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> North America
> United States
> Florida
> Gulf Gate Branch

Vacation homes - vacation rentals

Price per day

$1 $750 -

Bedrooms

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  • 4 and above
  • 3 and above
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Filtered properties are rated either by Tripadvisor Vacation Rentals users, or by Vrbo users. Both rating systems are separate, and are depicted differently as shown in the key above. Tripadvisor performs checks on its reviews. Holiday Lettings and companies under Tripadvisor Group do not check Vrbo reviews.
Property type
  • Apartment (107)
  • Villa (2)
  • Cottage (2)
  • House (65)
  • Townhouse (2)
  • Condo (93)
  • Guest house (1)

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272 Vacation rentals

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Private pool

Great rentals within 20 miles that match your search

Vacation apartment with swimming pool in Siesta Key

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $290 / night

$2,030 - $3,070 / week

1 / 28

Great rentals within 20 miles that match your search

Vacation condo in Siesta Key

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $401 / night

$2,806 / week

1 / 27

Great rentals within 20 miles that match your search

Siesta Key Vacation apartment rental

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $167 / night

$1,170 - $2,025 / week

1 / 31

Great rentals within 20 miles that match your search

Vacation home with swimming pool in Siesta Key

Siesta Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

from $1,002 / night

$7,014 / week

1 / 49

Great rentals within 20 miles that match your search

Apartment rental in Siesta Key with swimming pool

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $249 / night

$1,740 - $2,525 / week

1 / 22

Great rentals within 20 miles that match your search

Apartment rental in Siesta Key with swimming pool

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $264 / night

$1,845 - $2,785 / week

1 / 26

Great rentals within 20 miles that match your search

Vacation apartment rental

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $264 / night

$1,845 - $2,785 / week

1 / 21

Great rentals within 20 miles that match your search

Vacation apartment with swimming pool in Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $249 / night

$1,740 - $2,525 / week

1 / 33

Great rentals within 20 miles that match your search

Vacation apartment with swimming pool in Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $142 / night

$995 - $1,835 / week

1 / 37

Great rentals within 20 miles that match your search

Vacation apartment with swimming pool in Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $264 / night

$1,845 - $2,785 / week

1 / 15

Great rentals within 20 miles that match your search

Siesta Key Vacation apartment rental

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $264 / night

$1,845 - $2,785 / week

1 / 29

Great rentals within 20 miles that match your search

Vacation apartment in Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $167 / night

$1,170 - $2,025 / week

1 / 26

Great rentals within 20 miles that match your search

Vacation apartment rental

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6
1 review

from $167 / night

$1,170 - $2,025 / week

1 / 39

Great rentals within 20 miles that match your search

Siesta Key Vacation apartment rental

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $171 / night

$1,200 - $2,135 / week

1 / 25

Great rentals within 20 miles that match your search

Vacation apartment with swimming pool in Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $264 / night

$1,845 - $2,785 / week

1 / 23

Great rentals within 20 miles that match your search

Apartment rental in Siesta Key with swimming pool

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $249 / night

$1,740 - $2,525 / week

1 / 24

Great rentals within 20 miles that match your search

Siesta Key Vacation apartment rental

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $249 / night

$1,740 - $2,525 / week

1 / 17

Great rentals within 20 miles that match your search

Vacation condo in Sarasota

Sarasota condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $115 / night

$802 / week

1 / 24

Great rentals within 20 miles that match your search

Vacation apartment in Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6
30 reviews

from $266 / night

$1,861 - $3,704 / week

1 / 38

Great rentals within 20 miles that match your search

Apartment rental in Siesta Key with swimming pool

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4
1 review

from $142 / night

$995 - $1,835 / week

1 / 24

Great rentals within 20 miles that match your search

Apartment rental in Siesta Key with shared pool

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $133 / night

$2,004 / week

1 / 38

Great rentals within 20 miles that match your search

Vacation apartment in Siesta Key

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $290 / night

$2,030 - $3,070 / week

1 / 32

Great rentals within 20 miles that match your search

Vacation apartment with swimming pool in Siesta Key

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $290 / night

$2,030 - $3,070 / week

1 / 23

Great rentals within 20 miles that match your search

Siesta Key Vacation apartment rental

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $290 / night

$2,030 - $3,070 / week

1 / 28

Great rentals within 20 miles that match your search

Vacation apartment with swimming pool in Siesta Key

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $205 / night

$1,435 - $2,445 / week

1 / 44

Great rentals within 20 miles that match your search

Vacation apartment with swimming pool in Siesta Key

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $290 / night

$2,030 - $3,070 / week

1 / 23

Great rentals within 20 miles that match your search

Vacation apartment with swimming pool in Siesta Key

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $290 / night

$2,030 - $3,070 / week

1 / 26

Great rentals within 20 miles that match your search

Apartment rental in Siesta Key with swimming pool

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $290 / night

$2,030 - $3,070 / week

1 / 31

Great rentals within 20 miles that match your search

Siesta Key Vacation apartment rental

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $290 / night

$2,030 - $3,070 / week

1 / 38

Great rentals within 20 miles that match your search

Siesta Key Vacation apartment rental

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $205 / night

$1,435 - $2,445 / week

1 / 27

Great rentals within 20 miles that match your search

Vacation apartment in Siesta Key

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $193 / night

$1,350 - $2,310 / week

1 / 38

Great rentals within 20 miles that match your search

Vacation apartment with swimming pool in Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $249 / night

$1,740 - $2,525 / week

1 / 24

Great rentals within 20 miles that match your search

Siesta Key Vacation apartment rental

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $137 / night

$960 - $1,650 / week

1 / 30

Great rentals within 20 miles that match your search

Vacation apartment with swimming pool in Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from $142 / night

$995 - $1,835 / week

1 / 19

Great rentals within 20 miles that match your search

Vacation apartment with swimming pool in Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $137 / night

$960 - $1,650 / week

1 / 20

Great rentals within 20 miles that match your search

Siesta Key Vacation apartment accommodation

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from $142 / night

$995 - $1,835 / week

1 / 26

Great rentals within 20 miles that match your search

Vacation apartment with swimming pool in Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from $142 / night

$995 - $1,835 / week

1 / 31

Great rentals within 20 miles that match your search

Sarasota Vacation apartment rental

Sarasota apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $142 / night

$995 - $1,835 / week

1 / 32

Great rentals within 20 miles that match your search

Vacation apartment with swimming pool in Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $236 / night

$1,655 - $2,285 / week

1 / 20

Great rentals within 20 miles that match your search

Siesta Key Vacation apartment rental

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from $249 / night

$1,740 - $2,525 / week

1 / 20