Search Vacation Homes in Key West

Check prices for these dates

Next weekend
Sep 5 - Sep 7
In two weeks
Sep 12 - Sep 14
In one month
Sep 26 - Sep 28
In two months
Oct 24 - Oct 26

Vacation Homes in Key West

Kingfish Keep | Lively Escape on Duval! Balcony!
Living area

Kingfish Keep | Lively Escape on Duval! Balcony!

10.0 out of 10, Exceptional, (18)
"Awesome location with excellent communication. "
$328 nightly
The price is $361
Sep 8 - Sep 9
Total with taxes and fees
Kingfish Keep | Lively Escape on Duval! Balcony!
Poolside Cottage #411
Outdoor dining

Poolside Cottage #411

9.8 out of 10, Exceptional, (52)
"Lovely home to stay in for a couple of nights on Key West"
$266 nightly
The price is $296
Sep 1 - Sep 2
Total with taxes and fees
Poolside Cottage #411
Poolside Cottage #412
Outdoor dining

Poolside Cottage #412

9.2 out of 10, Wonderful, (25)
"The property and our place was really nice. Would definitely stay again. "
$266 nightly
The price is $296
Sep 1 - Sep 2
Total with taxes and fees
Poolside Cottage #412
Duval Hideaway | Dog-Friendly Home w/ Shared Hot Tub, Patio & Prime Location
Terrace/patio

Duval Hideaway | Dog-Friendly Home w/ Shared Hot Tub, Patio & Prime Location

9.6 out of 10, Exceptional, (18)
"Perfect location for enjoying Duval Street. "
$395 nightly
The price is $435
Sep 7 - Sep 8
Total with taxes and fees
Duval Hideaway | Dog-Friendly Home w/ Shared Hot Tub, Patio & Prime Location
Charming 1-Bedroom, 1-Beth Sailboat in wonderful Key West
Outdoor pool

Charming 1-Bedroom, 1-Beth Sailboat in wonderful Key West

$394 nightly
The price is $439
Sep 4 - Sep 5
Total with taxes and fees
Charming 1-Bedroom, 1-Beth Sailboat in wonderful Key West
Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED
Property grounds

Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED

9.8 out of 10, Exceptional, (112)
"Very comfortable house in a great location. "
$486 nightly
The price is $539
Sep 10 - Sep 11
Total with taxes and fees
Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED
Balcony, Pool, & Near Duval - Curry House Room 9
Terrace/patio

Balcony, Pool, & Near Duval - Curry House Room 9

7.4 out of 10, Good, (13)
"Perfect spot to plop down while bar hopping and seeing key west. Would return again for quick trip. Owners sent email and day of, text with access codes making it very easy. Happy we could drop our luggage prior to check-in"
$272 nightly
The price is $302
Sep 9 - Sep 10
Total with taxes and fees
Balcony, Pool, & Near Duval - Curry House Room 9
Poolside Suite with Direct Pool Access
Beach nearby

Poolside Suite with Direct Pool Access

10.0 out of 10, Exceptional, (1)
"amazing spot close to everything "
$307 nightly
The price is $342
Sep 1 - Sep 2
Total with taxes and fees
Poolside Suite with Direct Pool Access
Docked in Paradise
Terrace/patio

Docked in Paradise

$383 nightly
The price is $425
Sep 4 - Sep 5
Total with taxes and fees
Docked in Paradise
Luxury two floor apartment in prime location of famous Duval Street
Beach towels

Luxury two floor apartment in prime location of famous Duval Street

9.6 out of 10, Exceptional, (82)
"Perfect place to stay. Great location. "
$517 nightly
The price is $576
Sep 2 - Sep 3
Total with taxes and fees
Luxury two floor apartment in prime location of famous Duval Street
NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location
Exterior

NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location

10.0 out of 10, Exceptional, (3)
"This was the perfect cottage for our stay. Very clean, nicely remodeled, great location to everything. It had everything we needed for or stay."
$429 nightly
The price is $476
Sep 10 - Sep 11
Total with taxes and fees
NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location
Wahoo Way | Charming Hideaway On Duval Street!
1 bedroom, free WiFi, bed sheets

Wahoo Way | Charming Hideaway On Duval Street!

9.0 out of 10, Wonderful, (17)
"Small place, but clean and everything needed for 2 people to stay I "
$250 nightly
The price is $275
Sep 7 - Sep 8
Total with taxes and fees
Wahoo Way | Charming Hideaway On Duval Street!
Harbor Walk Hideaways | Group Compound In Old Town!
Outdoor dining

Harbor Walk Hideaways | Group Compound In Old Town!

9.8 out of 10, Exceptional, (6)
"I come to Key West often. This is the best location and property I’ve stayed in. Everything was wonderful. I will book this every single time I come. it is perfect for big families, couples or a group of friends. "
$799 nightly
The price is $878
Sep 7 - Sep 8
Total with taxes and fees
Harbor Walk Hideaways | Group Compound In Old Town!
Party Like A Local in Key West, 1 bedroom 1 bath yacht at marina.
Interior

Party Like A Local in Key West, 1 bedroom 1 bath yacht at marina.

$422 nightly
The price is $468
Aug 29 - Aug 30
Total with taxes and fees
Party Like A Local in Key West, 1 bedroom 1 bath yacht at marina.
Capmar House by Brightwild Huge Home Pool
House | 4 bedrooms, Internet

Capmar House by Brightwild Huge Home Pool

2.0 star property
10.0 out of 10, Exceptional, (1)
"Wonderful property, 4 large bedroom and en suite bathroom, private pool we really liked our stay"
$1,717 nightly
The price is $1,931
Sep 8 - Sep 9
Total with taxes and fees
Capmar House by Brightwild Huge Home Pool
FREE TIME 50’ 2 Cabin Yacht Key West
Property grounds

FREE TIME 50’ 2 Cabin Yacht Key West

$475 nightly
The price is $529
Sep 2 - Sep 3
Total with taxes and fees
FREE TIME 50’ 2 Cabin Yacht Key West
Atlantis House Suites
Outdoor dining

Atlantis House Suites

2.0 star property
10.0 out of 10, Exceptional, (1)
$691 nightly
The price is $767
Sep 2 - Sep 3
Total with taxes and fees
Atlantis House Suites
Sweet Caroline by Brightwild Pool Parking
House | 2 bedrooms, Internet

Sweet Caroline by Brightwild Pool Parking

2.0 star property
$769 nightly
The price is $865
Sep 8 - Sep 9
Total with taxes and fees
Sweet Caroline by Brightwild Pool Parking
Parking, Pet Friendly, Pool - Crestwood House
Fridge, microwave, oven, stovetop

Parking, Pet Friendly, Pool - Crestwood House

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."
$2,050 nightly
The price is $2,274
Sep 7 - Sep 8
Total with taxes and fees
Parking, Pet Friendly, Pool - Crestwood House
Palmgale House in Key West
House | 6 bedrooms, Internet

Palmgale House in Key West

2.0 star property
$2,278 nightly
The price is $2,563
Sep 8 - Sep 9
Total with taxes and fees
Palmgale House in Key West
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.
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

Price trends for Vacation Homes in Key West

Price trends for Vacation Homes in Key West

Less expensive
More expensive
Next month
September
February
$625
Month
Price
January
$1,167
February
$1,537
March
$1,325
April
$950
May
$940
June
$774
July
$647
August
$667
September
$625
October
$846
November
$916
December
$949
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

Find out more about Key West

Key West Vacation Homes information

Number of reviews
977
Accommodation
1050 Vacation Homes
Lowest Price
$361
Highest Price
$1,732

Explore a world of travel with Expedia

Explore a world of travel with Expedia