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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Southernmost Hospitality V $1,765.50 - $5,802.50 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Nightly, Weekly, Monthly
    • 5Bedrooms:
    • 5.5Baths:
    • 12Sleeps:
    16 people are interested in this property!
  • Description:
    2-Story 5BR/5.5BA Private Home w/ Private Pool & Fully Fenced Yard on Duval Street. Sleeps 10-12 Available Nightly, We...Read More

Suzy's Parrot Perch $280.50 - $935.00 Nightly

  • Property Highlights
    Type: Apartment
    Pets Allowed: No
    Neighborhood: Old Town
    Stay Type: Nightly, Weekly, Monthly
    • 2Bedrooms:
    • 1Baths:
    • 6Sleeps:
    32 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

Southernmost Solace $3,498.00 - $10,604.00 Monthly

  • 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

Mahogany House $8,607.50 - $21,697.50 Monthly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Monthly
    • 3Bedrooms:
    • 2.5Baths:
    • 6Sleeps:
  • Description:
    2-Story Private Corner Estate in Old Town + Private Pool, Media Room, & Office, 3 Bedrooms, 2 Bathrooms (Sleeps 6). Avai...Read More

Southernmost Hospitality VII $2,172.50 - $6,946.50 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Nightly, Weekly, Monthly
    • 7Bedrooms:
    • 7.5Baths:
    • 16Sleeps:
    16 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

La Casita En Cima $4,669.50 - $12,501.50 Monthly

  • Property Highlights
    Type: House
    Pets Allowed: No
    Neighborhood: Old Town
    Stay Type: Monthly
    • 2Bedrooms:
    • 2Baths:
    • 6Sleeps:
    15 people are interested in this property!
  • Description:
    1-Story Private Cottage in Old Town with Private Pool, 2 Bedrooms, 2 Bathrooms, (Sleeps 2-4) Available Monthly....Read More

Conch Contempo $11,110.00 - $24,722.50 Monthly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Monthly
    • 4Bedrooms:
    • 3.5Baths:
    • 10Sleeps:
  • Description:
    Two Story Private Home in Old Town w/ Large Private Pool, 4 Bedrooms, 3.5 Bathrooms (Sleeps 10) Available Monthly....Read More

Casa Oliviana $9,900.00 - $29,518.50 Monthly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Monthly
    • 6Bedrooms:
    • 6Baths:
    • 12Sleeps:
    11 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

Conch Casita $2,975.50 - $7,617.50 Monthly

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

Puerta Coralina $495.00 - $1,650.00 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Nightly, Weekly, Monthly
    • 2Bedrooms:
    • 3Baths:
    • 6Sleeps:
    33 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