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 Miami

4.96 out of 5 average rating, 167 reviews

Cozy private guest studio

Welcome! This is a private guesthouse located in a quiet neighborhood. Accommodations are with a private entrance and parking space to make you feel at home. We are located near a major expressway. We have a pool; The POOL is a SWIM AT YOUR OWN RISK. It is shared with Owner. Enjoy a smoke free cottage. Ashtrays are provided outside for those guest that do smoke. We provide a queen size bed and a couch/bed. This space is perfect and comfortable for two guest.Please NO children and NO animals.

Sep 10 – 17

G$21,219 GYD per night

Superhost

Guesthouse in Naples

4.8 out of 5 average rating, 297 reviews

Waterfront Sea Cottage

*Newly rebuilt after Hurricane Ian. Expect some construction within the main home. Enjoy Naples in this private waterfront tiny cottage conveniently located on the Gordon River with gulf access near the heart of Downtown 5th Avenue. Our cottage is only 1.5 miles (2.4 km) from the beach and is located within walking distance to parks, shopping, bars, restaurants, and many outdoor activities. Located in a safe, vibrant, and transitioning community full of life and the true flavor of old Naples.

Dec 8 – 15

G$19,787 GYD per night

Guest favorite

Guesthouse in Hollywood

4.94 out of 5 average rating, 187 reviews

La Moderna: A Private Guesthouse

Getaway in this cozy modern-minimalist guest-loft, tastefully designed with your comfort and privacy in mind. You'll enjoy SUPER-FAST 1 Gb internet, a SMART TV that you can watch from bed, new washer & dryer, and a well stocked kitchenette. Over-the-top amenities are yours to enjoy, courtesy of your 5-Star Superhost! Ask about our Exclusive Guestbook! Sparkling Clean & fully compliant with all of AirBnb's sanitation & safety protocols. Only 5 min from the beach and 15-20 min from airports.

Sep 29 – Oct 6

G$20,855 GYD per night

Guest favorite

Guesthouse in Biscayne Park

4.94 out of 5 average rating, 450 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.

Dec 16 – 23

G$32,503 GYD per night

Superhost

Guesthouse in Miami

4.85 out of 5 average rating, 451 reviews

Tropical Elegence 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!

Jun 27 – Jul 4

G$26,216 GYD per night

Guest favorite

Guesthouse in Miami

5.0 out of 5 average rating, 131 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.

Aug 21 – 28

G$22,740 GYD per night

Guest favorite

Guesthouse in Fort Lauderdale

4.94 out of 5 average rating, 547 reviews

Little Cottage By The Pine Tree -

Quaint cottage just a stone throw away from FLL Airport and downtown Fort Lauderdale (5 mins). Short drive from beaches, bars, restaurants & malls. Quick access to major freeways Miami in 30 mins & Palm Beach in 40 mins. *Please complete profile verification and send an introduction with a brief description and your purpose of visiting* Our commitment to cleanliness: We use the highest classification of disinfectants recommended by the CDC and and WHO to treat known pathogens.

Dec 21 – 28

G$25,558 GYD per night

Guest favorite

Guesthouse in Key West

4.93 out of 5 average rating, 527 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.

Jun 22 – 29

G$70,615 GYD per night

Guest favorite

Guesthouse in El Portal

4.93 out of 5 average rating, 148 reviews

Chic Studio | Mins to Wynwood,Brickell,South Beach

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.

Feb 14 – 21

G$20,753 GYD per night

Superhost

Guesthouse in Key Largo

4.87 out of 5 average rating, 378 reviews

Guesthouse Tropical Paradise Beach sunset fishing

The Guesthouse/Cabin romantic *sunsets beach, docks and fishing pier, on a peaceful lush gardens with private parking enjoy and relax, surrounded by nature wildlife at its best birds, iguanas, manatees, dolphin’s, eagles only a short walk to the beach from the guesthouse fishing pier, boats cruising by, relax enjoying sipping cocktail. FYI a guesthouse is part as on a state, small separate dwelling on the grounds of a larger one, used for accommodating guests.

Jul 5 – 12

G$49,259 GYD per night

Guest favorite

Guesthouse in Coral Gables

4.96 out of 5 average rating, 262 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).

Jul 19 – 26

G$19,464 GYD per night

Guest favorite

Guesthouse in Key Largo

4.91 out of 5 average rating, 192 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.

Oct 5 – 12

G$42,350 GYD per night