Vacation Rentals & House Rentals in Sugarloaf Key

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278 house rentals

Tranquility in Paradise - Sugarloaf

Sugarloaf Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$384

$and D0llar$: Indulge in Luxury & Spectacular Open Water Views, Pool, Hot Tub, D

Sugarloaf Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

Responds fast! avg. 2 hours 40 minutes

Price per night from

$179

Cassie's Paradise

Sugarloaf Key house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Responds fast! avg. 24 minutes

Price per night from

$5,720

Tiki Palms - Amazing 4 Bedroom Sugarloaf Key Canal Home, Private Pool and Dockag

Sugarloaf Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 40 minutes

Price per night from

$179

Bungalows at Sugarloaf Beach - The Lighthouse

Sugarloaf Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 24 minutes

Price per night from

$1,140

Beautiful quiet neighborhood. Sunsets! Huge Pool!

Sugarloaf Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 30 minutes

Price per night from

$320

Tropical Serenity in Sugarloaf: Waterfront 2BR Paradise, Pool, Tiki, Dockage & D

Sugarloaf Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 40 minutes

Price per night from

$179

Green Turtle Oasis: Lovely 4BR Canal Front Home, Pool, Dockage, Tiki, Outdoor Di

Sugarloaf Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 40 minutes

Price per night from

$179

Bayside Beauty: Tropical Paradise 3BR Home, Panoramic Open Water Views, Private

Sugarloaf Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 40 minutes

Price per night from

$179

Great rentals within 20 miles that match your search

Cozy Key West Hideaway with a Pool, Digital Workspace, and Privacy

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Price per night from

$343

Blackbeard's Escape

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$358

Waterfront Anchor House with Boat Basin and Ramp!

Little Torch Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$756

Pirates Paradise

Cudjoe Key house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Price per night from

$433

Blackbeard's Bounty

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$233

Boaters Dream House in the Water with 175’ of Sea Wall

Big Pine Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$772

Into the Mystic

Summerland Key house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Price per night from

$465

Lower Keys PARADISE 200 Ft of Dockage, Heated Pool, Quick Atlantic Access

Little Torch Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 24 minutes

Price per night from

$401

Price per night from

$612

Noah, Family Ocean Paradise

Key West house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$1,333

Private House Facing the Ocean with Heated Pool/Spa

Ramrod Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$409

Lobster Lagoon

Stock Island house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

Price per night from

$972

SEAPORT SAILING—Beach-Pool-BBQ-55”TV-HotTub

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$995

Historic Carriage House

Key West cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$229

Coconuts on the Water

Stock Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$205

Island Time on Cudjoe Key! 20 miles from Key West. Quick open water access.

Cudjoe Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$515

Price per night from

$262

Luxury waterfront rental awaits you. Stunning backyard oasis with a private pool

Stock Island house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

Price per night from

$1,030

Price per night from

$853

Price per night from

$745

Get an exclusive look at our updated property featuring dockage and dog-friendly

Big Coppitt Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$693

Experience the tranquility of this 3BR home near Old Town attractions

Key West house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$739

Big Pine Key/Hot tub/Canal Home/updated

Big Pine Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

Price per night from

$228

Island Suite @ KW Vacation

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$401

Moveable Feast

Key West house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

Price per night from

$430

Luxury Oceanview Pool Eco-friendly Villa Near Key West

Summerland Key villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$677

salty slumber get away

Summerland Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$395

Waterfront Captain House with Boat Basin and Ramp!

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$744

Living On the Hook in Key West Harbour

Key West houseboat

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 2

Price per night from

$441

Viewing 38 of 278
rentals in Sugarloaf Key

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