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Sugarloaf Key Rentals

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Price range

Per night

$10 - $500

Sugarloaf Key Rentals

219 house rentals

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

Sugarloaf Key house

5 bedrooms / 4 bathrooms / Sleeps 10

$179

1 / 45

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

Sugarloaf Key house

2 bedrooms / 2 bathrooms / Sleeps 6

$137

1 / 27

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

Sugarloaf Key house

1 bedroom / 1 bathroom / Sleeps 4

$172

1 / 25

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

Sugarloaf Key house

7 bedrooms / 8 bathrooms / Sleeps 18

$878

1 / 31

Gorgeous historic home with a private pool - great for large groups!

Sugarloaf Key house

9 bedrooms / 9 bathrooms / Sleeps 18

$890

1 / 33

Dog-friendly cottage w/ private hot tub & garden - great downtown location!

Sugarloaf Key house

2 bedrooms / 1 bathroom / Sleeps 6

$228

1 / 30

Welcoming home w/ shared pool boasts great Old Town location - dogs welcome!

Sugarloaf Key house

2 bedrooms / 3 bathrooms / Sleeps 4

$114

1 / 26

Cozy studio condo w/ shared pool & courtyard - easy beach access! Dogs OK!

Sugarloaf Key studio

Studio / 1 bathroom / Sleeps 2

$123

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

Sunny condo w/ amazing views features shared pool & hot tub - dogs welcome!

Sugarloaf Key house

2 bedrooms / 2 bathrooms / Sleeps 6

$137

1 / 27

Dog-friendly condo w/ shared pool, private balcony, and beach access

Sugarloaf Key house

2 bedrooms / 2 bathrooms / Sleeps 6

$229

1 / 26

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

Sugarloaf Key house

1 bedroom / 1 bathroom / Sleeps 4

$168

1 / 26

Colorful condo w/ shared pool & hot tub, parking spot, & balcony - one dog ok!

Sugarloaf Key house

2 bedrooms / 2 bathrooms / Sleeps 6

$137

1 / 26

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

Sugarloaf Key house

2 bedrooms / 2 bathrooms / Sleeps 6

$137

1 / 24

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

Sugarloaf Key house

2 bedrooms / 2 bathrooms / Sleeps 6

$137

1 / 27

Quaint romantic cottage with street parking, close to the beach & adventure!

Sugarloaf Key house

1 bedroom / 1 bathroom / Sleeps 2

$78

1 / 24

Lovely home w/ private pool and hot tub near shops and the beach - dogs OK!

Sugarloaf Key house

2 bedrooms / 2 bathrooms / Sleeps 6

$115

1 / 28

Dog-friendly home w/ private pool - one block from Duval Street, near Old Town!

Sugarloaf Key house

2 bedrooms / 1 bathroom / Sleeps 4

$74

1 / 26

Studio w/ balcony, central location, dog-friendly - beach nearby!

Sugarloaf Key studio

Studio / 1 bathroom / Sleeps 2

$99

1 / 31

Cozy, dog-friendly condo with views - walk to beach, dining, & attractions

Sugarloaf Key studio

Studio / 1 bathroom / Sleeps 2

$90

1 / 33

Dog-friendly Key West cottage with a private hot tub & an unbeatable location!

Sugarloaf Key house

3 bedrooms / 2 bathrooms / Sleeps 8

$352

1 / 27

Breezy dog-friendly condo w/ private deck, shared pool/hot tub, & parking space

Sugarloaf Key house

2 bedrooms / 2 bathrooms / Sleeps 6

$137

1 / 28

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

Sugarloaf Key house

2 bedrooms / 2 bathrooms / Sleeps 6

$137

1 / 29

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

Sugarloaf Key house

3 bedrooms / 2 bathrooms / Sleeps 8

$370

1 / 24

Dog-friendly, cozy home w/ private pool & hot tub - walk to must-see attractions

Sugarloaf Key house

3 bedrooms / 2 bathrooms / Sleeps 6

$171

1 / 39

Breezy condo w/ shared pool, hot tub, tennis courts, & balcony - dogs OK!

Sugarloaf Key house

2 bedrooms / 2 bathrooms / Sleeps 6

$137

1 / 29

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

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

Dog-friendly condo with tennis, shared pool, hot tub, and private balcony

Sugarloaf Key house

2 bedrooms / 2 bathrooms / Sleeps 6

$137

1 / 24

Breezy home w/central location in Key West near shopping, dining, etc. - dogs OK

Sugarloaf Key house

2 bedrooms / 2 bathrooms / Sleeps 6

$90

1 / 25

Fully-renovated home w/ yard, porch, shared pool - one block from Duval Street

Sugarloaf Key house

3 bedrooms / 2 bathrooms / Sleeps 8

$150

1 / 30

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

Sugarloaf Key house

1 bedroom / 1 bathroom / Sleeps 4

$172

1 / 27

Lovely condo w/ a private patio, shared pool & perfectly walkable location!

Sugarloaf Key house

2 bedrooms / 1 bathroom / Sleeps 4

$137

1 / 33

Dog-friendly condo w/ shared pool & hot tub perfect for exploring Key West!

Sugarloaf Key house

2 bedrooms / 2 bathrooms / Sleeps 6

$137

1 / 26

Charming, dog-friendly cottage with shared refreshing pool and easy beach access

Sugarloaf Key studio

Studio / 1 bathroom / Sleeps 2

$145

1 / 29

Breezy condo w/ shared pool & hot tub, tennis courts, & parking space

Sugarloaf Key house

2 bedrooms / 2 bathrooms / Sleeps 6

$137

1 / 30

Studio suite w/ shared hot tubs, patio, kitchenette - steps from beach. Dogs OK!

Sugarloaf Key studio

Studio / 1 bathroom / Sleeps 4

$122

1 / 26
Viewing 38 of 219
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