Skip to main content

The best vacation homes in Florida Keys

Check out our selection of great vacation homes in Florida Keys

Filter by:


Review score

Wonderful: 9+ Very Good: 8+ Good: 7+ Pleasant: 6+
Our top picks Lowest Price First Star rating and price Top reviewed

See the latest prices and deals by choosing your dates.

Key West Villas

Duval, Key West

Located in the heart of historic Key West, guests will be 1 minutes’ walk from Duval Street. A heated pool, daily continental breakfast, and free WiFi are provided.

All rooms feature a private bath, small refrigerator, and microwave. Apartments at Key West Villas include a fully-equipped kitchen and seating area. great location, nice service ,

Show more Show less
9.7
Exceptional
379 reviews
Price from
$229
per night

Newly renovated and cozy home in the Florida Keys

Marathon

This holiday home comes with 2 bedrooms, a kitchen with an oven and a microwave, a flat-screen TV, a seating area and 2 bathrooms equipped with a walk-in shower. Towels and bed linen are featured in the holiday home. For added privacy, the accommodation has a private entrance and soundproofing. I love that the house had 2 bathrooms & 2 bedrooms outside was very nice pool was great very clean host was very fast on responding to any questions love that we could have a small dog she loved having a fenced in yard.

Show more Show less
9.2
Wonderful
5 reviews
Price from
$171
per night

Sun Outdoors Sugarloaf Key

Summerland Key

Situated within 32 km of Ernest Hemingway Home and Museum and 32 km of Duval Street, Sun Outdoors Sugarloaf Key features rooms with air conditioning and a private bathroom in Summerland Key. Both free WiFi and parking on-site are accessible at the holiday home free of charge. Key West Aquarium is 32 km from the holiday home and Mallory Dock is 32 km away. We had a great stay here. The staff were all very friendly and helpful. The grounds were beautiful and very clean. Our bungalow was very cute and beautifully decorated.

Show more Show less
9.3
Wonderful
87 reviews
Price from
$199
per night

Casa Blue Pelican.

Marathon

Boasting a Blu-ray player, the spacious holiday home has a fully equipped kitchen with a dishwasher, an oven and a microwave, a living room with a seating area and a dining area, 3 bedrooms, and 2 bathrooms with a hot tub and a bath. The unit is air conditioned and is comprised of a balcony with an outdoor dining area as well as a flat-screen TV with streaming services. The holiday home offers bed linen, towels and laundry service. Home was amazing and just as pictured. Entering the property was easy and seamless it was well maintained and clean. Lots of activities for kids and adults and awesome fishing off the back dock. Home was well stocked with everything you could need for your stay including a well stocked kitchen with pots and pans. Beds were comfortable AC stayed cold on extremely hot days and it was centrally located for all of our family’s needs will stay here again.

Show more Show less
9.5
Exceptional
6 reviews
Price from
$451.25
per night

Pelican's Roost, Waterfront comfort at Venture Out

Cudjoe Key

Set in Cudjoe Key, 37 km from Ernest Hemingway Home and Museum and 37 km from Duval Street, Pelican's Roost, Waterfront comfort at Venture Out offers a private beach area and air conditioning. This beachfront property offers access to a balcony, tennis at the tennis court, free private parking and free WiFi. The holiday home offers a pool with a view with a fence, as well as a hot tub and a 24-hour front desk. Very nice on the water with view of Atlantic

Show more Show less
9.2
Wonderful
13 reviews
Price from
$286.35
per night

Just steps to Duval- Sleeps 10- Heated Pool House

Duval, Key West

Popular points of interest near the holiday home include Ernest Hemingway Home and Museum, Duval Street and Southernmost Point. The nearest airport is Key West International Airport, 4 km from Just steps to Duval- Sleeps 10- Heated Pool House. Location was awesome. Beds comfortable. Had everything we needed.

Show more Show less
9.7
Exceptional
6 reviews
Price from
$390
per night

New Casa Caribe by Brightwild- Two-Story Condo Rooftop Pool

Duval, Key West

The spacious holiday home is equipped with 2 bedrooms, a TV with cable channels and a fully equipped kitchen that provides guests with an oven, a microwave, a washing machine, a fridge and a stovetop. Towels and bed linen are provided in the holiday home. For added privacy, the accommodation features a private entrance. It was close to everything. It was clean and very roomy. There was a bike rental across the street (a must)

Show more Show less
9
Wonderful
6 reviews
Price from
$236
per night

Sunrise on the Atlantic

Key West

The holiday home is equipped with 2 bedrooms, 2 bathrooms, bed linen, towels, a flat-screen TV with cable channels, a dining area, a fully equipped kitchen, and a balcony with sea views. For added privacy, the accommodation features a private entrance. I loved everything about it.The place was so gorgeous and clean.The customer service was excellent.The master bedroom has a his and hers sink in the bathroom the shower was very big and nice.If I come back to Key West again I will choose to stay at this beautiful condo again.

Show more Show less
9.4
Wonderful
7 reviews
Price from
$335.91
per night

Julia Whitehead Guest Suites

Duval, Key West

The spacious holiday home features 3 bedrooms, a TV, a fully equipped kitchen with an oven and a microwave, and 4 bathrooms with an a bath or shower. Towels and bed linen are provided in the holiday home. For added privacy, the accommodation features a private entrance. This is a perfect spot to stay in Key West. Great location - just a couple minutes walk to Duval Street. We rent entire unit and it was amazing. Apartments are clean, beautiful cuban style. we spend there only 2 night but it was amazing experience. Highly recommend it!

Show more Show less
9.8
Exceptional
6 reviews

Leaward Isle Island Retreat

Key West

The spacious holiday home features 2 bedrooms, a flat-screen TV with cable channels, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 2 bathrooms with a bath. Towels and bed linen are featured in the holiday home. For added privacy, the accommodation features a private entrance. Close to the ocean. Large rooms

Show more Show less
9.5
Exceptional
8 reviews
Price from
$225.38
per night

Most booked vacation homes in Florida Keys this month

FAQs about vacation homes in Florida Keys

Vacation Homes that guests love in Florida Keys

Research, refine, and make plans for your whole trip