Key West Vacation Rentals, Homes, & More

1-50 of 92 Key West Rentals

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Key West Florida Vacation Rentals - Yacht
1 / 10

Key West Yacht
2 Bedrooms / 2 Bathrooms / Sleeps 4

from

$300

/ night

Email Owner
Key West Florida Vacation Rentals - Villa
1 / 28

Key West Villa
6 Bedrooms / 7 Bathrooms / Sleeps 16

Key West Florida Vacation Rentals - Condo
1 / 22

Key West Condo
2 Bedrooms / 2.5 Bathrooms / Sleeps 6

“ Excellent ”3 Reviews

from

$250

/ night

Email Owner
Key West Florida Vacation Rentals - Home
1 / 15

Key West Home
3 Bedrooms / 2.5 Bathrooms / Sleeps 6

“ Excellent ”2 Reviews

from

$358

/ night

Email Owner
Key West Florida Vacation Rentals - Home
1 / 25

Key West Home
5 Bedrooms / 5.5 Bathrooms / Sleeps 12

“ Excellent ”1 Review

from

$865

/ night

Email Owner
Key West Florida Vacation Rentals - Condo
1 / 1

Key West Condo
2 Bedrooms / 2 Bathrooms / Sleeps 6

from

$259

/ night

Email Owner
Key West Florida Vacation Rentals - Home
1 / 27

Key West Home
3 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”1 Review

from

$100

/ night

Email Owner
Key West Florida Vacation Rentals - Condo
1 / 20

Key West Condo
2 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”50 Reviews

from

$198

/ night

Email Owner
Key West Florida Vacation Rentals - Home
1 / 37

Key West Home
2 Bedrooms / 2.5 Bathrooms / Sleeps 6

“ Excellent ”1 Review

from

$340

/ night

Email Owner
Key West Florida Vacation Rentals - Condo
1 / 36

Key West Condo
2 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”35 Reviews

from

$189

/ night

Email Owner
Key West Florida Vacation Rentals - Yacht
1 / 24

Key West Yacht
1 Bedroom / 1 Bathroom / Sleeps 2

from

$175

/ night

Email Owner
Key West Florida Vacation Rentals - Apartment
1 / 8

Key West Apartment
Studio / 1 Bathroom / Sleeps 2

“ Excellent ”5 Reviews

from

$269

/ night

Email Owner
Key West Florida Vacation Rentals - Villa
1 / 4

Key West Villa
1 Bedroom / 1 Bathroom / Sleeps 2

from

$170

/ night

Email Owner
Key West Florida Vacation Rentals - Townhouse
1 / 17

Key West Townhouse
2 Bedrooms / 2.5 Bathrooms / Sleeps 6

“ Excellent ”12 Reviews

from

$158

/ night

Email Owner
Key West Florida Vacation Rentals - Townhouse
1 / 21

Key West Townhouse
2 Bedrooms / 2 Bathrooms / Sleeps 4

from

$225

/ night

Email Owner
Key West Florida Vacation Rentals - Home
1 / 21

Key West Home
1 Bedroom / 1.5 Bathrooms / Sleeps 4

“ Excellent ”2 Reviews

from

$210

/ night

Email Owner
Key West Florida Vacation Rentals - Townhouse
1 / 28

Key West Townhouse
2 Bedrooms / 2.5 Bathrooms / Sleeps 6

“ Excellent ”3 Reviews

from

$225

/ night

Email Owner
Key West Florida Vacation Rentals - Townhouse
1 / 26

Key West Townhouse
2 Bedrooms / 2.5 Bathrooms / Sleeps 6

“ Excellent ”1 Review

from

$236

/ night

Email Owner
Key West Florida Vacation Rentals - Apartment
1 / 16

Key West Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 4

from

$215

/ night

Email Owner
Key West Florida Vacation Rentals - Cottage
1 / 8

Key West Cottage
4 Bedrooms / 3 Bathrooms / Sleeps 8

“ Excellent ”8 Reviews

from

$540

/ night

Email Owner
Key West Florida Vacation Rentals - Home
1 / 21

Key West Home
3 Bedrooms / 4 Bathrooms / Sleeps 8

from

$572

/ night

Email Owner
Key West Florida Vacation Rentals - Condo
1 / 22

Key West Condo
2 Bedrooms / 2.5 Bathrooms / Sleeps 6

from

$175

/ night

Email Owner
Key West Florida Vacation Rentals - Condo
1 / 12

Key West Condo
2 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”8 Reviews

from

$250

/ night

Email Owner
Key West Florida Vacation Rentals - Guesthouse
1 / 3

Key West Guesthouse
2 Bedrooms / 2 Bathrooms / Sleeps 4

“ Excellent ”1 Review

from

$393

/ night

Email Owner
Key West Florida Vacation Rentals - Home
1 / 12

Key West Home
3 Bedrooms / 3 Bathrooms / Sleeps 6

“ Excellent ”1 Review

from

$400

/ night

Email Owner
Sunset at PirateHead Cove
1 / 29

Key West Home
2 Bedrooms / 2 Bathrooms / Sleeps 4

“ Excellent ”7 Reviews

from

$249

/ night

Email Owner
Key West Florida Vacation Rentals - Condo
1 / 12

Key West Condo
2 Bedrooms / 2 Bathrooms / Sleeps 6

from

$100

/ night

Email Owner
Key West Florida Vacation Rentals - Townhouse
1 / 11

Key West Townhouse
2 Bedrooms / 1.5 Bathrooms / Sleeps 6

“ Excellent ”13 Reviews

from

$258

/ night

Email Owner
Key West Florida Vacation Rentals - Townhouse
1 / 3

Key West Townhouse
2 Bedrooms / 2 Bathrooms / Sleeps 4

“ Excellent ”9 Reviews

from

$205

/ night

Email Owner
Key West Florida Vacation Rentals - Home
1 / 8

Key West Home
3 Bedrooms / 3 Bathrooms / Sleeps 8

from

$127

/ night

Email Owner
Key West Florida Vacation Rentals - Apartment
1 / 12

Key West Apartment
1 Bedroom / 1 Bathroom / Sleeps 2

“ Excellent ”1 Review

from

$120

/ night

Email Owner
Key West Florida Vacation Rentals - Home
1 / 23

Key West Home
3 Bedrooms / 2 Bathrooms / Sleeps 6

from

$134

/ night

Email Owner
Key West Florida Vacation Rentals - Home
1 / 16

Key West Home
2 Bedrooms / 2 Bathrooms / Sleeps 4

“ Excellent ”15 Reviews

from

$300

/ night

Email Owner
Key West Florida Vacation Rentals - Home
1 / 17

Key West Home
2 Bedrooms / 2 Bathrooms / Sleeps 4

“ Excellent ”30 Reviews

from

$350

/ night

Email Owner
Key West Florida Vacation Rentals - Home
1 / 12

Key West Home
1 Bedroom / 1 Bathroom / Sleeps 1

“ Excellent ”28 Reviews

from

$200

/ night

Email Owner
Key West Florida Vacation Rentals - Home
1 / 13

Key West Home
2 Bedrooms / 1 Bathroom / Sleeps 4

“ Excellent ”1 Review

from

$280

/ night

Email Owner
Key West Florida Vacation Rentals - Home
1 / 9

Key West Home
2 Bedrooms / 1 Bathroom / Sleeps 4

from

$280

/ night

Email Owner
Key West Florida Vacation Rentals - Home
1 / 13

Key West Home
2 Bedrooms / 1 Bathroom / Sleeps 4

from

$280

/ night

Email Owner
Key West Florida Vacation Rentals - Home
1 / 10

Key West Home
3 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”26 Reviews

from

$360

/ night

Email Owner
Key West Florida Vacation Rentals - Home
1 / 10

Key West Home
4 Bedrooms / 4 Bathrooms / Sleeps 8

from

$786

/ night

Email Owner
Key West Florida Vacation Rentals - Home
1 / 14

Key West Home
2 Bedrooms / 2 Bathrooms / Sleeps 4

“ Excellent ”18 Reviews

from

$240

/ night

Email Owner
Key West Florida Vacation Rentals - Home
1 / 28

Key West Home
4 Bedrooms / 2 Bathrooms / Sleeps 8

from

$530

/ night

Email Owner
Key West Florida Vacation Rentals - Home
1 / 21

Key West Home
-1 Bedroom / 2 Bathrooms / Sleeps 1

from

$280

/ night

Email Owner
Key West Florida Vacation Rentals - Home
1 / 34

Key West Home
4 Bedrooms / 4 Bathrooms / Sleeps 8

“ Excellent ”15 Reviews

from

$850

/ night

Email Owner
Key West Florida Vacation Rentals - Home
1 / 18

Key West Home
3 Bedrooms / 3 Bathrooms / Sleeps 6

“ Excellent ”34 Reviews

from

$460

/ night

Email Owner
Key West Florida Vacation Rentals - Home
1 / 23

Key West Home
4 Bedrooms / 4 Bathrooms / Sleeps 8

“ Excellent ”27 Reviews

from

$780

/ night

Email Owner
1  2 
Amenity-rich Key West vacation rentals are a superb way to enhance a visit to the southernmost city in the US. A wonderland of open-air bistros and bars, Euro-style cafes, hip boutiques, trendy art galleries, dynamic festivals, and seemingly every water sport imaginable, this island is a one-of-a-kind tropical city paradise.

One of the most prized experiences in the city is watching a sunset, which is possible from the balcony or patio of the many Key West condo rentals available in the area.

For the ultimate sunset celebration, of course, head to Mallory Square Dock, where a nightly arts festival attended by flocks of tourists from around the world features jugglers and fire eaters, art and jewelry exhibitors, local delicacies like Conch Fritters and Key Lime Tea, and Tarot card readers, hypnotists, and astrologers.

Beyond the glorious colors of a stunning Key West, FL sunset, there is much to see and do in the city. To immerse yourself in the laid-back, party lifestyle made famous by singer Jimmy Buffett, head to his restaurant, Jimmy Buffett's Margaritaville, where you'll find frosty margaritas and courtyard dining. Atop your sightseeing hit list should be the Ernest Hemingway Home and Museum, Harry S. Truman Little White House, the Aquarium, and the Shipwreck Historeum Museum.

When it's time to enjoy the blue-green waters encircling the city, your options range from snorkel and Scuba dive tours, parasailing, and jet skiing to deep sea fishing charters, dolphin cruises, and sailboat rentals.

If you're seeking Key West condo rentals on the beach, you'll find a selection of options with features like large porches with spectacular views, outdoor entertainment areas, and spacious dining areas. Vacation home rentals include everything from small, two-bedroom, pastel colored cottages to expansive homes that can accommodate more than a dozen people.

Many Key West rentals by owner come equipped with luxury amenities such as private pools and expansive outdoor veranda dining areas, multiple DVD players, flat-screen televisions, game rooms, and high-speed Internet access. Increasing the appeal is a fully equipped kitchen, which allows you to prepare money-saving meals and snacks.

The convenience and home-like comfort of Key West vacation rentals will make your visit to this special tropical town one to thoroughly enjoy and fondly remember.
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