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Best Vacation Rentals in Upper Matecumbe Key - Holiday Lettings - Cabins

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460 Vacation rentals

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Vacation home in Upper Matecumbe Key

Upper Matecumbe Key house

  • 9 bedrooms
  • 12 bathrooms
  • sleeps 18

from $2,349 / night

$16,443 / week

1 / 30

Ski apartment to rent in Upper Matecumbe Key

Upper Matecumbe Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $604 / night

$4,228 / week

1 / 30

Ski apartment to rent in Upper Matecumbe Key

Upper Matecumbe Key apartment

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 16

from $1,878 / night

$13,146 / week

1 / 30

Vacation villa in Upper Matecumbe Key

Upper Matecumbe Key villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 12

Pricing unknown

1 / 11

Upper Matecumbe Key Vacation home rental

Upper Matecumbe Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from $901 / night

$6,307 / week

1 / 30

Upper Matecumbe Key ski apartment to rent.

Upper Matecumbe Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $508 / night

$3,556 / week

1 / 30

Upper Matecumbe Key ski home to rent.

Upper Matecumbe Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from $404 / night

$2,828 / week

1 / 24

Vacation home in Upper Matecumbe Key

Upper Matecumbe Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $690 / night

$4,830 / week

1 / 25

Vacation home rental

Upper Matecumbe Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $476 / night

$3,332 / week

1 / 30

Upper Matecumbe Key Vacation home rental

Upper Matecumbe Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $514 / night

$3,598 / week

1 / 9

Upper Matecumbe Key Vacation home rental

Upper Matecumbe Key house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

from $1,289 / night

$9,023 / week

1 / 30

Upper Matecumbe Key Vacation home rental

Upper Matecumbe Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $1,016 / night

$7,112 / week

1 / 30

Vacation home in Upper Matecumbe Key

Upper Matecumbe Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 16

from $1,962 / night

$13,734 / week

1 / 30

Ski apartment to rent in Upper Matecumbe Key

Upper Matecumbe Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $442 / night

$3,094 / week

1 / 28

Vacation home in Upper Matecumbe Key

Upper Matecumbe Key house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

from $835 / night

$5,845 / week

1 / 30

Vacation home in Upper Matecumbe Key

Upper Matecumbe Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $787 / night

$5,509 / week

1 / 30

Vacation home rental

Upper Matecumbe Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from $1,777 / night

$12,439 / week

1 / 30

Upper Matecumbe Key ski apartment to rent.

Upper Matecumbe Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

from $655 / night

$4,585 / week

1 / 24

Vacation home in Upper Matecumbe Key

Upper Matecumbe Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

from $687 / night

$4,809 / week

1 / 20

Home rental in Upper Matecumbe Key

Upper Matecumbe Key house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

from $515 / night

$3,605 / week

1 / 30

Vacation home in Upper Matecumbe Key

Upper Matecumbe Key house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

from $440 / night

$3,080 / week

1 / 30

Vacation home in Upper Matecumbe Key

Upper Matecumbe Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $547 / night

$3,829 / week

1 / 30

Vacation home in Upper Matecumbe Key

Upper Matecumbe Key house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

from $517 / night

$3,619 / week

1 / 30

Vacation home in Upper Matecumbe Key

Upper Matecumbe Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $494 / night

$3,458 / week

1 / 30

Ski home to rent in Upper Matecumbe Key

Upper Matecumbe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $174 / night

$1,218 / week

1 / 30

Ski apartment to rent in Upper Matecumbe Key

Upper Matecumbe Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $560 / night

$3,920 / week

1 / 30

Vacation home in Upper Matecumbe Key

Upper Matecumbe Key house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

from $2,406 / night

$16,842 / week

1 / 30

Vacation condo in Upper Matecumbe Key

Upper Matecumbe Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $220 / night

$1,540 / week

1 / 23

Upper Matecumbe Key Vacation home rental

Upper Matecumbe Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $823 / night

$5,761 / week

1 / 30

Upper Matecumbe Key ski apartment to rent.

Upper Matecumbe Key apartment

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

from $1,309 / night

$9,163 / week

1 / 30

Vacation home in Upper Matecumbe Key

Upper Matecumbe Key house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

from $1,122 / night

$7,854 / week

1 / 30

Ski apartment to rent in Upper Matecumbe Key

Upper Matecumbe Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $542 / night

$3,794 / week

1 / 30

Ski home to rent in Upper Matecumbe Key

Upper Matecumbe Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $498 / night

$3,486 / week

1 / 30

Vacation villa in Upper Matecumbe Key

Upper Matecumbe Key villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

from $800 / night

$5,600 / week

1 / 30

Upper Matecumbe Key Vacation villa rental

Upper Matecumbe Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $1,117 / night

$7,819 / week

1 / 30

Vacation home in Upper Matecumbe Key

Upper Matecumbe Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 16

from $1,902 / night

$13,314 / week

1 / 30

Vacation home in Upper Matecumbe Key

Upper Matecumbe Key house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

from $892 / night

$6,244 / week

1 / 30

Upper Matecumbe Key Vacation condo accommodation

Upper Matecumbe Key condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $206 / night

$1,442 / week

1 / 29

Vacation home rental

Upper Matecumbe Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 8

from $917 / night

$6,419 / week

1 / 30

Upper Matecumbe Key ski home to rent.

Upper Matecumbe Key house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

from $560 / night

$3,920 / week

1 / 30