Find Vacation Rentals in Key West, Florida Keys

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Popular Key West Vacation Rentals

Find the perfect Key West vacation rental

House Key West
from $332 per night
House ∙ 2 guests ∙ 1 bedroom

68 m² House

4.8
Outstanding(15 ratings)
Key West, Monroe County, Florida, United States
Vacasa
Details
Villa Key West
from $1,595 per night
Villa ∙ 16 guests ∙ 7 bedrooms

418 m² Villa

4.9
Outstanding(88 ratings)
Key West, Monroe County, Florida, United States
Vrbo
Details
House Key West
from $533 per night
10 guests ∙ 6 bedrooms

House

4.7
Excellent(12 ratings)
Key West, Monroe County, Florida, United States
Vrbo
Details
House Key West
from $496 per night
House ∙ 10 guests ∙ 4 bedrooms

232 m² House

5.0
Outstanding(33 ratings)
Key West, Monroe County, Florida, United States
Vrbo
Details
House Key West
from $223 per night
House ∙ 6 guests ∙ 3 bedrooms

112 m² House

5.0
Outstanding(25 ratings)
Key West, Monroe County, Florida, United States
Vrbo
Details
House Key West
from $703 per night
12 guests ∙ 6 bedrooms

House

5.0
Outstanding(50 ratings)
Key West, Monroe County, Florida, United States
Vrbo
Details
House Key West
from $191 per night
House ∙ 6 guests ∙ 3 bedrooms

153 m² House

5.0
Outstanding(8 ratings)
Key West, Monroe County, Florida, United States
Vrbo
Details
House Key West
from $216 per night
House ∙ 6 guests ∙ 3 bedrooms

186 m² House

5.0
Outstanding(2 ratings)
Key West, Monroe County, Florida, United States
Vrbo
Details
Condo Key West
from $333 per night
5 guests ∙ 2 bedrooms

Condo

4.3
Very good(57 ratings)
Key West, Monroe County, Florida, United States
Vrbo
Details
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Vacation rentals and apartments with air conditioning

Condo Key West
from $322 per night
Condo ∙ 6 guests ∙ 2 bedrooms

126 m² Condo

4.0
Very good(5 ratings)
Key West, Monroe County, Florida, United States
Air conditioning
Vacasa
Details
House Key West
from $191 per night
House ∙ 6 guests ∙ 3 bedrooms

153 m² House

5.0
Outstanding
Key West, Monroe County, Florida, United States
Air conditioning
Vacasa
Details
House Key West
from $269 per night
House ∙ 4 guests ∙ 2 bedrooms

118 m² House

5.0
Outstanding(16 ratings)
Key West, Monroe County, Florida, United States
Air conditioning
Vrbo
Details
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Vacation rentals with Wi-Fi

House Key West
-10%
$863
from $780 per night
House ∙ 6 guests ∙ 3 bedrooms

149 m² House

4.6
Excellent(89 ratings)
Key West, Monroe County, Florida, United States
Internet
Vacasa
Details
Condo Key West
from $696 per night
Condo ∙ 8 guests ∙ 4 bedrooms

186 m² Condo

4.5
Excellent(169 ratings)
Key West, Monroe County, Florida, United States
Internet
Vrbo
Details
House Key West
from $492 per night
House ∙ 10 guests ∙ 5 bedrooms

251 m² House

5.0
Outstanding(2 ratings)
Key West, Monroe County, Florida, United States
Internet
Vrbo
Details
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Apartments and vacation rentals with a kitchen

Condo Key West
-13%
$267
from $231 per night
Condo ∙ 6 guests ∙ 2 bedrooms

72 m² Condo

4.4
Very good(131 ratings)
Key West, Monroe County, Florida, United States
Kitchen
Vacasa
Details
House Key West
from $618 per night
6 guests ∙ 3 bedrooms

House

Key West, Monroe County, Florida, United States
Kitchen
Vrbo
Details
Condo Key West
from $334 per night
Condo ∙ 6 guests ∙ 2 bedrooms

72 m² Condo

4.5
Excellent(5 ratings)
Key West, Monroe County, Florida, United States
Kitchen
Vacasa
Details
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Frequently Asked Questions

Can I find cheap vacation rentals in Key West?

Usually, a stay in Key West starts at $154 per night.

Can I book a vacation rental in Key West?

On tripping.com, you will find 6,863 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

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