Vacation rentals with a pool in Clearwater Beach Island

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Clearwater Beach Island

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Clearwater Beach

4.97 out of 5 average rating, 198 reviews

Clearwater Beach Townhome w/Game Room & Boat Slip!

PLEASE ASK ABOUT OUR OTHER 2 WATERFRONT PROPERTIES ON CLEARWATER BEACH IF YOUR DATES ARE NOT AVIALABLE!! Welcome to Brightwater Blue, our newer vacation Town Home in Clearwater Beach! 3 floors of fun, elegance & relaxation await you. Custom interior decorated with Restoration Hardware & other high end furnishings. Located on Clearwater Bay & within easy walking distance to Clearwater Beach, Beach Walk, restaurants, shopping & everything Clearwater Beach has to offer! Why book 3 hotel rooms when

Sep 3 – 10

€ 759 per night

Guest favorite

Tiny home in Dunedin

4.95 out of 5 average rating, 105 reviews

Sleeps5-Tiny Home-Pool-10min2Beach-Balcony

Fabulous newly built luxury tiny home in the heart of Downtown Dunedin! This charming 2 bedroom 1 bath home has everything you need for a perfect stay in our perfect little town. This home has an upstairs loft with King and Queen beds at opposite ends. Steps from all the best restaurants, breweries, shops and activities in Dunedin. Voted one of the best walking towns in America! Short drive to beaches! Or simply stay home and chill by the pool that's great too! This location can't be beat!!

Aug 30 – Sep 6

€ 195 per night

Guest favorite

Guesthouse in Palm Harbor

4.97 out of 5 average rating, 204 reviews

Private Suite, 1 bedroom, 1 bathroom, pool, patio

Private suite located in Palm Harbor with king-size bed, Split unit A/C Amenities include: Large Bathroom with Jacuzzi, Walk-in Shower, Double sink Vanity. Access to Patio, Swimming Pool , Backyard and Sundeck. Room includes small refrigerator/freezer, Microwave, Coffee maker, Espresso, Iron and much more. Bistro set in room. Private entrances to room and patio/backyard. Cable TV, Netflix and Wi-Fi included. Centrally located to Restaurants and shopping. 10 mins. to the beach/Pinellas Trail.

Nov 15 – 22

€ 129 per night

Guest favorite

Apartment in Clearwater

4.99 out of 5 average rating, 356 reviews

Private studio attached to house. Pool&bikes

Completely private A/C studio, bathroom & your own private saltwater pool. Studio attached to house. No cleaning fee. 1 block W to Edgewater trail. Beautiful sunsets on water. 1 block E to famous Pinellas trail. Stroll to downtown Dunedin or TD Stadium. Cruiser bikes provided. Drive, Uber, trolley or bike 4.5 miles to Clearwater Beach or Honeymoon Island. Near restaurants, shops, dancing, kayaking, fishing, boating, biking, baseball, etc! Space is not appropriate for under 18, pets, parties.

Dec 15 – 22

€ 147 per night

Guest favorite

Guest suite in Largo

4.95 out of 5 average rating, 234 reviews

"Twilight Sands Stud" Prvt Ent,Pool,Pk,Keyless Ent

Welcome to your private Studio located 10 minutes from Indian Rocks Beach FL. Come stay with us and dip your toes in the warm white sugar sands of the Gulf of Mexico. Our beautiful cozy studio has private parking, entrance and keyless entry, cozy cal king bed, on suite bath/shower w/bidet, sweet retro kitchenette including mini fridge/freezer, microwave and Keurig coffee/tea express. Beat the crowd, book your stay, relax at the best beaches in the country or explore Tampa Bay or St.Pete!

Apr 6 – 13

€ 104 per night

Guest favorite

Condo in Clearwater

4.97 out of 5 average rating, 103 reviews

Come and relax in a stylish art deco condo !

This amazing organic-modern decorated 1 BD condo is 5 min drive to the beautiful Clearwater Beach, bars & restaurants, and lots of family attractions. Unit is located in a beautiful resort-style gated community, which offers a clubhouse, heated pool, gym, wi-fi and free parking. This perfect retreat offers full privacy as each room provides separate access to the bathroom. The suite is on the main floor, with no stairs to climb, easy access in-out, and includes a laptop-friendly workspace.

Jul 4 – 11

€ 154 per night

Guest favorite

Condo in Clearwater

4.91 out of 5 average rating, 235 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.

Nov 2 – 9

€ 696 per night

Guest favorite

Apartment in Dunedin

4.95 out of 5 average rating, 169 reviews

Mermaid cottage

Watch this video first to experience the property https://vimeo.com/444390022 Cute little cottage poolside with a pond out front, great kitchen, plenty of space to kick back and relax, private front porch with a table and two chairs NOTE: If booking 28 days or more Please be advised this listing has a 45 DAY cancellation policy which is less strict than the airbnb cancellation policy that is listed , Airbnb will call and confirm that I honor this less punitive cancellation policy.

Dec 17 – 24

€ 197 per night

Guest favorite

Condo in Clearwater

4.89 out of 5 average rating, 166 reviews

Happy getaway nest. Very cozy & high quality

Modern and very cozy one-bedroom condo, clean, quiet, and comfortable. Convenient big kitchen space and bathroom. King bed in master. Sleeping sofa in the living room. All appliances, kitchen pots, and all you need to make yourself home. TV in the living room and Master. Full cable. Fast WiFi. Roku. Beach towels, umbrella, chairs, cooler. 10 min from Clearwater Beach. 20 min from the airport. I put a lot of <3 INTO! You feel at home in my place because I take care of myself!

Dec 3 – 10

€ 148 per night

Guest favorite

Condo in Clearwater

4.99 out of 5 average rating, 106 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.

Apr 29 – May 6

€ 635 per night

Guest favorite

Bungalow in Dunedin

4.89 out of 5 average rating, 186 reviews

Cozy Park Model RV with Sun Room. No pets

A relaxing space great for beach lovers, cyclist , and people who love the outdoors. Close to beaches restaurants and historic Downtown Dunedin. Located in the Dunedin RV Resort . Honeymoon Island State Park is 3 miles, Clearwater Beach is about 9 miles. Jolly Trolley goes to Clearwater Beach St Petersburg , Tarpon Springs where the sponge docks are. Greek Food and pastries are amazing in Tarpon Springs. NO PETS

Aug 13 – 20

€ 90 per night

Superhost

Apartment in Clearwater

4.78 out of 5 average rating, 236 reviews

Surf n Sand Studio Apartment by the Water 2

Our goal is to preserve the old Florida and to offer you the opportunity to experience a stay at a vintage themed motel. Our Airbnbs are all unique. Some include neon signs, some the original colorful subway tiles, and others terrazzo floors. You will be staying at the exact Airbnb as pictured on the listing. We seek to keep the properties original and authentic by implementing repairs instead of replacements.

Sep 19 – 26

€ 95 per night