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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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

4.94 out of 5 average rating, 280 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

A spacious outdoor pool area features a large swimming pool and a inviting hot tub. Palm trees provide shade, and waterways with lush vegetation are visible in the background. Loungers surround the pool for relaxation under the clear blue sky.

Townhouse in Clearwater

5 out of 5 average rating, 118 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 favorite

Condo in Clearwater

4.9 out of 5 average rating, 370 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.

Guest favorite

An aerial view showcases the proximity to Clearwater Beach, highlighted by a prominent arrow indicating a 2-minute walk to the soft sands. The surrounding area includes colorful buildings, green spaces, and the inviting coastline, providing a clear sense of location and ease of access.

Apartment in Clearwater

4.83 out of 5 average rating, 110 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 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

4.88 out of 5 average rating, 124 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

A community pool area is highlighted in a softly lit setting at night, surrounded by palm trees. Loungers are arranged around the pool, offering a space for relaxation. The clear sky features light cloud cover, creating a serene ambiance over the inviting waters.

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 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, 148 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

The image features a resort-style pool surrounded by lush palm trees and neatly arranged lounge chairs. A sunshade and a tropical atmosphere are visible, complemented by landscaped greenery and a fenced area, creating a serene and inviting outdoor space.

Condo in Clearwater

5 out of 5 average rating, 48 reviews

Avalon Sunshine: Summer Special + Free Parking

Welcome ! This is your Home away from Home ! Impeccably maintained and updated one bedroom/ one bath ( one king size bed and a queen pull out sofa) this condo is a gem ! Free parking and a beautiful pool for the resort style living at its best! Clearwater beach famous Pier 60 is only 3 miles away, beautiful natural Parks, an attractive Marine Aquarium and lots of activities at your finger tips for exciting moments and unforgettable memories. And more...

Superhost

The image showcases a sparkling heated pool adjacent to a white modern building. Lounge chairs are positioned around the pool, with expansive glass railings providing unobstructed views of Clearwater Beach and the Gulf of Mexico in the background.

Condo in Clearwater

4.84 out of 5 average rating, 103 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 favorite

A thatched-roof pavilion with a picnic table is set by the poolside, offering a shaded spot for gatherings. The shimmering pool reflects clear blue skies, and the beach is visible in the background, framed by lush greenery and swaying grasses.

Apartment in Belleair Beach

5 out of 5 average rating, 10 reviews

NEW Beachfront Oasis with Pool in Belleair Beach

BEACH ACCESS a few steps away from your front door! Views of the beach included with an in-ground pool and picnic area on one of the most beautiful beaches on Florida's Gulf Coast! Our fully renovated apartment is fully equipped with a combo kitchenette, dining space, living room with smart tv, and bedroom with smart tv. If you're looking for a peaceful and fun beach getaway, you've come to the right place!

Guest favorite

A rectangular pool is surrounded by palm trees and tropical plants, offering a refreshing escape. Lounge chairs are positioned near the water, with an inflatable float resting on the pool's surface. The cheerful, yellow building features balconies and invites relaxation in a vibrant atmosphere.

Apartment in Clearwater

4.8 out of 5 average rating, 264 reviews

Surf n Sand Studio Apartment by the Water 9

We were hit by 2 powerful hurricanes in the past month. As of now we are estimating to fully re-open on December 20th. In the meantime our upstairs rooms will stay open for guests who need a place to stay. Our rooms upstairs haven’t been damaged however, we will be working on fixing the rooms downstairs. Thank you for your understanding, and we really appreciate all the kind massages during this time.

Guest favorite

A clear view of the pool area features a well-maintained heated pool surrounded by paved walkways. Lounge chairs are positioned nearby, with lush greenery and well-kept bushes framing the scene, enhancing the tranquil outdoor environment.

Condo in Clearwater

4.93 out of 5 average rating, 141 reviews

Beachfront Condo with Centerline Sunsets

Stunning beachfront condo on the gulf. Beautiful white sand beach with an on-site heated pool. Unit is located on the fourth floor with gorgeous views of the Gulf. The balcony has a unobstructed beautiful view of the entire beach. Walk right onto the sand and let the stress melt away !!