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

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En Plein Air – MONTHLY Rental

  • 2
  • 4
  • 30 nights min

$130

Details

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Amelia's Hideaway ~ Weekly Rental

  • 4
  • 10
  • Min stay varies

$851

Details

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Tree House

  • 3
  • 6
  • 30 nights min

$100

Details

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Pelican Landing Florida Retreat

  • 2
  • 8
  • Min stay varies

$300

Details

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30 night minimum stay requirement. The Pearl in Paradise - 2 Bedroom House w

  • 2
  • 4
  • 30 nights min

$134

Details

1 / 11

Vintage Luxury Cottage ~ Weekly Rental

  • 1
  • 4
  • Min stay varies

$401

Details

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Reel Paradise - Big Pine Key

  • 3
  • 6
  • Min stay varies

$134

Details

1 / 25

Campbell Suite

  • 1
  • 2
  • Min stay varies

$201

Details

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Hyatt Sunset Harbor Resort

  • 2
  • 6
  • 4 nights min

$196

Details

1 / 6

Southernmost Beauty

  • 3
  • 6
  • 30 nights min

$268

Details

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3 BR (4bed) 2 BA Luxury Yacht-Sunset Cruise avail

  • 3
  • 8
  • 3 nights min

$650

Details

1 / 20

Key Z Cottage Romantic Getaway

  • 2
  • 6
  • 3 nights min

$238

Details

1 / 16

Ocean front Condo

  • 2
  • 6
  • 30 nights min

$134

Details

1 / 27

New Listing! - Mid Town Getaway with pool & jacuzzi

  • 3
  • 6
  • 28 nights min

$150

Details

1 / 6

The Galleon Resort - Friday, Saturday, Sunday Check Ins Only!

  • 2
  • 6
  • 7 nights min

$558

Details

1 / 25

Pelican Landing St. Thomas Penthouse

  • 4
  • 12
  • Min stay varies

$501

Details

1 / 33

"Not Big Enough"

  • 3
  • 8
  • Min stay varies

$396

Details

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Grande & Petite Maisons: Sleeps 12, Pool & Parking, Best Key West Location

  • 6
  • 12
  • Min stay varies

$1503

Details

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Beach Club #408 - Unique Oceanfront living

  • 4
  • 8
  • Min stay varies

$435

Details

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Hermitage South

  • 4
  • 8
  • Min stay varies

$726

Details

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Beautiful Townhome at the entrance to Key West

  • 2
  • 5
  • Min stay varies

$201

Details

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Shelleys Rooftop Hideaway

  • 2
  • 4
  • 7 nights min

$270

Details

1 / 15

Coral Hammock - Comfortable 3 Bedroom Home

  • 3
  • 6
  • 3 nights min

$250

Details

1 / 24

Dancing Palms Villa ~ Weekly Rental

  • 2
  • 4
  • 7 nights min

$264

Details

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Galleon Resort & Marina

  • 2
  • 6
  • 7 nights min

$258

Details

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Luxury 2 Bedroom with Full Kitchen - Sleeps 5 - Walk to the Beach & Nightlife

  • 2
  • 5
  • Min stay varies

$412

Details

1 / 15

737 The Place, a Monthly Rental Old Town Key West

  • 1
  • 2
  • 30 nights min

$61

Details

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Magnificent Ocean view with 35' dock , Canal home in gated Venture Out Resort

  • 2
  • 6
  • 3 nights min

$150

Details

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Coral Hammock 34- 3 Bedroom Townhouse with a Shared Pool

  • 3
  • 6
  • Min stay varies

$300

Details

1 / 23

Pete's East Cottage: Cypress east cottage steps from Duval

  • 2
  • 4
  • Min stay varies

$288

Details

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30 night Minimum Stay Heart of Historic downtown 238 2 bed 2 1/2 Bath

  • 2
  • 4
  • 30 nights min

$134

Details

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HISTORIC KEY WEST - Cigar House - Sleeps 4

  • 1
  • 4
  • 30 nights min

$99

Details

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Escape On Fleming: A charming 2 bedroom home

  • 2
  • 4
  • 28 nights min

$98

Details

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Island Days: Parking and Pool - Fishing, Boating, Golfing, Dining, Shopping!

  • 3
  • 7
  • Min stay varies

$450

Details

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Sparkling canalfront house surrounded by palms

  • 2
  • 4
  • 30 nights min

$108

Details

1 / 14

Center of It All - Paradise Island Suite

  • 2
  • 6
  • Min stay varies

$249

Details

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Kali Zoi House - 28 Day Minimum

  • 3
  • 6
  • 28 nights min

$233

Details

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