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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Coastal Cabana $192.50 - $506.00 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Monthly
    • 3Bedrooms:
    • 2.5Baths:
    • 6Sleeps:
    14 people are interested in this property!
  • Description:
    Ranch-Style 3BR/2.5BA Old Town Home on Quiet Lane (Sleeps 6)...Read More

Villa Cubana $220.00 - $880.00 Nightly

  • Property Highlights
    Type: Townhouse
    Pets Allowed: No
    Neighborhood: Old Town
    Stay Type: Weekly, Monthly
    • 2Bedrooms:
    • 2Baths:
    • 4Sleeps:
    23 people are interested in this property!
  • Description:
    Two Story Tropical Cottage in Gated Community Near Duval Street, 2 Bedrooms, 2 Bathrooms, Sleeps 4. Available Weekly & ...Read More

Southernmost Solace $125.40 - $397.10 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Monthly
    • 2Bedrooms:
    • 2Baths:
    • 6Sleeps:
  • Description:
    One-Story Private Home in Old Town, 2 Bedrooms, 2 Bathrooms (Sleeps 4-6.) Available Monthly....Read More

The Lime & The Coconut $1,006.50 - $5,252.50 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Nightly, Weekly, Monthly
    • 6Bedrooms:
    • 7Baths:
    • 16Sleeps:
    11 people are interested in this property!
  • Description:
    Two Side-by-Side 2-Story Private Homes, each with a Private Pool, Total of 6 Bedrooms, 6 Bathrooms + 2 Half Bathrooms (S...Read More

Sweet Home Angelita $440.00 - $3,448.50 Nightly

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

The Contented Crane $385.00 - $2,398.00 Nightly

  • Property Highlights
    Type: Townhouse
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Nightly, Weekly, Monthly
    • 3Bedrooms:
    • 3.5Baths:
    • 8Sleeps:
    13 people are interested in this property!
  • Description:
    2-Story 3BR/3.5BA Private Townhome w/ Private Pool in Old Town. Sleeps 6-8. Available Nightly, Weekly, Monthly....Read More

Good Vibrations $495.00 - $3,151.50 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Nightly, Weekly, Monthly
    • 4Bedrooms:
    • 4.5Baths:
    • 10Sleeps:
    23 people are interested in this property!
  • Description:
    2-Story Private Home with Heated Pool, 4 Bedrooms, 4.5 Baths (Sleeps 8-10) Available Nightly, Weekly, Monthly....Read More

The Artists' Muse $464.20 - $825.00 Nightly

Historic Florida Keys Foundation Award Winner
  • Property Highlights
    Type: House
    Pets Allowed: No
    Neighborhood: Old Town
    Stay Type: Monthly
    • 4Bedrooms:
    • 4Baths:
    • 8Sleeps:
    14 people are interested in this property!
  • Description:
    1-Story Immaculate Estate in Old Town + Private Pool, 4 Bedrooms, 4 Bathrooms (Sleeps 8). Available Monthly....Read More

Southernmost Hospitality VII $990.00 - $4,950.00 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Nightly, Weekly, Monthly
    • 7Bedrooms:
    • 7.5Baths:
    • 16Sleeps:
    22 people are interested in this property!
  • Description:
    2-Story 7BR/7.5BA Private Home + Guest House w/ Private Pool & Fully Fenced Yard on Duval Street. Sleeps 14-16 Availab...Read More

Conch Casita $106.70 - $280.50 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Monthly
    • 1Bedrooms:
    • 1Baths:
    • 4Sleeps:
    10 people are interested in this property!
  • Description:
    1-Story Private 1BR/1BA Cottage + Fully Fenced Yard & Spa, Sleeps 2-4. Available Monthly....Read More