Holiday rentals with a pool in Clearwater Beach Island

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Top-rated rentals with a pool in Clearwater Beach Island

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Guest favourite

Condo in Clearwater

4.94 out of 5 average rating, 283 reviews

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!

Top Guest favourite

Townhouse in Clearwater

5 out of 5 average rating, 123 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

Guest favourite

Condo in Clearwater

4.9 out of 5 average rating, 377 reviews

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.

Superhost

Apartment in Clearwater

4.8 out of 5 average rating, 158 reviews

Renovated 2025 - Retro Beach Oasis with Color Pop

Book with confidence—our property is in great shape and ready to host your Clearwater Beach getaway! -No hidden fees -No chores Just a breezy, beachy stay with: -2-minute walk to the beach -Beach Chairs -Free parking -Heated pool -Cold AC -Easy self check-in -Pet friendly (One Pet max -$150 fee) We provide essentials (linens, towels, toilet paper, soap etc.) to get you started. For longer stays, we recommend buying additional supplies. 📍648 Poinsettia Ave, Clearwater Beach, FL 33767

Guest favourite

Condo in Clearwater

5 out of 5 average rating, 5 reviews

Welcome to Sun Haven~Newly Remodeled! Waterfront!

Welcome to your luxury condo in Clearwater Beach! This 3 bd/3 full bath non-smoking, top-floor unit is located in the heart of south Clearwater Beach with a private balcony overlooking the intracoastal waterway and an easy 1.5 block walk to the beach. No need for a car during your stay as dining, entertainment, and the famous Pier 60 are all within walking distance! We rent Saturday to Saturday. Please contact the property manager if you wish to book during a different timeframe.

Guest favourite

Cottage in Clearwater

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

Apartment in Clearwater

4.89 out of 5 average rating, 218 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.

Top Guest favourite

Townhouse in Clearwater

4.99 out of 5 average rating, 110 reviews

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.

Guest favourite

Condo in Clearwater

4.99 out of 5 average rating, 150 reviews

Newly Reno Luxury Condo 30 Steps to Paradise

Welcome to our serene top-floor beach condo. This is a two-bedroom, two-bathroom condo in the heart of Clearwater Beach. This ocean-side condo is steps from the country's #1-rated beach and less than a five-minute walk from top restaurants and shopping. Clearwater Beach is renowned for its award-winning beaches, incredible restaurants, and lively nightlife. We have made every effort to make this condo a home away from home! We hope you enjoy our piece of paradise.

Superhost

Condo in Clearwater

4.85 out of 5 average rating, 105 reviews

Clearwater Beach,Stunning2/2.5, CityView condo,304

On Clearwater Beach! New and stunning 2/2.5 condo! This newer 2 bedroom, 2 and a half bath condo at Avalon (new in October of 2021) is a little piece of heaven on Clearwater Beach! It is a City view 3rd floor unit. There is a heated pool and sundeck on the 5th floor which has a beautiful view of Clearwater beach, as well as a 5th floor pool, pool bar, and sun deck. The layout of the bedrooms are a split plan for privacy on your vacation adventure!

Top Guest favourite

Loft in Clearwater

4.92 out of 5 average rating, 143 reviews

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. One free, dedicated parking space per unit. 57 Baymont Street to map. New pool available at 617 Bay Esplanade you can walk to.