Vacation rentals in Clearwater Beach Island

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Top-rated vacation rentals in Clearwater Beach Island

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Top guest favorite

The exterior of a charming blue beach house is surrounded by lush palm trees and vibrant landscaping. A spacious front yard features a green lawn and neatly trimmed bushes, while a driveway accommodates parked vehicles. Sunlight filters down, creating a warm atmosphere.

Home in Clearwater Beach

4.98 out of 5 average rating, 123 reviews

THE HOUSE - 32 Steps to the Beach - Beautiful Clearwater Beach Home just across from the Beach - Drive to your door.

House sleeps 6 - Private patio and Hot Tub, Wifi, Grill . '32 Steps to the Beach' is a charming and cozy Clearwater Beach retreat in a TOP LOCATION. The pristine Gulf Beach is just across the street! We also have a Cottage at the same address and they can be rented separately or together. Covid-19 UPDATE - See below. To book the House & Cottage or the Cottage on its own please see the links to their descriptions at the right of this page. THE HOUSE is a tastefully decorated, upscale and well-equipped beach home that has been completely remodeled. It sleeps 6 guests and offers 3 bedrooms, 2 bathrooms, an open kitchen and a cozy living/dining area with a sofa sleeper. You will love the secluded, tropical patio which offers a hot tub and a BBQ for relaxing moments. The property is located in a quiet and upscale, residential neighborhood of Clearwater North Beach, just across the street of the beautiful and pristine Gulf Beach. Clearwater Beach with its vibrant public beach life, various shopping opportunities and diverse restaurants is just a mile away. The House and Cottage can be BOOKED TOGETHER OR SEPARATELY and are the perfect place for families, family get togethers or romantic get-aways. It is NOT SUITABLE FOR SPRINGBREAKERS or any group that wants an environment that allows loud parties. THE AWARD-WINING GULF BEACH IS ONLY 32 STEPS AWAY! Grill, TVs, cable, WIFI, multiple driveways for parking, beautiful landscaping. Walk to shopping, dining or island attractions. Take the public trolley around the island or go as far south as Treasure Island! Check-in is 4:00pm or later; check-out is promptly at 10:00am to leave time for cleaning crew. IMPORTANT: We do not advertise on Craigslist! Be safe and only deal with the owner. COVID-19 Pinellas County is open for short term vacation rentals with guidelines that we are following in full. We take the safety of our guest and cleaning staff extremely seriously. Our cleaning crews are using sanitizer and disinfectant on all surfaces before your arrival and as cleaning is taking longer than previously it is unlikely that we can offer early check-ins or late checkouts. Our houses have well equipped kitchens and we believe that separate units are the best option for vacationing in the time of Covid-19. Florida is seeing an increase in cases at the moment and we stress the importance of guests taking travel insurance that would cover them in the event that they no longer want to travel to Florida. In the event that the administration halts vacation rentals we would of course refund guests as we could no longer accept them. We have to stress that after two months of cancellations and re-bookings we will not be able to offer refunds if Clearwater Beach remains open for vacation rentals but guests decide not to travel.

Superhost

A spacious living area features soft gray couches, a coffee table, and a large television. Natural light filters through the partially transparent window coverings. A dining table with chairs is visible in the corner, complemented by light-colored hardwood flooring throughout the space.

Apartment in Clearwater

4.9 out of 5 average rating, 167 reviews

NEW! Luxurious King Bed! 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 gate you can see the beach entrance. Locate 1 house from the sugary white sands of the world famous Clearwater Beach! Also located within walking distance of practically everything including many great restaurants, bars, shops, Pier 60, the marina 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!

Top guest favorite

A private backyard space is highlighted, featuring a heated swimming pool surrounded by lounge chairs and a shaded seating area. Lush greenery and tropical plants frame the space, creating a tranquil outdoor retreat with a colorful sunset sky overhead.

Home in Clearwater

5 out of 5 average rating, 23 reviews

4-Bed Beach Retreat: Steps to Sand + Private Pool

Relax, Unwind, and Make Memories at Our Clearwater Retreat This spacious 4-bedroom home sleeps 10 and is just 200 steps to the white sands of Clearwater Beach. Enjoy a private heated pool, BBQ grill, and outdoor shower in your backyard paradise. Inside, bright and airy spaces offer modern comfort with coastal charm. Walk to top restaurants, shops, and Pier 60. Perfect for families or groups, our home has earned 5-star reviews for its comfort, cleanliness, and unbeatable location. Book now!

Top guest favorite

A bright and airy living room features a large, blue sectional couch adorned with decorative pillows. A flat-screen TV is mounted on a stone accent wall, while natural light filters in through sheer white curtains. A wooden coffee table displays a small decorative tray.

Home in Clearwater

4.94 out of 5 average rating, 113 reviews

Best Location in Clw! Near Beach & Saltwater Pool!

PRIME LOCATION NEAR BEACH! Welcome to our newly renovated vacation home in beautiful Clearwater, FL. Located in the heart of downtown Clearwater within walking distance to several restaurants and shops and just a few mins drive to Clearwater Beach. This coastal styled home comes with a heated pool (at no extra charge), putting green, and a fun little game room for kids! The entire home is yours to enjoy and comes fully stocked with everything you need for a relaxing beach getaway vacation.

Guest favorite

A set of two white wicker chairs and a small table are positioned on a balcony, providing views of the Gulf of Mexico. The ocean and sandy beach stretch into the distance, with clear blue skies overhead.

Condo in Clearwater

4.9 out of 5 average rating, 383 reviews

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.

Superhost

A cozy bedroom features a king-sized bed with soft linens, alongside a nightstand illuminated by a gentle lamp. A window allows natural light to enter, framing a view of palm trees outside. Walls are painted in a warm tone, creating a relaxed atmosphere.

Apartment in Clearwater

4.79 out of 5 average rating, 168 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 favorite

A sandy path leads through lush greenery towards the beach, framed by overhanging branches. The ocean is visible in the distance, with light reflecting off the water. Shadows create a peaceful atmosphere as the sun casts a warm glow.

Cottage in Indian Shores

4.96 out of 5 average rating, 163 reviews

Beautiful Beachfront Cottage on the Water

Renovated, romantic 1937 beach front cottage. Last of its kind in the quiet family setting of Indian Shores Florida, halfway between Clearwater Beach and Treasure Island/John's Pass. Truly an "Old Florida" experience with original pine floors, Florida room and covered porches, as well as updated kitchen and bathroom. This house, uniquely built near ground level, allows it to be waterfront on the beach while shaded by huge pine trees. You won't find a more tranquil setting on the beach.

Superhost

A sandy pathway leads through beach grass and wildflowers, with palm trees framing the scene. The azure ocean and clear blue sky serve as a backdrop, inviting guests to enjoy the nearby beach.

Cottage in Clearwater

4.87 out of 5 average rating, 134 reviews

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.

Guest favorite

A modern dining area features a round glass table set for six, surrounded by white chairs. A unique blue chandelier hangs above, while large windows offer a view of the water. The kitchen area is equipped with white cabinetry and stainless steel appliances.

Apartment in Clearwater

4.89 out of 5 average rating, 227 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.

Guest favorite

A spacious bed is positioned in front of large windows offering views of the Gulf of Mexico. Soft blue accent pillows complement the bedding. Outside, two chairs on the balcony overlook the sandy beach, creating a serene coastal ambiance.

Condo in Clearwater

4.96 out of 5 average rating, 75 reviews

#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!

Top guest favorite

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, 113 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 favorite

A balcony view features two cushioned chairs adorned with pink pillows, overlooking a quiet street leading to the beach. Palm trees and lush greenery frame the scene, while the ocean is visible in the distance. Bright blue skies enhance the coastal atmosphere.

Condo in Clearwater

4.99 out of 5 average rating, 157 reviews

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.