Holiday rentals 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.

4.92 out of 5 average rating, 105 reviews

Sweet Air! 10 Steps to beach! Luxurious King Bed!

Welcome to Sweet Air! Where the air is sweet and the living is easy! Located within crawling distance of the sugary white sands of the world famous Clearwater Beach! Equipped with a Premium Organic Hybrid Pillow Top King Size Mattress to ensure an amazing nights sleep. Located in a small building with just 6 units, only 1 house from the beach. You can walk to beach or the street to many great restaurants, bars, shops & more, yet you are still located on a quiet street away from the noise.

4.9 out of 5 average rating, 374 reviews

Apartment 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.

4.9 out of 5 average rating, 134 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 house in Clearwater

4.98 out of 5 average rating, 125 reviews

Cozy 2 Bedroom - 12 Minutes from Clearwater Beach

Make your vacation relaxing, fun and easy! - Kick back in the hammock or have some coffee with loved ones in the peaceful private backyard. - Take the 12 minute drive to the beach with the provided boogie boards, chairs and sand toys. - Take a walk or bike ride on the gorgeous Pinellas Trail. You'll also find some of the best coffee, food and ice cream on the way. -Golf courses close by. This is a separate unit that shares a driveway and parking area with the front house.

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, 216 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.

4.93 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!

4.99 out of 5 average rating, 149 reviews

Apartment in Clearwater

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.

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! 🌅🏝️🚤

4.74 out of 5 average rating, 404 reviews

Surf n Sand Studio by the Water 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.

5 out of 5 average rating, 14 reviews

Flat in Belleair Beach

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!

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Popular amenities for Clearwater Beach Island holiday rentals

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Other great holiday rentals in Clearwater Beach Island

4.82 out of 5 average rating, 139 reviews

Parker Manor Apartment

MiaRating, 5 stars1 week ago

Our stay was great! We were able to check in earlier than 3 PM which was great and Anna was super responsive. The walk to the beach wasn’t bad at all! It only took us about 5 minutes. Everything is very walkable and there are plenty of restaurant options within minutes. Would definitely book again!

4.95 out of 5 average rating, 113 reviews

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

KobeRating, 5 stars1 week ago

This place was perfect for a weeklong getaway for two! The location is absolutely perfect being 30 steps from the beach! It is also located right in between North Beach and Clearwater Beach, so you get the best of both worlds. This worked well for us as we like the restaurants and shopping that Clearwater Beach provides but love the relaxation and peacefulness of North Beach. The room itself was very clean and well set up for two travelers. The king bed is truly comfortable. Mike and Alex have a lot of beach accessories that they provide as well, such as beach chairs, a cooler, towels, etc. which was extremely convenient for us as we flew in and could not fly with these items. They also have fun miscellaneous stuff like boogie boards, volleyballs, and even a fishing rod! The kitchen has everything needed to cook. Parking on the island is extremely limited so having a dedicated parking space was absolutely amazing! We can't wait for our next trip and would stay here again for sure!

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!

4.85 out of 5 average rating, 179 reviews

Hotel room in Clearwater

Bay Apartment 1

JacksonRating, 5 stars2 weeks ago

Located in a great spot within walking distance of the beach and all sorts of restaurants and attractions in the Clearwater Beach area. The room was clean with everything you would expect in a standard hotel room (including beach towels which were very useful!).

4.7 out of 5 average rating, 458 reviews

Hotel room in Clearwater

Bay Apartment 19

JadynRating, 5 stars4 days ago

This place was perfect for our quick getaway! The location is so nice, just like a 5 min walk to the beach. It also included chairs and an umbrella to take as well. You could easily walk down the strip to all the restaurants and shops. I also felt very safe as well! The a/c and fan works well and the room is a perfect stay for 2. I love this place and would totally stay again. The only issue I would have is I wish there was a broom in the room for all the sand haha!

4.74 out of 5 average rating, 292 reviews

Hotel room in Clearwater

Bay Apartment with Water View 6b

TraciRating, 5 stars2 days ago

The place was exactly as the pictures looked and the location was great. Would definitely stay again. The only issue was the lack dish towels in the kitchen and not a lot of kitchen supplies for cooking. We needed to wash dishes but no sponges or dish cloths provided and only one towel. Other than that, absolutely loved our stay!

4.75 out of 5 average rating, 267 reviews

Surf n Sand 1 Bedroom Apartment by the Water 19

JosephineRating, 5 stars1 week ago

Great quiet place to stay! Close enough to both beach and restaurants, no car needed. Beach was awesome!