
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 Coastal Bliss at Brightwater w/ Heated
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

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.

Waterfront • 2 King Suites • Walk to Beach • Pool
Escape to Dock of the Bay! ✅ Two KING suites + sofa bed ✅ 5-minute walk to beach ✅ Waterfront views ✅ Full kitchen ✅ Heated pool & sun deck ✅ Beach gear & wagon ✅ Free parking! Discover your perfect couples or family retreat at Dock of the Bay! Enjoy spacious king suites with split layouts for privacy and extras including beach chairs, a beach wagon, and pack & play. Just steps from the beach, this condo offers many amenities, serene views, and warm hospitality for memorable vacations.

Beautiful Tampa Bay Pool Home Near Gulf Beaches
A beautiful Gulf Coast residence with many amenities to offer. Bright and open furnished spaces, for relaxing and entertaining up to 10 guests. A quiet, upscale neighborhood , your just 6 minutes from Madeira Beach and many other Gulf of Mexico beaches. Or, fun & sun in the private pool outback. 20 minutes from Downtown St Pete, which offers restaurants, museums, the new Pier, and excellent night life. Very close to countless restaurants, shopping, coffee shops, and grocery stores.

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

Beachfront Condo in Exclusive Resort
The most stunning views from this brand new condo directly on Treasure Island Beach. This lovely unit is on the 4th, 5th, or 6th floor and provides sweeping views of the ocean. This units has 2 bedrooms and 2 full bathrooms. The inviting open concept living area has one of the best views of the ocean, especially when the retractable sliding doors are opened. The dining table on your private balcony provides a perfect dining area, with the ocean providing a beautiful backdrop.

Sandy Feet Retreat
Enjoy your stay with STUNNING VIEWS from your Very Own Balcony! This home is Fully Equipped and designed for your convenience. The Master Suite overlooks the Intra-Coastal & has its own Jacuzzi tub w/ separate shower. This End Unit allows ample lighting throughout. Located directly across the street from the infamous Shephards, and just steps to the Sugary White Sand, Clearwater Beach is known for! Walking distance to several Restaurants, Bars, Shops, & Tourist Attractions!

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.

Sleeps 8 Near Beach | Pool + Game Retreat
Discover your tropical retreat at Paradise Palms in Seminole! This newly renovated, pet-friendly home features a game room, outdoor dining, and a sparkling, saltwater swimming pool - with heating provided at no extra cost. mid Oct- April. Just minutes from Madeira Beach, we've equipped you with all the beach essentials for your convenience. Professionally hosted by Tropical Oasis, FL, we've meticulously prepared all the essentials to ensure a memorable stay.

"Jewel At The Shores" Gulf Front, sleeps 5
"Jewel at the shore"feels like you are in a snug resting place, your own nest, very homey with a breath taking Gulf view from the balcony. The gulf is right outside your door along with a year round heated pool, great on cool winter days. The unit is stocked with things you’ll need; linens, towels, shampoo et., necessities for the beach, keurig and drip coffee, some pods to get you started. New balcony and sliders. Just beautiful and comfy

New! Condo in exclusive Avalon Club
This 3-bedroom, 2-1/2-bathroom modern chic condo hotel suite offers stunning views of the Bay, Honeymoon Island, and Dunedin. It has room for 8 with one King bed, 2 Queen beds, plus a full-sized sofa bed. The private balcony provides the perfect place for people watching in the street below and south, down Mandalay Ave., or to enjoy watching the sun rise over Mandalay Bay. Please note that one of the queen bedrooms does not have a window.

Boutique Bungalow with Private Saltwater Pool
Relax in a crisp Florida bungalow with a private saltwater pool set in a fully private backyard oasis. Whether you are coming to Tampa for an event, extending your cruise vibe, or coming to Tampa for work, this home has got you covered. You’ll be 15 minutes from the Tampa Convention Center and the Port Tampa Bay Cruise Terminal, close to South Tampa dining and nightlife, 10 minutes to TPA, and an easy drive to award-winning Gulf beaches.
Popular amenities for Clearwater Beach rentals with a pool
House rentals with a pool

Hibernate in our Bear Creek Home

*Apollo Escape* – Canalfront Home + Private Pool

The Palm House | Free Heated Pool!

Heated Pool Oasis • 5 min to Beach • Sleeps 11

4BR Family Home • Heated Pool •Game Room

Spacious family home ~ heated pool, King beds!

Tropical Pool Retreat in Tarpon Springs

Walk to Beach | Private Pool • Mini Golf • Firepit
Apartment rentals with a pool

Relax in a Newly Renovated Beach Front Paradise

Sun Haven~Remodeled~Waterfront~Walk to Beach

Lovely-2 bedroom condo with 2 pools, Madeira beach

Ocean Breeze • Easy - Heated Pool Access

Captain's Cove Waterside Condo 103 We are open!

Best of the Gulf with a View - Sand Castle 1

Beachfront 3-Bedroom Condo in Indian Shores

Penthouse Condo on Water Steps to Beach+Johns Pass
Other holiday rentals with a pool

Hgtv Style Pool Home, Across the Street from Beach

Fantastic Condo at Avalon - Fully Renovated

Heated Pool & Spa Oasis Near Clearwater Beach

Pool home pet friendly close to Mad beach

Awesome Condo in Clearwater, FL

Near Clearwater Beach - Pool Home Retreat

Organic & Modern~90° Heated Salt Pool~Walk 2 beach

Private Heated Pool/Waterfront/5-mins to Beach
When is the best time to visit Clearwater Beach?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £159 | £197 | £238 | £183 | £147 | £155 | £157 | £132 | £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
- Cortez Beach
- Bean Point Beach
- Anna Maria Public Beach
- Jannus Live
- ZooTampa at Lowry Park
- Tampa Palms Golf & Country Club
- Hard Rock Casino
- River Strand Golf and Country Club
- Tampa Convention Center
- North Beach At Fort DeSoto Park
- Busch Gardens
- Splash Harbour Water Park
- Adventure Island
- Lakewood National Golf Club




