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Sugarloaf Key Rentals

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Price range

Per night

$10 - $500

Sugarloaf Key Rentals

216 house rentals

Dog-friendly, tropical escape with central location, hot tub, and shared pool

Sugarloaf Key house

1 bedroom / 1 bathroom / Sleeps 4

$142

1 / 25

Large, dog-friendly home on three secluded acres w/ balconies, deck, views

Sugarloaf Key house

5 bedrooms / 4 bathrooms / Sleeps 10

$179

1 / 45

Cute, colorful, & updated Key West home w/ private pool - close to Duval Street

Sugarloaf Key house

3 bedrooms / 2 bathrooms / Sleeps 10

$309

1 / 25

Colorful, dog-friendly condo w/ private balcony, views, & shared pool/hot tub

Sugarloaf Key house

2 bedrooms / 2 bathrooms / Sleeps 6

$137

1 / 24

Newly furnished suite w/ shared pool & hot tub, tennis, balcony, parking, dog ok

Sugarloaf Key house

2 bedrooms / 2 bathrooms / Sleeps 6

$137

1 / 25

Restored historic home w/ private pool & reserved off-street parking - Dogs OK!

Sugarloaf Key house

3 bedrooms / 2 bathrooms / Sleeps 8

$370

1 / 24

Welcoming, dog-friendly suite w/ balcony views & shared pool/hot tub, & more!

Sugarloaf Key house

2 bedrooms / 2 bathrooms / Sleeps 6

$137

1 / 29

Sunny condo w/ private balcony, shared pool & hot tub, tennis, parking, 1 dog ok

Sugarloaf Key house

2 bedrooms / 2 bathrooms / Sleeps 6

$137

1 / 26

Cozy, dog-friendly suite w/ shared hot tubs, grill, and patio space to relax

Sugarloaf Key studio

Studio / 1 bathroom / Sleeps 4

$117

1 / 27

Beautiful, dog-friendly home w/ private pool & patio - in Old Town, near beach!

Sugarloaf Key house

2 bedrooms / 3 bathrooms / Sleeps 6

$99

1 / 28

Spacious home w/ private hot tub, back patio, and awesome location!

Sugarloaf Key house

8 bedrooms / 7 bathrooms / Sleeps 24

$770

1 / 37

A Key West gem w/ a private pool - close to shops & restaurants, dog-friendly

Sugarloaf Key house

2 bedrooms / 2 bathrooms / Sleeps 6

$328

1 / 27

Penthouse w/ private hot tub & shared pool - close to beaches, dogs OK.

Sugarloaf Key house

2 bedrooms / 3 bathrooms / Sleeps 6

$228

1 / 33

West-facing, dog-friendly condo w/ shared pool & hot tub, tennis, & parking

Sugarloaf Key house

2 bedrooms / 2 bathrooms / Sleeps 6

$137

1 / 27

Sunny condo w/ entertainment, balcony, & great location near the beach! Dogs OK!

Sugarloaf Key house

1 bedroom / 1 bathroom / Sleeps 4

$168

1 / 26

Dog-friendly seaside escape with shared pool, hot tub, tennis courts, and more!

Sugarloaf Key house

2 bedrooms / 2 bathrooms / Sleeps 4

$64

1 / 32

Dog-friendly studio condo w/ deck & free WiFi, in the heart of Old Town Key West

Sugarloaf Key studio

Studio / 1 bathroom / Sleeps 2

$99

1 / 29

East-facing dog-friendly condo w/ shared pool, hot tub, tennis, private balcony

Sugarloaf Key house

2 bedrooms / 2 bathrooms / Sleeps 6

$137

1 / 26

Dog-friendly condo w/ water views, shared pool & hot tub, and free shuttle

Sugarloaf Key house

2 bedrooms / 2 bathrooms / Sleeps 6

$137

1 / 27

Cozy, dog-friendly suite w/ shared hot tubs, patio space, grill, and kitchenette

Sugarloaf Key studio

Studio / 1 bathroom / Sleeps 4

$123

1 / 24

Freshly renovated condo w/ shared pool & full kitchen - great location!

Sugarloaf Key house

1 bedroom / 1 bathroom / Sleeps 4

$172

1 / 27

Charming attic studio suite in historic inn w/ a shared pool & a great location!

Sugarloaf Key studio

Studio / 1 bathroom / Sleeps 2

$128

1 / 24

Oceanview home w/ shared pool & hot tub - near golf & more. Dogs OK!

Sugarloaf Key house

2 bedrooms / 2 bathrooms / Sleeps 6

$123

1 / 24

Dog-friendly suite w/ balcony, shared pool & hot tub, tennis, & covered parking

Sugarloaf Key house

2 bedrooms / 2 bathrooms / Sleeps 6

$137

1 / 27

Quiet condo w/ shared pool & hot tub, private balcony - dog-friendly!

Sugarloaf Key house

2 bedrooms / 2 bathrooms / Sleeps 6

$137

1 / 26

Sunny tropical condo with a shared pool, close to all of the beachside action

Sugarloaf Key house

2 bedrooms / 1 bathroom / Sleeps 4

$133

1 / 28

Bright, clean home w/private hot tub & shared pool, close to everything, dogs ok

Sugarloaf Key house

2 bedrooms / 3 bathrooms / Sleeps 6

$228

1 / 27

Stylish condo with shared swimming pool moments from popular attractions!

Sugarloaf Key house

2 bedrooms / 3 bathrooms / Sleeps 4

$358

1 / 27

Tropical getaway w/private balcony, shared pool/hot tub - dog-friendly!

Sugarloaf Key house

2 bedrooms / 2 bathrooms / Sleeps 6

$137

1 / 27

Historic house w/ private pool & easy beach access - ideal for groups! Dogs OK!

Sugarloaf Key house

7 bedrooms / 8 bathrooms / Sleeps 18

$924

1 / 31

Charming cottage w/a private parking spot and private hot tub

Sugarloaf Key house

2 bedrooms / 2 bathrooms / Sleeps 6

$99

1 / 25

Dog-friendly condo w/ scenic views, shared pool & hot tub, balcony & parking

Sugarloaf Key house

2 bedrooms / 2 bathrooms / Sleeps 6

$137

1 / 25

Cozy, dog-friendly suite with balcony, shared hot tub/pool, and private parking!

Sugarloaf Key house

2 bedrooms / 2 bathrooms / Sleeps 6

$137

1 / 31

Nautical-themed home w/ private pool & gorgeous outdoor area - dogs OK!

Sugarloaf Key house

2 bedrooms / 2 bathrooms / Sleeps 6

$99

1 / 25

Dog-friendly retreat w/shared pool & hot tub, tennis, & balcony w/pool views

Sugarloaf Key house

2 bedrooms / 2 bathrooms / Sleeps 6

$137

1 / 25

Dog-friendly getaway, w/ separate living spaces, shared pool & hot tub

Sugarloaf Key house

3 bedrooms / 3 bathrooms / Sleeps 12

$432

1 / 35

Studio condo w/ entertainment, full kitchen & private parking - central location

Sugarloaf Key studio

Studio / 1 bathroom / Sleeps 2

$136

1 / 24

Cozy, dog-friendly home w/ patio & private pool - walk to dining & shopping!

Sugarloaf Key house

2 bedrooms / 2 bathrooms / Sleeps 5

$121

1 / 29
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