Vacation rentals in Clearwater

4.91 out of 5 average rating, 204 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

4.97 out of 5 average rating, 392 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 comfortable stay. Fully stocked. Walk to dining, shops, breweries, and Dunedin’s stunning waterfront sunsets, then drive minutes to the beaches. Pet-friendly. Every detail beautifully done—reserve the Barefoot Parrot today.

Condo 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, 183 reviews

Condo in Clearwater Beach

A private balcony is seen featuring two white chairs and a table, offering uninterrupted views of the Gulf of Mexico. The calming blue sky meets the horizon, enhancing the serene beachfront experience.

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.

4.91 out of 5 average rating, 338 reviews

4.94 out of 5 average rating, 102 reviews

PVT Heated Pool + Spa + Game Room, Dream VacaHome

🏊Private saltwater heated pool with built-in spa. 🎮Newly added air-conditioned game room with pool, ping-pong, foosball, air hockey and a classic arcade cabinet. 🌴 Fenced yard with cornhole, covered lanai and grill. 🛏️ This 5-bedroom, 3-bath home comfortably hosts up to 10 guests, with two living rooms, a full kitchen, WiFi, laundry and parking for four.—all a short drive from Clearwater Beach and Indian Rocks Beach. 🏡 Bring the whole crew to a Clearwater retreat built for fun!

Townhouse in Clearwater Beach

A modern kitchen showcases white cabinetry with marble countertops and stainless steel appliances. Natural light floods through large windows, highlighting decorative accents and elegant floral arrangements. A central island is surrounded by bar stools, complemented by stylish area rugs beneath.

Waterfront Beach House Steps Away from #1 Beach!

Welcome to The Bombshell Beach House! This 3 story, 3 bedroom luxury water-front townhouse located in Clearwater Beach, FL has been a childhood dream come true for me as a Clearwater native! As avid travelers, my husband and I wanted to create a STAY-CATION spot that mixed in all of the comforts of HOME with all of the luxuries of a 5 star vacation & this beach house is JUST THAT! This listing is brand new and we are expecting dates to book extremely fast! Book now to secure your GETAWAY!

5.0 out of 5 average rating, 152 reviews

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.

4.88 out of 5 average rating, 8 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

4.93 out of 5 average rating, 122 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

4.97 out of 5 average rating, 62 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, 237 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

Townhouse in Clearwater Beach

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.

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.

4.99 out of 5 average rating, 148 reviews

Popular amenities for Clearwater vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Clearwater

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)

4.98 out of 5 average rating, 94 reviews

A spacious living area features a comfortable gray sofa adorned with colorful pillows, complemented by a wooden coffee table. A large piece of coastal art hangs on a teal wall, while light streams in from the open dining area, showcasing bar stools and a bright kitchen beyond.

Condo in Clearwater

Key West Oasis, Chic 1 BR, A+ Pool, 3mi to Beach

5.0 out of 5 average rating, 22 reviews

Apartment in Clearwater

the Salty Pearl at Clearwater /Hot Tub/

4.98 out of 5 average rating, 50 reviews

Home in Oldsmar

Modern Private Estate | Central to Tampa & Beaches

4.88 out of 5 average rating, 41 reviews

Heated Pool, Games, Spa & 10 Min to Beach

4.93 out of 5 average rating, 29 reviews

Apartment in Clearwater

Cozy Modern Studio • Private • Central Clearwater

4.96 out of 5 average rating, 57 reviews

Pickleball-BBall-Volley-Bocce, Pool & Bar Resort