Key West holiday rentals
We found 2,757 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 AU$22,318
AU$22,318
AU$3,188 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 AU$23,045
AU$23,045
AU$3,292 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 AU$6,844
AU$6,844
AU$978 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 AU$5,322
AU$5,322
AU$760 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 AU$22,318
AU$22,318
AU$3,188 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 AU$26,139
AU$26,139
AU$3,734 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 AU$22,318
AU$22,318
AU$3,188 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 AU$21,279
AU$21,279
AU$3,040 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 AU$22,318
AU$22,318
AU$3,188 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 AU$29,793
AU$29,793
AU$4,256 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 AU$6,136
AU$6,136
AU$877 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 AU$3,208
AU$3,208
AU$458 per night
includes taxes & fees
Image gallery for Oceanfront
1010 out of 10 rating
Exceptional
(54 reviews)
Oceanfront
Key West, FL
12% off
Price is AU$8,447
AU$8,447
AU$1,207 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 AU$11,038
AU$11,038
AU$1,577 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 AU$3,459
AU$3,459
AU$494 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 AU$3,038
AU$3,038
AU$434 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 AU$3,994
AU$3,994
AU$571 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 AU$25,253
AU$25,253
AU$3,608 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 AU$3,221
AU$3,221
AU$460 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 AU$3,032
AU$3,032
AU$433 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 AU$7,476
AU$7,476
AU$1,068 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 AU$35,171
AU$35,171
AU$5,024 per night
includes taxes & fees
Image gallery for Fishermen’s Paradise
9.29.2 out of 10 rating
Wonderful
(97 reviews)
Fishermen’s Paradise
Summerland Key, FL
8% off
Price is AU$3,200
AU$3,200
AU$457 per night
includes taxes & fees
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
Price is AU$3,996
AU$3,996
AU$571 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
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West
Sleeps 8 · 4 bedrooms · 2+ bathrooms
8.08.0 out of 10
Very goodvery good
9 reviews(9 reviews)
Aqua Lodges at Hurricane Hole Marina
Sleeps 4 · 2 bedrooms
8.88.8 out of 10
Excellentexcellent
158 reviews(158 reviews)
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
Sleeps 6 · 2 bedrooms · 1 bathroom
8.88.8 out of 10
Excellentexcellent
50 reviews(50 reviews)
Luxurious "Atlantia" 2020 6-bedrooms 64ft yacht with full time crew
Sleeps 12 · 6 bedrooms · 6 bathrooms
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)
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
208 reviews(208 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, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value