Vacation rentals with a pool in Clearwater Beach Island

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.

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!

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.

A set of two white wicker chairs and a small table are positioned on a balcony, providing views of the Gulf of Mexico. The ocean and sandy beach stretch into the distance, with clear blue skies overhead.

4.9 out of 5 average rating, 393 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.

4.88 out of 5 average rating, 163 reviews

An aerial view highlights the proximity of the property to Clearwater Beach, with a marked path indicating a 2-minute walk. The beach is visible in the background, showcasing white sand and calm waters. Surrounding buildings reflect a mix of residential and commercial spaces.

Apartment in Clearwater

Fresh for 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

Apartment in Clearwater Beach

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.

4.9 out of 5 average rating, 141 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.

Hotel room in Clearwater Beach

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.

4.88 out of 5 average rating, 420 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!)

4.94 out of 5 average rating, 100 reviews

Apartment in Clearwater

The Breezeway #6 only a 2 min walk to the Beach!

Our studio has a King Bed, as well as a microwave, mid-size fridge, regular coffeemaker and toaster. We do not provide kitchen utensils, paper towels etc. but you’ll find tons of amazing local restaurants just a short walk away. We offer a heated Pool and free parking for our guests on site. We have a brand-new Pickle ball court and Playground on one side and a public pool and tennis court on the other. We are just short stroll to historic Pier 60 and vibrant beach nightlife.

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.

4.99 out of 5 average rating, 113 reviews

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

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.

A well-appointed bedroom features a spacious queen bed with a striped blanket. Two bedside tables with lamps are positioned on either side. Natural light fills the room through a window adorned with light curtains, while tasteful artwork hangs on the concrete wall.

4.98 out of 5 average rating, 130 reviews

Seasalt Breeze, by the pool, NO PETS

The Avalon at Clearwater is a gated community with a nice size heated pool and community gym. Parking space is not assigned and it’s free of charge. Location is central with short distance to nearby beaches, attractions and other nearby towns. Unit is approximately 500 square feet with a living room-kitchen open concept and One bedroom - bathroom open concept. Great access from Tampa Airport 20 minutes and 1.5/hours drive from Orlando airport

4.99 out of 5 average rating, 115 reviews

2 King Suites | Stunning Views | Walk Everywhere!

Escape to Dock of the Bay! ✅ Two KING suites + sofa bed ✅ 5-minute walk to beach ✅ Stunning waterfront views ✅ Full kitchen ✅ Heated pool & sun deck ✅ Beach gear & wagon ✅ Free parking! 👨‍👩‍👧 Traveling with a group? We also own the condo next door -- “Dock Holiday” (www.airbnb.com/h/dockholiday-clearwaterbeach). Tell your friends or book both together—Dockside Duo (www.airbnb.com/h/docksideduo). Double the space and double the fun!