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698 Houses

12

Green Turtle Landing

Florida Keys / Sugarloaf

Sugarloaf house

3 6 30 nights min

  • 3 bedrooms
  • sleeps 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet Friendly

Price per night from

$139

Price per night from

$139

31

Canal-Front Paradise! Spacious 3BR w/ Private Pool, Boat Dock & Deck

Florida Keys / Sugarloaf

Sugarloaf house

3 6 30 nights min

  • 3 bedrooms
  • sleeps 6
  • 30 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$319

Price per night from

$319

8

Bay Pointe

Florida Keys / Sugarloaf

Sugarloaf house

3 6 30 nights min

  • 3 bedrooms
  • sleeps 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet Friendly

Price per night from

$139

Price per night from

$139

17

South Point Shores

Florida Keys / Sugarloaf

Sugarloaf house

3 6 30 nights min

  • 3 bedrooms
  • sleeps 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

Price per night from

$160

Price per night from

$160

19

Bow Channel Manor

Florida Keys / Sugarloaf

Sugarloaf house

3 6 30 nights min

  • 3 bedrooms
  • sleeps 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

Price per night from

$187

Price per night from

$187

11

Tranquility in Paradise - Sugarloaf Key (17 miles to Key West)

Florida Keys / Sugarloaf

Sugarloaf house

5 9 28 nights min

  • 5 bedrooms
  • sleeps 9
  • 28 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$280

Price per night from

$280

Great rentals within 20 miles that match your search

Distance approx 12.28 km from Sugarloaf

(19) Excellent 

26

Spectacular Atlantic Ocean View Condo (MONTHLY)

Florida Keys / Key West

Key West apartment

2 6 28 nights min

  • 2 bedrooms
  • sleeps 6
  • 28 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“Amazing Views And A Great Condo” My wife and I stayed here on our honeymoon and were absolutely 100% pleased with the condo. I have to honestly say it was the nicest condo either of us have stayed in. The view was amazing and the patio was very tranqu
…see more

Price per night from

$134

Price per night from

$134

Distance approx 6.42 km from Sugarloaf

38

Shark Key Home with beach 10 Min from Duval St

Florida Keys / Key West

Key West house

3 8 21 nights min

  • 3 bedrooms
  • sleeps 8
  • 21 nights min
  • Child Friendly
  • Ask about pets

Price per night from

$289

Responds fast!
avg. 3 hours 15 minutes

Price per night from

$289

Distance approx 17.09 km from Sugarloaf

(2) Excellent 

25

The Water's Edge

Florida Keys / Key West

Key West house

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“Perfect for a Memorable Key West Experience!” My family and I absolutely loved staying in this beautiful Key West home. Located in Truman Annex (a quiet, private community in Old Town Key West), the location is perfect for whatever you wish to do duri
…see more

Price per night from

$837

Price per night from

$837

Distance approx 16.87 km from Sugarloaf

(9) Very Good 

33

Heavenly Hideout at Rainbow's End ~ Weekly Rental

Florida Keys / Key West

Key West house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Ask about children
  • Air conditioning
  • Private garden

Price per night from

$745

Price per night from

$745

Distance approx 4.06 km from Sugarloaf Show on Map

(2) Excellent 

22

Oksana's Tropical Beach Oasis

Florida Keys / Cudjoe Key

Cudjoe Key house

5 14 7 nights min

  • 5 bedrooms
  • sleeps 14
  • 7 nights min
  • Nearest beach 10 mi
  • Swimming pool
  • Child Friendly

Price per night from

$592

Price per night from

$592

Distance approx 16.77 km from Sugarloaf

(3) Very Good 

31

Key West Wabi Sabi ~ Weekly Rental

Florida Keys / Key West

Key West house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$745

Price per night from

$745

Distance approx 16.68 km from Sugarloaf

(1) Excellent 

19

Villa Nouveau Key West ~ Weekly Rental

Florida Keys / Key West

Key West house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$839

Price per night from

$839

Distance approx 16.83 km from Sugarloaf

24

Old Town Eyebrow:Luxurious/Private Home

Florida Keys / Key West

Key West house

3 8 30 nights min

  • 3 bedrooms
  • sleeps 8
  • 30 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$424

Price per night from

$424

Distance approx 17 km from Sugarloaf

6

Garden Oasis at Truman Annex

Florida Keys / Key West

Key West condo

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$272

Price per night from

$272

Distance approx 16.63 km from Sugarloaf

(4) Excellent 

17

Twice as Nice ~ Weekly Rental

Florida Keys / Key West

Key West house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“Couldn't have chosen a better place!” We traveled with a group of 4 couples and stayed in both cottages. We couldn't haven chosen a better location or better homes. These homes were in an awesome location on Duval St. close enough to the crowds, but f
…see more

Price per night from

$839

Price per night from

$839

Distance approx 17 km from Sugarloaf

(1) Excellent 

21

Truman Annex 2 Bedroom 1 Bath

Florida Keys / Key West

Key West apartment

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$303

Price per night from

$303

Distance approx 16.68 km from Sugarloaf

(2) Average 

55

The Meeting Point - Key West ~ Weekly Rental

Florida Keys / Key West

Key West house

11 24 min stay varies

  • 11 bedrooms
  • sleeps 24
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$2,418

Price per night from

$2,418

Distance approx 9.07 km from Sugarloaf

19

Bahia Azul

Florida Keys / Ramrod Key

Ramrod Key house

4 8 30 nights min

  • 4 bedrooms
  • sleeps 8
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

Price per night from

$227

Price per night from

$227

Distance approx 4.71 km from Sugarloaf

11

Mermaid's Rest

Florida Keys / Cudjoe Key

Cudjoe Key house

3 6 30 nights min

  • 3 bedrooms
  • sleeps 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

Price per night from

$132

Price per night from

$132

Distance approx 16.84 km from Sugarloaf

(1) Excellent 

34

Seaport Treasure Estate ~ Monthly Rental

Florida Keys / Key West

Key West house

6 12 30 nights min

  • 6 bedrooms
  • sleeps 12
  • 30 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$592

Price per night from

$592

Distance approx 10.47 km from Sugarloaf

15

Island Chalet

Lower Keys / Little Torch Key

Little Torch Key house

3 6 30 nights min

  • 3 bedrooms
  • sleeps 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet Friendly

Price per night from

$116

Price per night from

$116

Distance approx 16.87 km from Sugarloaf

(7) Very Good 

16

The Tree House Old Town 2 Bedroom MONTHLY Rental

Florida Keys / Key West

Key West house

2 7 30 nights min

  • 2 bedrooms
  • sleeps 7
  • 30 nights min
  • Ask about children
  • Car not necessary
  • Air conditioning
“Wonderful” Close to everything! Furnishings just the best. We stayed upstairs in the 2 bedroom 1 large bath. Great wrap around porch up stairs and down. Our key Westies were welcomed which was a plus for us! Overall Stephanie has done a great job an
…see more

Price per night from

$112

Price per night from

$112

Distance approx 5.01 km from Sugarloaf

12

Cudjoe Ocean Shores

Florida Keys / Cudjoe Key

Cudjoe Key house

3 6 30 nights min

  • 3 bedrooms
  • sleeps 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

Price per night from

$96

Price per night from

$96

Distance approx 11.35 km from Sugarloaf

10

Mango House

Lower Keys / Little Torch Key

Little Torch Key house

2 4 30 nights min

  • 2 bedrooms
  • sleeps 4
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

Price per night from

$67

Price per night from

$67

Distance approx 4.87 km from Sugarloaf

(3) Very Good 

19

Charming 3bedroom/2bath home in the Florida Keys

Florida Keys / Cudjoe Key

Cudjoe Key house

3 6 30 nights min

  • 3 bedrooms
  • sleeps 6
  • 30 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$92

Price per night from

$92

Distance approx 6.33 km from Sugarloaf

12

Caribbean House

Lower Keys / Summerland Key

Summerland Key house

2 4 30 nights min

  • 2 bedrooms
  • sleeps 4
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

Price per night from

$82

Price per night from

$82

Distance approx 4.86 km from Sugarloaf

15

Pirate's Cove

Florida Keys / Cudjoe Key

Cudjoe Key house

2 4 30 nights min

  • 2 bedrooms
  • sleeps 4
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet Friendly

Price per night from

$69

Price per night from

$69

Distance approx 13.2 km from Sugarloaf

16

Island Time 2 (half of duplex)

Florida Keys / Big Pine Key

Big Pine Key house

3 6 30 nights min

  • 3 bedrooms
  • sleeps 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet Friendly

Price per night from

$92

Price per night from

$92

Distance approx 13.75 km from Sugarloaf

(16) Very Good 

19

Elegant, Two Bedroom Condo Close to the Ocean

Florida Keys / Key West

Key West apartment

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Nearest beach 2 mi
  • Swimming pool
  • Child Friendly
“We'll be back...” We found this condo to be very clean and comfortable. We enjoyed sitting at the pool as well. Paul, the caretaker, was very pleasant and most accommodating. We shared the condo with another couple for our two night stay. It was
…see more

Price per night from

$258

Responds fast!
avg. 1 hour 34 minutes

Price per night from

$258

Distance approx 15.47 km from Sugarloaf

24

By The Beautiful Sea ~ A Key West Beach Front Condo ~ Weekly Rental

Florida Keys / Key West

Key West house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Ask about children

Price per night from

$474

Price per night from

$474

Distance approx 13.09 km from Sugarloaf

7

Atlantis

Florida Keys / Big Pine Key

Big Pine Key house

3 6 30 nights min

  • 3 bedrooms
  • sleeps 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

Price per night from

$103

Price per night from

$103

Distance approx 11.63 km from Sugarloaf

10

Blue Heron

Florida Keys / Big Pine Key

Big Pine Key house

2 4 30 nights min

  • 2 bedrooms
  • sleeps 4
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet Friendly

Price per night from

$85

Price per night from

$85

Distance approx 16.07 km from Sugarloaf

5

Vacation house for a family for oct

Florida Keys / Key West

Key West house

3 5 6 nights min

  • 3 bedrooms
  • sleeps 5
  • 6 nights min
  • Child Friendly

Price per night from

$497

Price per night from

$497

Distance approx 13.75 km from Sugarloaf

(69) Excellent 

Certificate of Excellence

25

Sunrise Suite Key West 2 Bed Rooms 2 Full Baths

Florida Keys / Key West

Key West condo

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Great condo- great vacation!!” Very nice condo, it accommodated 5 of comfortably. Condo is a quick 10 minute Uber/ taxi ride to town. My wife & I took a break from the action on Duval St to enjoy the heated pool & hot tub. Ed the owner was very easy t
…see more

Certificate of Excellence

Price per night from

$197

Responds fast!
avg. 2 hours 58 minutes

Price per night from

$197

Distance approx 5.2 km from Sugarloaf

17

Paradise Palms

Lower Keys / Summerland Key

Summerland Key house

3 6 30 nights min

  • 3 bedrooms
  • sleeps 6
  • 30 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$146

Price per night from

$146

Distance approx 1.03 km from Sugarloaf Show on Map

(4) Excellent 

11

Key West's only Real Beach House

Florida Keys / Key West

Key West guest house

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Ask about children

Price per night from

$388

Price per night from

$388

Distance approx 4.82 km from Sugarloaf

(2) Very Good 

29

Tropical Blue Adventure Waterfront at Venture Out

Florida Keys / Cudjoe Key

Cudjoe Key house

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 30 mi
  • Swimming pool

Price per night from

$173

Price per night from

$173