
Holiday rentals with a pool in Clearwater Beach
Find and book unique homes with a pool on Airbnb
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 $65 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!
Top-rated rentals with a pool in Clearwater Beach
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Heated Pool and Spa | 5 min to beach
Welcome to our home in Largo, Florida. This is a modern and comfortable place with a heated pool and spa, just minutes from Clearwater and Indian Rocks beaches. The kitchen has everything you need, and the living spaces are meant for relaxed stays with family or friends. The house has 3 bedrooms and 2 bathrooms and sleeps up to 6 guests comfortably. Whether you spend the day at the beach or by the pool, you’ll have an easy place to unwind and enjoy your time here. We hope you feel at home.

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

BEACHFRONT Condo - Belleair Beach Club - RENOVATED
No impact from hurricanes! - RECENTLY RENOVATED. This cozy 1 bedroom condo with a kitchen in Belleair Beach just steps from the sugar-white sand and crystal clear waters that are consistently ranked among America's most beautiful beaches! It has a lovely pool area that overlooks the gulf with a patio, chairs and grills. You’ll love the beachfront views and quiet ambiance. 3rd Floor, balcony with DIRECT BEACH/GULF VIEW. Minutes away from Clearwater Beach. Perfect for couples! ONE parking spot.

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.

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!

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.

Tiny Oasis | Pool | Stocked Stay Near Indian Rocks
Welcome to The Tiny Oasis! A cozy boutique style retreat in Largo, FL, near Indian Rocks and Clearwater Beach that’s packed with luxury. Lounge by the plunge pool, fire up the Blackstone or enjoy an outdoor movie night. Unique touches and a 5-star experience prove that small spaces make big memories! Tap ‘Show More’ below! What’s There To Look Forward to? 👙Plunge Pool 🚿Outdoor Shower 🔴 Corn Hole ⛱️ Beach Gear 🍔Grill 🅿️ Private Parking 🍳Cook at Home 🧺 Your own private Washer/Dryer

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.

CWB Retreats at Baymont Lofts - Loft A
Loft A at Baymont is one block from the Sand Pearl entrance to the beach. Walk down the stairs from the spacious 2 bedroom loft, with private patio, and enjoy the local restaurants and convenient shops. Additionally, there is a queen sleeper sofa in living room. Washer and dryer in the unit is a huge perk. Full kitchen. One free, dedicated parking space per unit. 57 Baymont Street to map. New pool available at 617 Bay Esplanade you can walk to.
Popular amenities for Clearwater Beach rentals with a pool
House rentals with a pool

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

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

Hannah’s beachside resort Saltwater Heated Pool

Sandy Morning Restored | Pool Spa

Best Celebration - Heated Pool - Hot Tub - Arcade

Heated Pool Home | Close to Clearwater Beach

Clearwater Gameroom- Pool/Mini golf/Home Theatre

Family/Group Getaway w/ Pool Near Clearwater Beach
Apartment rentals with a pool

Oceanfront View, Spacious Townhouse, Heated Pool

Newly Reno Condo! Spot Dolphins from Your Balcony!

Ocean Breeze • Easy - Heated Pool Access

Modern and Cozy Condo 6 Minutes from the Beach !

Indian Shores Awesome Coastal Beach Condo! 2Br/2Ba

Beach Front at “The Shore”

Spectacular beach to bay views from this resort.

Beach, dolphin/manatee sightings, fishing, sunsets
Other holiday rentals with a pool

Luxury Poolside Paradise

Yachtsman Beachfront Cottage w/ Heated Pool

Waterfront/ Sunsets/ Heated Pool/ Tiki Bar/ Dock

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

Four Bedroom Presidential, Clearwater A820

GulfPort Paradise, Bali-like Oasis with Pool

Oceanfront Condo - Beach front• Free parking

Beachfront Luxury Corner Unit, Balcony, Pool
When is the best time to visit Clearwater Beach?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $262 SGD | $338 SGD | $401 SGD | $318 SGD | $255 SGD | $268 SGD | $272 SGD | $228 SGD | $217 SGD | $214 SGD | $236 SGD | $255 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 |
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- Anna Maria Island
- Raymond James Stadium
- Weeki Wachee Springs
- 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
- Weeki Wachee Springs State Park
- Epperson Lagoon
- River Strand Golf and Country Club
- MidFlorida Credit Union Amphitheatre
- Jannus Live





