Holiday houses in Clearwater Beach Island

4.95 out of 5 average rating, 73 reviews

CWB Retreats at Bayside Villas - Bayside 6

Relax in this second-floor space. Situated right on the water, only 5-minute walk to the beach, the recreation center, and all that Clearwater Beach has to offer. Featuring a king-size bedroom. Queen sleeper sofa in living room. Dining area seats four. Full galley style kitchen includes appliances and cutlery. Grill your fresh seafood outside. Enjoy water views and dolphins from our bay front dock. Free washer and dryer next door. Pool construction may be ongoing between April and August 2025.

4.95 out of 5 average rating, 114 reviews

NEW! High End King Mattress! 10 Steps to the beach

AMAZING LOCATION! Located within crawling distance of the sugary white sands of the world famous Clearwater Beach! Equipped with a Premium King Casper Wave Hybrid Snow Mattress which retails at $4,000, to ensure an amazing nights sleep. Located in a small building with just 6 units, only 1 house from the beach. Walking distance to practically everything in town including many great restaurants, bars, shops, Pier 60, the marina & more, yet still located on a quiet street. No car is necessary!

4.9 out of 5 average rating, 374 reviews

Condo in Clearwater

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.

4.82 out of 5 average rating, 110 reviews

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

4.87 out of 5 average rating, 126 reviews

Cottage in Clearwater

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.

4.89 out of 5 average rating, 217 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.

4.98 out of 5 average rating, 40 reviews

Condo in Clearwater

2/2 JW Marriott Resort/Spa Clearwater Beach, 811

Relax and unwind at this luxurious condo located at the JW Marriott Resort and Spa on Clearwater Beach. This privately owned 2-bedroom, 2-bathroom residence features stunning views of the Gulf of Mexico from your 8th floor private balcony, which is accessible from both bedrooms and the living room. The unit sleeps up to 6. The secluded, private beach allows guests to enjoy the pristine white sand and sparkling water of Clearwater Beach without the hassle of the crowds!

4.93 out of 5 average rating, 73 reviews

Home in Clearwater

Beachfront Getaway with Patio – Perfect For 6

Welcome to the piece of paradise you’ve been dreaming of!! This charming seaside townhouse is located just 70 STEPS from the beautiful white sand of Clearwater Beach. Enjoy the convince of it's prime location, cook great seafood at the grill, and truly live the Florida beach lifestyle. Walking distance from bars, restaurants, and stores. This house has been entirely renovated and furnished so it can offer an outstanding beach experience. Don't delay and enjoy Florida!

Holiday home in Clearwater

4.87 out of 5 average rating, 139 reviews

Waterfront Courtyard Condo 2 Blocks to Beach

🌊 Ultimate Waterfront Escape – Adventure Awaits! 🚴‍♂️🏄‍♂️ Welcome to your dream beach getaway! This stunning waterfront rental puts you right on the water with breathtaking views and endless adventure. Paddle on a kayak or stand-up paddleboard, then cruise around town on our complimentary beach bikes. Jet ski island tours, parasailing, and more—all available right from the property! This is the perfect spot to make unforgettable beach memories! 🌅🏝️🚤

4.85 out of 5 average rating, 179 reviews

Hotel room in Clearwater

Bay Apartment 1

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.

Apartment in Belleair Beach

5 out of 5 average rating, 14 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!

Top Guest favourite

Townhouse in Dunedin

5 out of 5 average rating, 22 reviews

Rooftop+Balcony! Luxury Stay in Downtown Dunedin

***NEW AIRBNB PRICING STRUCTURE: Effective mid-April 2025 Airbnb displays all-in pricing to guests, which includes a 14.2% service fee charged directly by Airbnb (we have no control over), the $180 cleaning fee, & pet fees if applicable. Comfort meets elegant, modern luxury in this stunning brand new 2 bedroom, 2 bath second story townhome unit in the heart of Downtown Dunedin!

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Popular amenities for Clearwater Beach Island holiday rentals

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Other great holiday rentals in Clearwater Beach Island

4.79 out of 5 average rating, 218 reviews

Surf n Sand Water View Studio Apartment 17

DanielaRating, 5 stars1 week ago

We enjoyed our stay at Lea’s! It was clean and well located. We will definitely be back.

4.9 out of 5 average rating, 134 reviews

Renovated 2025 - Retro Beach Oasis with Color Pop

AnthonyRating, 5 stars6 days ago

Antonis place was super clean, was even better in person. looks just like the photos. Me and my wife had a great honeymoon. The beach is 2 min away by foot. you can literally walk everywhere. Pool was super nice and private. Just wow.

4.81 out of 5 average rating, 242 reviews

Surf n Sand Studio Apartment by the Water 16

StewartRating, 5 stars1 week ago

This was our 2nd year in a row that we have stayed and I give it a 9.8 out of 10 with the only setback was that the pool had a pump issue and wasnt as clean as the result but mechanical things break .. We will be booking more stays in the future,,, we'll done

Holiday home in Clearwater

4.9 out of 5 average rating, 105 reviews

Coastal Waterfront Condo 2 blocks to Beach

JenniferRating, 5 stars1 week ago

Great location, cute place, clean, and easy access to all the fun spots on Clearwater beach! Also a great perk having the Stay and Play amenities right there - highly recommended!

4.87 out of 5 average rating, 160 reviews

Bright Waterfront Studio Walk to Sand

AudreyRating, 5 stars2 days ago

We had a really nice stay. It was a great walk to the beach and local restaurants near by. Definitely recommend for anyone who wants to stay on the beach without the outrageous prices. The air b and b was also stocked full of anything you could need and the host was very responsive.

4.9 out of 5 average rating, 268 reviews

Condo in Clearwater

Beachfront in exclusive resort

JenniferRating, 5 stars2 months ago

My family and I love staying at the Avalon. This is our go-to place when we’re visiting Clearwater.

4.85 out of 5 average rating, 119 reviews

Intracoastal Waterside Studio 2 Blocks to Beach

ElishaRating, 5 stars2 weeks ago

This place was perfect for the 2 of us! It’s very close walking distance to the beach and restaurants. There are bikes on site that you can use, which was so nice for going to dinner/shops. Andrew was very responsive and helpful during our stay. Would definitely recommend!