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.

0 of 0 items showing

1 of 3 pages

Top guest favourite

Home in Palm Harbor

5 out of 5 average rating, 107 reviews

Coastal Escape: heated saltwater pool & beaches

★ Close to beaches - Honeymoon Island: just 6 miles away. - Clearwater Beach: 15 miles away - crowned the nation's #1 beach Trip Advisor in 2018 ★ Heated saltwater pool ★ Screened-in lanai ★ BBQ grill ★ Large backyard w/ playground ★ Outdoor dining area ★ 3 bedrooms New Mattresses - California king size bed - Queen size bed - Kid-friendly room w/ two bunk beds ★ Renovated kitchen and bathrooms ★ Open living space - great for family gatherings, movie nights ★ Children toys and games

Top guest favourite

Apartment in Treasure Island

4.99 out of 5 average rating, 191 reviews

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.

Guest favourite

Home in Treasure Island

4.84 out of 5 average rating, 170 reviews

Eiko Beach House 4BR/3BA Heatd Pool*Hot Tub* Pets

BEACHFRONT HOUSE Private Heated Pool & Spa, Pets OK *** Photos updated Jan 26th 2025 Enjoy amazing sunsets & white sandy beaches from this unique property. About 1/4 acre, beach front property directly on the Gulf of Mexico. Located on a quiet street in Treasure Island, just a few blocks to John's Pass shops. ENJOY great family times, never ending views of sunsets, boating, dolphins, sea birds. Great location walk to John's Pass for great shopping, restaurants, boat rentals, fishing trips.

Top guest favourite

Cottage in Indian Rocks Beach

4.99 out of 5 average rating, 176 reviews

Luxury Beach Bungalow | Walk to Dining & Sunset

Escape to paradise at Sunshine Escapes! Welcome to #CocoPalmsIRB, 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, #CocoPalmsIRB invites you to immerse yourself in the laid-back beachy vibes of IRB. Your perfect getaway awaits!

Top guest favourite

Apartment in Clearwater Beach

4.99 out of 5 average rating, 110 reviews

Dock of the Bay, Coastal Elegance | Walk to Beach!

Dockside 204 -- Sittin’ on the Dock of the Bay … at Dockside Condominiums. Looking for a beautiful beach home on one of the top-rated beaches on the Gulf coast? Check out our exquisitely-decorated condo located in the heart of Clearwater Beach. We’re right on the bay and within 100 yards of the sugar sand beach, beachwalk, restaurants, shops, night life, and more. The views are spectacular and you will enjoy watching the boats, dolphins, and manatees from your dining room window and balcony.

Top guest favourite

Townhouse in Clearwater Beach

5 out of 5 average rating, 124 reviews

Waterfront Beach House Steps Away from #1 Beach!

Welcome to The Bombshell Beach House! This 3 story, 3 bedroom luxury water-front townhouse located in Clearwater Beach, FL has been a childhood dream come true for me as a Clearwater native! As avid travelers, my husband and I wanted to create a STAY-CATION spot that mixed in all of the comforts of HOME with all of the luxuries of a 5 star vacation & this beach house is JUST THAT! This listing is brand new and we are expecting dates to book extremely fast! Book now to secure your GETAWAY!

Guest favourite

Bungalow in Indian Shores

4.95 out of 5 average rating, 153 reviews

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 + heated pool

Top guest favourite

Home in Seminole

4.99 out of 5 average rating, 110 reviews

Tootsie’s Beachside Retreat

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.

Superhost

Apartment in Treasure Island

4.9 out of 5 average rating, 124 reviews

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.

Top guest favourite

Home in Clearwater

4.98 out of 5 average rating, 134 reviews

Fun Funky Pool Fire Pit 4m to Beach

Welcome to The Merry Mint! A family & pet friendly 2/1 oasis located 4mi from the #1 beach in America; Clearwater This colorful & whimsical property is just minutes from grocery, 5 star restaurants, & every convenience. Only a short drive to the beach! Or stay in & enjoy: ★ 24x12 Pool w/LED multicolor pool light ★ 34X18 Pool Deck ★ Loungers ★ 16x20 Grill Deck ★ Fire-Pit w/grill grate ★ Yard Games (regulation corn hole, jenga, connect four, etc) ★ BBQ Grill ★ string lights

Guest favourite

Cottage in Clearwater Beach

4.88 out of 5 average rating, 129 reviews

Mermaid Cottage

Located in a three unit 'Olde Florida Style Complex' and just 45 steps to Clearwater Beach! The Mermaid Cottage is located on the 1st floor at the back of the complex. This Florida style unit is adorned wood floors and charming island decor. Open to an outdoor patio with furniture. The cottage has two bedrooms, two full baths and an outdoor shower! Living room has a queen pull-out bed. The patio area is completely fenced for private use. Nice, park like charcoal grill.

Guest favourite

Flat in Clearwater Beach

4.89 out of 5 average rating, 219 reviews

Waterfront Modern Chic #1 Clearwater Beach

Ultra Modern renovated & decorated Industrial-Chic apartment on the water! A spacious layout of about 1200 square feet, porcelain tile floors, fully equipped kitchen - Italian cabinetry, Quartz counter tops, top of the line full size Samsung appliances, refrigerator, stove, dishwasher, and microwave. Large family room flows into the dinning area making it the center of the home. The split floor plan accommodates guests on either side of the apartment allowing for privacy.