Key West holiday lettings
We found 2,876 holiday rentals — enter your dates for availability
Choose the right private holiday rental that's close to Key West, FL (EYW-Key West Intl.). Holiday homes provide the amenities that you need and want for you and your friends, family or even pets, such as air conditioning and cable TV. No matter what you're looking for, you'll be able to choose a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.
Holiday rentals with weekly discounts - Key West, FL (EYW-Key West Intl.)
Showing deals for:25 Jul - 1 Aug
Image gallery for Steps from Duval with Private Pool – Southern Palms
8.08.0 out of 10 rating
Very good
(7 reviews)
Steps from Duval with Private Pool – Southern Palms
Key West, Florida
8% off
Price is £17,405
£17,405
£2,486 per night
includes taxes & fees
Image gallery for Namaste 'The Spirit Within Me Salutes The Spirit Within You'
1010 out of 10 rating
Exceptional
(43 reviews)
Namaste 'The Spirit Within Me Salutes The Spirit Within You'
Key West, FL
8% off
Price is £3,739
£3,739
£534 per night
includes taxes & fees
Image gallery for Ocean views! <br>Luxury suites
1010 out of 10 rating
Exceptional
(26 reviews)
Ocean views! <br>Luxury suites
Key West, FL
11% off
Price is £3,192
£3,192
£456 per night
includes taxes & fees
Image gallery for Old Town Bali Hideaway For 2, Just Steps From Duval
1010 out of 10 rating
Exceptional
(87 reviews)
Old Town Bali Hideaway For 2, Just Steps From Duval
Key West, Fl
8% off
Price is £2,559
£2,559
£366 per night
includes taxes & fees
Image gallery for Two Bedroom Residence
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Two Bedroom Residence
Key West, Florida
8% off
Price is £4,309
£4,309
£616 per night
includes taxes & fees
Image gallery for Pool, Parking, & Pet Friendly - Sunnyside Up
1010 out of 10 rating
Exceptional
(7 reviews)
Pool, Parking, & Pet Friendly - Sunnyside Up
Key West, Florida
8% off
Price is £7,602
£7,602
£1,086 per night
includes taxes & fees
Image gallery for Charming Studio in Historic Key West, 5-Min Bike Ride to Beach & Bikes Included!
1010 out of 10 rating
Exceptional
(115 reviews)
Charming Studio in Historic Key West, 5-Min Bike Ride to Beach & Bikes Included!
Key West, FL
8% off
Price is £1,909
£1,909
£273 per night
includes taxes & fees
Image gallery for Private Parking & Near Downtown - Sea Breeze
9.49.4 out of 10 rating
Exceptional
(40 reviews)
Private Parking & Near Downtown - Sea Breeze
Key West, Florida
8% off
Price is £4,434
£4,434
£633 per night
includes taxes & fees
Image gallery for Beach Paradise in the Keys! Location! Location! 2 Blocks to Duval St
9.49.4 out of 10 rating
Exceptional
(47 reviews)
Beach Paradise in the Keys! Location! Location! 2 Blocks to Duval St
Key West, FL
7% off
Price is £4,083
£4,083
£583 per night
includes taxes & fees
Image gallery for Balcony, Pool, & Pet Friendly - The Grand Turk
8.48.4 out of 10 rating
Very good
(18 reviews)
Balcony, Pool, & Pet Friendly - The Grand Turk
Key West, Florida
8% off
Price is £3,477
£3,477
£497 per night
includes taxes & fees
Image gallery for Prime location, stunning views from 2 decks—walk or ride to explore the island!
1010 out of 10 rating
Exceptional
(113 reviews)
Prime location, stunning views from 2 decks—walk or ride to explore the island!
Key West, FL
8% off
Price is £2,399
£2,399
£343 per night
includes taxes & fees
Image gallery for Newly Updated! The Grand Cayman Suite
9.29.2 out of 10 rating
Wonderful
(22 reviews)
Newly Updated! The Grand Cayman Suite
Key West, Florida
8% off
Price is £3,829
£3,829
£547 per night
includes taxes & fees
Image gallery for Crystal Clear Water Getaway!
9.89.8 out of 10 rating
Exceptional
(70 reviews)
Crystal Clear Water Getaway!
Summerland Key, FL
8% off
Price is £2,430
£2,430
£347 per night
includes taxes & fees
Image gallery for Happy’s Houseboat Key West
9.29.2 out of 10 rating
Wonderful
(20 reviews)
Happy’s Houseboat Key West
Key West, FL
8% off
Price is £3,112
£3,112
£445 per night
includes taxes & fees
Image gallery for Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
9.89.8 out of 10 rating
Exceptional
(230 reviews)
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
Summerland Key, FL
7% off
Price is £3,515
£3,515
£502 per night
includes taxes & fees
Image gallery for DUVAL SQUARE, KEY WEST Lovely 2 Bedroom 2.5 Bath Condo in a GREAT Location!
9.29.2 out of 10 rating
Wonderful
(192 reviews)
DUVAL SQUARE, KEY WEST Lovely 2 Bedroom 2.5 Bath Condo in a GREAT Location!
Key West, FL
8% off
Price is £2,585
£2,585
£369 per night
includes taxes & fees
Image gallery for Balcony, Pool, & Pet Friendly - The Grenada Suite
8.68.6 out of 10 rating
Excellent
(9 reviews)
Balcony, Pool, & Pet Friendly - The Grenada Suite
Key West, Florida
8% off
Price is £3,495
£3,495
£499 per night
includes taxes & fees
Image gallery for Shared Pool & Near Duval - Road's End
9.69.6 out of 10 rating
Exceptional
(156 reviews)
Shared Pool & Near Duval - Road's End
Key West, Florida
8% off
Price is £4,076
£4,076
£582 per night
includes taxes & fees
Image gallery for Poolside Paradise | Heated Pool, Steps to Duval St!
9.09.0 out of 10 rating
Wonderful
(13 reviews)
Poolside Paradise | Heated Pool, Steps to Duval St!
Key West, Florida
8% off
Price is £9,217
£9,217
£1,317 per night
includes taxes & fees
Image gallery for Ocean views! <br>I didn’t do it too
1010 out of 10 rating
Exceptional
(19 reviews)
Ocean views! <br>I didn’t do it too
Key West, FL
7% off
Price is £2,821
£2,821
£403 per night
includes taxes & fees
Image gallery for Near Duval: Hot Tub, Sleeps 6, Top Location
9.89.8 out of 10 rating
Exceptional
(16 reviews)
Near Duval: Hot Tub, Sleeps 6, Top Location
Key West, FL
8% off
Price is £5,868
£5,868
£838 per night
includes taxes & fees
Image gallery for Henry's Piece of Paradise on the Ocean in Key West - Weekly / Nightly
9.69.6 out of 10 rating
Exceptional
(96 reviews)
Henry's Piece of Paradise on the Ocean in Key West - Weekly / Nightly
Key West, FL
8% off
Price is £2,813
£2,813
£402 per night
includes taxes & fees
Image gallery for 20 MINUTES TO KEY WEST , BOATERS PARADISE
9.49.4 out of 10 rating
Exceptional
(52 reviews)
20 MINUTES TO KEY WEST , BOATERS PARADISE
Summerland Key, FL
8% off
Price is £2,742
£2,742
£392 per night
includes taxes & fees
Image gallery for ATLANTIS...Ocean Front Cottage Retreat!
9.89.8 out of 10 rating
Exceptional
(13 reviews)
ATLANTIS...Ocean Front Cottage Retreat!
Summerland Key, FL
5% off
Price is £6,987
£6,987
£998 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Key West
Ultimate Beach Adventure! Pool, Restaurant, Bar, Bike Rental, Gym,
Sleeps 3 · 1 bedroom · 1 bathroom
8.08.0 out of 10
Very goodvery good
47 reviews(47 reviews)
Aqua Lodges at Hurricane Hole Marina
Sleeps 4 · 2 bedrooms
9.09.0 out of 10
Wonderfulwonderful
131 reviews(131 reviews)
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West
Sleeps 8 · 4 bedrooms · 2+ bathrooms
9.29.2 out of 10
Wonderfulwonderful
5 reviews(5 reviews)
Cottage with Pool and Boat Dockage just minutes to Key West!
Sleeps 2 · 1 bedroom · 1 bathroom
8.68.6 out of 10
Excellentexcellent
134 reviews(134 reviews)
RV Lot 502 Venture Out, Located on a boating canal
Sleeps 6 · 1 bedroom · 1 bathroom
Cottage with Pool and Dockage, just minutes to Key West
Sleeps 4 · 2 bedrooms · 1 bathroom
9.29.2 out of 10
Wonderfulwonderful
137 reviews(137 reviews)
Top rated rentals - Key West
Perfect
1010 out of 10
Exceptionalexceptional
22 reviews(22 reviews)
Perfect stay
1010 out of 10
Exceptionalexceptional
134 reviews(134 reviews)
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value