Sugarloaf Vacation Rentals, Houses & More


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Areas near Sugarloaf

1 / 19

Bow Channel Manor

  • 3
  • 6
  • 30 nights min

$188

Details

Great rentals within 20 miles that match your search

1 / 30

Classic Key West Estate ~ Weekly Rental

  • 7
  • 14
  • Min stay varies

$1400

Details

1 / 15

Coral Hammock - Comfortable 3 Bedroom Home

  • 3
  • 6
  • 3 nights min

$250

Details

1 / 19

Royal Palm

  • 2
  • 5
  • 7 nights min

$250

Details

1 / 24

Poinciana Place Garden: First Floor, Hot Tub, Walk to Beach & Downtown!

  • 1
  • 3
  • Min stay varies

$218

Details

1 / 9

Half a block away from Duval St and one block from the Hemingway House house!

  • 1
  • 2
  • 30 nights min

$114

Details

1 / 18

Yellow Fin

  • 4
  • 8
  • 30 nights min

$100

Details

1 / 21

The Meadows House

  • 2
  • 6
  • Min stay varies

$401

Details

1 / 13

3 bedroom canal front home minutes from open Water!

  • 3
  • 10
  • 30 nights min

$100

Details

1 / 17

Two Story Stilt Home with a Wraparound Deck in a Tropical Paradise in Fl Keys

  • 2
  • 6
  • 30 nights min

$108

Details

1 / 13

Bali Hideaway: A studio cottage that's perfect for two

  • Studio
  • 2
  • Min stay varies

$250

Details

1 / 37

Galleon Key West 2/2 Oceanfront Condo

  • 2
  • 6
  • 7 nights min

$537

Details

1 / 24

Dancing Palms Villa ~ Weekly Rental

  • 2
  • 4
  • 7 nights min

$264

Details

1 / 25

Quilted Giraffe

  • 2
  • 4
  • 14 nights min

$401

Details

1 / 10

Foundry on the Waterfront ~ Weekly Rental

  • 2
  • 6
  • 7 nights min

$272

Details

1 / 6

Galleon Resort & Marina

  • 2
  • 6
  • 7 nights min

$258

Details

1 / 12

The Tree House Old Town 2 Bedroom MONTHLY Rental

  • 2
  • 7
  • 30 nights min

$100

Details

1 / 15

Shelleys Rooftop Hideaway

  • 2
  • 4
  • 7 nights min

$270

Details

1 / 45

Family Reunion ~ Weekly Rental

  • 9
  • 22
  • Min stay varies

$1400

Details

1 / 33

Duval Square Penthouse: A large, beautiful condo steps from the action

  • 4
  • 10
  • Min stay varies

$527

Details

1 / 16

Beautiful Townhome at the entrance to Key West

  • 2
  • 5
  • Min stay varies

$201

Details

1 / 17

Twice as Nice ~ Weekly Rental

  • 4
  • 8
  • Min stay varies

$844

Details

1 / 37

Beach Club #408 - Unique Oceanfront living

  • 4
  • 8
  • Min stay varies

$435

Details

1 / 20

Beautiful Oceanfront 4/2 Home With Heated Pool/Spa

  • 4
  • 8
  • 30 nights min

$233

Details

1 / 17

Key West Seashell Cottage-1 block to Duval, spa

  • 1
  • 2
  • Min stay varies

$200

Details

1 / 16

Private Key West Sunset ~ Weekly Rental

  • 3
  • 6
  • 7 nights min

$543

Details

1 / 10

Starlight Siesta ~ Weekly Rental

  • 2
  • 4
  • Min stay varies

$376

Details

1 / 21

Exclusive Key West Beach Front ~ Weekly Rental

  • 2
  • 6
  • Min stay varies

$480

Details

1 / 4

Key West Hyatt Windward Pointe

  • 2
  • 6
  • 7 nights min

$229

Details

1 / 19

Fantasy Resort Villa ~ Weekly Rental

  • 3
  • 8
  • Min stay varies

$851

Details

1 / 5

One-bedroom suite in the heart of Old Key West

  • 1
  • 4
  • 3 nights min

$191

Details

1 / 23

Captain Rons Tropical Vacation Hideaway

  • 2
  • 4
  • 30 nights min

$90

Details

1 / 24

Admiral's Lane

  • 4
  • 8
  • 7 nights min

$750

Details

1 / 10

Mango House

  • 2
  • 4
  • 30 nights min

$68

Details

1 / 12

Green Turtle Landing

  • 3
  • 6
  • 30 nights min

$140

Details

1 / 8

Bay Pointe

  • 3
  • 6
  • 30 nights min

$140

Details

1 / 36

Beautifully landscaped & appointed canal-front home w/beach access & views!

  • 3
  • 8
  • Min stay varies

$135

Details

1 / 17

South Point Shores

  • 3
  • 6
  • 30 nights min

$160

Details

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