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 $1,941.50 - $3,751.00 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Nightly, Weekly, Monthly
    • 5Bedrooms:
    • 5.5Baths:
    • 12Sleeps:
    26 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

Pilar's Secret $1,056.00 - $3,118.50 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Nightly, Weekly, Monthly
    • 3Bedrooms:
    • 2Baths:
    • 8Sleeps:
    52 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

La Grande Reunion $11,000.00 - $25,135.00 Monthly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Monthly
    • 5Bedrooms:
    • 5.5Baths:
    • 10Sleeps:
    23 people are interested in this property!
  • Description:
    3-Story Private Home with Private Pool in Old Town, 5 Bedrooms, 5.5 Bathrooms, Sleeps 10. Available Monthly....Read More

The Ultimate Pool Cottage $6,600.00 - $13,123.00 Monthly

  • Property Highlights
    Type: Cottage
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Monthly
    • 3Bedrooms:
    • 3Baths:
    • 6Sleeps:
    27 people are interested in this property!
  • Description:
    Modern Clean Pool Cottage on Large Lot + Large Pool (Sleeps 6) Available Monthly...Read More

Heavenly Zen $12,705.00 - $25,905.00 Monthly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Monthly
    • 4Bedrooms:
    • 3Baths:
    • 8Sleeps:
    30 people are interested in this property!
  • Description:
    2-Story 4BR/3BA Private Home w/ Private Pool in Old Town, Sleeps 8, Available Monthly....Read More

Southernmost Vistas $11,000.00 - $18,903.50 Monthly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Monthly
    • 4Bedrooms:
    • 3.5Baths:
    • 10Sleeps:
    31 people are interested in this property!
  • Description:
    New Two-Story Private Home + Pool & Rooftop Sun Deck in Old Town, 4 Bedrooms, 3.5 Bathrooms (Sleeps 8). Available Monthl...Read More

Casa Plumeria $8,882.50 - $18,188.50 Monthly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Monthly
    • 4Bedrooms:
    • 3.5Baths:
    • 10Sleeps:
    31 people are interested in this property!
  • Description:
    2-Story 4BR/3.5BA Private Home with Guest Cottage & Private Pool in Old Town, (Sleeps 8-10) Available Monthly....Read More

That's Amore! $7,001.50 - $18,502.00 Monthly

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

Havana House $5,500.00 - $13,337.50 Monthly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Monthly
    • 3Bedrooms:
    • 2Baths:
    • 8Sleeps:
    35 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

Endless Summer $1,078.00 - $3,465.00 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Nightly, Weekly, Monthly
    • 5Bedrooms:
    • 5Baths:
    • 12Sleeps:
    61 people are interested in this property!
  • Description:
    Private Home with Private Pool Half Block from Duval Street, 5 Bedrooms, 5 Bathrooms, Sleeps 10-12. Pets Considered....Read More