Updating...

Enter dates for more accurate prices

Sugarloaf Key Rentals

Filter

Bedrooms

  • Any
  • 1+ Bedrooms
  • 2+ Bedrooms
  • 3+ Bedrooms
  • 4+ Bedrooms
  • 5+ Bedrooms
  • 6+ Bedrooms
  • 7+ Bedrooms
  • 8+ Bedrooms
  • 9+ Bedrooms
  • 10+ Bedrooms
  • 11+ Bedrooms
  • 12+ Bedrooms
  • 13+ Bedrooms
  • 14+ Bedrooms
  • 15+ Bedrooms

Price range

Per night

$10 - $500

Sugarloaf Key Rentals

710 house rentals

$126

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 10 minutes

$126

1 / 26

$166

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 10 minutes

$166

1 / 44

$158

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

Sugarloaf Key house

2 bedrooms / 2 bathrooms / Sleeps 6

Responds fast! avg. 2 hours 10 minutes

$158

1 / 24

$91

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 10 minutes

$91

1 / 29

$134

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

Sugarloaf Key house

2 bedrooms / 3 bathrooms / Sleeps 6

Responds fast! avg. 2 hours 10 minutes

$134

1 / 36

$157

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

Sugarloaf Key house

1 bedroom / 1 bathroom / Sleeps 4

Responds fast! avg. 2 hours 10 minutes

$157

1 / 27

$735

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 10 minutes

$735

1 / 37

$151

Dog-friendly condo w/ shared pool & hot tub & complimentary shuttle.

Sugarloaf Key house

2 bedrooms / 2 bathrooms / Sleeps 6

Responds fast! avg. 2 hours 10 minutes

$151

1 / 30

$154

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 10 minutes

$154

1 / 25

$364

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

Sugarloaf Key house

4 bedrooms / 3 bathrooms / Sleeps 12

Responds fast! avg. 2 hours 10 minutes

$364

1 / 30

$151

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 10 minutes

$151

1 / 26

$81

Tropical condo for two with a great location in the heart of Old Town Key West

Sugarloaf Key studio

Studio / 1 bathroom / Sleeps 2

Responds fast! avg. 2 hours 10 minutes

$81

1 / 30

$395

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 10 minutes

$395

1 / 35

$473

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 10 minutes

$473

1 / 24

$277

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 10 minutes

$277

1 / 25

$149

Key West home w/ private hot tub - close to notable attractions

Sugarloaf Key house

5 bedrooms / 2 bathrooms / Sleeps 9

Responds fast! avg. 2 hours 10 minutes

$149

1 / 33

$195

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

Sugarloaf Key house

2 bedrooms / 1 bathroom / Sleeps 4

Responds fast! avg. 2 hours 10 minutes

$195

1 / 24

$493

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 10 minutes

$493

1 / 24

$190

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

Sugarloaf Key house

2 bedrooms / 1 bathroom / Sleeps 6

“Super little Key West house” Three friends had a splendid three nights at Windward Isle over Superbowl weekend in January. Two large and very comfortable beds, nice hot tub out the back. There's access to two pools nearby, which are good for a dip if

Responds fast! avg. 2 hours 10 minutes

$190

1 / 30

$182

Condo on Duval w/shared hot tub & private parking - dogs OK

Sugarloaf Key house

2 bedrooms / 1 bathroom / Sleeps 4

“LOVED IT!!!” My fiance and I absolutely LOVED our stay at Buena Vista cottage. There was a VERY PRIVATE jacuzzi, very romantic! Found the cottage to be very clean. Location was absolutely fantastic in relation to Duval Street, Mallory Square, and bea

Responds fast! avg. 2 hours 10 minutes

$182

1 / 29

$74

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

Sugarloaf Key house

2 bedrooms / 1 bathroom / Sleeps 4

Responds fast! avg. 2 hours 10 minutes

$74

1 / 26

$157

Dog-friendly condo w/ complimentary shuttle, shared pool, & hot tub

Sugarloaf Key house

2 bedrooms / 2 bathrooms / Sleeps 6

Responds fast! avg. 2 hours 10 minutes

$157

1 / 28

$159

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

Sugarloaf Key house

2 bedrooms / 2 bathrooms / Sleeps 6

Responds fast! avg. 2 hours 10 minutes

$159

1 / 27

$150

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

Sugarloaf Key house

2 bedrooms / 2 bathrooms / Sleeps 6

Responds fast! avg. 2 hours 10 minutes

$150

1 / 27

$151

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. 2 hours 10 minutes

$151

1 / 26

$249

~ CASABLANCA GRANDE ~ 2 'Old Town' Cottages w/ Pvt Pool, Hot Tub, & Parking!

Sugarloaf Key apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$249

1 / 26

$126

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

Sugarloaf Key house

2 bedrooms / 1 bathroom / Sleeps 4

Responds fast! avg. 2 hours 10 minutes

$126

1 / 33

$160

Lovely condo w/ shared pool & hot tub right nearby the beach - dogs OK!

Sugarloaf Key house

2 bedrooms / 2 bathrooms / Sleeps 6

Responds fast! avg. 2 hours 10 minutes

$160

1 / 27

$123

Condo on Duval Street - walk to beach & Southernmost Point, dogs OK

Sugarloaf Key house

1 bedroom / 1 bathroom / Sleeps 3

Responds fast! avg. 2 hours 10 minutes

$123

1 / 28

$98

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

Sugarloaf Key studio

Studio / 1 bathroom / Sleeps 2

Responds fast! avg. 2 hours 10 minutes

$98

1 / 27

$106

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

Sugarloaf Key studio

Studio / 1 bathroom / Sleeps 2

Responds fast! avg. 2 hours 10 minutes

$106

1 / 30

$239

Colorful condo w/ deck, balcony & shared pool - near downtown & beaches

Sugarloaf Key house

2 bedrooms / 3 bathrooms / Sleeps 6

“Excellent Location and accomodations” We had a great experience with Casa Cubana and the folks at Key West Vacation Rentals. The apartment itself was well furnished, spacious, and in a prime location walking distance to shopping and dining. Rick at Ke

Responds fast! avg. 2 hours 10 minutes

$239

1 / 27

$166

Stylish, dog-friendly condo with shared pool, hot tub, and complimentary shuttle

Sugarloaf Key house

2 bedrooms / 2 bathrooms / Sleeps 6

Responds fast! avg. 2 hours 10 minutes

$166

1 / 27

$130

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 10 minutes

$130

1 / 30

$106

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

Sugarloaf Key house

2 bedrooms / 3 bathrooms / Sleeps 4

Responds fast! avg. 2 hours 10 minutes

$106

1 / 26

$156

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

Sugarloaf Key house

2 bedrooms / 2 bathrooms / Sleeps 6

Responds fast! avg. 2 hours 10 minutes

$156

1 / 27

$138

Island condo w/ balcony & great central location - beach nearby! Dogs OK!

Sugarloaf Key house

1 bedroom / 1 bathroom / Sleeps 4

“Awesome” The location Is close to the beach as well as restaurants and shops. It was clean and had everything we needed. Very cute. The veranda was nice to sit out in the morning and evening

Responds fast! avg. 2 hours 10 minutes

$138

1 / 25

$110

Cozy, tropical getaway w/ shared pool - close to shopping and restaurants

Sugarloaf Key studio

Studio / 1 bathroom / Sleeps 2

Responds fast! avg. 2 hours 10 minutes

$110

1 / 30
Viewing 38 of 710
Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more