Guesthouse vacation rentals in Clearwater

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Top-rated guesthouse rentals in Clearwater

Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Guesthouse in Clearwater

4.92 out of 5 average rating, 332 reviews

Clearwater Guesthouse w/ King Bed, Near Beaches

This private home away from home sits behind the main house in a quiet neighborhood conveniently located near downtown Clearwater, Clearwater Beach, Tampa, St Petersburg, Dunedin, Tarpon Springs, and other great towns. Located near Beaches, restaurants, shopping, & entertainment venues. • Clearwater Beach= 4 miles / 8 minutes • Downtown Dunedin= 3 miles • Honeymoon Island= 9 miles • Tarpon Springs Sponge docks= 14 miles • Tampa Airport (TPA)= 14 miles • St Pete/Clearwater Airport (PIE)= 9 miles

Jun 6 – 13

G$16,657 GYD per night

Guest favorite

Guesthouse in Largo

4.99 out of 5 average rating, 300 reviews

Paradise Cottage Largo 2 miles to beach private+

We are PARADISE COTTAGE and the standards of super host are status quo! Come on down - we're ready for you! Although only 2 miles from the Gulf, we're on high ground! We are on a Priority One Energy Grid. With over 300 plants, many trees, we live in a lush tropical "Paradise". Our guests' highest praises include the private, quiet, serene, safe and secluded attributes we're fortunate to claim, no neighbors while being so close to so much. Read on in the next section "The Space" to learn more

Oct 29 – Nov 5

G$29,246 GYD per night

Guest favorite

Guesthouse in St. Petersburg

4.89 out of 5 average rating, 140 reviews

Casa Magnolia- Cute and spacious remodeled unit

Perfect St. Petersburg getaway! This spacious and completely remodeled unit is located in a quiet residential area but is close to everything the area has to offer. Downtown St. Pete with it's new pier, spa beach, waterfront parks, many restaurants and breweries is less than 5 miles away. Sawgrass Park and Weedon Island Nature Preserve (~2 miles) offers great nature trails, kayaking, fishing and birding options. Some of the best beaches in the world are less than 30 minutes away. TPA is 20 mins.

Jul 5 – 12

G$20,858 GYD per night

Guest favorite

Guesthouse in Gulfport

4.92 out of 5 average rating, 729 reviews

graceful haven...

This boutique-sized, moon-drenched studio is more than just a place to lay your head. From the delicate metal birds swirling above your bed, to the tender light reflecting off the burnished aluminum countertop, your senses will be soothed and tickled by its quietly exuberant design & decor. Nestled in a lush tropical garden, the space is just a block away from Gulfport's Art Village with its sunset waterfront, delightful shops, and many fine restaurants. (or, see my “bohemian treat” listing)

Sep 8 – 15

G$23,769 GYD per night

Guest favorite

Guesthouse in Tampa

4.99 out of 5 average rating, 100 reviews

Cozy-Private apartment, private entrance & parking

A cozy place to have your vacation in Tampa, private entrance and parking. Cozy and romantic to enjoy as a couple to your liking. Located in a central area of Tampa, close to Bush Garden, Adventure Island, Raymond James Stadium, Tampa International Airport, Ybor City, Downtown Tampa, Amalie Arena, River Walk, Internacional Mall, Citrus Park Town Center,Aquarium,Lowry Park Zoo, Clearwater Beach and more! Peaceful and centrally-located place with very good restaurants and a wide variety of shops.

Feb 24 – Mar 3

G$15,543 GYD per night

Guest favorite

Guesthouse in Palm Harbor

4.97 out of 5 average rating, 200 reviews

Private Suite, 1 bedroom, 1 bathroom, pool, patio

Private suite located in Palm Harbor with king-size bed, Split unit A/C Amenities include: Large Bathroom with Jacuzzi, Walk-in Shower, Double sink Vanity. Access to Patio, Swimming Pool , Backyard and Sundeck. Room includes small refrigerator/freezer, Microwave, Coffee maker, Espresso, Iron and much more. Bistro set in room. Private entrances to room and patio/backyard. Cable TV, Netflix and Wi-Fi included. Centrally located to Restaurants and shopping. 10 mins. to the beach/Pinellas Trail.

Nov 26 – Dec 3

G$24,540 GYD per night

Guest favorite

Guesthouse in Clearwater

4.9 out of 5 average rating, 124 reviews

Cozy Clearwater Apt w/ King Bed & Private Balcony

This is a pet-friendly 1/1 apartment with a private balcony to hang out. The apartment is located at the second floor of a duplex residence completely separate from the ground floor apartment with its own entrance. Guests need to climb two flights of stairs to reach the main door of the apartment. **Because pets live on the property and the yard is shared with other guests, we MUST know of animals included in bookings. Animals are to be leashed when outdoors. 2 animal max unless we give the ok

Sep 11 – 18

G$18,010 GYD per night

Guest favorite

Guesthouse in Seminole

4.95 out of 5 average rating, 144 reviews

Quiet & Cozy Guesthouse minutes to the beach.

Newly remodeled, quiet and cozy guest house on a cul de sac. Great location close to shopping/restaurants, 4 miles to Gulf Blvd where you will find many beautiful beaches. 4 Miles to Madeira Beach/Treasure Island, 9 miles to Clearwater and St Pete Beach. 1 Bedroom, queen bed, and sofa bed in living room which pulls out to a queen bed. Full kitchen with all the extras. Cable TV, WiFi, 1 private parking spot and access to washer/dryer for stays 4 nights or more. No pets, no children under 12.

Jun 26 – Jul 3

G$17,595 GYD per night

Guest favorite

Guesthouse in Clearwater

4.93 out of 5 average rating, 369 reviews

Magical Garden Paradise: Hunt Haven Hideaway.

In the heart of Clearwater, a peaceful artists' retreat that will remind you of TN or North Carolina. If you like nature, this is the spot for you! Wander through the "Florida natural" garden and find spots for relaxation or conversation. If you like baseball, we are close to two SPRING TRAINING stadiums and 25 minutes from Raymond James Stadium. About 20 minutes from the beach, if you prefer fun in the sun. Safe, clean gated property centrally located for shopping and activities.

Jan 13 – 20

G$36,436 GYD per night

Guest favorite

Guesthouse in St. Petersburg

4.98 out of 5 average rating, 131 reviews

Central Cozy Cottage w/ Heated Pool & Hot Tub!

Welcome to cute & cozy Turtle Cottage located right in the center of St. Pete, close to both Downtown AND several gorgeous Florida beaches. NO CLEANING FEE with competitive, seasonal pricing = a FANTASTIC DEAL for this space! A BEAUTIFUL NEW HEATED POOL & HOT TUB await in the private, fenced-in tropical backyard. Sorry, no pets/animals or babies/children/teens. Adults 21+ only and limited to 2 verified guests. 100% smoke-free property, inside & out. DEI honored here. Come & enjoy!

Aug 4 – 11

G$25,815 GYD per night

Guest favorite

Guesthouse in Clearwater

4.96 out of 5 average rating, 117 reviews

Studio Bedroom - Private Bathroom , Full Kitchen.

Enjoy your stay in Clearwater, Florida at this cozy, newly remodeled studio! The sanctuary is a place for you to retreat, relax, reset and revive yourself. It is a mini-retreat especially designed for you to come alone, or with a friend or partner. This studio is centrally located near downtown, and a a short drive from the beaches. Don't want to go out? There is everything you need - access to a full patio, jacuzzi, bar, and outdoor dining area is also available during your stay!

Jul 6 – 13

G$38,381 GYD per night

Guest favorite

Guesthouse in Clearwater

4.9 out of 5 average rating, 182 reviews

Cottage on Pinellas Bike Trail

This cottage on the trail is a gem. It is an easy one mile bicycle ride to downtown Dunedin and a quick stroll to waterfront Edgewater Park to watch sunsets or see the lights of Clearwater Beach across the intracoastal waterway. Circular driveway with a carport for off street parking. The cottage is equipped with a Keurig, microwave, mini fridge, as well as beach amenities and wifi. There's a fenced back patio for you to enjoy our beautiful weather!

Sep 27 – Oct 4

G$22,420 GYD per night