Key West holiday homes
We found 2,760 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:17 Oct - 24 Oct
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
8% off
Price is NZ$25,320
NZ$25,320
NZ$3,617 per night
includes taxes & fees
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
8% off
Price is NZ$25,893
NZ$25,893
NZ$3,699 per night
includes taxes & fees
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
8% off
Price is NZ$7,527
NZ$7,527
NZ$1,075 per night
includes taxes & fees
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
7% off
Price is NZ$5,853
NZ$5,853
NZ$836 per night
includes taxes & fees
Image gallery for Waterfront, Pool & Dock - Spindrift House
1010 out of 10 rating
Exceptional
(27 reviews)
Waterfront, Pool & Dock - Spindrift House
Key West, Florida
8% off
Price is NZ$25,320
NZ$25,320
NZ$3,617 per night
includes taxes & fees
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
8% off
Price is NZ$29,759
NZ$29,759
NZ$4,251 per night
includes taxes & fees
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
8% off
Price is NZ$25,320
NZ$25,320
NZ$3,617 per night
includes taxes & fees
Image gallery for Parking, Pet Friendly, Pool & Dock - Aquaria House
9.89.8 out of 10 rating
Exceptional
(37 reviews)
Parking, Pet Friendly, Pool & Dock - Aquaria House
Key West, Florida
8% off
Price is NZ$24,112
NZ$24,112
NZ$3,445 per night
includes taxes & fees
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
8% off
Price is NZ$25,320
NZ$25,320
NZ$3,617 per night
includes taxes & fees
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
8% off
Price is NZ$33,988
NZ$33,988
NZ$4,855 per night
includes taxes & fees
Image gallery for Luxurious Oceanfront Home on Beach, Dock, Heat/Cool Pool, Kayaks, Bikes, Views!
1010 out of 10 rating
Exceptional
(193 reviews)
Luxurious Oceanfront Home on Beach, Dock, Heat/Cool Pool, Kayaks, Bikes, Views!
Summerland Key, FL
8% off
Price is NZ$6,748
NZ$6,748
NZ$964 per night
includes taxes & fees
Image gallery for Lower Keys paradise
1010 out of 10 rating
Exceptional
(34 reviews)
Lower Keys paradise
Summerland Key, FL
8% off
Price is NZ$3,528
NZ$3,528
NZ$504 per night
includes taxes & fees
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
8% off
Price is NZ$12,347
NZ$12,347
NZ$1,764 per night
includes taxes & fees
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
Price is NZ$3,804
NZ$3,804
NZ$543 per night
includes taxes & fees
Image gallery for 34’ Catamaran Sailboat
9.49.4 out of 10 rating
Exceptional
(35 reviews)
34’ Catamaran Sailboat
Key West, FL
8% off
Price is NZ$3,341
NZ$3,341
NZ$477 per night
includes taxes & fees
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
8% off
Price is NZ$4,393
NZ$4,393
NZ$628 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
10% off
Price is NZ$28,655
NZ$28,655
NZ$4,094 per night
includes taxes & fees
Image gallery for Island Therapy
9.89.8 out of 10 rating
Exceptional
(57 reviews)
Island Therapy
Summerland Key, FL
8% off
Price is NZ$3,752
NZ$3,752
NZ$536 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
(97 reviews)
Henry's Piece of Paradise on the Ocean in Key West - Weekly / Nightly
Key West, FL
8% off
Price is NZ$7,598
NZ$7,598
NZ$1,085 per night
includes taxes & fees
Image gallery for Relax by Florida Keys Beaches, just a 7-min drive away
9.89.8 out of 10 rating
Exceptional
(194 reviews)
Relax by Florida Keys Beaches, just a 7-min drive away
Summerland Key, FL
8% off
Price is NZ$3,543
NZ$3,543
NZ$506 per night
includes taxes & fees
Image gallery for Waterfront home with numerous amenities on popular Cudjoe Key!
9.49.4 out of 10 rating
Exceptional
(18 reviews)
Waterfront home with numerous amenities on popular Cudjoe Key!
Summerland Key, FL
15% off
Price is NZ$3,334
NZ$3,334
NZ$476 per night
includes taxes & fees
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
8% off
Price is NZ$40,194
NZ$40,194
NZ$5,742 per night
includes taxes & fees
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
8% off
Price is NZ$8,222
NZ$8,222
NZ$1,175 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 NZ$13,292
NZ$13,292
NZ$1,899 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: 14 Oct - 17 Oct
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 NZ$1,328
NZ$1,328
for 3 nights, 1 houseboat
NZ$443 per night
includes taxes & fees
Luxurious "Atlantia" 2020 6-bedrooms 64ft yacht with full time crew
Sleeps 12 · 6 bedrooms · 6 bathrooms
The current price is NZ$37,034
NZ$37,034
for 3 nights, 1 houseboat
NZ$12,345 per night
includes taxes & fees
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 NZ$1,799
NZ$1,799
for 3 nights, 1 apartment
NZ$600 per night
includes taxes & fees
Key West Wabi Sabi - Authentic Downtown Cottage w Pool - Steps Off Duval
Sleeps 8 · 4 bedrooms · 3+ bathrooms
9.29.2 out of 10
Wonderfulwonderful
43 reviews(43 reviews)
The current price is NZ$5,799
NZ$5,799
for 3 nights, 1 home
NZ$1,933 per night
includes taxes & fees
Cottage with Pool and Boat Dockage just minutes to Key West!
Sleeps 2 · 1 bedroom · 1 bathroom
8.68.6 out of 10
Excellentexcellent
143 reviews(143 reviews)
The current price is NZ$938
NZ$938
for 3 nights, 1 cottage
NZ$313 per night
includes taxes & fees
Decorators own Coastal Chic home
Sleeps 6 · 3 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
97 reviews(97 reviews)
The current price is NZ$3,612
NZ$3,612
for 3 nights, 1 home
NZ$1,204 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