Guesthouse vacation rentals in Florida Keys

Find and book unique guesthouse rentals on Airbnb

Top-rated guesthouse rentals in Florida Keys

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

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Guest favorite

Guesthouse in Naples

4.9 out of 5 average rating, 105 reviews

Ecofriendly Yoga Retreat 6 min to Beach

Guests can enjoy an adult only, clean, quiet, TV-free, 300 sq. ft indoor space and a tropical bathhouse surrounded by a serene garden setting, and private entrance. Entire property is non-smoking. Perfect for yoga, meditation, creative work and nature lovers. Garden and patios can be enjoyed between 7 am and 10 pm. Guests have free use of bikes. Property does not accept third party bookings, guest must be at least 21 years, no animals (no exceptions) or guests that like to party or smoke.

Guest favorite

Guesthouse in Naples

5 out of 5 average rating, 151 reviews

By the Beach and 5th - Studio Home with Pool

Great location! Newly renovated! A studio guest home with your own private entrance & your own full kitchen & bath! A non-smoking home only 1 mile from the beach, 5th Ave dining and shops, the mall, the zoo, beautiful Baker Park, and that's not all- Only steps away are local restaurants and shops! Bikes and beach equipment included! Did we mention the pool? Or that you can sing along to your fave tunes in the shower via a Bluetooth shower speaker? This home is 350 square feet of clean cuteness!

Guest favorite

Guesthouse in Miami

4.94 out of 5 average rating, 551 reviews

Brand NEW Cottage with Gorgeous Patio! 5 mi Beach!

"The Atelier" is a charming and rustic cottage inspired by an artist. It is a very private, peaceful & cute studio. Small space yet fully equipped for solo travelers or couples (4 can sleep but snuggly). It has a queen bed with a twin trundle bed (plus a foldable bed in the walk-in closet). Enjoy a cute backyard with a sofa under the avocado tree and a small grill. Plenty of free street parking. Best central location nearby all main Miami attractions. Between Little Havana and Brickell.

Guest favorite

Guesthouse in Biscayne Park

4.95 out of 5 average rating, 470 reviews

Cozy and charming cottage

Our cottage is located in a very quiet residential area, 15mn to the beach (Bal Harbor area).20mn from both Miami and Fort Lauderdale Airports, Located in the backyard of the main house but separate and with an independent entry. Enjoy our tropical garden and beautiful pool, in the back of our house. Share with owner only, we give priority to our guests to enjoy it! Parking available in our front yard. No kitchen but microwave and fridge. TV, cable and WIFI. It is suggested to have a car.

Guest favorite

Guesthouse in Miami

4.86 out of 5 average rating, 490 reviews

Tropical Paradise in Miami Brickell

You will appreciate your private entrance and space that Casa Roja has to offer. It is a stylish studio with a tropical elegance. The large room has a nice sitting area with a queen bed, sofa bed , desk, nice closet, large shower, microwave, kurig coffee maker and mini fridge. Located in one of Miami's best neighborhoods. RIght off I95 a short walk to Brickell Village ,Key Biscayne beaches, and Calle Ocho. Close to metrorail & a short uber to SOBE. Tropical paradise...location, location!

Guest favorite

Guesthouse in Miami

4.98 out of 5 average rating, 158 reviews

Casanessa - a private cottage among the gardens

102 years old with a fresh new look! Come we just revamped our gardens! Relax in this spacious, recently renovated one bedroom cottage detached from the main house with its own living room & kitchen. Surround yourself with peaceful greenery & gardens while being steps away from the heart of Calle Ocho's art galleries & restaurants. Local bakery, grocery store, & laundromat are around the corner at your convenience. We offer coffee, tea , 2 water bottles, snacks & free street parking.

Guest favorite

Guesthouse in Key West

4.94 out of 5 average rating, 563 reviews

Old Town - Room Opens to Pool and Garden

Located in the heart of Old Town, we are three blocks from Duval Street, a 10-minute walk to Higgs Beach, and around the corner from the best, least-expensive meal in town--El Siboney Cuban Restaurant. We suggest bicycling around Key West. Rentals from We-Cycle Bike Shop can be delivered to our door. Two blocks away, The Duval Loop offers free air-conditioned bus service 7 a.m. until midnight. We also offer a link with recommendations for excursions, tours, & restaurants.

Guest favorite

Guesthouse in El Portal

4.93 out of 5 average rating, 169 reviews

Queen Bed | Mins to South Beach | Wynwood| Brickel

Enjoy a stylish stay in Miami at our Boho cottage centrally located in a BEAUTIFUL, QUIET and SAFE neighborhood. We are less than 10 minutes drive from Wynwood and the Design District. 15 minutes to Downtown and South Beach. 18 minutes from the Airport. This boho retreat offers a fully equipped kitchen, WiFI, Free Parking, independent A/C and Netflix. Enjoy Complementary Coffee, Shampoo, Conditioner, Soap and plenty of clean towels & sheets. PRIVATE/INDEPENDENT ENTRANCE.

Guest favorite

Guesthouse in Sunrise

4.95 out of 5 average rating, 111 reviews

Private Dahl•House River Cabins

Take it easy at this tranquil getaway. Guests receive access to private cabins, outdoor bathroom, outdoor kitchen, tree house, koi pond, lounge, zen garden and a floating dock. It's a mix of modern amenities with a Bohemian edge. This unique artist’s retreat feels like a different world. The property was built by hand with influences of the travels of the owner always with sustainability in mind. This hideaway is the pure expression of glamping and a resort spa.

Guest favorite

Guesthouse in Coral Gables

4.96 out of 5 average rating, 274 reviews

Cozy Cottage in quiet neighborhood.

Refurbished, SMALL DETACHED STUDIO (no kitchen, and sitting area is outside) with King sized bed, Wifi, microwave, kettle, French Press, small TV with premium channels, mini fridge, and private shower. Our peaceful backyard sanctuary is perfect for relaxing with a glass of wine (complimentary bottle upon arrival!) music,and/or a book. 2 miles to Miracle Mile restaurants / 12 miles to South Beach (20 - 30 mins.)/ Wynwood / Little Havana (3 miles).

Guest favorite

Guesthouse in Naples

4.87 out of 5 average rating, 115 reviews

Coastal Cabana - 2 Miles to Beach and 5th Ave

The Coastal Cabana is an adorable one-bedroom guest house less than two miles to the beach and the best shopping and dining in Naples. This downtown location in the 34102 zip is unmatched when it comes to beach accessibility and the best of everything downtown Naples has to offer. The Cabana is tucked away in a small, quiet coastal neighborhood walking distance to the Naples Zoo and Conservancy of Southwest Florida, and Gordon River Greenway!

Superhost

Guesthouse in Key Largo

4.9 out of 5 average rating, 216 reviews

Oceanside, 1 bedroom, Bungalow in Key Largo

Canal front bungalow with beautiful views of the ocean. Private water front and pergola with steamer chairs and hammock. BBQ your fresh catch while lounging on the back porch, relaxing in the tropical landscape. One bedroom with Queen bed. Queen size pull-out couch in the living-room. Full kitchen boasting high-end appliances. One Car Parking by unit. Centrally located between shopping centers and destination activities.