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Vacation Rentals & House Rentals in Sugarloaf Key

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Price range

Per night

$10 - $500

Vacation Rentals & House Rentals in Sugarloaf Key

696 house rentals

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

Sugarloaf Key house

5 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 2 hours 52 minutes

Price per night from

$143

1 / 44

Comfortable condo w/ shared pool, private balcony, and beach access

Sugarloaf Key house

2 bedrooms / 2 bathrooms / sleeps 6

“Relaxing and Fun” Very good location..steps away from Smathers beach. Parked car then rode bikes, scooters, and walked around the entire Key. Condo was very nice and comfortable with everything needed for a week or more stay. The only negative is t

Responds fast! avg. 2 hours 52 minutes

Price per night from

$227

1 / 26

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

Sugarloaf Key house

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 52 minutes

Price per night from

$117

1 / 25

Cute, updated Key West home w/ private pool - close to Duval Street, dogs ok!

Sugarloaf Key house

3 bedrooms / 2 bathrooms / sleeps 10

“What a fun time !!!” I brought my daughter & her boyfriend, my middle daughter and her boyfriend, my son who is a freshman at psu, my girlfriend suzie & myself. We golfed( great golf course ) !!! We jet skiied around key west... you guys have to do

Responds fast! avg. 2 hours 52 minutes

Price per night from

$323

1 / 25

Dog-friendly Sunrise Suites condo w/ private balcony, views, shared pool/hot tub

Sugarloaf Key house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 52 minutes

Price per night from

$105

1 / 24

Family friendly condo w/ shared pool, hot tub, & complimentary shuttle! Dogs ok!

Sugarloaf Key house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 52 minutes

Price per night from

$105

1 / 27

Recently renovated home w/ shared pool, furnished patio area - in town, dogs ok

Sugarloaf Key house

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 52 minutes

Price per night from

$154

1 / 28

NEW LISTING! Adorable studio in Historic Seaport -walking distance to waterfront

Sugarloaf Key studio

Studio / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 52 minutes

Price per night from

$60

1 / 24

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

Sugarloaf Key studio

Studio / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 52 minutes

Price per night from

$72

1 / 29

Sprawling condo w/ ocean views, dock, & shared pool - dog-friendly!

Sugarloaf Key house

2 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 2 hours 52 minutes

Price per night from

$113

1 / 36

Dog-friendly home in a quiet neighborhood w/ shared pool & private hot tub!

Sugarloaf Key house

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 2 hours 52 minutes

Price per night from

$159

1 / 26

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

Sugarloaf Key house

8 bedrooms / 7 bathrooms / sleeps 24

Responds fast! avg. 2 hours 52 minutes

Price per night from

$730

1 / 35

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

Sugarloaf Key house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 52 minutes

Price per night from

$108

1 / 25

Dog-friendly, colorful cottages w/ pool & hot tub in a fabulous location!

Sugarloaf Key house

5 bedrooms / 4 bathrooms / sleeps 16

“Love Key West” We had a group of 10 people and we stayed at almost Southernmost Retreat. The property consisted of 2 homes that were connected with a pool and hot tub. The property was fantastic. Great location and the property was well kept and ver

Responds fast! avg. 2 hours 52 minutes

Price per night from

$278

1 / 47

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

Sugarloaf Key house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 52 minutes

Price per night from

$106

1 / 25

Shared pool & hot tub, parking spot, balcony - one dog ok! Family friendly!

Sugarloaf Key house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 52 minutes

Price per night from

$114

1 / 25

Sunrise Suites condo w/balcony, shared pool & hot tub, tennis, & covered parking

Sugarloaf Key house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 52 minutes

Price per night from

$122

1 / 24

Beautiful condo with a deck/patio & shared pool - walk to beaches, Duval & more!

Sugarloaf Key house

2 bedrooms / 1 bathroom / sleeps 4

“Key West Vacation Rentals was great to work with.” We loved our stay at Truman annex at the Secret Garden. Working with Key West Vacation Rentals was awesome. Had a little problem when we first checked in with construction going on in the unit next d

Responds fast! avg. 2 hours 52 minutes

Price per night from

$137

1 / 24

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

Sugarloaf Key house

3 bedrooms / 3 bathrooms / sleeps 12

Responds fast! avg. 2 hours 52 minutes

Price per night from

$452

1 / 35

Dog-friendly Sunrise Suites condo w/ shared pool, hot tub & free parking

Sugarloaf Key house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 52 minutes

Price per night from

$100

1 / 29

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

Sugarloaf Key house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 52 minutes

Price per night from

$411

1 / 24

Dog-friendly home w/ private pool - walk to the beach and restaurants!

Sugarloaf Key house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 52 minutes

Price per night from

$409

1 / 26

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

Sugarloaf Key house

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 52 minutes

Price per night from

$170

1 / 26

Breezy Florida home with shared swimming pool, dog-friendly - walk to beach!

Sugarloaf Key house

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 52 minutes

Price per night from

$97

1 / 29

Four condos w/ entertainment, private parking & beach nearby - great for groups!

Sugarloaf Key house

4 bedrooms / 4 bathrooms / sleeps 14

Responds fast! avg. 2 hours 52 minutes

Price per night from

$520

1 / 24

Peaceful, dog-friendly home in a residential neighborhood w/ a shared pool

Sugarloaf Key house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 52 minutes

Price per night from

$174

1 / 26

Ocean view home with kayak near beaches, parks, shops & restaurants!

Sugarloaf Key house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 52 minutes

Price per night from

$100

1 / 37

Dog-friendly studio in the heart of Old Town - walk to beach & attractions!

Sugarloaf Key studio

Studio / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 52 minutes

Price per night from

$74

1 / 27

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

Sugarloaf Key house

7 bedrooms / 9 bathrooms / sleeps 18

Responds fast! avg. 2 hours 52 minutes

Price per night from

$1,030

1 / 31

Cozy ground-floor suite in historic home w/ shared pool - close to boardwalk!

Sugarloaf Key studio

Studio / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 52 minutes

Price per night from

$107

1 / 29

Dog-friendly home w/ detached cottage, private pool, & walk to beach!

Sugarloaf Key house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 2 hours 52 minutes

Price per night from

$168

1 / 24

Stylish, dog-friendly condo w/ balcony - in the heart of the historic district

Sugarloaf Key house

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 52 minutes

Price per night from

$126

1 / 26

Dog-friendly getaway in a quiet, residential neighborhood w/ a shared pool

Sugarloaf Key house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 52 minutes

Price per night from

$165

1 / 29

Spectacular, oceanfront, dog-friendly home w/ private pool & boat docks

Sugarloaf Key house

5 bedrooms / 3 bathrooms / sleeps 18

Responds fast! avg. 2 hours 52 minutes

Price per night from

$166

1 / 36

Cozy, dog-friendly retreat w/ shared hot tubs, patio, great location in Old Town

Sugarloaf Key studio

Studio / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 52 minutes

Price per night from

$89

1 / 29

Cozy, dog-friendly suite for two in the heart of historic Key West!

Sugarloaf Key house

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 52 minutes

Price per night from

$84

1 / 28

Spacious home w/ private pool - close to attractions & beach, dog OK!

Sugarloaf Key house

4 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 2 hours 52 minutes

Price per night from

$234

1 / 31

Dog-friendly home w/ private pool offers fantastic location in central Key West

Sugarloaf Key house

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 52 minutes

Price per night from

$97

1 / 26
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