Vacation 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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Top guest favorite
Gentle waves lapping against a sandy shore create a serene coastal scene. The sky is filled with wispy clouds and varying shades of blue, reflecting the tranquil atmosphere of the beach. The shoreline reveals patterns in the wet sand as the water recedes.
Condo in Clearwater
4.95 out of 5 average rating, 297 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!

Guest favorite
Condo in Clearwater
4.97 out of 5 average rating, 131 reviews

2 BR/2 BA Key West Retreat, A+Pool, 3m 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.

Superhost
A private balcony is seen featuring two white chairs and a table, offering uninterrupted views of the Gulf of Mexico. The calming blue sky meets the horizon, enhancing the serene beachfront experience.
Condo in Clearwater
4.9 out of 5 average rating, 276 reviews

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.

Top guest favorite
A modern kitchen showcases white cabinetry with marble countertops and stainless steel appliances. Natural light floods through large windows, highlighting decorative accents and elegant floral arrangements. A central island is surrounded by bar stools, complemented by stylish area rugs beneath.
Townhouse in Clearwater
5 out of 5 average rating, 130 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!

Superhost
A tranquil heated pool is surrounded by palm trees and lounge chairs. Umbrellas provide shade near the pool's edge, and a pink inflatable float rests gently on the water's surface. The vibrant colors of a sunset are reflected in the sky, enhancing the serene atmosphere.
Apartment in Clearwater
4.82 out of 5 average rating, 199 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 favorite
A spacious living area is presented with a modern sofa adorned with decorative pillows. Two comfortable armchairs complement a circular coffee table. Natural light floods the space through sliding glass doors, leading to an outdoor patio with water views. Soft, neutral tones and contrasting textures are visible.
Apartment in Clearwater Beach
4.9 out of 5 average rating, 143 reviews

Waterfront Industrial Chic #2 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.

Guest favorite
A welcoming living space is highlighted by a blend of light and muted tones on the wooden accent wall. A spacious sofa and a white coffee table are arranged in the room, accompanied by a television mounted on the wall. A fully equipped kitchen is visible in the background.
Hotel room in Clearwater Beach
4.88 out of 5 average rating, 422 reviews

Boutique Stay on Clw Beach 1BR Suite w/full Kit

🐬 The Porpoise Inn & Suites is a charming boutique motel located right on world-famous Clearwater Beach. Just steps from the sand, shops, restaurants, attractions, and even a recreation pool, it’s the perfect spot for your next Florida getaway. Newly renovated suites feature the stylish touches of coastal living you’ll love, creating a cozy and welcoming space couples, Come for the location, stay for the charm 🏖️✨ (4 Max. Guest/Strictly Enforced & No Pets Strictly Enforced!)

Superhost
A sandy pathway leads through beach grass and wildflowers, with palm trees framing the scene. The azure ocean and clear blue sky serve as a backdrop, inviting guests to enjoy the nearby beach.
Cottage in Clearwater
4.87 out of 5 average rating, 139 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.

Top guest favorite
The image captures a spacious townhouse community, featuring white architectural designs. A clear view of the intercoastal waterway is presented, with boats visible in the distance. A community pool is seen among vibrant greenery, inviting leisure and relaxation.
Townhouse in Clearwater
4.99 out of 5 average rating, 113 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.

Top guest favorite
A balcony view features two cushioned chairs adorned with pink pillows, overlooking a quiet street leading to the beach. Palm trees and lush greenery frame the scene, while the ocean is visible in the distance. Bright blue skies enhance the coastal atmosphere.
Condo in Clearwater
4.99 out of 5 average rating, 163 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.

Top guest favorite
A cozy sitting area is featured on the private balcony, highlighted by a circular rattan chair adorned with soft cushions. Green plants provide a touch of nature, while water views and boats can be seen beyond the railing, enhancing the relaxing atmosphere.
Condo in Clearwater
4.99 out of 5 average rating, 135 reviews

Waterfront Condo | Steps to Clearwater Beach 2King

Wake up to stunning waterfront views in this luxurious 3BR/2BA intercoastal condo, just steps from Clearwater Beach! Watch dolphins from your private balcony, relax in the pool or hot tub, and enjoy a spacious kitchen perfect for family meals. Walk to white-sand beaches, 5-star dining, and local attractions, close to the action, yet peacefully tucked away. Modern decor, 1,650 sqft of comfort, and unforgettable sunsets await. Book your beach escape now!

Top guest favorite
A living room features exposed wooden beams and a brick accent wall, enhancing the cozy environment. A flat-screen television is mounted on one wall, and a coffee table sits centrally on a patterned rug. A lounge sofa and a chair provide comfortable seating options.
Loft in Clearwater
4.93 out of 5 average rating, 152 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. 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.

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