Holiday Homes in Florida Keys

Find and book unique holiday homes on Airbnb

Top-rated Holiday Homes in Florida Keys

Guests agree: These holiday homes are highly rated for location, cleanliness and more.

1 of 1 pages1 / 1

Guest favourite

Holiday home in Hollywood

4.8 out of 5 average rating, 326 reviews

Private Tropical Paradise+Pool❤Near Beach+Parking

Safe, upscale neighborhood near Hollywood Beach, walk to downtown. Entire upper level of a detached cottage at the rear of a classic Hollywood property. No other guests. Beautiful large, heated swimming pool with spa and covered cabana, surrounded by lush landscaping, all for guest use. Master BR has queen bed, second BR has two twin beds. Fully equipped kitchen with dishwasher, micro, coffee/espresso/tea maker, cookware. Central A/C, HIGH SPEED wifi, RokuTV + free Netflix, Amazon Prime and more

Top Guest favourite

Holiday home in Key Largo

4.95 out of 5 average rating, 154 reviews

Ocean Shores Villa 3 with pool and boat slip

This centrally located boater's paradise is the perfect place to relax. Walk to restaurants, cook in kitchen or grill downstairs. With only 4 units in the building the guests have half an acre of waterfront entertainment (boat slip, Kayaks, Bikes, Hammock and Pool). 32ft Dock Slip and Trailer Parking are included in the rental. Relaxing Balcony that looks down the Ocean Canal is the perfect place to have your morning coffee. Conveniently located near Sandbars, State parks and many attractions.

Guest favourite

A three-story historic building is framed by palm trees and tropical foliage. White decorative railings and an ornate archway lead to the entrance, while soft sunlight brightens the exterior's yellow siding. The inviting architecture complements the serene surroundings.

Holiday home in Key West

4.85 out of 5 average rating, 387 reviews

Historic Cigar House. 3rd floor Suite W/Kitchen

This unit is located in the historic "Cigar House" of the Island City House Hotel. Unit 12 is on the 3rd floor and is one of the most requested units in the entire hotel. Your private balcony overlooks the pool. Only 3 blocks from Duval street so close everything, yet quiet enough for a good nights sleep. You will have your own private entrance and use of all the hotel amenities. The space is a private 1BR with a kitchen and NEW sleeper sofa (12/23). In Old Town, walk to everything.

Guest favourite

A spacious living area features a gray sectional sofa adorned with blue accent pillows. Light wood tables complement the hardwood floor. A large painting of a coastal scene is displayed on the wall, and natural light filters in through shuttered windows.

Holiday home in Marathon

4.93 out of 5 average rating, 54 reviews

Cabana Club Condo: Key Colony Beach, FL

Located on the Atlantic Ocean in the middle keys. Accommodations for up to 10 people. Waking up to the sounds of ocean waves and the beautiful waters of the Florida Keys is breath taking. Very few are on a private beach. The unit is very spacious and well kept. Large master closet for storage. Private entrance and Cabana Club access during operating hours: ( Monday 10-5, Tuesday-Sunday 10-7 ). New furnishings, full kitchen, clothes washer and dryer. Minimum one week rental, seven nights.

Guest favourite

The exterior of the property showcases a well-maintained two-story house surrounded by lush greenery and palm trees. A spacious driveway leads to the entrance, which is flanked by landscaping that creates a welcoming atmosphere. The clear blue sky complements the well-kept facade.

Holiday home in Marco Island

4.91 out of 5 average rating, 33 reviews

Waterfront Home - Walk to Beach & Restaurants

Enjoy a large open 1st floor flat (no stairs) with a pool table, 65" TV, full kitchen, and dining table. The backyard pool, dock and patio are in a fenced-in area for fishing, grilling, and playing with your pets. Walk to Tigertail Beach, grocery store and the best restaurants on Marco. Water sports, Everglades tours, shopping, farmers market and art fairs are all within a short walk. There is a 2nd floor that only my family uses; however, we don’t use it when hosting guests (100% privacy).

Guest favourite

The bedroom features a spacious bed with decorative pillows and soft linens. Two bedside lamps sit on matching nightstands, while a piece of wall art adds a touch of color. Natural light enters through two vertical-blind-covered windows, enhancing the calming atmosphere.

Holiday home in Miami

4.82 out of 5 average rating, 120 reviews

Coral Gables Paradise 2

This property is centrally-located minutes away from South Beach, Miami Design District/Wynwood, Merrick Park , Miracle Miles and Coconut Grove. Perfect for families who want to walk in shopping malls, restaurants and the beautiful beaches Miami offers. For those who want to enjoy the nightlife, you will find Coconut Grove, South Beach, Wynwood, and Miami Design District between 10 and 20 minutes away. Here you will find the top-rated restaurants & most desirable lounges and clubs.

Superhost

Holiday home in Miami

4.87 out of 5 average rating, 122 reviews

Dreams Villa | Pool | 12 PPL | Games |Top Location

Welcome to Dream Stays Villa in Miami Florida! Why you should book with us? - 2000 ft2 ground floor house - Top Location: Next to Hard Rock Stadium - 20 Min Miami Beach - 30 Min to Downtown and Brickell - 4 Bedrooms - 1 King, 2 Queen Beds, 1 Bunk Bed and two sofa beds - Heated and Salted Private Pool - Games Room - Fast WIFI - Fully equipped kitchen - BBQ - Outdoor Dining - Dedicated Work Space - Onsite parking - Washer & Dryer - Kids friendly - Mini Golf - Hammocks - Pool Table

Guest favourite

Holiday home in Key Largo

4.89 out of 5 average rating, 292 reviews

6. Adventurer's Waterfront Cabana | Key Largo

Unwind in this Modern Key Largo waterfront studio, nestled on a canal with ocean access near Rodriguez Key, Mosquito Bank, and shipwrecks. Just minutes from John Pennekamp Park. Enjoy a full kitchen, ice-cold A/C, Smart TV, Wi-Fi, and assigned parking. Boaters can reserve our dock or use nearby Pilot House Marina. Snorkel reefs, kayak mangroves, or dine at local favorites like The Fish House, Sundowners, and Key Largo Fisheries. Comfort, adventure, and location in one perfect stay.

Guest favourite

A heated pool is enclosed with a mesh screen, surrounded by lush greenery. Two lounge chairs sit to the side, while a seating area with chairs is positioned nearby. Large glass doors lead into the interior space, allowing natural light to flow in.

Holiday home in Hollywood

4.89 out of 5 average rating, 117 reviews

Heated Pool | Soundproof Home | Firepit | 630Mbps

★ "The most comfortable mattresses and blankets I have ever slept in. " ☞ Patio w/ outdoor dining + BBQ + firepit ☞ Heated enclosed pool* w/ toys ☞ Screened-in back porch + lounge ☞ King in master bedroom ☞ 65” Smart TVs + Netflix ☞ Fully equipped + stocked kitchen ☞ Parking → driveway (2 cars) ☞ 630 mbps wifi 4 mins → DT Hollywood (cafes, dining, shopping) 12 mins → Hollywood Beach ⛱ + FLL International Airport ✈ 20 mins → DT Miami + Miami International Airport ✈

Guest favourite

A spacious living area features a comfortable blue sofa and a white coffee table at its center. Modern appliances are visible in the adjacent kitchen, along with a dining area. Natural light flows in through sliding doors leading to the outdoor space.

Holiday home in Marathon

4.93 out of 5 average rating, 95 reviews

Perfect Paradise

Relax with family and friends at this newly renovated Marathon getaway! Located minutes from Sombrero Beach, boat ramps, restaurants, shopping, and local attractions, it’s the perfect base for your Florida Keys adventure. Enjoy boat and trailer parking, complimentary kayaks, a fire pit, grill, patio dining area, and a fully stocked kitchen. After a day on the water, unwind in the king suite or relax under the stars. Perfect for families, anglers, and beach lovers.

Top Guest favourite

A private porch overlooks the tranquil harbor, featuring blue chairs beside a white railing. A boat is secured at the dock, with sailboats moored in the distance. Bright sunlight reflects off the water's surface, creating a serene atmosphere.

Holiday home in Key Largo

4.99 out of 5 average rating, 267 reviews

Waterfront, GROUND LEVEL, Awesome Sunsets!!!

This ground level unique location is close to everything. Walk to some of the most iconic restaurants and bars Key Largo has to offer for fresh seafood and awesome drinks! We Do Not allow fishing on our Property! Enjoy the amazing sunsets over the water from your private porch and dock. John Pennekamp Coral Reef State Park close by. Walk to dolphin research center!! 28 day rental I am a licensed charter boat captain and offer discounts for all guests

Guest favourite

The exterior of a two-story apartment is shown, featuring a white facade with a gabled roof. A two-car garage door is present, along with a small area for outdoor storage. The driveway leads to a clean, spacious concrete surface under a partly cloudy sky.

Holiday home in Homestead

4.87 out of 5 average rating, 257 reviews

Beautiful Cozy Apartment.

Bring the whole family to this great place with lots of room for fun. Located in Homestead, you are in the central location for outlets, The Florida Keys, and Miami. 2 floor apartment with the main bedroom on the second floor. Also located on the second floor is the bathroom and shower. All Televisions are brand new smart Tv's. Avocado Villas is a quiet neighborhood, and the house is surrounded with security cameras for your protection.