Guesthouse holiday rentals in Clearwater

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Top-rated Guesthouses in Clearwater

Guests agree: These guesthouses are highly rated for location, cleanliness and more.

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Guest favourite

Guesthouse in Tampa

4.93 out of 5 average rating, 322 reviews

Beautiful, cozy guesthouse in the heart of Tampa

Enjoy a stylish experience at this centrally-located guesthouse with much of what Tampa has to offer, just a short ride away. Perfect for 3 adults w/ 1 queen bed & a futon. Guest add. available for a fee. 8 min - Tampa International Airport 4 min - Bucs Stadium 8 min - Amalie Arena 8 min - downtown Tampa 7 min - International Mall 9 min - Ybor City 8 min - Soho 16 min - Busch Gardens 30 min - both Clearwater and St. Pete Beaches Many of Tampa's best restaurants and bars within a 3 mile radius!

Guest favourite

Guesthouse in Riverview

4.89 out of 5 average rating, 120 reviews

Spacious Industrial Style Studio Guesthouse

Welcome to Riverview Cottage - A beautiful, fully renovated, industrial/modern guest house only 10 miles from Tampa Bay! In this 450 square foot guest house, you'll enjoy all the regular luxuries of a full-size home without sacrificing comfort! Best of all enjoy a FULLY fenced-in entrance and private yard + parking for up-to 2 vehicles! Whether stopping by for work or leisure, you are sure to enjoy this thoughtfully designed space complete with full-size kitchen, bathroom, and living space.

Guest favourite

Guesthouse in Historic Old Northeast

4.88 out of 5 average rating, 285 reviews

Private Guest Studio w/Courtyard

Enjoy your own private guest studio separate from the main house (no main house access). Located 1 mile from downtown and 1/2 mile from Tampa Bay. Guest studio includes one queen size bed, one full bathroom with shower (no tub), brand new air conditioner, mini fridge, 32" smart TV (login to your favorite streaming options and enjoy, no cable provided), a microwave and a coffeemaker. Great walking ability. We do not allow animals, any pet related questions please inquire with us prior to booking!

Guest favourite

Guesthouse in St. Petersburg

4.98 out of 5 average rating, 207 reviews

Cozy Guesthouse Near Downtown (Non-Toxic)

Come relax in this calm, newly renovated guest suite. Clean, natural, & chemical free - diffusers and oils available on site. Amenities like central a/c, laundry, private patio, full kitchen, Netflix & Hulu. A short 5 minute drive from downtown - near tons of local restaurants, entertainment, and beaches. St. Pete loves the local vibe, be sure to check out our visitors guide for suggestions on spots to see while you’re here. It doesn’t get any better than St Pete! Book your stay with us today!

Superhost

Guesthouse in Old Seminole Heights

4.91 out of 5 average rating, 192 reviews

Guest House close to Attractions

Our guesthouse is a great space for a couple or two friends traveling together. We have two beds for your stay. One is a traditional queen in the back bedroom space and the other is a queen foldout couch in the living room space. There is a small kitchenette with sink, refrigerator/freezer, microwave, coffee maker and toaster. You will enjoy many great independent restaurants and breweries my neighborhood has within a short distance. Plenty of space in yard to relax and hang out as well.

Superhost

Guesthouse in Tampa

4.74 out of 5 average rating, 132 reviews

Cozy guesthouse, 1 Bed, 2 miles from Busch Gardens

This cozy 1-bedroom guesthouse has everything you need for your TAMPA trip. The unit comes with Wi-Fi, free coffee and tea, and a TV. During your stay, you can also enjoy using a convenient private bathroom, kitchen, and living room. Our house is within 5 miles driving distance from Seminole Hard Rock Casino, only 1.5 miles driving distance from Busch Gardens Tampa Bay, as close as 1.3 miles from University of South Florida and several popular restaurants. An ideal base to explore TAMPA.

Superhost

Guesthouse in Tarpon Springs

4.83 out of 5 average rating, 293 reviews

Papa Bear's Cottage Two Bedroom Vacation Rental

A simple, yet magical second-story guesthouse, nestled into a yard of Spanish Moss and Magnolia trees, above a garage (no one will be in the guest house but you!). Minutes from downtown Tarpon Springs and the famous Sponge Docks, and 15 minutes from beautiful Gulf beaches, 30 minutes from Clearwater Beach. Hunkered in at the end of a private drive, on over two acres of quiet, enchanting land. You and your crew will enjoy the respite, nature, and coziness of Papa Bear's Cottage!

Guest favourite

Guesthouse in Tampa Heights

4.97 out of 5 average rating, 114 reviews

Cute Guesthouse by the Riverwalk, w/patio and WFH

Enjoy a stylish experience at this centrally-located detached guesthouse with patio and fire pit. Fully equipped with a WFH setup for your workcation and close to all Tampa has to offer. The Riverwalk as well as Armature Works is close. It’s a quick ride to the stadium. A walk on the beach is a drive away. Easy access to Tampa International airport . Quiet guesthouse recently refurbished with a full kitchen and a dedicated work space. Wifi and air conditioning.

Guest favourite

Guesthouse in Old Seminole Heights

4.87 out of 5 average rating, 886 reviews

Seminole Heights Riverside Paradise w/Pool

Whether you're traveling for business, seeking a FL adventure or a short getaway staycation, the stunning waterfront views, pool & incredible amenities with convenient proximity to downtown Tampa, airport & area attractions, the guesthouse at Isla de Dij is the perfect accommodation. You'll fall in love with the massive live oaks that line the brick paved streets, the glassy waters of the Hillsborough River and the brilliant sunsets that paint the evening sky.

Guest favourite

Guesthouse in Old Seminole Heights

4.81 out of 5 average rating, 140 reviews

Cozy Cottage in Seminole Heights

The Hiawatha House is a one bedroom one bathroom suite with a full kitchen. This space is newly renovated with all new stainless steel appliances! The outdoor deck is beautiful with an area to sit and enjoy a cup of coffee or tea. The property is located in charming Seminole Heights. It is within walking distance of some of the best restaurants in Tampa. A short drive from downtown and Raymond James stadium, this is the perfect place for any Tampa trip.

Guest favourite

Guesthouse in Palma Ceia

4.93 out of 5 average rating, 107 reviews

Spacious Charming Hyde Park Cottage

Our spacious 850sf Historic Hyde Park cottage is blocks from Bayshore, a short walk to Bern’s, Hyde Park Village, and numerous restaurants and bars! This charming 2/1 (queen/twin), 2nd story carriage house is in the heart of Hyde Park! Please send a message if you do not see your dates available. Note that the cottage is not next to the highway as the map view may suggest. Ask about amenities in our well-equipped kitchen and longer-term stays.

Guest favourite

Guesthouse in Pass-a-Grille Beach

4.9 out of 5 average rating, 186 reviews

A Hidden Gem Steps to Pass-a-Grille Beach Dogs Ok!

We are grateful to share that this beautiful upstairs cottage unit is Guest Ready!! It was not damaged by the storms and we are excited to start taking reservations again! Many establishments throughout the Gulf beach areas have reopened. Your stay provides the much needed support our local businesses appreciate and need as they recover. Please note that there is renovation work ongoing to the downstairs cottage.