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Vacation Rentals & Vacation Rentals in Sugarloaf Key

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Per night

$10 - $500

Vacation Rentals & Vacation Rentals in Sugarloaf Key

693 house rentals

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 22 minutes

Price per night from

$110

1 / 26

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. 3 hours 38 minutes

Price per night from

$225

1 / 26

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

Sugarloaf Key house

5 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 3 hours 38 minutes

Price per night from

$139

1 / 44

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

Sugarloaf Key house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 38 minutes

Price per night from

$126

1 / 24

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 22 minutes

Price per night from

$144

1 / 25

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

Sugarloaf Key house

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 38 minutes

Price per night from

$136

1 / 26

Studio condo w/ shared courtyard & pool - walk to everything - dogs welcome!

Sugarloaf Key studio

Studio / 1 bathroom / sleeps 2

Responds fast! avg. 3 hours 38 minutes

Price per night from

$91

1 / 29

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 22 minutes

Price per night from

$381

1 / 27

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

Sugarloaf Key studio

Studio / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 38 minutes

Price per night from

$87

1 / 26

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 22 minutes

Price per night from

$435

1 / 24

Bright and sunny condo with patio, shared pool, and hot tub

Sugarloaf Key house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 22 minutes

Price per night from

$123

1 / 26

Dog-friendly home on a private beach with private pool & hot tub

Sugarloaf Key house

5 bedrooms / 6 bathrooms / sleeps 12

Responds fast! avg. 2 hours 22 minutes

Price per night from

$261

1 / 51

Cute, dog-friendly condo w/ free shuttle, private patio, shared pool and hot tub

Sugarloaf Key house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 38 minutes

Price per night from

$123

1 / 24

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. 3 hours 38 minutes

Price per night from

$127

1 / 25

Classic Key West cottage featuring shared pool, courtyard, covered front porch

Sugarloaf Key house

2 bedrooms / 2 bathrooms / sleeps 6

“Wonderful Place.” The Key Box was a little hard to see at night. We had never been in Key West before. The lighting by the Key Box was not very good to read the keypad. the directions to the House were very good if you were following them in the dayli

Responds fast! avg. 3 hours 38 minutes

Price per night from

$239

1 / 27

Elegant condo w/ entertainment & private parking - great central location!

Sugarloaf Key house

1 bedroom / 1 bathroom / sleeps 4

“Orchid Suite” This suite is a one bedroom suite with a pull out couch and a small kitchen but with no stove. It does have a microwave that was useful. It is very close to everything and one can walk to most stores, restaurants etc... The parking is b

Responds fast! avg. 2 hours 22 minutes

Price per night from

$112

1 / 17

Tropical condo w/ private patio & shared pool - walk to beaches, Duval & more!

Sugarloaf Key house

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 22 minutes

Price per night from

$177

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. 3 hours 38 minutes

Price per night from

$82

1 / 29

Cozy home w/ private pool & hot tub - walk to must-see attractions

Sugarloaf Key house

3 bedrooms / 4 bathrooms / sleeps 6

Responds fast! avg. 3 hours 38 minutes

Price per night from

$219

1 / 39

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

Sugarloaf Key studio

Studio / 1 bathroom / sleeps 2

Responds fast! avg. 3 hours 38 minutes

Price per night from

$73

1 / 27

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

Sugarloaf Key house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 38 minutes

Price per night from

$142

1 / 33

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

Sugarloaf Key house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 38 minutes

Price per night from

$143

1 / 26

Cute condo w/ front porch and optimal location, great for couples

Sugarloaf Key house

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 38 minutes

Price per night from

$125

1 / 27

Historic dog-friendly condo w/ hot tub and private balcony

Sugarloaf Key house

4 bedrooms / 3 bathrooms / sleeps 12

Responds fast! avg. 3 hours 38 minutes

Price per night from

$344

1 / 30

Spacious room in historic Curry House - shared pool & semi-private front balcony

Sugarloaf Key studio

Studio / 1 bathroom / sleeps 2

Responds fast! avg. 3 hours 38 minutes

Price per night from

$82

1 / 28

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

Sugarloaf Key studio

Studio / 1 bathroom / sleeps 2

Responds fast! avg. 3 hours 38 minutes

Price per night from

$103

1 / 27

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. 3 hours 38 minutes

Price per night from

$146

1 / 23

Comfy dog-friendly condo w/ balcony, shared pool & hot tub, tennis, & parking

Sugarloaf Key house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 22 minutes

Price per night from

$128

1 / 25

West-facing, bright and sunny condo w/ shared pool & hot tub, tennis, & parking

Sugarloaf Key house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 38 minutes

Price per night from

$128

1 / 27

Charming condo w/ entertainment & private parking - great location in town!

Sugarloaf Key house

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 38 minutes

Price per night from

$106

1 / 31

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. 3 hours 38 minutes

Price per night from

$220

1 / 26

Welcoming, budget-friendly studio w/ shared heated pool & home comforts

Sugarloaf Key studio

Studio / 1 bathroom / sleeps 2

Responds fast! avg. 3 hours 38 minutes

Price per night from

$80

1 / 25

Vibrant home w/hot tub & private pool blocks from the beach - dog-friendly!

Sugarloaf Key house

2 bedrooms / 3 bathrooms / sleeps 4

Responds fast! avg. 2 hours 22 minutes

Price per night from

$138

1 / 30

Beautiful top-floor room in historic inn w/ a shared pool & a semi-private deck!

Sugarloaf Key studio

Studio / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 22 minutes

Price per night from

$95

1 / 28

Cozy cottage w/ private hot tub, tranquil garden & parking - dogs OK!

Sugarloaf Key house

2 bedrooms / 1 bathroom / sleeps 6

“helpful and courteous” The service we received was excellent. The check in was easy to find and the help was very friendly and courteous. We loved the fact that we could leave our luggage between check in and check out time instead of having to carry

Responds fast! avg. 3 hours 38 minutes

Price per night from

$171

1 / 32

Centrally located home w/ private pool 3 blocks to Duval St - dogs OK!

Sugarloaf Key house

2 bedrooms / 2 bathrooms / sleeps 6

“5 star place to stay!” What could be better in Key West than your own pool, adorable kitchen and updated baths, and a great location, a few blocks from Duval. Kw Vacation Rentals couldn't have been nicer, thanks Thomas, Keith and Rick!

Responds fast! avg. 3 hours 38 minutes

Price per night from

$145

1 / 25

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

Sugarloaf Key house

4 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 3 hours 38 minutes

Price per night from

$234

1 / 31

Relax on historic inn's top floor - shared pool & semi-private deck!

Sugarloaf Key studio

Studio / 1 bathroom / sleeps 2

Responds fast! avg. 3 hours 38 minutes

Price per night from

$100

1 / 30
Viewing 38 of 693
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