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 Oliviana $9,900.00 - $29,518.50 Monthly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Monthly
    • 6Bedrooms:
    • 6Baths:
    • 12Sleeps:
    15 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

Star of the Seaport $1,650.00 - $4,950.00 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Nightly, Weekly, Monthly
    • 5Bedrooms:
    • 5Baths:
    • 10Sleeps:
    25 people are interested in this property!
  • Description:
    Grand Spacious Home + Private Pool & Grounds, 5 Bedrooms, 5 Bathrooms (Sleeps 10) Available Nightly, Weekly, Monthly....Read More

Casa Feliz $7,067.50 - $19,470.00 Monthly

  • Property Highlights
    Type: House
    Pets Allowed: No
    Neighborhood: Old Town
    Stay Type: Monthly
    • 3Bedrooms:
    • 4Baths:
    • 8Sleeps:
    10 people are interested in this property!
  • Description:
    2-Story 3BR/3.5BA Private Historic Home w/ Private Pool in Old Town. Sleeps 8. Available Monthly. No Pets....Read More

The Lilac Cottage $4,537.50 - $13,387.00 Monthly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Monthly
    • 2Bedrooms:
    • 2Baths:
    • 7Sleeps:
    10 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

Keys to Happiness $3,630.00 - $8,470.00 Monthly

  • Property Highlights
    Type: Condominium
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Monthly
    • 2Bedrooms:
    • 1Baths:
    • 6Sleeps:
    11 people are interested in this property!
  • Description:
    First Floor Condo in Renovated Old Town Home + Large Front Porch & Shared Pool, 2 Bedrooms, 1 Bathroom, Great Location, ...Read More

A Most Southern Peach $5,296.50 - $18,870.50 Monthly

  • Property Highlights
    Type: House
    Pets Allowed: No
    Neighborhood: Old Town
    Stay Type: Monthly
    • 3Bedrooms:
    • 2.5Baths:
    • 6Sleeps:
    22 people are interested in this property!
  • Description:
    2-Story Private Home in the Historic Seaport neighborhood of Old Town, 3 Bedrooms, 2.5 Baths (Sleeps 6)....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:
    30 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

Casita Angelita $456.50 - $1,512.50 Nightly

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

The Ibis & The Crane $1,606.00 - $5,940.00 Nightly

  • Property Highlights
    Type: Townhouse
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Nightly, Weekly, Monthly
    • 6Bedrooms:
    • 7Baths:
    • 16Sleeps:
    19 people are interested in this property!
  • Description:
    Two Side By Side Homes With A Total of Six Bedrooms, Six Full Bathrooms and 2 Half Bathrooms, Each with a Private Pool i...Read More

Pilar's Secret $962.50 - $2,970.00 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Nightly, Weekly, Monthly
    • 3Bedrooms:
    • 2Baths:
    • 8Sleeps:
    45 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