Holiday rentals in Monroe County

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Monroe County

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

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Top guest favourite

Hotel room in Key West

The Sanchez House Room #2

There is no better welcome to Key West than staying in local and famous folk artist Mario Sanchez's birth home. This home was built in the 1860's in the heart of the historic Gato and Merrero cigar factory villages. Featuring original Dade County pine construction, and located right on historic Duval Street, the Sanchez House is guaranteed to offer the historic atmosphere and living a part of Key West many visitors want to experience. Sit on the balcony and enjoy the trade winds & Ocean Breeze.

ValueLocationWalkability

4.85 out of 5 average rating, 711 reviews

Superhost

Houseboat in Marathon

Tiny Home Aqua Lodges 2/1

This memorable place is anything but ordinary. Stay in our fully equipped aqua lodge with private surroundings. This lodge has 1 queen bed, 1 full bed, a sofa sleeper full size on the main floor, and 1 twin in the loft. It has a full kitchen, mini split ac, and full bathroom with hot water. This location has great sunset views and private BBQ waterfront area. All lodges have all bedding and dishes and cooking utensils. You will also have access to the Cabana Club located in Key Colony Beach.

FamilyValuePets

4.77 out of 5 average rating, 162 reviews

Guest favourite

Home in Cutler Bay

Miami 6BR Resort • Pool_Spa • Pickleball & Games

Experience a 6B private resort-style retreat in Miami designed for families, groups, and unforgettable gatherings. Enjoy a stay where every part of the home adds to the experience: 💦 Heated Pool + Waterfall ♨️ Jacuzzi /hot tub 🏓 Pickleball court 🌳 Private Forest Oasis 🎱 Game Lounge 🔥 Outdoor Kitchen & BBQ 🛋️ Sunken Fire Pit 🏖️ Beach-Style Sand Area The outdoor spaces are a highlight of the stay, thoughtfully designed for relaxing, playing, dining, and spending quality time together.

FamilyLocationBack garden

4.87 out of 5 average rating, 30 reviews

Top guest favourite

Home in Marathon

Marathon Oceanfront 4BR Private Pool 60’ Boat Dock

Wake up to open-water views at your private oceanfront retreat in Marathon. Bring the boat, step into your private pool, Perfect for families and boating groups.Your private 60' dock offers direct water access, freshwater for rinsing gear and flushing engines, while parking accommodates up to 4 vehicles. • Direct oceanfront setting • Private swimming pool • Private 60' boat dock • Complimentary kayaks • Sleeps up to 10 • Parking for 4 vehicles • Wi-Fi + dedicated workspace

FamilyLocationCondition

5.0 out of 5 average rating, 6 reviews

Top guest favourite

Home in Key Largo

Las Olas: waterfront home, private pool & dock

Experience Key Largo from this beautiful waterfront home, perfect for families and groups of up to 8 guests. Relax by the private pool, enjoy the dock, play a game of pool, or unwind in the spacious outdoor living areas and balconies. The home features a modern kitchen, comfortable living spaces, and everything you need for an unforgettable Florida Keys getaway. The perfect place to enjoy the sunshine, waterfront lifestyle, and quality time with family and friends.

LocationFamilyGrill

5.0 out of 5 average rating, 12 reviews

A charming floating bungalow rests on calm waters, surrounded by an expansive horizon. Its thatched roof and large windows reflect a serene setting, while the gentle ripples of the water enhance the peaceful atmosphere.

Houseboat in Buttonwood Sound

Premium Floating Bungalow by Stay Ombi

Welcome to Stay Ombi, a fully off-grid micro-resort and escape on the gentle waters of Buttonwood Sound in the Florida Keys. Ombi offers three bungalows, crafted to immerse you in nature - without compromising on comfort. Guests are transported to the bungalow by boat (10-minute trip), which will be pre-stocked with all of your requested comforts. Our concierge team will work with you upon booking to plan one of the most unique experiences in the Keys.

ValueLocationGetting around

4.92 out of 5 average rating, 37 reviews

Superhost

Home in Miami

Tropical Miami 5BR Retreat • Pool_BBQ & Game Room

Perfect escape in paradise. This majestic 5-bedroom home combines luxury, comfort, and entertainment . Dive into a private, heated pool, relax in the spacious social areas, fully equipped with a pool table, and more. Accommodating large families or groups of friends, each room has been designed with style and comfort. Enjoy a modern kitchen, outdoor lounge areas, a barbecue grill, and details that will make you never want to leave.

ValueLocationCheck-in

4.88 out of 5 average rating, 41 reviews

Top guest favourite

Flat in Downtown Miami

Breathtaking Views Studio Suite | Downtown Miami

"Spectacular apartment with breathtaking views, amazing amenities, and perfect functionality." This contemporary studio suite offers stunning Downtown Miami & Biscayne Bay views. Steps away from Bayfront Park (2 min walk), it’s built for solo travelers seeking truly effortless stays. Perfect for post-procedure relaxation or a comfortable temporary base. Enjoy zero-hassle hospitality and ultimate convenience.

ValueLocationWifi

4.89 out of 5 average rating, 626 reviews

Top guest favourite

Guest suite in Homestead

Hacienda Paraíso | Private Queen Suite |

Welcome to the original suite at Hacienda Paraíso! This cozy private retreat features a queen bed, private bathroom, kitchenette and separate exterior entrance. Step outside and enjoy our beautiful one-acre tropical property and shared pool. Hacienda Paraíso is home to five independent Airbnb stays, making it a unique place to relax, explore South Florida and experience the peaceful Miami Redlands.

ValueLocationAccess

5.0 out of 5 average rating, 222 reviews

Townhouse in Miami

Architectural Mid-Century Home w/ Moody Interiors

Welcome to Casa Mia, a fully curated 2-bedroom, 2-bath home in the heart of Kendall. The home features soaring 14-foot vaulted wood ceilings, a skylight that fills the kitchen with natural light, and an open layout designed for both comfort and entertaining. Guests can enjoy a private zen patio with a BBQ, as well as access to the community pool, tennis, basketball, and pickleball courts.

FamilyLocationAmenities

5.0 out of 5 average rating, 3 reviews

Top guest favourite

Home in Miami

Miami Lux Lake Front Retreat

A destination on its own: 1. Spacious home- over 5500 sqft of living space. 2. Gym with sauna and steam shower. 3. Pool table 4. Gourmet kitchen. 5. Formal dining room. 6. Large TV room with leather sectional, all recliner. 7. Karaoke 8. Kayaks to enjoy the lake 9. Heated Pool 10. Outdoor ping pong 🏓 table 11. Gym 12. Sauna and steam Room

FamilyValueTV

4.97 out of 5 average rating, 164 reviews

Guest favourite

The Tiki Suite is presented on a wooden platform, showcasing thatched roofing and an inviting porch area. Two stand-up paddleboards are placed alongside the structure, with calm waters reflecting the clear sky.

Houseboat in Key West

Tiki Suites ~ Original Tiki ~ Floating Bungalows

Stay on the water in this one-of-a-kind Tiki Suite in Key West. This private floating bungalow blends boat life with comfort, featuring a custom bed, panoramic views, and direct access to the ocean. Swim, paddle, or relax in a hammock surrounded by nature. A peaceful, off-grid glamping experience you won’t find anywhere else. Accessible by boat only.

ValueLocationLayout

4.91 out of 5 average rating, 562 reviews