Vacation Rentals by Historic Key West Vacation Rentals - Boutique Luxury Vacation Rentals in Key West Florida!

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  Air Conditioning
  Dishwasher
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Activities and Interests
  Beach
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  Over 55 Community
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  Spa
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  Wineries and Vineyards
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  Hang Gliding
  Disney
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  Hiking
  Rental Exchange
  Specials
  Ultra Luxury
  Family Vacations
  Kayaking

Vacation Rental Travel Guide

The Truman Suites -  All 4 Suites
$795/night
Home in Key West Florida
6 Beds • 4 Full Baths • Sleeps 15
Historic Key West Vacation Rentals

Grand Maison
$749/night
Home in Key West Florida
4 Beds • 4 Full Baths • Sleeps 8
Historic Key West Vacation Rentals

$1,575/week
Home in Key West Florida
4 Beds • 4 Full Baths • Sleeps 8
Historic Key West Vacation Rentals

Bahama Getaway - Monthly Rental
Home in Old Town Key West Florida
4 Beds • 3 Full Baths • Sleeps 8
Historic Key West Vacation Rentals

Casa Del Rio - Monthly Rental
Home in Truman Annex of Key West Florida
4 Beds • 2 Full Baths • Sleeps 8
Historic Key West Vacation Rentals

Chick-a-Pea's Cottage
$510/night
Cottage in Key West Florida
4 Beds • 2 Full Baths • Sleeps 7
Historic Key West Vacation Rentals

Island Days
$299/night
Townhouse in Key West Florida
3 Beds • 3 Full Baths • Sleeps 7
Historic Key West Vacation Rentals

Steamplant 208
$1,575/week
Condo in Key West Florida
3 Beds • 3 Full Baths • Sleeps 7
Historic Key West Vacation Rentals

Steamplant 209
$1,575/week
Condo in Key West Florida
3 Beds • 3 Full Baths • Sleeps 7
Historic Key West Vacation Rentals

Steamplant 210
$1,575/week
Condo in Key West Florida
3 Beds • 3 Full Baths • Sleeps 7
Historic Key West Vacation Rentals

Steamplant 212
$1,575/week
Condo in Key West Florida
3 Beds • 3 Full Baths • Sleeps 7
Historic Key West Vacation Rentals

Sea Vista
$1,127/week
Home in Key West Florida
3 Beds • 2 Full Baths • Sleeps 7
Historic Key West Vacation Rentals

Chavez House
$739/night
Home in Key West Florida
3 Beds • 2 Full Baths • Sleeps 7
Historic Key West Vacation Rentals

Cloud 9
$699/night
Home in Key West Florida
3 Beds • 3 Full Baths • Sleeps 6
Historic Key West Vacation Rentals

Casa Key West
$4,470/month
Home in Key West Florida
3 Beds • 3 Full Baths • Sleeps 6
Historic Key West Vacation Rentals

Ashe House - Monthly Rental
Home in Key West Florida
3 Beds • 3 Full Baths • Sleeps 6
Historic Key West Vacation Rentals

Southard Comfort
$499/night
Home in Key West Florida
3 Beds • 2 Full Baths • Sleeps 6
Historic Key West Vacation Rentals

Little Miss Magic
$4,950/month
Key West Florida
3 Beds • 2 Full Baths • Sleeps 6
Historic Key West Vacation Rentals

Fairwinds at the Foundry
$1,463/week
Condo in Key West Florida
2 Beds • 2 Full Baths • Sleeps 6
Historic Key West Vacation Rentals

Cayo Limon
$4,500/month
Home in Key West Florida
2 Beds • 2 Full Baths • Sleeps 6
Historic Key West Vacation Rentals

Casablanca Grande - Nightly Rental
Villa in Old Town Key West Florida
2 Beds • 2 Full Baths • Sleeps 6
Historic Key West Vacation Rentals

Steamplant 211
$1,575/week
Condo in Key West Florida
2 Beds • 3 Full Baths • Sleeps 5
Historic Key West Vacation Rentals

Potter's Cottage
$399/night
Home in Key West Florida
2 Beds • 2 Full Baths • Sleeps 5
Historic Key West Vacation Rentals

The Pink House
$1,127/week
Home in Key West Florida
2 Beds • 2 Full Baths • Sleeps 5
Historic Key West Vacation Rentals

Lemonade Mermaid
$1,001/week
Cottage in Key West Florida
2 Beds • 2 Full Baths • Sleeps 5
Historic Key West Vacation Rentals

Inn Cogneato
$875/week
Home in Key West Florida
2 Beds • 2 Full Baths • Sleeps 5
Historic Key West Vacation Rentals

Harry Suite - First Floor Front 2 Bedroom 1 Bath
$269/night
Home in Key West Florida
2 Beds • 1 Full Bath • Sleeps 5
Historic Key West Vacation Rentals

Petite Maison
$289/night
Home in Key West Florida
2 Beds • 2 Full Baths • Sleeps 4
Historic Key West Vacation Rentals

Lola’s Place
$3,570/month
Home in Key West Florida
2 Beds • 2 Full Baths • Sleeps 4
Historic Key West Vacation Rentals

Bohemian House - Monthly Rental
Home in Old Town Key West Florida
2 Beds • 2 Full Baths • Sleeps 4
Historic Key West Vacation Rentals

Coconut Cottage - Monthly Rental
Condo in Key West Florida
2 Beds • 2 Full Baths • Sleeps 4
Historic Key West Vacation Rentals

$265/night
Home in Key West Florida
2 Beds • 1 Full Bath • Sleeps 4
Historic Key West Vacation Rentals

Petunia Cottage
$700/week
Home in Key West Florida
2 Beds • 1 Full Bath • Sleeps 4
Historic Key West Vacation Rentals

Seas The Day
$1,533/week
Condo in Key West Florida
2 Beds • 1 Full Bath • Sleeps 4
Historic Key West Vacation Rentals

Castaway Cove - Monthly Rental
Townhouse in Key West Florida
2 Beds • 1 Full Bath • Sleeps 4
Historic Key West Vacation Rentals

Copa Cabana - Monthly Rental
Home in Old Town Key West Florida
2 Beds • 1 Full Bath • Sleeps 4
Historic Key West Vacation Rentals

Horse Conch - Nightly Rental
Condo in Old Town Key West Florida
1 Bed • 1 Full Bath • Sleeps 4
Historic Key West Vacation Rentals

Martha Suite -Second Floor Rear 1 Bedroom 1 Bath
$189/night
Home in Key West Florida
1 Bed • 1 Full Bath • Sleeps 3
Historic Key West Vacation Rentals

$159/night
Home in Key West Florida
1 Bed • 1 Full Bath • Sleeps 3
Historic Key West Vacation Rentals

Poinciana Place Treetop
$159/night
Home in Key West Florida
1 Bed • 1 Full Bath • Sleeps 3
Historic Key West Vacation Rentals

Casablanca
$229/night
Condo in Key West Florida
1 Bed • 1 Full Bath • Sleeps 3
Historic Key West Vacation Rentals

Bess Truman Suite - Nightly Rental
Home in Old Town Key West Florida
1 Bed • 1 Full Bath • Sleeps 3
Historic Key West Vacation Rentals

Poppy Cottage
$560/week
Cottage in Key West Florida
1 Bed • 1 Full Bath • Sleeps 2
Historic Key West Vacation Rentals

Solaris Cottage
$149/night
Home in Key West Florida
1 Bed • 1 Full Bath • Sleeps 2
Historic Key West Vacation Rentals

Casablanca Too
$179/night
Condo in Key West Florida
1 Bed • 1 Full Bath • Sleeps 2
Historic Key West Vacation Rentals

Solaris Garden Cottage
Cottage in Key West Florida
1 Bed • 1 Full Bath • Sleeps 2
Historic Key West Vacation Rentals

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Historic Key West Vacation Rentals

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Historic Key West Vacation Rentals