Key West holiday rentals
We found 2,773 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:19 Dec - 26 Dec
Image gallery for Floralee House | Stunning Estate w/ Heated Pool
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Floralee House | Stunning Estate w/ Heated Pool
Key West, FL
8% off
Price is AU$42,420
AU$42,420
for 7 nights, 1 home
AU$6,060 per night
includes taxes & fees
Image gallery for Parking, Heated Pool & Pet Friendly - Altair House
1010 out of 10 rating
Exceptional
(11 reviews)
Parking, Heated Pool & Pet Friendly - Altair House
Key West, FL
8% off
Price is AU$42,420
AU$42,420
for 7 nights, 1 home
AU$6,060 per night
includes taxes & fees
Image gallery for Parking, Pet Friendly, Pool, Dock - Suncoast House
9.69.6 out of 10 rating
Exceptional
(40 reviews)
Parking, Pet Friendly, Pool, Dock - Suncoast House
Key West, FL
8% off
Price is AU$46,353
AU$46,353
for 7 nights, 1 home
AU$6,622 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, FL
8% off
Price is AU$31,945
AU$31,945
for 7 nights, 1 home
AU$4,564 per night
includes taxes & fees
Image gallery for Waterfront Home, Heated Pool - The Seagate Estate
1010 out of 10 rating
Exceptional
(17 reviews)
Waterfront Home, Heated Pool - The Seagate Estate
Key West, FL
8% off
Price is AU$31,945
AU$31,945
for 7 nights, 1 home
AU$4,564 per night
includes taxes & fees
Image gallery for Atlantic Paradise by AvantStay | Great Location w/ & Shared Pool and hot tub!
9.69.6 out of 10 rating
Exceptional
(88 reviews)
Atlantic Paradise by AvantStay | Great Location w/ & Shared Pool and hot tub!
Key West, FL
6% off
Price is AU$7,781
AU$7,781
for 7 nights, 1 home
AU$1,112 per night
includes taxes & fees
Image gallery for Aug 3-8 Special only 399, Oceanfront Home on Beach, Pool, Kayaks, Bikes, Views!
1010 out of 10 rating
Exceptional
(195 reviews)
Aug 3-8 Special only 399, Oceanfront Home on Beach, Pool, Kayaks, Bikes, Views!
Summerland Key, FL
8% off
Price is AU$6,819
AU$6,819
for 7 nights, 1 home
AU$974 per night
includes taxes & fees
Image gallery for Luxury Home with Heated Pool - The Ebberly Estate
9.09.0 out of 10 rating
Wonderful
(12 reviews)
Luxury Home with Heated Pool - The Ebberly Estate
Key West, FL
8% off
Price is AU$42,420
AU$42,420
for 7 nights, 1 home
AU$6,060 per night
includes taxes & fees
Image gallery for TRAVEL THE KEYS OR JUST RELAX AT THE DOCK
9.49.4 out of 10 rating
Exceptional
(28 reviews)
TRAVEL THE KEYS OR JUST RELAX AT THE DOCK
Key West, FL
8% off
Price is AU$17,602
AU$17,602
for 7 nights, 1 houseboat
AU$2,515 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
(196 reviews)
Relax by Florida Keys Beaches, just a 7-min drive away
Summerland Key, FL
8% off
Price is AU$3,318
AU$3,318
for 7 nights, 1 home
AU$474 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
6% off
Price is AU$11,202
AU$11,202
for 7 nights, 1 home
AU$1,600 per night
includes taxes & fees
Image gallery for Fully Updated 2/2 Condo! The Grand Cayman Suite
9.29.2 out of 10 rating
Wonderful
(25 reviews)
Fully Updated 2/2 Condo! The Grand Cayman Suite
Key West, FL
8% off
Price is AU$7,100
AU$7,100
for 7 nights, 1 apartment
AU$1,014 per night
includes taxes & fees
Image gallery for Comfortable Waterfront Vacation Rental minutes from key west w boat dock 35 ft
9.49.4 out of 10 rating
Exceptional
(162 reviews)
Comfortable Waterfront Vacation Rental minutes from key west w boat dock 35 ft
Summerland Key, FL
5% off
Price is AU$3,256
AU$3,256
for 7 nights, 1 home
AU$465 per night
includes taxes & fees
Image gallery for Private Heated Pool & Near Duval - The Curry House
1010 out of 10 rating
Exceptional
(6 reviews)
Private Heated Pool & Near Duval - The Curry House
Key West, FL
8% off
Price is AU$33,954
AU$33,954
for 7 nights, 1 home
AU$4,851 per night
includes taxes & fees
Image gallery for waterfront cottage near key west, sleeps 6
9.49.4 out of 10 rating
Exceptional
(24 reviews)
waterfront cottage near key west, sleeps 6
Summerland Key, FL
7% off
Price is AU$3,735
AU$3,735
for 7 nights, 1 cottage
AU$534 per night
includes taxes & fees
Image gallery for 1 Block to Duval St | Banana's Foster Guesthouse
1010 out of 10 rating
Exceptional
(6 reviews)
1 Block to Duval St | Banana's Foster Guesthouse
Key West, FL
8% off
Price is AU$34,712
AU$34,712
for 7 nights, 1 home
AU$4,959 per night
includes taxes & fees
Image gallery for Pet Friendly, Pool, Free Parking - The Grand Turk
8.48.4 out of 10 rating
Very good
(18 reviews)
Pet Friendly, Pool, Free Parking - The Grand Turk
Key West, FL
8% off
Price is AU$5,798
AU$5,798
for 7 nights, 1 apartment
AU$828 per night
includes taxes & fees
Image gallery for Casa Calypso- Beautiful Tropical 3 KING Beds, 3 baths - 2 miles to beach
1010 out of 10 rating
Exceptional
(206 reviews)
Casa Calypso- Beautiful Tropical 3 KING Beds, 3 baths - 2 miles to beach
Key West, FL
8% off
Price is AU$7,348
AU$7,348
for 7 nights, 1 home
AU$1,050 per night
includes taxes & fees
Image gallery for Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!
9.69.6 out of 10 rating
Exceptional
(12 reviews)
Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!
Summerland Key, FL
8% off
Price is AU$5,135
AU$5,135
for 7 nights, 1 cottage
AU$734 per night
includes taxes & fees
Image gallery for Steps from Duval with Private Pool – Southern Palms
9.09.0 out of 10 rating
Wonderful
(12 reviews)
Steps from Duval with Private Pool – Southern Palms
Key West, FL
8% off
Price is AU$36,676
AU$36,676
for 7 nights, 1 home
AU$5,239 per night
includes taxes & fees
Image gallery for Ocean views! <br>I didn’t do it too
1010 out of 10 rating
Exceptional
(21 reviews)
Ocean views! <br>I didn’t do it too
Key West, FL
7% off
Price is AU$5,469
AU$5,469
for 7 nights, 1 houseboat
AU$781 per night
includes taxes & fees
Image gallery for Epic location, Private Parking - Commodore's Cove
8.68.6 out of 10 rating
Excellent
(14 reviews)
Epic location, Private Parking - Commodore's Cove
Key West, FL
8% off
Price is AU$17,848
AU$17,848
for 7 nights, 1 apartment
AU$2,550 per night
includes taxes & fees
Image gallery for Duval Sea Turtle by AvantStay | Great Location | Close to Shops | Shared Pool!
9.69.6 out of 10 rating
Exceptional
(70 reviews)
Duval Sea Turtle by AvantStay | Great Location | Close to Shops | Shared Pool!
Key West, FL
6% off
Price is AU$10,089
AU$10,089
for 7 nights, 1 home
AU$1,441 per night
includes taxes & fees
Image gallery for Classic King & Private Balcony - Curry Mansion Inn
8.48.4 out of 10 rating
Very good
(5 reviews)
Classic King & Private Balcony - Curry Mansion Inn
Key West, FL
8% off
Price is AU$5,204
AU$5,204
for 7 nights, 1 apartment
AU$743 per night
includes taxes & fees
Find spaces that suit your style
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Cottage
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Chalet
Find the best place to stay - Key West
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
Sleeps 6 · 2 bedrooms · 1 bathroom
8.88.8 out of 10
Excellentexcellent
56 reviews(56 reviews)
Aqua Lodges at Hurricane Hole Marina
Sleeps 4 · 2 bedrooms
9.09.0 out of 10
Wonderfulwonderful
162 reviews(162 reviews)
Oceanfront Marina Condo With All Luxuries
Sleeps 6 · 3 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
151 reviews(151 reviews)
Newly Remodeled! Gated Community on Open Water, Dock, Heated Pool, Kayaks, Bikes
Sleeps 6 · 2 bedrooms · 3 bathrooms
9.89.8 out of 10
Exceptionalexceptional
237 reviews(237 reviews)
INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!
Sleeps 6 · 2 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
51 reviews(51 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
146 reviews(146 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