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11/06/2026
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11/07/2026

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51 villas found

Showing 1 - 30 of 51 Villas
Luxury Key West 1BR Cottage with Private Hot Tub
$2.004 /night
Luxury Key West 1BR Cottage with Private Hot Tub
Florida Keys
5.0/5 Excellent 3 Reviews
3 1 1
Luxury Pet-Friendly 1BR Retreat with Pool in Old Town Key West
$726 /night
Luxury Pet-Friendly 1BR Retreat with Pool in Old Town Key West
Florida Keys
4.7/5 Excellent 3 Reviews
2 1 1
Luxury Romantic 1BR Conch Cottage w/ Pool in Old Town Key West
$1.062 /night
Luxury Romantic 1BR Conch Cottage w/ Pool in Old Town Key West
Florida Keys
4.7/5 Excellent 3 Reviews
2 1 1
Luxury 1BR Key West Retreat with Shared Pool
$1.200 /night
Luxury 1BR Key West Retreat with Shared Pool
Florida Keys
5.0/5 Excellent 3 Reviews
4 1 1
Key West Villa with Private Pool & Shared Pool | Old Town
$1.740 /night
Key West Villa with Private Pool & Shared Pool | Old Town
Florida Keys
4.8/5 Excellent 6 Reviews
4 1 2
Luxury Villa | 2BR Key West Retreat with Private Pool & Golf
$702 /night
Luxury Villa | 2BR Key West Retreat with Private Pool & Golf
Florida Keys
4.8/5 Excellent 6 Reviews
5 2 1
Luxury 2-Bed Key West Retreat with Pool & Parking
$1.098 /night
Luxury 2-Bed Key West Retreat with Pool & Parking
Florida Keys
5.0/5 Excellent 3 Reviews
4 2 1
Key West 38: 2-Bed Villa with Private Pool in Old Town
$874 /night
Key West 38: 2-Bed Villa with Private Pool in Old Town
Florida Keys
4.8/5 Excellent 4 Reviews
6 2 3
Key West 25 - 2 Bed Villa with Private Pool in Key West
$1.038 /night
Key West 25 - 2 Bed Villa with Private Pool in Key West
Florida Keys
5.0/5 Excellent 3 Reviews
4 2 1
Key West 36: 2-Bed Villa with Private Pool & Beach Access
$1.530 /night
Key West 36: 2-Bed Villa with Private Pool & Beach Access
Florida Keys
4.8/5 Excellent 6 Reviews
6 2 2
Luxury 2BR Private Pool Retreat in Key West
$1.038 /night
Luxury 2BR Private Pool Retreat in Key West
Florida Keys
5.0/5 Excellent 3 Reviews
6 2 3
Luxury 2BR Key West Retreat with Private Pool & Deck
$1.206 /night
Luxury 2BR Key West Retreat with Private Pool & Deck
Florida Keys
5.0/5 Excellent 3 Reviews
5 2 2
Oceanfront 2-Bed Villa with Private Pool in Key West
$732 /night
Oceanfront 2-Bed Villa with Private Pool in Key West
Florida Keys
4.3/5 Very Good 4 Reviews
6 2 2
Key West 62: 2-Bed Villa with Private Pool & Golf Views
$702 /night
Key West 62: 2-Bed Villa with Private Pool & Golf Views
Florida Keys
4.7/5 Excellent 6 Reviews
4 2 2
Luxury 2BR Oceanfront Key West Villa with Pool & Tennis
$978 /night
Luxury 2BR Oceanfront Key West Villa with Pool & Tennis
Florida Keys
5.0/5 Excellent 3 Reviews
4 2 2
Luxury 2BR Key West Retreat with Pool & Balcony
$1.302 /night
Luxury 2BR Key West Retreat with Pool & Balcony
Florida Keys
5.0/5 Excellent 5 Reviews
6 2 3
Key West 42: 2-Bed Villa with Private Pool & Pet-Friendly
$1.374 /night
Key West 42: 2-Bed Villa with Private Pool & Pet-Friendly
Florida Keys
4.8/5 Excellent 5 Reviews
4 2 1
Luxury Villa | 2BR Key West Retreat with Pool & Balcony
$1.068 /night
Luxury Villa | 2BR Key West Retreat with Pool & Balcony
Florida Keys
5.0/5 Excellent 5 Reviews
4 2 2
Luxury 2BR Key West Retreat with Pool & Terrace
$1.038 /night
Luxury 2BR Key West Retreat with Pool & Terrace
Florida Keys
5.0/5 Excellent 3 Reviews
4 2 1
Luxury Villa | 2BR Key West Villa with Pool & Balcony
$738 /night
Luxury Villa | 2BR Key West Villa with Pool & Balcony
Florida Keys
4.7/5 Excellent 3 Reviews
6 2 2
Key West 47: 2-Bed Villa with Private Pool & Pet-Friendly Charm
$1.212 /night
Key West 47: 2-Bed Villa with Private Pool & Pet-Friendly Charm
Florida Keys
5.0/5 Excellent 3 Reviews
4 2 2
Key West Charm: 2BR Villa with Private Pool & Patio
$1.038 /night
Key West Charm: 2BR Villa with Private Pool & Patio
Florida Keys
5.0/5 Excellent 4 Reviews
4 2 1
Key West 21: 2-Bed Villa with Private Pool & Island Charm
$1.062 /night
Key West 21: 2-Bed Villa with Private Pool & Island Charm
Florida Keys
4.7/5 Excellent 6 Reviews
6 2 2
Key West 48 | 2-Bed Villa with Private Pool & Courtyard
$852 /night
Key West 48 | 2-Bed Villa with Private Pool & Courtyard
Florida Keys
5.0/5 Excellent 5 Reviews
4 2 1
Luxury 2BR Key West Retreat with Pool & Patio
$966 /night
Luxury 2BR Key West Retreat with Pool & Patio
Florida Keys
5.0/5 Excellent 4 Reviews
4 2 1
Key West 49: 2-Bed Villa with Private Pool & Courtyard
$990 /night
Key West 49: 2-Bed Villa with Private Pool & Courtyard
Florida Keys
5.0/5 Excellent 3 Reviews
4 2 1
Key West 27: 2-Bed Villa with Private Pool & Communal Pool
$966 /night
Key West 27: 2-Bed Villa with Private Pool & Communal Pool
Florida Keys
5.0/5 Excellent 3 Reviews
5 2 1
Key West 33: 2-Bed Villa with Private Pool & Ocean Views
$1.416 /night
Key West 33: 2-Bed Villa with Private Pool & Ocean Views
Florida Keys
5.0/5 Excellent 3 Reviews
6 2 2
Luxury 2BR Key West Cottage with Private Pool & Charm
$984 /night
Luxury 2BR Key West Cottage with Private Pool & Charm
Florida Keys
5.0/5 Excellent 3 Reviews
6 2 2
Luxury 2BR Key West Retreat with Pool & Balcony
$720 /night
Luxury 2BR Key West Retreat with Pool & Balcony
Florida Keys
4.7/5 Excellent 3 Reviews
5 2 2

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