Search Vacation Homes in Key West

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Dec 19 - Dec 21
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In four months
Mar 27 - Mar 29

Vacation Homes in Key West

Outdoor dining
Poolside Cottage #411

Vacation Home in Key West

9.8 out of 10, Exceptional, (53)
"Perfect for our family! Recommend 10/10!"
United States
Melissa F.
$268 nightly
The price is $298
Dec 14 - Dec 15
Total with taxes and fees
Poolside Cottage #411
Outdoor dining
Poolside Cottage #412

Vacation Home in Key West

9.2 out of 10, Wonderful, (28)
"The property and our place was really nice. Would definitely stay again. "
United States
Sarah M.
$316 nightly
The price is $350
Dec 21 - Dec 22
Total with taxes and fees
Poolside Cottage #412
Property grounds
Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED

Vacation Home in Stock Island

9.8 out of 10, Exceptional, (115)
"Great location, close to everything family had a great time."
United States
rafael m.
$534 nightly
The price is $593
Dec 8 - Dec 9
Total with taxes and fees
Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED
Living area
Kingfish Keep | Lively Escape on Duval! Balcony!

Vacation Home in Old Town Key West

9.8 out of 10, Exceptional, (24)
"Luxury unit with eclectic art work. Super clean. Comfortable bed. Walking distance to many restaurants."
United States
David D.
$394 nightly
The price is $433
Dec 8 - Dec 9
Total with taxes and fees
Kingfish Keep | Lively Escape on Duval! Balcony!
Terrace/patio
The Seagate Estate at Lunara Bay

Vacation Home in Raccoon Key

10.0 out of 10, Exceptional, (18)
"The perfect House , everything was good "
United States
CARLOS G.
$1,446 nightly
The price is $1,608
Dec 8 - Dec 9
Total with taxes and fees
The Seagate Estate at Lunara Bay
House | 8 bedrooms, Internet
Waterfront Luxury Home - Tidelands House

Vacation Home in Raccoon Key

2.0 star property
$2,326 nightly
The price is $2,617
Dec 14 - Dec 15
Total with taxes and fees
Waterfront Luxury Home - Tidelands House
Pool
The Dreamside House at Lunara Bay

Vacation Home in Raccoon Key

10.0 out of 10, Exceptional, (1)
"This was a beautiful property and was everything I expected. Staff took great care making sure it was ready for us."
United States
Tony H.
$2,347 nightly
The price is $2,609
Dec 14 - Dec 15
Total with taxes and fees
The Dreamside House at Lunara Bay
Fridge, microwave, oven, stovetop
Springtide House at Lunara Bay

Vacation Home in Raccoon Key

9.8 out of 10, Exceptional, (43)
"It was great. House was amazing"
United States
Ernest H.
$1,484 nightly
The price is $1,646
Dec 8 - Dec 9
Total with taxes and fees
Springtide House at Lunara Bay
Fridge, microwave, oven, stovetop
Crestwood House at Lunara Bay

Vacation Home in Raccoon Key

10.0 out of 10, Exceptional, (1)
"The house and property was perfect for 4 adults and 4 kids. Gourmet kitchen for great breakfasts to start the day. Grill for cookouts and swimming in the early evenings. Good proximity to downtown key west, but far enough away for quiet time. Would stay again."
United States
Vicki L.
$1,998 nightly
The price is $2,217
Dec 8 - Dec 9
Total with taxes and fees
Crestwood House at Lunara Bay
3 bedrooms, iron/ironing board, WiFi, bed sheets
Spacious 3-bedroom townhome on Stock Island with resort style pool.

Vacation Home in Stock Island

2.0 star property
$470 nightly
The price is $523
Dec 8 - Dec 9
Total with taxes and fees
Spacious 3-bedroom townhome on Stock Island with resort style pool.
Pool
Great Family Vacation Rental.

Vacation Home in Stock Island

8.8 out of 10, Excellent, (15)
"Enjoyed staying here super clean and well stocked!"
Canada
Kirsty E.
$674 nightly
The price is $748
Dec 24 - Dec 25
Total with taxes and fees
Great Family Vacation Rental.
2 bedrooms, iron/ironing board, WiFi, bed sheets
Private Parking, Heated Pool - Sweet Caroline

Vacation Home in Key West Historic District

8.6 out of 10, Excellent, (20)
"It is definitely an historic property with some cracks in the floor boards and bathrooms but it has its charms and the location is excellent! I would stay there again!"
United States
Martha B.
$678 nightly
The price is $753
Dec 10 - Dec 11
Total with taxes and fees
Private Parking, Heated Pool - Sweet Caroline
Outdoor dining
The Starboard House at Solaire Lunara Bay

Vacation Home in Raccoon Key

$2,398 nightly
The price is $2,660
Dec 8 - Dec 9
Total with taxes and fees
The Starboard House at Solaire Lunara Bay
Pool
The Greenmoor House at Lunara Bay

Vacation Home in Raccoon Key

$2,055 nightly
The price is $2,280
Dec 8 - Dec 9
Total with taxes and fees
The Greenmoor House at Lunara Bay
Pool
Altair House at Lunara Bay

Vacation Home in Raccoon Key

10.0 out of 10, Exceptional, (11)
"Great house. Large space, everything you need is there. "
United States
CRIMSON A.
$1,998 nightly
The price is $2,217
Dec 8 - Dec 9
Total with taxes and fees
Altair House at Lunara Bay
House | 8 bedrooms, Internet
The Fairhaven House at Solaire Lunara Bay

Vacation Home in Raccoon Key

2.0 star property
$2,425 nightly
The price is $2,729
Dec 9 - Dec 10
Total with taxes and fees
The Fairhaven House at Solaire Lunara Bay
Fridge, microwave, oven, stovetop
Capmar House at Lunara Bay

Vacation Home in Raccoon Key

9.8 out of 10, Exceptional, (28)
"The property had all the comforts of home. Plus, being able to enjoy the heated pool even through the overcast and windy conditions! The tropical landscaping and the dock on the bay was awesome!Would definitely recommend!!!"
United States
Anonymous traveler
$1,541 nightly
The price is $1,710
Dec 17 - Dec 18
Total with taxes and fees
Capmar House at Lunara Bay
TV, offices
Spindrift House at Lunara Bay

Vacation Home in Raccoon Key

10.0 out of 10, Exceptional, (28)
"The BrightWild team is very professional and responsive. Always a great stay every year!"
United States
Chris S.
$1,446 nightly
The price is $1,608
Dec 8 - Dec 9
Total with taxes and fees
Spindrift House at Lunara Bay
Pool
Palmgale Estate at Lunara Bay

Vacation Home in Raccoon Key

2.0 star property
10.0 out of 10, Exceptional, (7)
"Very clean and stocked. Pleasant experience!"
United States
Iris H.
$1,998 nightly
The price is $2,217
Dec 8 - Dec 9
Total with taxes and fees
Palmgale Estate at Lunara Bay
Fridge, microwave, stovetop, dishwasher
Suncoast House at Lunara Bay

Vacation Home in Raccoon Key

9.6 out of 10, Exceptional, (41)
"Beautiful House, super clean, perfect location "
United States
carlos s.
$1,924 nightly
The price is $2,135
Dec 8 - Dec 9
Total with taxes and fees
Suncoast House at Lunara Bay
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Key West Hotel Reviews

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

10/10 Excellent
"Facilities were great. Enjoyed the b&b feel. Staff was nice and professional."
Daniel 6-night trip
Posted 23 hours ago
Southernmost Beach Resort and Guesthouses

Price trends for Vacation Homes in Key West

Less expensive
More expensive
This month
Next month
September
February
$829
$1,108
Month
Price
January
$1,108
February
$1,542
March
$1,411
April
$1,076
May
$985
June
$775
July
$721
August
$668
September
$542
October
$738
November
$657
December
$829
Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed Vacation Homes in Key West. Select dates and complete search for nightly totals inclusive of taxes and fees.

Find out more about Key West

Key West Vacation Homes information

Number of reviews
331
Accommodation
1043 Vacation Homes
Lowest Price
$298
Highest Price
$2,729

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