Historic Old Town - Key West Rentals

This neighborhood encompasses the western part of Key West to White Street. The World-famous Duval Street runs through the center of Old Town. Here, you will find numerous waterfront restaurants and bars, retail stores, museums, fishing and sailing charters. There are many upscale Victorian homes available for vacation rental in this district. If you want to experience what it’s really like to live in the “Conch Republic”, Old Town is where you should look.

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Pilar's Secret $825.00 - $4,550.70 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Nightly, Weekly, Monthly
    • 3Bedrooms:
    • 2Baths:
    • 8Sleeps:
    61 people are interested in this property!
  • Description:
    2-Story Private Home with Private Pool off Duval St, 3 Bedrooms, 2 Baths (Sleeps 6-8) Available Nightly, Weekly, Monthly...Read More

Casa Oliviana $354.20 - $742.50 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Monthly
    • 6Bedrooms:
    • 6Baths:
    • 12Sleeps:
    16 people are interested in this property!
  • Description:
    3-Story Large Private 6BR/6BA Home w/ Private Resort-Style Pool in Old Town. Sleeps 12. Available Monthly. Also Availa...Read More

The Commodore's Manor $825.00 - $3,778.50 Nightly

  • Property Highlights
    Type: Townhouse
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Nightly, Weekly, Monthly
    • 5Bedrooms:
    • 4Baths:
    • 14Sleeps:
    19 people are interested in this property!
  • Description:
    3-Story 5BR/4BA Waterfront Home w/ Private Pool & Boat Slip on Garrison Bight in Old Town. Sleeps 14. Available Nightly...Read More

Suzy's Parrot Perch $198.00 - $1,225.40 Nightly

  • Property Highlights
    Type: Apartment
    Pets Allowed: No
    Neighborhood: Old Town
    Stay Type: Nightly, Weekly, Monthly
    • 2Bedrooms:
    • 1Baths:
    • 6Sleeps:
    11 people are interested in this property!
  • Description:
    2nd Story 2BR/1BA Apartment in Old Town Near Duval Street. Sleeps 4-6. Available Nightly, Weekly, Monthly....Read More

Havana House $195.80 - $476.30 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Monthly
    • 3Bedrooms:
    • 2Baths:
    • 8Sleeps:
    24 people are interested in this property!
  • Description:
    1.5 Story Private Home + Private Pool in Old Town, 3 Bedrooms, 2 Baths, Sleeps 6-8. Available Monthly....Read More

Villa Olivietta $334.40 - $577.50 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Monthly
    • 4Bedrooms:
    • 5Baths:
    • 8Sleeps:
  • Description:
    Private Home with Private Resort-Style Pool, 4 Bedrooms, 5 Baths (Sleeps 8) Available Monthly....Read More

Sweet Home Angelita $440.00 - $3,492.50 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Nightly, Weekly, Monthly
    • 5Bedrooms:
    • 4Baths:
    • 13Sleeps:
    12 people are interested in this property!
  • Description:
    Spacious and Modern 5 Bedroom, 4 Bathroom Home just off Duval Street...Read More

The Mellow Macaw $211.20 - $1,469.60 Nightly

  • Property Highlights
    Type: Apartment
    Pets Allowed: No
    Neighborhood: Old Town
    Stay Type: Nightly, Weekly, Monthly
    • 2Bedrooms:
    • 1Baths:
    • 6Sleeps:
    24 people are interested in this property!
  • Description:
    1st Floor 2BR/1BA Apartment just off Duval Street with Private Garden & Spa. Sleeps 4-6. Available Nightly, Weekly, Mont...Read More

Puerta Coralina $275.00 - $1,917.30 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Nightly, Weekly, Monthly
    • 2Bedrooms:
    • 3Baths:
    • 6Sleeps:
    16 people are interested in this property!
  • Description:
    2-Story Private Home in Old Town, 2 Bedrooms + Sleeper Sofa, 3 Baths, Private Pool (Sleeps 4-6) Available Nightly, Weekl...Read More

Southernmost Bliss $370.70 - $828.30 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: No
    Neighborhood: Old Town
    Stay Type: Monthly
    • 3Bedrooms:
    • 3Baths:
    • 8Sleeps:
    17 people are interested in this property!
  • Description:
    1-Story 3BR/3BA Private Home + Loft & Private Pool in Old Town. Sleeps 6-8. Available Monthly....Read More