Vacation Rentals by Historic Hideaways - The Finest Vacation Rental Homes in Key West!

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Number of Guests

Bedrooms

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Price Range

Amenities
  Air Conditioning
  Dishwasher
  Fireplace
  Grill
  Hot Tub (Private)
  Luxury
  Pets Allowed
  Pool (Private)
  Ski-in/Ski-out
  Washer/Dryer
  Wheelchair Accessible

Activities and Interests
  Beach
  Biking
  Boating
  Canoeing
  Casino
  Corporate and Executive
  Disney
  Family Vacations
  Fishing
  Deep Sea Fishing
  Fly Fishing
  For Sale
  Golfing
  Group and Reunion
  Hang Gliding
  Hiking
  Honeymoon
  Horseback Riding
  Hunting
  Kayaking
  Lake
  LegoLand
  Mountain Biking
  Nightclub and Disco
  Over 55 Community
  Rental Exchange
  Sailing
  Scuba Diving
  Skiing
  State National Parks
  Cross Country Skiing
  Snowmobiling
  Spa
  Specials
  Surfing
  Theatre
  Ultra Luxury
  Wedding
  White Water Rafting
  Wind Surfing
  Wineries and Vineyards


The Sanctuary
$6,000/month
Home in Key West Florida
5 Beds • 5 Full Baths • Sleeps 10
Historic Hideaways

Paradise Grand
$9,900/month
Home in Key West Florida
5 Beds • 4 Full Baths • Sleeps 10
Historic Hideaways

Truman House
$770/night
Home in Key West Florida
4 Beds • 3 Full Baths • Sleeps 10
Historic Hideaways

Pool Area
$625/night
Home in Key West Florida
4 Beds • 3 Full Baths • Sleeps 8
Historic Hideaways

Admiral's Lane
$4,200/week
Home in Key West Florida
4 Beds • 3 Full Baths • Sleeps 8
Historic Hideaways

Key West vacation home with pool and 4 bedrooms close to the beach and Duval Street : Island Style
$695/night
Home in Key West Florida
4 Beds • 3 Full Baths • Sleeps 8
Historic Hideaways

Lady Emma
$600/night
Home in Key West Florida
4 Beds • 2 Full Baths • Sleeps 8
Historic Hideaways

Blackbeard's Treasure
$5,200/month
Townhouse in Key West Florida
3 Beds • 3 Full Baths • Sleeps 8
Historic Hideaways

Maximo Cabana
$5,950/month
Home in Key West Florida
3 Beds • 3 Full Baths • Sleeps 8
Historic Hideaways

Kemp House
$550/night
Home in Key West Florida
3 Beds • 3 Full Baths • Sleeps 6
Historic Hideaways

Casa Angelina
$4,500/month
Home in Key West Florida
3 Beds • 3 Full Baths • Sleeps 6
Historic Hideaways

Ultimate Pool Cottage
$3,950/month
Home in Key West Florida
3 Beds • 3 Full Baths • Sleeps 6
Historic Hideaways

Pool with Waterfall
$5,800/month
Home in Key West Florida
3 Beds • 2 Full Baths • Sleeps 6
Historic Hideaways

Hemingway's Library
$5,700/month
Home in Key West Florida
3 Beds • 2 Full Baths • Sleeps 6
Historic Hideaways

Amelia's Bungalow
$5,500/month
Home in Key West Florida
3 Beds • 2 Full Baths • Sleeps 6
Historic Hideaways

Serenity Now
$5,000/month
Home in Key West Florida
3 Beds • 2 Full Baths • Sleeps 6
Historic Hideaways

Azure Hideaway
$3,500/month
Cottage in Key West Florida
2 Beds • 2 Full Baths • Sleeps 8
Historic Hideaways

Private Spa Patio
$225/night
Townhouse in Key West Florida
2 Beds • 2 Full Baths • Sleeps 6
Historic Hideaways

The Meadows House
$325/night
Home in Key West Florida
2 Beds • 2 Full Baths • Sleeps 6
Historic Hideaways

Duval Street Suite
$250/night
Condo in Key West Florida
2 Beds • 2 Full Baths • Sleeps 6
Historic Hideaways

la Palm d'or
$3,500/month
Home in Key West Florida
2 Beds • 2 Full Baths • Sleeps 6
Historic Hideaways

Banana Key
$310/night
Condo in Key West Florida
2 Beds • 2 Full Baths • Sleeps 5
Historic Hideaways

Royal Palm
$250/night
Townhouse in Key West Florida
2 Beds • 2 Full Baths • Sleeps 5
Historic Hideaways

Havana Hideaway
$310/night
Condo in Key West Florida
2 Beds • 2 Full Baths • Sleeps 5
Historic Hideaways

La Prive
$200/night
Townhouse in Key West Florida
2 Beds • 2 Full Baths • Sleeps 4
Historic Hideaways

Old Town Key West
$4,500/month
Home in Key West Florida
2 Beds • 2 Full Baths • Sleeps 4
Historic Hideaways

Quilted Giraffe
$400/night
Home in Key West Florida
2 Beds • 2 Full Baths • Sleeps 4
Historic Hideaways

Valhalla
$400/night
Home in Key West Florida
2 Beds • 2 Full Baths • Sleeps 4
Historic Hideaways

La Hacienda
$4,500/month
Home in Key West Florida
2 Beds • 2 Full Baths • Sleeps 4
Historic Hideaways

Bahamian Rhapsody
$5,000/month
Home in Key West Florida
2 Beds • 2 Full Baths • Sleeps 4
Historic Hideaways

Shipyard
$185/night
Condo in Key West Florida
2 Beds • 1 Full Bath • Sleeps 4
Historic Hideaways

Hilltop Hideaway
$2,100/month
Home in Key West Florida
2 Beds • 1 Full Bath • Sleeps 4
Historic Hideaways

Private Pool
$3,900/month
Home in Key West Florida
2 Beds • 1 Full Bath • Sleeps 4
Historic Hideaways

Poinciana House
$385/night
Home in Key West Florida
1 Bed • 2 Full Baths • Sleeps 4
Historic Hideaways

Coral Condo
$160/night
Condo in Key West Florida
1 Bed • 1 Full Bath • Sleeps 4
Historic Hideaways

Welcome to Paradise!
$214/night
Condo in Key West Florida
1 Bed • 1 Full Bath • Sleeps 4
Historic Hideaways

Ann Street Gardens
$200/night
Cottage in Key West Florida
1 Bed • 1 Full Bath • Sleeps 3
Historic Hideaways

The Courtyard
$235/night
Condo in Key West Florida
1 Bed • 1 Full Bath • Sleeps 2
Historic Hideaways

Campbell Suite
$180/night
Condo in Key West Florida
1 Bed • 1 Full Bath • Sleeps 2
Historic Hideaways

Solares
$1,950/month
Home in Key West Florida
1 Bed • 1 Full Bath • Sleeps 2
Historic Hideaways

Living Area
$2,700/month
Home in Key West Florida
1 Bed • 1 Full Bath • Sleeps 2
Historic Hideaways

Large Heated Pool
$2,500/month
Home in Key West Florida
1 Bed • 1 Full Bath • Sleeps 2
Historic Hideaways

Rose Treehouse
$175/night
Home in Key West Florida
1 Bed • 1 Full Bath • Sleeps 2
Historic Hideaways

Bella Vita
$200/night
Condo in Key West Florida
1 Bed • 1 Full Bath • Sleeps 2
Historic Hideaways