Holiday rentals in Clearwater Beach Island

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Top-rated holiday rentals in Clearwater Beach Island

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Top guest favourite
Gentle waves lapping against a sandy shore create a serene coastal scene. The sky is filled with wispy clouds and varying shades of blue, reflecting the tranquil atmosphere of the beach. The shoreline reveals patterns in the wet sand as the water recedes.
Apartment in Clearwater
4.95 out of 5 average rating, 313 reviews

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!

Top guest favourite
A modern kitchen is presented with stylish white cabinetry and a spacious concrete countertop. Two pendant lights hang above the bar seating, which features four black chairs. Stainless steel appliances, including a refrigerator and microwave, are visible, providing a well-equipped cooking space.
Apartment in Clearwater
5 out of 5 average rating, 56 reviews

Wonderful Condo at Avalon - Fully Renovated

Ground Floor Completely RENOVATED!!! Amazing & Very cozy and it has a a 60” Fireplace. 1 king size bed and a queen pullout couch new style, 1 bathroom with the best water pressure including a rain shower and a hand held unit. This unit is very well equipped with everything you need and have at your home. The condo is great for a couple’s getaway or a nice family vacation. YOUR HOME AWAY FROM HOME!!! Steps to the POOL, beach chairs, Floaties, wagon, cooler, etc. The Beach is a 10 minutes!!

Top guest favourite
A spacious living area is presented with a modern sofa adorned with decorative pillows. Two comfortable armchairs complement a circular coffee table. Natural light floods the space through sliding glass doors, leading to an outdoor patio with water views. Soft, neutral tones and contrasting textures are visible.
Flat in Clearwater Beach
4.91 out of 5 average rating, 151 reviews

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.

Guest favourite
A wide view of Clearwater Beach showcases soft white sand lined with colorful umbrellas and beach towels. Bathers enjoy the warm waters where turquoise waves meet lighter green ones. In the background, beachgoers can be seen near the resorts and other structures along the shoreline.
Apartment in Clearwater
4.94 out of 5 average rating, 116 reviews

Beach Haven in South Clearwater Beach

This unique two-story vacation rental with a loft is perfect for a large family or two. It has large panoramic windows with incredible views of the harbor from every bedroom and living space. The Dockside Condos are centrally located in South Clearwater Beach close to all the action of Shephard's nightclub, restaurants, sports bars, miniature golf and more, as well as being only two blocks to the beach. Come and enjoy this condo just one block from the white sands of Clearwater Beach.

Top guest favourite
A covered patio features four comfortable wicker chairs surrounding a glass-top table. Large windows provide views of palm trees and the sunset over the water, creating a serene outdoor space for relaxation.
Flat in Clearwater
4.94 out of 5 average rating, 87 reviews

Gorgeous and Updated Waterfront Condo 2 Bed/2 Bath

Relax in this renovated waterfront apartment. Unwind after your day at the beach on the patio overlooking the sun setting over the water. This fresh space has everything you need for your stay; a full kitchen stocked with cooking supplies, two full bedrooms & bathrooms, a large living area with ocean views to name a few highlights. Only 5 miles to the #1 rated Clearwater Beach, 1.3 miles to the fun Downtown Dunedin, a block to the Pinellas Trail, & 1 mile to the Blue Jay’s stadium!

Top guest favourite
A bright and airy kitchen and living area are visible, featuring white cabinetry and modern stainless steel appliances. A cozy sectional sofa is positioned near a window, while a subtle area rug adds warmth to the space. A flat-screen television is mounted on the wall, enhancing the functional layout.
Guest house in Clearwater
4.97 out of 5 average rating, 39 reviews

New private guesthouse walk to downtown Dunedin

This new construction (July, 2024) unique and tranquil unit is perfect for your weekend getaway or a longer stay. Light, bright and neutral, 10 foot ceilings make property feel more spacious. Very quiet and private, concrete block construction provides solid insulation. Close to Clearwater and Honeymoon Island beaches, walking distance to TD Ballpark .6 miles, downtown Dunedin 1.2 miles to shops and restaurants, Pinellas Trail is across the street, easy transit to airport.

Guest favourite
A spacious living area showcases a dark gray sleeper couch adorned with decorative pillows, including one that reads 'Beach Life.' A light-colored wall provides a backdrop for a decorative sign that reads 'happy place.' Natural light filters in from windows leading to the kitchen.
Home in Clearwater
4.89 out of 5 average rating, 106 reviews

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!

Top guest favourite
The image captures a spacious townhouse community, featuring white architectural designs. A clear view of the intercoastal waterway is presented, with boats visible in the distance. A community pool is seen among vibrant greenery, inviting leisure and relaxation.
Townhouse in Clearwater
4.99 out of 5 average rating, 124 reviews

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.

Guest favourite
A living area features a navy blue sofa and wooden coffee table, with a decorative fish wall art and plants adding a coastal touch. A television is situated on a sleek white console. Light wood flooring enhances the spacious feel, complemented by a welcoming 'Welcome' sign.
Flat in Clearwater
4.85 out of 5 average rating, 170 reviews

Waterfront Courtyard Condo 2 Blocks to Beach

🌊 Ultimate Waterfront Escape – Adventure Awaits! πŸš΄β€β™‚οΈπŸ„β€β™‚οΈ 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. We are pet friendly! Pet fee is $150 for the first dog, $100 for the second dog.

Guest favourite
Apartment in Indian Shores
5 out of 5 average rating, 6 reviews

Oceanview Seaside Cottage | Walkout Beach Access

Wake up to the sound of the waves at this charming oceanfront cottage! Enjoy coffee on your ocean-view balcony or step right onto the sand with walk-out beach access. Inside, relax in the king bedroom or on the pullout sofa with inflatable topper. Smart TVs, an updated kitchen, and coastal dΓ©cor add comfort and charm. Outside, unwind on the patio with chairs and a picnic table. Beach essentials included for a stress-free stay.

Guest favourite
A private balcony offers a stunning view of the Gulf of Mexico, showcasing the shimmering water and distant shoreline. Comfortable seating provides a perfect spot to enjoy the serene surroundings, while the expansive sky features scattered clouds and sunlight reflecting off the water.
Apartment in Clearwater
4.93 out of 5 average rating, 30 reviews

1/1 located at JW Marriott on Clearwater Beach,914

JUST LISTED! Beach front, water and beach view! Relax and unwind at this luxurious condo located at the JW Marriott Resort and Spa on Clearwater Beach! This privately owned 1-bedroom, 1-bathroom residence features stunning views of the Gulf of Mexico from your 9th floor private balcony, which is accessible from both bedrooms and the living room. The unit sleeps up to 4.

Top guest favourite
A spacious bedroom features a king bed dressed in neutral linens, complemented by decorative pillows. A ceiling fan circulates air above, while sliding glass doors provide access to a private patio. A wall-mounted television is positioned for comfortable viewing.
Townhouse in Dunedin
5 out of 5 average rating, 45 reviews

Coastal Retreat in Downtown Dunedin w/ Yard+Grill

These luxury townhomes were thoughtfully built as vacation havens in the heart of Downtown Dunedin, a place we proudly call home. Designed with privacy in mind, each home features professionally built lockout units between floors and neighboring townhomes, allowing guests to book individual spaces or entire homes - while always maintaining complete privacy and comfort.

Popular amenities for Clearwater Beach Island holiday rentals

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Pinellas County
  5. Clearwater
  6. Clearwater Beach Island