Vacation rentals with a pool in Clearwater Beach Island

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!

Banana Breeze Cottage 2 pools steps from the beach

Banana Breeze is a 2-bedroom, 1-bath cottage just 2 blocks from Clearwater Beach. Freshly updated with modern tile, a bright living room, and a comfortable king bedroom, it also features a full kitchen and dining space. Guests enjoy tropical gardens, outdoor seating, and 2 heated pools in a peaceful, private setting. With shops, restaurants, and the beach just steps away, Banana Breeze offers the perfect balance of relaxation and convenience, cleaned to the highest standards for your comfort.

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.

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 dog 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

Waterfront Industrial Chic #2 Clearwater Beach

This prime location is on the bay just steps away from the beach and the main strip offering a complete home experience. This spacious apartment is equipped with a full kitchen, washer/dryer, two full bathrooms, a large family room, dining area, access to the pool and two assigned parking spaces. A split floor plan ensures privacy, accommodating guests on either side of the apartment. The private patio overlooks the bay, offering stunning views of the sunrise and the occasional dolphin.

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.

Beach 1BR Suite w/full kitchen on Clearwater Beach

🐬 The Porpoise Inn & Suites is a charming boutique motel located right on world-famous Clearwater Beach. Just steps from the sand, shops, restaurants, attractions, and even a recreation pool, it’s the perfect spot for your next Florida getaway. Newly renovated suites feature the stylish touches of coastal living you’ll love, creating a cozy and welcoming space. Come for the location, stay for the charm 🏖️✨ (4 Max. Guest/Strictly Enforced & No Pets Strictly Enforced!)

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.

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.

Family/Group Getaway w/ Pool Near Clearwater Beach

🏖️ Private pool + 4BR | 9 mins to Clearwater Beach Bring the whole group to this spacious 4-bedroom home designed for relaxing and entertaining. Enjoy a private pool, oversized backyard, and plenty of room for families and friends to spread out. ✔ Sleeps large groups comfortably ✔ Private pool + outdoor space ✔ Fully equipped kitchen + fast WiFi Just minutes from Clearwater Beach, dining, and attractions—your ideal home base for a fun, easy Gulf Coast getaway.

Clearwater Beach, Stunning 2/2.5, City View, 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!