Sugarloaf Key Vacation Rentals, Vacation Home Rentals & more


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Areas near Sugarloaf Key

Travelers going to Sugarloaf Key are booking December dates now. Secure your vacation rental today and have the perfect trip.

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

  • 5
  • 10
  • Min stay varies

$178

Details

Great rentals within 20 miles that match your search

1 / 13

Oceanfront Home Rental in Ramrod Key, Florida

  • 3
  • 6
  • Min stay varies

Inquire for Rates

Details

1 / 17

Sunrise off Southard- A Tropical Sanctuary Newly Remodeled in May

  • 1
  • 3
  • 7 nights min

$140

Details

1 / 22

Catherine House: A charming Old Town Key West cottage

  • 2
  • 4
  • Min stay varies

$326

Details

1 / 19

Fantasy Resort Villa ~ Weekly Rental

  • 3
  • 8
  • Min stay varies

$851

Details

1 / 37

Beach Club #408 - Unique Oceanfront living

  • 4
  • 8
  • Min stay varies

$435

Details

1 / 24

HISTORIC KEY WEST - Turtle House - Sleeps 6

  • 2
  • 6
  • 30 nights min

$131

Details

1 / 24

Garden Home Paradise in Midtown Key West

  • 2
  • 6
  • 30 nights min

$128

Details

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Sunrise At Seaside Condo 2 bedroom 2 bath

  • 2
  • 5
  • Min stay varies

$160

Details

1 / 14

53' Hatteras 3 Bedroom

  • 3
  • 6
  • 7 nights min

$401

Details

1 / 24

Banana Key

  • 2
  • 5
  • 7 nights min

$250

Details

1 / 24

Pelican Landing Harbor Island Retreat

  • 2
  • 6
  • Min stay varies

$300

Details

1 / 24

Admiral's Lane

  • 4
  • 8
  • 7 nights min

$750

Details

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The Meadows House

  • 2
  • 6
  • Min stay varies

$401

Details

1 / 15

House of the Sun

  • 3
  • 6
  • 30 nights min

$181

Details

1 / 30

Classic Key West Estate ~ Weekly Rental

  • 7
  • 14
  • Min stay varies

$1400

Details

1 / 38

Shark Key Home with beach 10 Min from Duval St

  • 3
  • 8
  • 21 nights min

$258

Details

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house boat Ramrod

  • 2
  • 4
  • 30 nights min

$118

Details

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Atlantic Breeze

  • 3
  • 6
  • 30 nights min

$134

Details

1 / 24

Shipyard

  • 2
  • 4
  • 7 nights min

$184

Details

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Sunshine, beaches, and ocean breezes at Ocean Vista (La Brisa #403E)

  • 2
  • 4
  • Min stay varies

$225

Details

1 / 24

Solaris Cottage: Historic Old Town Lane, 14 minute walk to Beach!

  • 1
  • 2
  • Min stay varies

$296

Details

1 / 24

Old Town Eyebrow:Luxurious/Private Home

  • 3
  • 8
  • 30 nights min

$426

Details

1 / 19

Royal Palm

  • 2
  • 5
  • 7 nights min

$249

Details

1 / 24

Pelican Landing Eleuthera Retreat

  • 2
  • 8
  • Min stay varies

$298

Details

1 / 23

Amelia's Hideaway ~ Weekly Rental

  • 4
  • 10
  • Min stay varies

$844

Details

1 / 14

On Hemingway's Rounds ~ Monthly Rental

  • 3
  • 6
  • 30 nights min

$149

Details

1 / 19

Big Water Views, New Dock With No Neighbors

  • 4
  • 8
  • 30 nights min

$167

Details

1 / 28

Florida Keys Fisherman and Divers Paradise

  • 4
  • 12
  • 30 nights min

$239

Details

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Pelican Landing Abaco Retreat

  • 2
  • 8
  • Min stay varies

$300

Details

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Architects Cottage on Quiet Lane in Old Town

  • 3
  • 8
  • 30 nights min

$149

Details

1 / 17

Twice as Nice ~ Weekly Rental

  • 4
  • 8
  • Min stay varies

$844

Details

1 / 13

Casa Rosa

  • 2
  • 4
  • 30 nights min

$107

Details

1 / 15

Beautiful, Oversize 2BR/King Beds w/ Large Outdoor Spaces, Location! Truman Annx

  • 2
  • 4
  • 7 nights min

$227

Details

1 / 31

Poinciana Place Treetop: Second Floor, Hot Tub, Walk to Beach & Downtown!

  • 1
  • 3
  • Min stay varies

$221

Details

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Catchin' Moments Charters

  • 4
  • 8
  • 3 nights min

$950

Details

1 / 31

30 night minimum stay requirement. Key Haven Retreat - 4 Bedroom House with

  • 4
  • 10
  • 30 nights min

$167

Details

1 / 20

Beautiful Oceanfront 4/2 Home With Heated Pool/Spa

  • 4
  • 8
  • 30 nights min

$233

Details

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