
Vacation 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

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!

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.

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.

Casa Palmera! *Heated Pool!
Step into relaxation as you enter this tropical pool home, centrally located to everything one would need staying in Clearwater! This 4 bedroom, 2 bath home has been meticulously curated to give our guests the best experience imaginable during their stay on the west coast of Florida. Only 5 miles from world renown Clearwater Beach, 1 mile from the Phillies spring training site, less than 2 miles from some of the best local eateries in Safety Harbor and Dunedin. Come stay at Casa Palmera!

Waterfront Modern Chic #1 Clearwater Beach
This prime location is on the bay just steps away from the beach and the main strip offering a complete home experience. This spacious apartment is equipped with a full kitchen, washer/dryer, two full bathrooms, a large family room, dining area, access to the pool and two assigned parking spaces. A split floor plan ensures privacy, accommodating guests on either side of the apartment. The private patio overlooks the bay, offering stunning views of the sunrise and the occasional dolphin.

Tootsie’s Beachside Retreat-New Heated Pool
LUXURY SALTWATER HEATED POOL HOME! JUST 1.5 MILES TO BEAUTIFUL REDINGTON BEACH. AMAZING REMODELED HOME WITH HIGH END FINISHES LOCATED ON 1/2 ACRE LOT. BRAND NEW CUSTOM POOL WITH PEBBLETECH FINISH AND BAJA SHELF. BEAUTIFUL WHITE SAND BEACHES ONLY 1.5 MILE RIDE! 5 MIN. FROM: 3 COFFEE SHOPS,OUTSIDE MALL WITH SHOPPING, RESTAURANTS AND MOVIES. HOUSE IS ON RARE 1/2 ACRE PROPERTY IN UPSCALE NEIGHBORHOOD. RENOVATED WITH HIGH END FURNITURE AND FIXTURES, SAMSUNG 4K LED T.V.’S IN EVERY ROOM.

Beach Haven in South Clearwater Beach
This unique two-story vacation rental with a loft is perfect for a large family or two. It has large panoramic windows with incredible views of the harbor from every bedroom and living space. The Dockside Condos are centrally located in South Clearwater Beach close to all the action of Shephard's nightclub, restaurants, sports bars, miniature golf and more, as well as being only two blocks to the beach. Come and enjoy this condo just one block from the white sands of Clearwater Beach.

Luxury Beach Bungalow | Walk to Dining & Sunset
Escape to paradise at Sunshine Escapes IRB! Welcome to Mango, nestled in the heart of Indian Rocks Beach. IRB is a hidden gem radiating a whimsical, small-town charm that evokes nostalgic memories of carefree childhood summers by the shore. Just ✌🏽 blocks away, the Gulf of Mexico beckons, offering pristine fluffy sand and unforgettable sunsets. As the sister cottage of Coco, Mango invites you to immerse yourself in the laid-back beachy vibes of IRB. Your perfect beach getaway awaits!

Triplex- heated pool, bikes, walk to beach,
☀ Easy access to the beach; just walk across the street! ☀ Stylish shared heated pool with sun shelf and chaise loungers ☀ Fire pit with relaxing swivel lounge chairs, bikes ☀ Beach wagons, zero gravity chairs, cooler, ice, umbrellas, towels, speakers ☀ 3 hole glow in the dark putt putt ☀ Amazon Dots with Unlimited Amazon Music ☀ Fenced-in courtyard w/ outdoor seating, umbrellas, and BBQ grills ☀ Triplex with 3 uniquely decorated suites- private interiors, shared exterior

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
House rentals with a pool

The Jungalow SOHO - Pool/Hot Tub

Paradise Cove-Designer Home | Pool+Spa | Arcade

Endless Summer in Clearwater-HeatedPool-Golf-Beach

Largo Poolside Paradise Heated Pool 10Min To Beach

Sunshine, Beaches & Refreshing Pool/Screen Patio

Heated Pool | 2BD 2BA | Home near Beaches

UTOPIA!Heated Pool &Hot Tub 2 master suites w KING

Belleair Beach Oasis w/ Heated Pool - 3mi to Beach
Condo rentals with a pool

Gulf-View 2BR/2BA Beach Condo!

Renovated Condo! Across the Street From The Beach

Royal Orleans at Redington Beach ( Studio )

Modern and Cozy Condo 6 Minutes from the Beach !

850 Sqft - 1 Bedroom 1.5 Bath (GULF FACING!) Condo

Beachfront in exclusive resort

2 King Suites • Waterfront • Walk to Beach

Beachfront Condo with Centerline Sunsets
Other vacation rentals with a pool

Luxury Tiny Home 1 Bed - 1 Bath Unit B "Sandy"

Chateaux Beachfront Condo/Top Unit - Indian Shores

Condo Conveniently located to Clearwater Beach

Cozy Waterfront Condo - Pool & Hot Tub!

Waterfront Clearwater Beach #16| Pool | Parking

Beachfront with Oceanview Balcony in Quiet Area

Sea Side Sunsets Unit C

Ram Sea 1-302 Beachfront with pool & Hot tub!
When is the best time to visit Clearwater Beach?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $287 CAD | $357 CAD | $431 CAD | $332 CAD | $267 CAD | $281 CAD | $285 CAD | $239 CAD | $226 CAD | $224 CAD | $247 CAD | $267 CAD |
| 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 vacation rentals with a pool in Clearwater Beach

Total vacation rentals
Explore 1,070 vacation rentals in Clearwater Beach

Nightly prices starting at
Clearwater Beach vacation rentals start at $68 CAD per night before taxes and fees

Verified guest reviews
Over 40,930 verified reviews to help you choose

Family-friendly vacation rentals
560 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 250 rentals that welcome pets

Rentals with dedicated workspaces
580 properties have a dedicated workspace

Wifi availability
1,070 of Clearwater Beach vacation 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
- Dunedin Beach
- Coquina Beach
- Vinoy Park
- Lido Key Beach
- Amalie Arena
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- Jannus Live
- ZooTampa at Lowry Park
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- The Don CeSar
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