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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Casa Victoria $770.00 - $4,537.50 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Nightly, Weekly, Monthly
    • 5Bedrooms:
    • 7Baths:
    • 12Sleeps:
    21 people are interested in this property!
  • Description:
    3-Story Private Home + Guest House & Private Pool & Spa in Old Town, 5 Bedrooms, 7 Bathrooms, Sleeps 12. Available Nigh...Read More

The Mellow Macaw $198.00 - $1,182.50 Nightly

  • Property Highlights
    Type: Apartment
    Pets Allowed: No
    Neighborhood: Old Town
    Stay Type: Nightly, Weekly, Monthly
    • 2Bedrooms:
    • 1Baths:
    • 6Sleeps:
    28 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

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

Casa Oliviana $354.20 - $742.50 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Monthly
    • 6Bedrooms:
    • 6Baths:
    • 12Sleeps:
    14 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 Lilac Cottage $161.70 - $501.60 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Monthly
    • 2Bedrooms:
    • 2Baths:
    • 7Sleeps:
    18 people are interested in this property!
  • Description:
    2-Story 2BR/2BA Private Home + Private Pool & Large Fenced Yard in Old Town. Sleeps 4-6. Available Monthly....Read More

Casa Serendipity $324.50 - $1,540.00 Nightly

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

Casita Angelita $220.00 - $1,512.50 Nightly

  • Property Highlights
    Type: Condominium
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Nightly, Weekly, Monthly
    • 2Bedrooms:
    • 2Baths:
    • 6Sleeps:
    23 people are interested in this property!
  • Description:
    Fully Renovated 1st Floor 2 Bedroom, 2 Bathroom Condo just off Duval Street...Read More

Americana Tropicale $550.00 - $3,300.00 Nightly

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

That's Amore! $249.70 - $660.00 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Monthly
    • 3Bedrooms:
    • 3.5Baths:
    • 8Sleeps:
  • Description:
    Stunning 3BR/3.5BA Private Old Town Home & Pool (Sleeps 6-8) Available Monthly....Read More

The Royal Compound $392.70 - $1,141.80 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Monthly
    • 5Bedrooms:
    • 6Baths:
    • 14Sleeps:
    17 people are interested in this property!
  • Description:
    Two Story Private Estate w/ 2 Guest Houses + Large Private Pool in Old Town Near Historic Seaport, 5 Bedrooms, 5 Bathroo...Read More