50 Best Key West Vacation rentals on Holiday Lettings - House rentals

Close

Key West

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

Payment Protection
To book this vacation rental you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

187 Vacation rentals

Travelers going to Key West are booking December dates now. Secure your vacation rental today and have the perfect trip.

(31) Very Good 

14

Florida Keys / Key West

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Car not necessary

 …see more

from $332 / night

$2322 / week

Book View

from $332 / night

(2) Excellent 

21

USA East Coast Vacation houseboat rental

Florida Keys / Key West

4 9 2 nights min

  • 4 bedrooms
  • Sleeps 9
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Ocean view yacht with beautiful sunsets and sunrises. Underwater windows in the forward cabins makes this yacht unbelievable. Located in the finest most elegant first class member only marinas. Guests have access to private pool, tiki bar, fine dining restaurant and fre  …see more

from $409 / night

$2520 - $4410 / week

Book View

from $409 / night

(1) Very Good 

24

USA East Coast Vacation home rental

Florida Keys / Key West

3 8 30 nights min

  • 3 bedrooms
  • Sleeps 8
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
28 DAY MINIMUM STAY IS MANDATED BY COUNTY LAW. PLEASE DO NOT SEND ENQUIRIES FOR SHORTER PERIODS!! Charted back in the 1800's, Shark Key was named by early explorers for its shark-like shape. This exclusive island boasts more than 2 miles of pristine shoreline, lush  …see more

from $270 / night

$1884 / week

Book View

from $270 / night

(27) Very Good 

17

Florida Keys / Key West

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Car not necessary

 …see more

from $262 / night

$1828 / week

Book View

from $262 / night

(22) Excellent 

14

Florida Keys / Key West

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Car not necessary

 …see more

from $251 / night

$1757 / week

Book View

from $251 / night

(13) Excellent 

17

Florida Keys / Key West

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Car not necessary
  • Air conditioning

 …see more

from $282 / night

$1969 / week

Book View

from $282 / night

(4) Excellent 

15

Florida Keys / Key West

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from $273 / night

$1890 / week

Book View

from $273 / night

6

Florida Keys / Key West

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $227 / night

$1588 / week

Book View

from $227 / night

6

Florida Keys / Key West

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

 …see more

from $216 / night

$1512 / week

Book View

from $216 / night

(9) Excellent 

14

Florida Keys / Key West

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 2 mi
  • Swimming pool
  • Child friendly

 …see more

from $171 / night

$1210 - $2816 / week

Book View

from $171 / night

(1) Excellent 

22

Florida Keys / Key West

2 6 5 nights min

  • 2 bedrooms
  • Sleeps 6
  • 5 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from $252 / night

$1613 - $2520 / week

Book View

from $252 / night

(4) Excellent 

14

Florida Keys / Key West

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Air conditioning

 …see more

from $201 / night

$2016 - $2369 / week

Book View

from $201 / night

15

Florida Keys / Key West

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from $302 / night

$2117 - $3239 / week

Book View

from $302 / night

(10) Excellent 

23

Florida Keys / Key West

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from $278 / night

$1613 - $3194 / week

Inquire View

from $278 / night

(2) Excellent 

24

Florida Keys / Key West

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from $670 / night

$4687 - $10670 / week

Inquire View

from $670 / night

16

Florida Keys / Key West

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $227 / night

$1210 - $1714 / week

Book View

from $227 / night

(52) Excellent 

28

Florida Keys / Key West

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from $192 / night

$1412 - $3032 / week

Inquire View

from $192 / night

(8) Very Good 

14

Florida Keys / Key West

3 6 30 nights min

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from $404 / night

$2823 / week

Book View

from $404 / night

(48) Very Good 

22

Florida Keys / Key West

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from $242 / night

$1396 - $3179 / week

Inquire View

from $242 / night

(1) Excellent 

24

Florida Keys / Key West

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden

 …see more

from $680 / night

$4760 / week

Book View

from $680 / night

(2) Excellent 

32

Florida Keys / Key West

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly

 …see more

from $299 / night

$1699 - $2451 / week

Book View

from $299 / night

(15) Very Good 

13

Florida Keys / Key West

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $201 / night

$1008 - $2520 / week

Book View

from $201 / night

(2) Excellent 

24

Florida Keys / Key West

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from $247 / night

$1391 - $2804 / week

Inquire View

from $247 / night

(22) Very Good 

24

Florida Keys / Key West

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from $232 / night

$1437 - $3266 / week

Inquire View

from $232 / night

(25) Very Good 

24

Florida Keys / Key West

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from $328 / night

$2037 - $5225 / week

Inquire View

from $328 / night

(3) Very Good 

6

Florida Keys / Key West

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from $298 / night

$2082 / week

Book View

from $298 / night

(1) Very Good 

6

Florida Keys / Key West

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Air conditioning
  • Private garden

 …see more

from $404 / night

$1512 - $3024 / week

Book View

from $404 / night

7

Florida Keys / Key West

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly

 …see more

from $269 / night

$1877 / week

Book View

from $269 / night

16

Florida Keys / Key West

1 2 30 nights min

  • 1 bedroom
  • Sleeps 2
  • 30 nights min
  • Beach/lakeside relaxation
  • Car not necessary
  • Air conditioning

 …see more

from $101 / night

$706 / week

Book View

from $101 / night

(1) Good 

20

Florida Keys / Key West

Studio 3 Min stay varies

  • Studio
  • Sleeps 3
  • Min stay varies
  • Child friendly
  • Air conditioning

 …see more

from $131 / night

$911 / week

Book View

from $131 / night

(32) Very Good 

24

Florida Keys / Key West

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from $207 / night

$1245 - $2850 / week

Inquire View

from $207 / night

6

Florida Keys / Key West

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from $216 / night

$1512 / week

Book View

from $216 / night

(3) Very Good 

99

Florida Keys / Key West

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Child friendly

 …see more

from $432 / night

$2879 / week

Book View

from $432 / night

11

Florida Keys / Key West

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly

 …see more

from $260 / night

$1815 - $2319 / week

Book View

from $260 / night

(4) Very Good 

20

Florida Keys / Key West

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 3 mi
  • Swimming pool
  • Child friendly

 …see more

from $242 / night

$1613 - $1815 / week

Book View

from $242 / night

(6) Very Good 

24

Florida Keys / Key West

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from $378 / night

$2268 - $3982 / week

Inquire View

from $378 / night

(27) Very Good 

23

Florida Keys / Key West

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from $197 / night

$1074 - $2300 / week

Inquire View

from $197 / night

(26) Very Good 

24

Florida Keys / Key West

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from $207 / night

$1245 - $2850 / week

Inquire View

from $207 / night

(27) Very Good 

24

Florida Keys / Key West

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from $252 / night

$1477 - $3179 / week

Inquire View

from $252 / night

(36) Very Good 

23

Florida Keys / Key West

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from $278 / night

$1613 - $3194 / week

Inquire View

from $278 / night