Key West holiday homes
We found 2,826 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:15 Aug - 22 Aug
Image gallery for "Tranquility " At Ann Street Gardens Steps From Duval
1010 out of 10 rating
Exceptional
(78 reviews)
"Tranquility " At Ann Street Gardens Steps From Duval
Key West, FL
8% off
Price is NZ$6,864
NZ$6,864
NZ$981 per night
includes taxes & fees
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 NZ$28,080
NZ$28,080
NZ$4,011 per night
includes taxes & fees
Image gallery for Parking, Pet Friendly, Pool, Dock - Suncoast House
9.69.6 out of 10 rating
Exceptional
(36 reviews)
Parking, Pet Friendly, Pool, Dock - Suncoast House
Key West, Florida
8% off
Price is NZ$24,208
NZ$24,208
NZ$3,458 per night
includes taxes & fees
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
9% off
Price is NZ$12,923
NZ$12,923
NZ$1,846 per night
includes taxes & fees
Image gallery for Parking, Pet Friendly, Pool & Dock - Aquaria House
9.89.8 out of 10 rating
Exceptional
(34 reviews)
Parking, Pet Friendly, Pool & Dock - Aquaria House
Key West, Florida
8% off
Price is NZ$19,315
NZ$19,315
NZ$2,759 per night
includes taxes & fees
Image gallery for Old Town Bali Hideaway For 2, Just Steps From Duval
1010 out of 10 rating
Exceptional
(88 reviews)
Old Town Bali Hideaway For 2, Just Steps From Duval
Key West, Fl
8% off
Price is NZ$5,571
NZ$5,571
NZ$796 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 NZ$6,956
NZ$6,956
NZ$994 per night
includes taxes & fees
Image gallery for Key West 44ft Sailboat Wild Thing-Summer Fun Sandbar Motorboat Trips
9.49.4 out of 10 rating
Exceptional
(76 reviews)
Key West 44ft Sailboat Wild Thing-Summer Fun Sandbar Motorboat Trips
Key West, FL
8% off
Price is NZ$6,598
NZ$6,598
NZ$943 per night
includes taxes & fees
Image gallery for Pool View 3BR Residence | Beachside Resort
9.89.8 out of 10 rating
Exceptional
(47 reviews)
Pool View 3BR Residence | Beachside Resort
Key West, Florida
8% off
Price is NZ$9,318
NZ$9,318
NZ$1,331 per night
includes taxes & fees
Image gallery for Parking, Pool & Dock - Spindrift House
1010 out of 10 rating
Exceptional
(26 reviews)
Parking, Pool & Dock - Spindrift House
Key West, Florida
8% off
Price is NZ$19,145
NZ$19,145
NZ$2,735 per night
includes taxes & fees
Image gallery for Commodore's Compound - Epic Location Near Duval
9.09.0 out of 10 rating
Wonderful
(11 reviews)
Commodore's Compound - Epic Location Near Duval
Key West, Florida
8% off
Price is NZ$31,032
NZ$31,032
NZ$4,433 per night
includes taxes & fees
Image gallery for The Hollinsed House "Victorian Delights" - Large 1 Bedroom
9.89.8 out of 10 rating
Exceptional
(122 reviews)
The Hollinsed House "Victorian Delights" - Large 1 Bedroom
Key West, FL
7% off
Price is NZ$3,636
NZ$3,636
NZ$519 per night
includes taxes & fees
Image gallery for Hollinsed House Poolside / King Studio / sleeps 2
9.69.6 out of 10 rating
Exceptional
(106 reviews)
Hollinsed House Poolside / King Studio / sleeps 2
Key West, FL
5% off
Price is NZ$3,533
NZ$3,533
NZ$505 per night
includes taxes & fees
Image gallery for 3 Bedroom 2 Bath Oceanfront Condo quiet and secluded adjacent to Hotel/Marina
1010 out of 10 rating
Exceptional
(44 reviews)
3 Bedroom 2 Bath Oceanfront Condo quiet and secluded adjacent to Hotel/Marina
Key West, FL
8% off
Price is NZ$7,484
NZ$7,484
NZ$1,069 per night
includes taxes & fees
Image gallery for Key West dream townhouse * Sleeps 6 * Like new! Old Town * Perfect location
1010 out of 10 rating
Exceptional
(49 reviews)
Key West dream townhouse * Sleeps 6 * Like new! Old Town * Perfect location
Key West, FL
7% off
Price is NZ$5,930
NZ$5,930
NZ$847 per night
includes taxes & fees
Image gallery for The Island Suite at KW Vacation
1010 out of 10 rating
Exceptional
(107 reviews)
The Island Suite at KW Vacation
Key West, FL
8% off
Price is NZ$3,695
NZ$3,695
NZ$528 per night
includes taxes & fees
Image gallery for Tropical Key West out of the way
9.49.4 out of 10 rating
Exceptional
(164 reviews)
Tropical Key West out of the way
Key West, FL
8% off
Price is NZ$6,198
NZ$6,198
NZ$885 per night
includes taxes & fees
Image gallery for The Caribbean Suite - 2-K-bedroom /1 bath/ kitchenette/sleeps 6
9.89.8 out of 10 rating
Exceptional
(214 reviews)
The Caribbean Suite - 2-K-bedroom /1 bath/ kitchenette/sleeps 6
Key West, FL
6% off
Price is NZ$4,388
NZ$4,388
NZ$627 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 NZ$12,077
NZ$12,077
NZ$1,725 per night
includes taxes & fees
Image gallery for Key West Beachside Spacious Two Bedroom Condo in the Top Location on the Key
9.89.8 out of 10 rating
Exceptional
(183 reviews)
Key West Beachside Spacious Two Bedroom Condo in the Top Location on the Key
Key West, FL
8% off
Price is NZ$5,972
NZ$5,972
NZ$853 per night
includes taxes & fees
Image gallery for The Cozy Little Cottage!
9.69.6 out of 10 rating
Exceptional
(31 reviews)
The Cozy Little Cottage!
Key West, FL
8% off
Price is NZ$3,729
NZ$3,729
NZ$533 per night
includes taxes & fees
Image gallery for ISLAND PARADISE
1010 out of 10 rating
Exceptional
(32 reviews)
ISLAND PARADISE
Summerland Key, FL
8% off
Price is NZ$3,249
NZ$3,249
NZ$464 per night
includes taxes & fees
Image gallery for 'LA DOLCE VITA' OLD TOWN, STEPS TO DUVAL! SLEEPS 2-4, 3 BLOCKS TO SOUTH BEACH!
9.69.6 out of 10 rating
Exceptional
(33 reviews)
'LA DOLCE VITA' OLD TOWN, STEPS TO DUVAL! SLEEPS 2-4, 3 BLOCKS TO SOUTH BEACH!
Key West, FL
6% off
Price is NZ$2,857
NZ$2,857
NZ$408 per night
includes taxes & fees
Image gallery for A slice of paradise
9.09.0 out of 10 rating
Wonderful
(95 reviews)
A slice of paradise
Summerland Key, FL
8% off
Price is NZ$3,111
NZ$3,111
NZ$444 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
Showing deals for: 13 Aug - 16 Aug
Aqua Lodges at Hurricane Hole Marina
Sleeps 4 · 2 bedrooms
9.09.0 out of 10
Wonderfulwonderful
137 reviews(137 reviews)
The current price is NZ$1,206
NZ$1,206
for 3 nights, 1 houseboat
NZ$402 per night
includes taxes & fees
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West
Sleeps 8 · 4 bedrooms · 2+ bathrooms
9.69.6 out of 10
Exceptionalexceptional
7 reviews(7 reviews)
The current price is NZ$1,466
NZ$1,466
for 3 nights, 1 houseboat
NZ$489 per night
includes taxes & fees
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West
Sleeps 4 · 2 bedrooms · 2 bathrooms
9.09.0 out of 10
Wonderfulwonderful
204 reviews(204 reviews)
The current price is NZ$2,469
NZ$2,469
for 3 nights, 1 home
NZ$823 per night
includes taxes & fees
Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
7 reviews(7 reviews)
The current price is NZ$1,238
NZ$1,238
for 3 nights, 1 houseboat
NZ$413 per night
includes taxes & fees
Cottage with Pool and Dockage, just minutes to Key West
Sleeps 4 · 2 bedrooms · 1 bathroom
9.29.2 out of 10
Wonderfulwonderful
141 reviews(141 reviews)
The current price is NZ$1,154
NZ$1,154
for 3 nights, 1 cottage
NZ$385 per night
includes taxes & fees
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
Sleeps 6 · 2 bedrooms · 1 bathroom
8.88.8 out of 10
Excellentexcellent
47 reviews(47 reviews)
The current price is NZ$2,610
NZ$2,610
for 3 nights, 1 home
NZ$870 per night
includes taxes & fees
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, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value