Vacation rentals with outdoor seating in Clearwater Beach Island

1BR NEW Coastal Boutique Cottage Closest to Beach!

The one you've been dreaming of! Bright, modern, adorable cottage in the quieter North section of Clearwater Beach, just 50 steps from curb to the sand. Walk to all attractions, restaurants, shops & Pier 60. Modern kitchen w/ full-size appliances, wood-grained ceramic tile floors, calming colors throughout. Private BR w/Queen-size Casper cooling mattress. Queen sleeper sofa in living area. Sleeps up to 4. Outdoors a shared landscaped courtyard, BBQ and Treehouse Deck w/gulf views. Shared W/D.

THE SALT LIFE! 10 steps to the beach!

AMAZING LOCATION! This vacation rental is located within crawling distance of the beach. As soon as you open the front door, you can see the beach. The apartment is located in a small building with just 6 units and is 1 house from the sugary white sands of the world famous Clearwater Beach! Also located within walking distance of many great restaurants, bars, shops and much more, yet still located on a quiet street. Once you park your car in your reserved spot, you probably won't need it again!

Beachfront in exclusive resort

This upper floor, 3-bedroom modern chic condo hotel suite offers sweeping views of the Gulf of Mexico from private balconies. While preparing your morning coffee on the spacious kitchen island, you can see the shrimp trawlers making their way out to sea. Enjoy a cocktail while watching the sunset over the open water of the Gulf of Mexico. This suite can sleep 8, with King or Queen-size beds in each of the three bedrooms, a comfortable full-sized sofa bed in the living room & 3-1/2 bathrooms.

Upgraded 3 Bed, 3 Bath Corner Water Front Condo!

Stylish & Sunny Corner Unit On Dolphin Faved Inlet Across The Street From Florida's #1 Beach. This all-inclusive unit allows you to walk everywhere and enjoy all Clearwater Beach has to offer from sand & sun to restaurants & shopping. Updated & upgraded 3 bedroom, all with connected bathrooms offers amazing space, a chef's kitchen as well as bright & beautiful dining & living rooms. Private balcony to relax & watch the sunset. Beach concessions include sea kayaks, jet ski's, boating & more.

Walk Downtown and to Waterfront, Mins to Beaches

Just steps to Main Street Dunedin and minutes to Honeymoon Island and Clearwater Beach, this stylish upstairs 2-bedroom cottage blends modern coastal design with exceptional comfort. Tropical murals, treetop views, two king beds, and a sleeper sectional create a chic and indulgent stay. Fully stocked. Walk to dining, shops, breweries, and Dunedin’s stunning waterfront sunsets, then drive minutes to the beaches. Pet-friendly. Every detail beautifully done—reserve the Barefoot Parrot today.

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

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.

Lemon Cottage Steps from Beach

1925 beach cottage with king size bed, new kitchen with granite countertops LG stainless steel double over, just 130 steps to the sand with no streets to cross. Sofa bed in living room total 2 sleeping areas. Great location with Frenchy s Rockaway Grill and Crabby s just 2 blocks away and Pier 60 5 blocks walk Enjoy a commercial size hot tub right out your back door with large wood party deck tin roof gazebo or private hot tub in Balinese style Cedarwood Hut

#1- SALE! Nice 2/2 Condo-Directly on the sand!

Kick back and relax in this calm & quiet beachfront condo, located directly on beautiful North Clearwater Beach! Unit is located on the 2nd floor with gorgeous views of the Gulf of Mexico. 2 Bedrooms, 2 bathrooms with a private balcony overlooking the beach. Sleeps 6 with the air mattress. WiFi included, Smart TV's, beach chairs, towels, toys, etc. Just bring yourselves and you are ready to go! Fully equipped full-sized kitchen with enough supplies to get you started!

Breathtaking Beachy Houseboat on Clearwater Island

🌊 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! 🌅🏝️🚤

CWB Retreats at Baymont Lofts - Loft A

Loft A at Baymont is one block from the Sand Pearl entrance to the beach. Walk down the stairs from the spacious 2 bedroom loft, with private patio, and enjoy the local restaurants and convenient shops. Additionally, there is a queen sleeper sofa in living room. Washer and dryer in the unit is a huge perk. Full kitchen. One free, dedicated parking space per unit. 57 Baymont Street to map. New pool available at 617 Bay Esplanade you can walk to.

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.