Guesthouse holiday rentals in Florida Keys

4.86 out of 5 average rating, 107 reviews

Guesthouse in Homestead

Keys Porch Experience New and Beautiful Unit 1

Modern country decoration, separate bedroom, bathroom, fully equipped kitchen, common area with sofa bed, washer and dryer, patio with barbecue and seats for your enjoyment. Everything you need to feel at home! This convenient location is near to the beautiful Everglades and Biscayne National Parks ( The largest subtropical wilderness in the United Sates) and many great beaches and entertaining night life in the Florida Keys! Location is a perfect choice for those traveling to Miami or the Keys!

4.87 out of 5 average rating, 460 reviews

Guesthouse in Key Largo

Romantic cozy peaceful Guesthouse beach Sunsets.

Private Romantic Bayside Cabin/Guesthouse, peaceful settings, lovely sunsets, beach, fishing pier, lush gardens surrounded by nature and wildlife, birds, iguanas, manatees, dolphin’s, eagles, the beach is just a short walk away from the Guesthouse enjoying a cocktail, fishing, boats cruising by, kayaking, snorkeling or an amazing sunset. *This Guesthouse is on bayside not Bayfront ! Same property but private from the residence! "No pets, Airbnb-granted pets Exemption cus allergies reasons"

Guesthouse in Biscayne Park

4.95 out of 5 average rating, 511 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.

4.97 out of 5 average rating, 196 reviews

Casanessa - a private cottage among the gardens

103 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.

4.94 out of 5 average rating, 156 reviews

Guesthouse in Key Largo

Seaside Bungalow

Very private entire Cottage brand new walking distance to world famous Tiki Bar jet ski rentals kayaks Extremely private surrounded by exotic flowers and orchids.Less than 2 miles from Baker's Cay and close to the Key Largo and Islamorada wedding venues. We have a fully stocked home size kitchen. All the condiments coffee creamers sugar ketchup mustard etc. Giant stone shower with shampoos and conditioner and plenty of plush towels. Beach towels and chairs as well as 2 bicycles.

4.86 out of 5 average rating, 546 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, 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!

4.94 out of 5 average rating, 206 reviews

Guesthouse in El Portal

South Beach | Wynwood| DesignDistrict| Brickell

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.

Superhost

Guesthouse in Key Largo

4.89 out of 5 average rating, 260 reviews

SaltSpray Bungalow Oceanside, 1 bedroom

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.

4.95 out of 5 average rating, 170 reviews

Cozy and private studio.

Step into your private oasis—where serenity meets charm. A gently swaying hammock beneath whispering palm trees invites you to slow down and soak in the calm. Tucked among lush greenery, a rustic metal bistro table sets the scene for dining under the stars. Whether it's a quiet morning coffee or an intimate alfresco dinner, this tranquil retreat offers the perfect backdrop for relaxation and unforgettable memories.

4.97 out of 5 average rating, 153 reviews

Guesthouse in Homestead

Villa Samsara - on a beautiful 5 acre farm

When you come and stay with us, it’s a deeply immersive experience with our horses. Often you will find them in your front door or window. There is something profoundly impactful about being around horses and sharing close-quarters with them. You are in their energy field, receiving all that they have to offer. Without even realizing it, your energies are being grounded and regulated through their presence.

4.97 out of 5 average rating, 179 reviews

Guesthouse in Homestead

Charming Private Pool house for two.

Charming private back pool house on a fenced property in a quiet neighborhood close to US 1, the Turnpike, the Keys, Nascar and the Homestead Speedway, and the Everglades. You are 15-20 minutes from the Speedway, 20 minutes from the Everglades, and 30 minutes from Key Largo. For guests wishing to stay a month or more, I would require you to provide a copy of your photo ID.