
- University of South Florida
- Hard Rock Casino
- John's Pass
- Tropicana Field
- Fort De Soto Park
- Sand Key Beach
- Anna Maria Public Beach
- Epperson Lagoon
- Weeki Wachee Springs State Park
- River Strand Golf and Country Club
- MidFlorida Credit Union Amphitheatre
- Cortez Beach





