Holiday rentals in Clearwater

4.9 out of 5 average rating, 189 reviews

Heated Pool & Spa • Pergola Swing

"Peaceful pool/spa haven with a responsive host." That's how a guest described Viewtop, our single-story Clearwater pool home with a heated pool and spa, and a pergola hung with two porch swings. Coffee in the pergola swings at sunrise, a dip in the spa, a game of pool or a round on the arcade in the game room, dinner under the chandelier, then a movie on the 65-inch Roku. King master, two queens, a queen, and two queen sleeper sofas in the second living room. Eleven minutes to Clearwater Beach.

4.98 out of 5 average rating, 366 reviews

A two-story beach-style house is depicted, featuring a covered porch with white railings and blue shutters on the windows. Potted plants adorn the porch, complementing the light exterior. Lush greenery is visible in the background, providing a tropical ambiance.

Home in Dunedin

Steps to Downtown, Mins. to Waterfront | Sleeps 8

Steps from Main Street Dunedin, a short walk to the waterfront and an easy drive to award-winning beaches, Honeymoon Island & Clearwater Beach. Experience the charm of the Barefoot Parrot House, a private pet friendly house with designer decor and abundant outdoor space. Walk, bike, or cart to stunning sunsets, shops, dining, breweries, and Pinellas Trail. Perfect for families, couples, groups. Loaded with beach gear, kids's items & pup supplies. Treat yourself to this Dunedin favorite today !

The exterior of a retro home is highlighted by a red vintage truck parked in the driveway. Lush greenery, including palm and flowering plants, surrounds the property, while two distinct pathways lead toward the entrance. The warm concrete driveway complements the inviting atmosphere.

5.0 out of 5 average rating, 122 reviews

Sleeps 10, pet friendly/ fenced yard, near beaches

Step into 1960, skip the ordinary vacation rental and stay somewhere your family will actually remember. From the colorful retro diner and vintage décor to the fenced backyard and playful details throughout the home, every room was designed to make you smile, walk to Publix. Just minutes from Clearwater Beach, you'll enjoy modern comforts wrapped in a one-of-a-kind nostalgic Florida experience. This is Not just a place to stay it’s an experience you’ll talk about long after your vacation ends.

Apartment in Clearwater Beach

A scenic view of a fishing pier extends into the water, framed by gentle waves and a sandy beach. The sky is filled with colorful clouds, reflecting hues of orange and blue as the sun sets on the horizon.

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.

4.98 out of 5 average rating, 184 reviews

4.89 out of 5 average rating, 179 reviews

Pool, King Bed, & Outdoor Kitchen - Near Beaches!

Relax by the pool, sit inside the screened in party room, with mini fridge, 55" smart TV, & BBQ grill, while enjoying the best weather Florida has to offer. Located 5 miles from the world famous Clearwater beach. Every restaurant, bar, and store you could possibly want within a 2-mile radius. Baseball fans will love catching Spring Training games at Spectrum Field, home of the Philadelphia Phillies, located just a short 10 minute WALK from the house. You will love making memories here!

4.91 out of 5 average rating, 11 reviews

Clearwater Pool Oasis|3 BR|2 King Beds|Near Beach

Welcome to "Isa" your Clearwater retreat! This fully remodeled 3-bedroom, 2-bath private pool home features 2 king suites, a fully equipped kitchen, a dedicated workspace with a desk, and a relaxing outdoor oasis with comfortable patio furniture. Conveniently located just minutes from Clearwater Beach and charming Downtown Dunedin, you’ll enjoy easy access to award-winning beaches, waterfront dining, breweries, shopping, and local attractions while returning home to your own private escape

5.0 out of 5 average rating, 19 reviews

Designer Home | 10 Min to Dunedin Waterfront

Designer home 10 min to Downtown Dunedin, 15 to Honeymoon Island and Clearwater Beach. Sleeps 6: king bed, queen bed, and queen sleeper in a flex/office room. Two renovated baths with rain shower, open kitchen with large granite island, Nespresso coffee bar, and dining for 6. Private fenced backyard with covered patio lounge, outdoor dining with grill, and a second lounge under the palms. Game room with ping pong. Your home base for beaches, spring training, and the best of the Gulf Coast.

Superhost

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.

Apartment in Clearwater Beach

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, 492 reviews

A well-lit bedroom features a spacious white bed with crisp linens and a decorative bedside lamp on a nightstand. A ceiling fan adds to the comfort, while windows with shutters allow natural light. The open doorway leads to a hallway, hinting at additional living spaces.

4.83 out of 5 average rating, 77 reviews

Spacious 3BR, Central Location MD.BNB-Indigo(6G)

Welcome to your tropical oasis! This charming 3-bedroom, 3-bathroom home is your gateway to a vacation filled with unforgettable experiences. Just 30 minutes away, discover some of the finest beaches in Florida, an exciting array of world-class entertainment, and a plethora of extraordinary activities. After a day of adventure, retreat to the serenity of your own private, fully fenced backyard. Embrace the perfect blend of relaxation and exhilaration. Don't miss out-reserve your stay now!

4.97 out of 5 average rating, 157 reviews

Apartment in Clearwater

Spacious Key West Retreat, Fun 2 BR, Resort Pool

🌴 😎 Stunning Key West Style Retreat featuring: - Memory Foam Queen bed - Covered porch for unwinding - Hotel linens, towels and many creature comforts. Enjoy beach 🏄‍♂️ vibes decor in this spacious two bed two bath property. Located less than three miles from the white, sugar sand of Clearwater Beach 😎 (rated #1 beach in the US by Trip Advisor). Relax by the oversized resort style pool and clubhouse. Convenient walking distance to nearby restaurants and grocery stores.

4.98 out of 5 average rating, 240 reviews

Specious home W/ Heated Pool ! ! ! Great Location.

Cozy, spacious home 🏡 w/ heated swimming 🏊‍♀️ pool, next to a golf ⛳️ course. Close to the famous beaches ⛱️, St.Pete and Tampa. This cozy open home has a large living room, big kitchen and pool deck patio. All 3 bedrooms have large TV's. The big back patio has a swimming 🏊‍♀️ pool, TV, fridge and BBQ for cook outs & R&R. Located in a quiet family-friendly neighborhood. Location! 15 min - Clearwater Beach, Dunedin, Safety Harbor 30 min from - St.Pete, TPA Airport, Tampa

The exterior of a single-story home is depicted, featuring a well-manicured lawn and palm trees. A driveway leads to a garage, while colorful plants border the walkway. The house's façade is painted in neutral tones, highlighted by bright wooden shutters on the windows.

5.0 out of 5 average rating, 52 reviews

Sea Turtle Cove

Welcome to Sea Turtle Cove! We are delighted to have you as our guest and hope that you have a fantastic stay with us. This 3 bed 2 bath home has been recently renovated to create a clean, cozy, and your home away from home experience close to Clearwater Beach! Take some time to settle in, explore the area, and make yourself at home. Clearwater and Tampa has so much to offer, from beautiful beaches to vibrant local attractions. Wishing you a fantastic time in Clearwater!

Popular amenities for Clearwater holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Clearwater

4.97 out of 5 average rating, 65 reviews

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Flat in Clearwater

Cozy Modern Studio • Private • Central Clearwater

4.97 out of 5 average rating, 66 reviews

Elegant Living: Spacious 4-Bedroom, 3-Bath Home

4.75 out of 5 average rating, 441 reviews

A waterfront balcony features wooden chairs and a small table, offering views of palm trees and the waterway. The area below includes a dock and a green landscaped space, highlighted by sunlight under a clear blue sky.

Flat in Clearwater Beach

Surf n Sand Townhouse 20

4.98 out of 5 average rating, 51 reviews

Home in Oldsmar

Modern Private Estate | Central to Tampa & Beaches