Find Vacation Rentals in Key West, Florida Keys

We have 5,648 properties to choose from
Anytime
Guests
Anytime
Guests

Popular Key West Vacation Rentals

Find the perfect Key West vacation rental

House Key West
from $1,041 per night
House ∙ 16 guests ∙ 8 bedrooms

372 m² House

Key West, Monroe County, Florida, United States
Details
House Key West
from $1,062 per night
16 guests ∙ 6 bedrooms

House

Key West, Monroe County, Florida, United States
Details
House Key West
from $418 per night
House ∙ 14 guests ∙ 5 bedrooms

186 m² House

4.9
Outstanding(14 ratings)
Key West, Monroe County, Florida, United States
Details
House Key West
from $215 per night
House ∙ 6 guests ∙ 2 bedrooms

88 m² House

4.4
Very good(96 ratings)
Key West, Monroe County, Florida, United States
Details
House Key West
from $1,058 per night
10 guests ∙ 4 bedrooms

House

4.7
Excellent(7 ratings)
Key West, Monroe County, Florida, United States
Details
House Key West
from $2,513 per night
House ∙ 21 guests ∙ 8 bedrooms

370 m² House

Key West, Monroe County, Florida, United States
Details
House Key West
from $464 per night
House ∙ 10 guests ∙ 4 bedrooms

232 m² House

5.0
Outstanding(36 ratings)
Key West, Monroe County, Florida, United States
Details
Accommodation Key West
from $258 per night
2 guests ∙ 1 bedroom

Accommodation

4.2
Very good(307 ratings)
Key West, Monroe County, Florida, United States
Details
House Key West
from $703 per night
House ∙ 12 guests ∙ 5 bedrooms

237 m² House

5.0
Outstanding(1 rating)
Key West, Monroe County, Florida, United States
Details
Show more

Vacation rentals and apartments with air conditioning

House Key West
from $322 per night
House ∙ 6 guests ∙ 3 bedrooms

132 m² House

4.4
Very good(153 ratings)
Key West, Monroe County, Florida, United States
Air conditioning
Details
House Key West
from $541 per night
House ∙ 8 guests ∙ 4 bedrooms

202 m² House

5.0
Outstanding(8 ratings)
Key West, Monroe County, Florida, United States
Air conditioning
Details
Condo Key West
from $510 per night
6 guests ∙ 2 bedrooms

Condo

5.0
Outstanding(2 ratings)
Key West, Monroe County, Florida, United States
Air conditioning
Details
Show more

Vacation rentals with Wi-Fi

House Key West
from $176 per night
House ∙ 5 guests ∙ 2 bedrooms

78 m² House

Key West, Monroe County, Florida, United States
Internet
Details
House Key West
from $189 per night
House ∙ 6 guests ∙ 3 bedrooms

96 m² House

Key West, Monroe County, Florida, United States
Internet
Details
Condo Key West
from $232 per night
6 guests ∙ 2 bedrooms

Condo

4.8
Outstanding(124 ratings)
Key West, Monroe County, Florida, United States
Internet
Details
Show more

Apartments and vacation rentals with a kitchen

House Key West
from $305 per night
House ∙ 6 guests ∙ 3 bedrooms

162 m² House

3.9
Good(12 ratings)
Key West, Monroe County, Florida, United States
Kitchen
Details
House Key West
from $247 per night
House ∙ 6 guests ∙ 2 bedrooms

105 m² House

4.9
Outstanding(129 ratings)
Key West, Monroe County, Florida, United States
Kitchen
Details
Accommodation Key West
from $352 per night
4 guests ∙ 1 bedroom

Accommodation

4.2
Very good(307 ratings)
Key West, Monroe County, Florida, United States
Kitchen
Details
Show more

Frequently Asked Questions

Can I find cheap vacation rentals in Key West?

Usually, a stay in Key West starts at $194 per night.

Can I book a vacation rental in Key West?

On tripping.com, you will find 5,648 available vacation rental offers in Key West.

Finding the perfect vacation home has never been easier. Tripping.com searches the world's top vacation rental sites to find the best properties in 190 countries worldwide. One search lets you filter, compare and sort over 10 million available vacation rentals from trusted partners including HomeAway, VRBO, TripAdvisor, Booking.com and more. When you use Tripping.com to plan your trip and book your vacation rental, you never have to wonder if you're getting the best deal.

Key West Information

About Key West

Key West is proud to be the southernmost city in the continental US. With such a prominent claim to fame, Key West has become a destination for those seeking a budget beach vacation. Off the tip of mainland Florida and hooked into the Gulf of Mexico, the climate is nearly tropical with mild winters and warm summers. A multitude of activities for everyone in the family makes Key West a wonderful place for anyone to travel to.

Things to Do in Key West

For pride’s sake, the first thing to do is check out the “Southernmost Point” buoy that marks Key West’s distinct location. After that, you can move on to attractions like the house of Ernest Hemingway or the Key West Aquarium on Mallory Square. Dry Tortugas Park has really cool marine life and for divers the Vandenberg Wreck is an underwater wonder. As with any Gulf of Mexico vacation destination, fishing and golfing activities are abundant! The location historically has been an important naval center, so for navy brats and Civil War buffs the Key West Naval Station and Fort Zachary Taylor State Park are the go to locations.

Key West Accommodations

In Key West, staying somewhat off the main streets will avoid the noise coming from the energetic nightlife crowd. You can find a lot of Key West vacation rentals that are situated right on the beach, sometimes even on a private beach. Criteria should be focused on amenities. You’ll want air conditioning to cool off, beach towels to bring to the beach, and a barbeque for your freshly caught fish.

Popular Day Trips Near Key West

image-tag