Key West vacation rentals
We found 2,767 vacation rentals — enter your dates for availability
Select the perfect private vacation rental within easy reach of Key West Intl. Airport (EYW). Vacation homes provide the amenities you need and want for your stay with friends, family, or just your pet, such as a hot tub and garden. At the end of the day, you'll be able to choose a rental to meet everyone's needs, including a place that is accessible or non-smoking.
Vacation rentals with weekly discounts - Key West, FL (EYW-Key West Intl.)
Showing deals for:Oct 17 - Oct 24
Image gallery for Waterfront Wellness Home w/Pool - Evershore Estate
9.89.8 out of 10 rating
Exceptional
(25 reviews)
Waterfront Wellness Home w/Pool - Evershore Estate
Key West, Florida
9% off
$14,025 for 7 nights
$14,025 for 7 nights
Price is $2,004
$2,004
Fees included upfront
Image gallery for Waterfront, Private Heated Pool - Capmar House
9.89.8 out of 10 rating
Exceptional
(27 reviews)
Waterfront, Private Heated Pool - Capmar House
Key West, Florida
9% off
$13,711 for 7 nights
$13,711 for 7 nights
Price is $1,959
$1,959
Fees included upfront
Image gallery for Waterfront, Pool & Dock - Spindrift House
1010 out of 10 rating
Exceptional
(27 reviews)
Waterfront, Pool & Dock - Spindrift House
Key West, Florida
9% off
$13,711 for 7 nights
$13,711 for 7 nights
Price is $1,959
$1,959
Fees included upfront
Image gallery for Parking, Pet Friendly, Pool, Dock - Suncoast House
9.69.6 out of 10 rating
Exceptional
(38 reviews)
Parking, Pet Friendly, Pool, Dock - Suncoast House
Key West, Florida
9% off
$16,943 for 7 nights
$16,943 for 7 nights
Price is $2,420
$2,420
Fees included upfront
Image gallery for Waterfront Home, Heated Pool - The Seagate Estate
1010 out of 10 rating
Exceptional
(15 reviews)
Waterfront Home, Heated Pool - The Seagate Estate
Key West, Florida
9% off
$13,711 for 7 nights
$13,711 for 7 nights
Price is $1,959
$1,959
Fees included upfront
Image gallery for Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes, Boat Dock
9.89.8 out of 10 rating
Exceptional
(235 reviews)
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes, Boat Dock
Summerland Key, FL
8% off
$3,169 for 7 nights
$3,169 for 7 nights
Price is $453
$453
Fees included upfront
Image gallery for WATERFRONT Seaside Sanctuary in the Keys with 35' SEAWALL FOR YOUR BOAT!
1010 out of 10 rating
Exceptional
(9 reviews)
WATERFRONT Seaside Sanctuary in the Keys with 35' SEAWALL FOR YOUR BOAT!
Summerland Key, FL
9% off
$4,044 for 7 nights
$4,044 for 7 nights
Price is $578
$578
Fees included upfront
Image gallery for Parking, Pool & Waterfront - Springtide House
9.89.8 out of 10 rating
Exceptional
(42 reviews)
Parking, Pool & Waterfront - Springtide House
Key West, Florida
9% off
$13,711 for 7 nights
$13,711 for 7 nights
Price is $1,959
$1,959
Fees included upfront
Image gallery for Parking, Pet Friendly, Pool & Dock - Aquaria House
9.89.8 out of 10 rating
Exceptional
(36 reviews)
Parking, Pet Friendly, Pool & Dock - Aquaria House
Key West, Florida
9% off
$13,711 for 7 nights
$13,711 for 7 nights
Price is $1,959
$1,959
Fees included upfront
Image gallery for Tropical Island Paradise W / Open Water Views!
9.69.6 out of 10 rating
Exceptional
(103 reviews)
Tropical Island Paradise W / Open Water Views!
Summerland Key, FL
8% off
$2,035 for 7 nights
$2,035 for 7 nights
Price is $291
$291
Fees included upfront
Image gallery for Parking, Heated Pool & Pet Friendly - Altair House
9.89.8 out of 10 rating
Exceptional
(8 reviews)
Parking, Heated Pool & Pet Friendly - Altair House
Key West, Florida
9% off
$19,303 for 7 nights
$19,303 for 7 nights
Price is $2,758
$2,758
Fees included upfront
Image gallery for July 19-25 special only 299! Luxurious Oceanfront, Pool, Dock, Kayaks, Views!
1010 out of 10 rating
Exceptional
(192 reviews)
July 19-25 special only 299! Luxurious Oceanfront, Pool, Dock, Kayaks, Views!
Summerland Key, FL
8% off
$3,648 for 7 nights
$3,648 for 7 nights
Price is $521
$521
Fees included upfront
Image gallery for 3 bedroom 2 bath Ocean front condo on marina with opt boat slip.
1010 out of 10 rating
Exceptional
(14 reviews)
3 bedroom 2 bath Ocean front condo on marina with opt boat slip.
Key West, FL
9% off
$6,519 for 7 nights
$6,519 for 7 nights
Price is $931
$931
Fees included upfront
Image gallery for Lower Keys paradise
1010 out of 10 rating
Exceptional
(34 reviews)
Lower Keys paradise
Summerland Key, FL
8% off
$1,886 for 7 nights
$1,886 for 7 nights
Price is $269
$269
Fees included upfront
Image gallery for 34’ Catamaran Sailboat
9.49.4 out of 10 rating
Exceptional
(35 reviews)
34’ Catamaran Sailboat
Key West, FL
9% off
$1,839 for 7 nights
$1,839 for 7 nights
Price is $263
$263
Fees included upfront
Image gallery for water at your back door
8.88.8 out of 10 rating
Excellent
(34 reviews)
water at your back door
Summerland Key, FL
9% off
$2,359 for 7 nights
$2,359 for 7 nights
Price is $337
$337
Fees included upfront
Image gallery for The Cathouse, an Old Town tropical poolside oasis with huge, heated pool
1010 out of 10 rating
Exceptional
(9 reviews)
The Cathouse, an Old Town tropical poolside oasis with huge, heated pool
Key West, FL
11% off
$15,668 for 7 nights
$15,668 for 7 nights
Price is $2,238
$2,238
Fees included upfront
Image gallery for NAUTILUS...ocean front cottage retreat ~
8.88.8 out of 10 rating
Excellent
(6 reviews)
NAUTILUS...ocean front cottage retreat ~
Summerland Key, FL
9% off
$4,437 for 7 nights
$4,437 for 7 nights
Price is $634
$634
Fees included upfront
Image gallery for Fishermen’s Paradise
9.29.2 out of 10 rating
Wonderful
(97 reviews)
Fishermen’s Paradise
Summerland Key, FL
8% off
$1,902 for 7 nights
$1,902 for 7 nights
Price is $272
$272
Fees included upfront
Image gallery for Paradise in the Lower Keys!
8.68.6 out of 10 rating
Excellent
(19 reviews)
Paradise in the Lower Keys!
Summerland Key, FL
5% off
$2,381 for 7 nights
$2,381 for 7 nights
Price is $340
$340
Fees included upfront
Image gallery for Gorgeous Ocean View in Paradise - Three Bedroom Condo - Minutes from Key West!
1010 out of 10 rating
Exceptional
(35 reviews)
Gorgeous Ocean View in Paradise - Three Bedroom Condo - Minutes from Key West!
Key West, FL
14% off
$4,563 for 7 nights
$4,563 for 7 nights
Price is $652
$652
Fees included upfront
Image gallery for Cozy and modern island living, Cudjoe Key
9.29.2 out of 10 rating
Wonderful
(88 reviews)
Cozy and modern island living, Cudjoe Key
Summerland Key, FL
15% off
$1,301 for 7 nights
$1,301 for 7 nights
Price is $186
$186
Fees included upfront
Image gallery for A slice of paradise
9.09.0 out of 10 rating
Wonderful
(96 reviews)
A slice of paradise
Summerland Key, FL
8% off
$1,672 for 7 nights
$1,672 for 7 nights
Price is $239
$239
Fees included upfront
Image gallery for Banana's Foster Guesthouse | 1 Block to Duval St
1010 out of 10 rating
Exceptional
(5 reviews)
Banana's Foster Guesthouse | 1 Block to Duval St
Key West, Florida
9% off
$21,797 for 7 nights
$21,797 for 7 nights
Price is $3,114
$3,114
Fees included upfront
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Key West
Showing deals for: Oct 11 - Oct 14
Aqua Lodges at Hurricane Hole Marina
Sleeps 4 · 2 bedrooms
8.88.8 out of 10
Excellentexcellent
158 reviews(158 reviews)
The current price is $226
$226
Fees included upfront
Luxurious "Atlantia" 2020 6-bedrooms 64ft yacht with full time crew
Sleeps 12 · 6 bedrooms · 6 bathrooms
The current price is $6,705
$6,705
Fees included upfront
Cottage with swimming pool and dockage, just minutes to Key West!
Sleeps 2 · 1 bedroom · 1 bathroom
9.09.0 out of 10
Wonderfulwonderful
152 reviews(152 reviews)
The current price is $167
$167
Fees included upfront
Steps from Duval, Pool on Site & Bikes Included!
Sleeps 2 · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
390 reviews(390 reviews)
The current price is $432
$432
Fees included upfront
Cottage with Pool and Boat Dockage just minutes to Key West!
Sleeps 2 · 1 bedroom · 1 bathroom
8.68.6 out of 10
Excellentexcellent
142 reviews(142 reviews)
The current price is $167
$167
Fees included upfront
Decorators own Coastal Chic home
Sleeps 6 · 3 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
97 reviews(97 reviews)
The current price is $666
$666
Fees included upfront
Top rated rentals - Key West
Cute community and perfect location
1010 out of 10
Exceptionalexceptional
78 reviews(78 reviews)
A Stay
1010 out of 10
Exceptionalexceptional
145 reviews(145 reviews)
Awesome Rental
1010 out of 10
Exceptionalexceptional
14 reviews(14 reviews)
When you walk in "WOW"
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Fantastic stay!
1010 out of 10
Exceptionalexceptional
120 reviews(120 reviews)
Exactly like photos
1010 out of 10
Exceptionalexceptional
48 reviews(48 reviews)
Perfect Keys Getaway
1010 out of 10
Exceptionalexceptional
192 reviews(192 reviews)
Amazing Beach House!
1010 out of 10
Exceptionalexceptional
34 reviews(34 reviews)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
More for lessMore space, more privacy, more amenities — more value
