Vacation Rentals & House Rentals in Sugarloaf Key

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62 house rentals

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Tranquility in Paradise - Sugarloaf

Sugarloaf Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Garden

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Price per night from

$385

Cassie's Paradise

Sugarloaf Key house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Garden

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Price per night from

$5,720

Beautiful quiet neighborhood. Sunsets! Huge Pool!

Sugarloaf Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 30 minutes

Match: Garden

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Price per night from

$320

Great rentals within 20 miles that match your search

The Mermaids House, Historic Old Town Key West

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Beautiful Home in Old Town Key West” Mermaid House is conveniently located in the heart of Old Town yet when you are there you are in your own private paradise. The house is beautifully appointed with anything you could need during your stay and has ample space for four people. It was the perfect spot for our stay in Key West and we plan to stay again when we return to the area. Thanks to Barbara for making us feel welcome and for sharing her beautiful home with us.

Match: Garden

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Price per night from

$328

Harbor Walk Hideaways

Key West b&b

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Location, Location, Location” We were a group of 8 and rented the entire compound! The place was in an amazing location that was easily accessible to everything. We had everything we needed onsite and if we had any questions, Phyllis was always just a phone call away. The music and talking at night from the cigar lounge was a bit loud, but nothing we couldn't tolerate. The only suggestion I'd make is to buy an ionizer for the first two units to help with the cigar smell....again, nothing intolerable, but could make a world of difference. Can't wait to come back for another visit! THANK YOU!

Match: Garden

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Price per night from

$1,303

Conch Haven Cottage Old Town Studio MONTHLY Rental

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Garden

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Price per night from

$108

Olivia Place

Key West house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Garden

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Price per night from

$345

Key West--20 min, Stunning Views, Private, Ocean Access, Spacious, Resort-like

Summerland Key house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Garden

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Price per night from

$766

"Little Paradise" Historic Seaport Old Town Key West

Key West house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Garden

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Price per night from

$493

New Listing! Beautiful Canal front , Key Deer and jacuzzi.

Big Pine Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Garden

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Price per night from

$287

Hogfish Retreat

Cudjoe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Garden

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Price per night from

$178

Key West Island Vacation

Key West house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 8 minutes

Match: Garden

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Price per night from

$481

Ohana Paradise At Historic Seaport ,Old Town, Key West. Private Home.

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Garden

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Price per night from

$259

Conch House - Dock Your Boat

Little Torch Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 7

Match: Garden

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Price per night from

$775

Blue Palms Retreat. ocean front w/pool and dock for your boat.

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Garden

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Price per night from

$574

5 Pirate's Hideaway Canal Front Home with Seawall & Kayaks

Little Torch Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Match: Garden

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Price per night from

$308

Key West Gulf front Home with private dock and pool.

Key West house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Garden

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Price per night from

$482

Match: Garden

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Price per night from

$210

Private, heated pool. Private yard.

Key West condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Garden

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Price per night from

$172

Hogfish Hideout

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Garden

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Price per night from

$379

Florida Keys at it's best

Sugarloaf house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Garden

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Price per night from

$241

$145 per night for months of Sep-Nov on Canal (fits 25-28 ft boat) and Pool.

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Garden

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Price per night from

$259

Charming House on deep clear canal

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 44 minutes

Match: Garden

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Price per night from

$201

Tranquility in Paradise - Cudjoe

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Garden

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Price per night from

$218

Oceanside, pet friendly, smart home with plenty of paddle equipment

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Garden

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Price per night from

$224

Lower Keys Retreat.....

Big Pine Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Garden

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Price per night from

$253

Eleanor's Place in Key West Old Town - Dogs Ok

Key West house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Garden

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Price per night from

$378

Upscale ocean front home & easy canal boat access to Gulf or Atlantic ocean

Big Pine Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Garden

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Price per night from

$240

Reel Paradise

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Garden

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Price per night from

$286

Agua Azul

Little Torch Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Garden

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Price per night from

$151

Match: Garden

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Price per night from

$333

Sweet Caroline Seaport Floor 2

Key West house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Garden

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Price per night from

$276

Entire House with Deep Water Dock & Heated Pool - 4 Min. to KW - Pets OK

Stock Island house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 11

Match: Garden

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Price per night from

$801

Key West House

Key West house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Garden

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Price per night from

$689

Palmetto Retreat

Big Pine Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Garden

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Price per night from

$144

Pirates Paradise

Cudjoe Key house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Match: Garden

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Price per night from

$434

Blackbeard's Bounty

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Garden

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Price per night from

$234

Private House Facing the Ocean with Heated Pool/Spa

Ramrod Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Garden

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Price per night from

$410

Viewing 38 of 62
rentals in Sugarloaf Key

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