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20 Best Summerland Key Vacation rentals on Holiday Lettings - House rentals

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112 Vacation rentals

Summerland Key Vacation home rental

Summerland Key house

4 bedrooms • 2 bathrooms • sleeps 8

1 review

from $556 / night

$3,888 / week

1 / 25

Vacation home in Summerland Key

Summerland Key house

3 bedrooms • 2 bathrooms • sleeps 6

from $129 / night

$899 / week

1 / 18

Vacation home in Summerland Key

Summerland Key house

3 bedrooms • 2 bathrooms • sleeps 6

from $244 / night

$1,704 / week

1 / 13

Vacation home rental

Summerland Key house

3 bedrooms • 3 bathrooms • sleeps 6

from $297 / night

$2,077 / week

1 / 23

Vacation home in Summerland Key

Summerland Key house

3 bedrooms • 2 bathrooms • sleeps 8

from $287 / night

$2,004 / week

1 / 22

Home rental in Summerland Key with swimming pool

Summerland Key house

5 bedrooms • 3 bathrooms • sleeps 8

from $229 / night

$1,890 - $5,153 / week

1 / 13

Vacation home in Summerland Key

Summerland Key house

4 bedrooms • 3 bathrooms • sleeps 8

from $330 / night

$2,310 / week

1 / 16

Vacation home in Summerland Key

Summerland Key house

2 bedrooms • 2 bathrooms • sleeps 4

from $150 / night

$1,050 / week

1 / 14

Summerland Key Vacation home rental

Summerland Key house

3 bedrooms • 3 bathrooms • sleeps 8

from $447 / night

$3,129 / week

1 / 21

Home rental in Summerland Key

Summerland Key house

2 bedrooms • 2 bathrooms • sleeps 6

1 review

from $161 / night

$1,123 / week

1 / 14

Vacation home in Summerland Key

Summerland Key house

3 bedrooms • 3 bathrooms • sleeps 6

from $220 / night

$1,540 / week

1 / 12

Summerland Key Vacation home rental

Summerland Key house

3 bedrooms • 3 bathrooms • sleeps 8

1 review

from $478 / night

$3,343 / week

1 / 51

Home rental in Summerland Key

Summerland Key house

5 bedrooms • 5 bathrooms • sleeps 10

from $764 / night

$5,344 / week

1 / 27

Vacation home in Summerland Key

Summerland Key house

3 bedrooms • 3 bathrooms • sleeps 6

from $230 / night

$1,610 / week

1 / 18

Vacation home in Summerland Key

Summerland Key house

4 bedrooms • 3 bathrooms • sleeps 10

from $430 / night

$3,010 / week

1 / 16

Vacation home in Summerland Key

Summerland Key house

3 bedrooms • 2 bathrooms • sleeps 8

from $179 / night

$1,251 / week

1 / 29

Summerland Key Vacation home rental

Summerland Key house

4 bedrooms • 2 bathrooms • sleeps 8

from $267 / night

$1,867 / week

1 / 19

Home rental in Summerland Key

Summerland Key house

3 bedrooms • 2 bathrooms • sleeps 9

from $297 / night

$2,077 / week

1 / 21

Vacation home with swimming pool in Summerland Key

Summerland Key house

4 bedrooms • 3 bathrooms • sleeps 9

from $179 / night

$1,251 / week

1 / 29

Vacation home rental

Summerland Key house

2 bedrooms • 2 bathrooms • sleeps 4

from $197 / night

$1,377 / week

1 / 14

Home accommodation in Summerland Key

Summerland Key house

2 bedrooms • 2 bathrooms • sleeps 10

from $174 / night

$1,219 / week

1 / 49

Summerland Key Vacation home rental

Summerland Key house

4 bedrooms • 3 bathrooms • sleeps 12

from $174 / night

$1,219 / week

1 / 48

Vacation home in Summerland Key

Summerland Key house

3 bedrooms • 3 bathrooms • sleeps 8

from $197 / night

$1,377 / week

1 / 17

Vacation home in Summerland Key

Summerland Key house

2 bedrooms • 2 bathrooms • sleeps 6

from $144 / night

$1,291 / week

1 / 31

Great rentals within 20 miles that match your search

Vacation home with golf nearby in Key West

Key West house

3 bedrooms • 2 bathrooms • sleeps 6

from $516 / night

$3,607 / week

1 / 18

Vacation yacht in Key West

Key West yacht

3 bedrooms • 3 bathrooms • sleeps 6

7 reviews

from $2,977 / night

$14,828 - $21,240 / week

1 / 70

Vacation home in Stock Island

Stock Island house

3 bedrooms • 4 bathrooms • sleeps 6

from $4,008 / night

$28,053 / week

1 / 4

Vacation home in Big Pine Key

Big Pine Key house

2 bedrooms • 2 bathrooms • sleeps 8

from $185 / night

$1,291 / week

1 / 12

Cudjoe Key Vacation home accommodation

Cudjoe Key house

3 bedrooms • 2 bathrooms • sleeps 6

3 reviews

from $130 / night

$909 / week

1 / 21

Vacation home in Ramrod Key

Ramrod Key house

2 bedrooms • 2 bathrooms • sleeps 6

from $130 / night

$909 / week

1 / 17

Vacation home in Big Pine Key

Big Pine Key house

5 bedrooms • 2 bathrooms • sleeps 10

from $227 / night

$1,587 / week

1 / 27

Vacation home in Cudjoe Key

Cudjoe Key house

2 bedrooms • 1 bathroom • sleeps 4

from $94 / night

$654 / week

1 / 15

Vacation home in Big Pine Key

Big Pine Key house

3 bedrooms • 1 bathroom • sleeps 6

from $122 / night

$852 / week

1 / 17

Vacation home in Cudjoe Key

Cudjoe Key house

2 bedrooms • 2 bathrooms • sleeps 4

from $114 / night

$794 / week

1 / 14

Cudjoe Key Vacation home rental

Cudjoe Key house

2 bedrooms • 2 bathrooms • sleeps 4

from $117 / night

$817 / week

1 / 16

Vacation home in Little Torch Key

Little Torch Key house

3 bedrooms • 2 bathrooms • sleeps 6

from $137 / night

$957 / week

1 / 15

Home rental in Little Torch Key

Little Torch Key house

3 bedrooms • 2 bathrooms • sleeps 6

from $164 / night

$1,144 / week

1 / 16

Vacation home in Cudjoe Key

Cudjoe Key house

3 bedrooms • 3 bathrooms • sleeps 6

from $194 / night

$1,354 / week

1 / 18

Vacation home rental

Little Torch Key house

3 bedrooms • 2 bathrooms • sleeps 6

1 review

from $145 / night

$1,015 / week

1 / 18

Vacation home in Big Pine Key

Big Pine Key house

2 bedrooms • 1 bathroom • sleeps 4

from $119 / night

$829 / week

1 / 16