Search Vacation Homes in Key West

Start date: Check-in selected.
To Date
End date: Check-out

Check prices for these dates

Next weekend
Nov 14 - Nov 16
In two weeks
Nov 21 - Nov 23
In one month
Dec 5 - Dec 7
In two months
Jan 2 - Jan 4

Vacation Homes in Key West

Outdoor dining
Poolside Cottage #411
Poolside Cottage #411
9.8 out of 10, Exceptional, (53)
"Nice area, quiet and clean"
United States
Gary S.
$274 nightly
The price is $304
Nov 16 - Nov 17
Total with taxes and fees
Poolside Cottage #411
Outdoor dining
Poolside Cottage #412
Poolside Cottage #412
9.2 out of 10, Wonderful, (26)
"very nice bungalow right in front of the pool. Well maintained and comfortable. Was a great place to stay."
United States
DONALD H.
$275 nightly
The price is $305
Nov 11 - Nov 12
Total with taxes and fees
Poolside Cottage #412
Outdoor dining
Paradise found
Paradise found
9.8 out of 10, Exceptional, (30)
"The property and location was great. I highly recommend"
United States
Clifton P.
$493 nightly
The price is $547
Nov 4 - Nov 5
Total with taxes and fees
Paradise found
House | 8 bedrooms, Internet
Waterfront Luxury Home - Tidelands House
Waterfront Luxury Home - Tidelands House
2.0 star property
$2,964 nightly
The price is $3,335
Nov 19 - Nov 20
Total with taxes and fees
Waterfront Luxury Home - Tidelands House
1 bedroom, free WiFi, bed sheets
Wahoo Way | Charming Hideaway On Duval Street!
Wahoo Way | Charming Hideaway On Duval Street!
9.0 out of 10, Wonderful, (17)
"Rating Details: The property manager was very helpful. The vacation rental was very clean. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Easy walks to everything!"
United States
Don N.
$297 nightly
The price is $326
Nov 17 - Nov 18
Total with taxes and fees
Wahoo Way | Charming Hideaway On Duval Street!
Terrace/patio
The Seagate Estate at Lunara Bay
The Seagate Estate at Lunara Bay
10.0 out of 10, Exceptional, (17)
"The perfect House , everything was good "
United States
CARLOS G.
$1,531 nightly
The price is $1,700
Nov 4 - Nov 5
Total with taxes and fees
The Seagate Estate at Lunara Bay
Terrace/patio
Duval Hideaway | Dog-Friendly Home w/ Shared Hot Tub, Patio & Prime Location
Duval Hideaway | Dog-Friendly Home w/ Shared Hot Tub, Patio & Prime Location
9.6 out of 10, Exceptional, (18)
"Great place!"
United States
Anonymous traveler
$498 nightly
The price is $547
Nov 19 - Nov 20
Total with taxes and fees
Duval Hideaway | Dog-Friendly Home w/ Shared Hot Tub, Patio & Prime Location
Fridge, microwave, oven, stovetop
Crestwood House at Lunara Bay
Crestwood House at Lunara Bay
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.
$2,031 nightly
The price is $2,255
Nov 4 - Nov 5
Total with taxes and fees
Crestwood House at Lunara Bay
Outdoor dining
Larkshine House at Lunara Bay
Larkshine House at Lunara Bay
2.0 star property
10.0 out of 10, Exceptional, (6)
"Great property and great management. Our trip could not have gone any better"
United States
William G.
$2,537 nightly
The price is $2,818
Nov 4 - Nov 5
Total with taxes and fees
Larkshine House at Lunara Bay
Pool
The Shellstone House at Solaire Lunara Bay
The Shellstone House at Solaire Lunara Bay
$2,708 nightly
The price is $3,007
Nov 4 - Nov 5
Total with taxes and fees
The Shellstone House at Solaire Lunara Bay
TV, stereo, offices
Tidelands House at Lunara Bay
Tidelands House at Lunara Bay
$2,594 nightly
The price is $2,881
Nov 4 - Nov 5
Total with taxes and fees
Tidelands House at Lunara Bay
Fridge, microwave, oven, stovetop
Capmar House at Lunara Bay
Capmar House at Lunara Bay
9.8 out of 10, Exceptional, (28)
"Beautiful property & great location! Well stocked with kitchen supplies, towels, etc. Property managers were readily available if we needed them, but everything was perfect. Check-in & check-out procedures were a breeze! Highly recommend."
United States
Summer W.
$1,531 nightly
The price is $1,700
Nov 4 - Nov 5
Total with taxes and fees
Capmar House at Lunara Bay
Terrace/patio
Catchlight House at Lunara Bay
Catchlight House at Lunara Bay
2.0 star property
9.8 out of 10, Exceptional, (6)
"Awesome place definitely recommend if going to key west "
United States
Brandon M.
$2,036 nightly
The price is $2,260
Nov 12 - Nov 13
Total with taxes and fees
Catchlight House at Lunara Bay
House | 8 bedrooms, Internet
New Waterfront Home - Dreamside House
New Waterfront Home - Dreamside House
2.0 star property
$3,664 nightly
The price is $4,122
Nov 10 - Nov 11
Total with taxes and fees
New Waterfront Home - Dreamside House
Pool
Altair House at Lunara Bay
Altair House at Lunara Bay
10.0 out of 10, Exceptional, (11)
" Very nice property in a great location"
United States
David G.
$2,050 nightly
The price is $2,274
Dec 1 - Dec 2
Total with taxes and fees
Altair House at Lunara Bay
Fridge, microwave, oven, stovetop
Springtide House at Lunara Bay
Springtide House at Lunara Bay
9.8 out of 10, Exceptional, (43)
"We loved many things about the house, especially how spacious it was/all on 1 level, size of bedrooms & all en-suite baths. Pool was perfect and fishing of backyard pier a bonus. We had a great time. "
United States
louise s.
$1,531 nightly
The price is $1,700
Nov 4 - Nov 5
Total with taxes and fees
Springtide House at Lunara Bay
Outdoor dining
The Starboard House at Solaire Lunara Bay
The Starboard House at Solaire Lunara Bay
$2,708 nightly
The price is $3,007
Nov 4 - Nov 5
Total with taxes and fees
The Starboard House at Solaire Lunara Bay
Pool
The Dreamside House at Lunara Bay
The Dreamside House at Lunara Bay
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.
$2,594 nightly
The price is $2,881
Nov 4 - Nov 5
Total with taxes and fees
The Dreamside House at Lunara Bay
Property grounds
Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED
Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED
9.8 out of 10, Exceptional, (114)
"Great location. Clean and beautifully decorated. "
United States
Dawn H.
$586 nightly
The price is $652
Nov 11 - Nov 12
Total with taxes and fees
Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED
Fridge, microwave, stovetop, dishwasher
Suncoast House at Lunara Bay
Suncoast House at Lunara Bay
9.6 out of 10, Exceptional, (40)
"I have to say, this has to be one of the best VRBO experiences I’ve ever had! The house was exactly as listed, if not better! The team at Bright wild was outstanding and met our every need! Highly recommend!!!"
United States
Michael P.
$1,919 nightly
The price is $2,129
Dec 1 - Dec 2
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Key West Hotel Reviews

Beachside Resort & Residences

Beachside Resort & Residences

10/10 Excellent
"Staff good but never clean our room"
Amanda 3-night trip
Posted 5 hours ago
Beachside Resort & Residences

Price trends for Vacation Homes in Key West

Less expensive
More expensive
This month
Next month
August
February
$676
$891
Month
Price
January
$1,032
February
$1,619
March
$1,246
April
$798
May
$805
June
$822
July
$596
August
$441
September
$457
October
$873
November
$676
December
$891
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
304
Accommodation
1055 Vacation Homes
Lowest Price
$304
Highest Price
$4,122

Explore a world of travel with Expedia