Holiday rentals in Clearwater

4.91 out of 5 average rating, 184 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.

4.91 out of 5 average rating, 200 reviews

Home in Largo

The Oasis - Arcades - Golf & Games - HTD Pool

Staying at The Oasis is the perfect blend of vacation and home. Every detail was carefully thought out to provide guests two things: comfort and fun. The ULTIMATE vacation awaits you. Whether a group of friends or your family vacation, this home was designed with relaxation AND fun in mind. Located within walking distance to Largo’s beautiful Central Park and a few miles to the beach, you can spend the day exploring the area or truly relax in the resort style, private backyard. BUT! No parties

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, 181 reviews

4.97 out of 5 average rating, 390 reviews

The exterior of a coastal cottage is shown, featuring a gravel driveway and tropical landscaping with palm trees. Two wicker chairs are positioned under a covered porch, inviting relaxation. Large windows allow natural light to brighten the welcoming facade.

Cottage in Dunedin

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 gorgeous waterfront sunsets, then drive minutes to the beaches. Pet-friendly. Every detail beautifully done—reserve the Barefoot Parrot today.

5.0 out of 5 average rating, 18 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.

Apartment in Clearwater Beach

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.

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, 482 reviews

A welcoming basket sits on a light-colored countertop, filled with snacks and bottled water. A decorative sign reads 'Welcome to Our Little Piece of Paradise.' A small potted plant is positioned nearby, and the kitchen's modern appliances are visible in the background.

4.98 out of 5 average rating, 106 reviews

Harbor Breeze Hideaway 4/2 King size bed!

Welcome to our beautiful city of Clearwater and to our unique Mid-Century modern style home. Centrally located within 20 minutes driving to the famous and award-winning Clearwater beach and 20 min driving to Tampa international airport. Easy access to local restaurants, bars, stores, super markets and mall. This comfortable home features unique design and layout with Mid-century modern furniture and decor, free Wi-Fi, smart TV’s, tile flooring; sleeps up to 10 people and has free parking.

4.94 out of 5 average rating, 116 reviews

Clearwater-Pickleball/SltPool/Golf/Theatre/Arcade

Welcome to Clearwater Tranquility- Our unique space offers endless amenities and fun! With over 5000sq ft there's room for the whole family to enjoy. Most rooms have a view of the yard &pool! Inside includes a movie theatre, 3 dining spaces, 2 living rooms, 2 primary bedrooms, game room, yoga studio,arcade games, home gym/sauna and a wet bar to make your favorite cocktails or juices. Outside presents an Olympic sized swimming pool, pickle ball, mini golf, outside dining, fire pit &more

5.0 out of 5 average rating, 56 reviews

Vacation At Lantana

Come enjoy our home, whether you are coming for the beach or the theme parks our home is conveniently located in the heart of Pinellas County. With the Inter-Coastal/Gulf Waters less then a mile away, a walk or bike ride will land you at marinas, beach’s and even Honeymoon island state park. But you can also take a short car ride with your friends or family to the theme parks, airports, Big city’s, Sport venues, State parks, Camping and all the beautiful activities Florida has to offer!

4.98 out of 5 average rating, 234 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

4.94 out of 5 average rating, 34 reviews

Clearwater-Dunedin Retreat-steps from water views

Welcome to your newly renovated duplex, designed for families and friends seeking comfort, convenience, and a bright coastal vibe. Enjoy modern open living, stylish finishes, and a warm, inviting atmosphere that feels like home from the moment you arrive. Perfectly located just 1.4 miles from Downtown Clearwater, 3 miles from Dunedin’s most charming, walkable downtown, and 4.2 miles from award-winning Clearwater Beach—experience the best of sun, sand, and city charm.

4.9 out of 5 average rating, 10 reviews

Providence Cove | Heated Salt Pool • Sleeps 12

Welcome to Providence Cove, your luxury retreat just minutes from Clearwater Beach! Relax in the heated saltwater pool, enjoy private mini golf, gather around the fire pit, and create unforgettable memories with family and friends. Sleeps up to 12 guests and features stylish bedrooms, a fully equipped kitchen, fast Wi-Fi, private parking, and a curated vacation guide with our favorite local beaches, restaurants, and attractions. 🌴✨🌊🫶🏻🌞

Popular amenities for Clearwater holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Clearwater

Superhost

4.87 out of 5 average rating, 38 reviews

Heated Pool, Games, Spa & 10 Min to Beach

5.0 out of 5 average rating, 71 reviews

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

Wonderful Condo at Avalon - Fully Renovated

4.97 out of 5 average rating, 29 reviews

Home in Ozona

Honeymoon Luxury Residence with Heated Pool &Sauna

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

4.94 out of 5 average rating, 70 reviews

Heated pool, pickleball, mini golf near beaches

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)

4.95 out of 5 average rating, 19 reviews

Home in Clearwater Beach

4 Bedroom, 3 Bathroom House 1 Block From The Beach