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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La Casa Roja $4,537.50 - $12,600.50 Monthly

  • Property Highlights
    Type: House
    Pets Allowed: No
    Neighborhood: Old Town
    Stay Type: Monthly
    • 2Bedrooms:
    • 2Baths:
    • 4Sleeps:
    10 people are interested in this property!
  • Description:
    One Story Private Home + Private Pool, 2 Bedrooms, 2 Bathrooms (Sleeps 4). Available Monthly....Read More

The Ibis & The Crane $1,600.50 - $5,197.50 Nightly

  • Property Highlights
    Type: Townhouse
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Nightly, Weekly, Monthly
    • 6Bedrooms:
    • 7Baths:
    • 16Sleeps:
    25 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

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:
    13 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

Sweet Home Angelita $1,116.50 - $3,492.50 Nightly

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

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:
    13 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

The Emerald Orchid $8,552.50 - $22,429.00 Monthly

  • Property Highlights
    Type: House
    Pets Allowed: No
    Neighborhood: Old Town
    Stay Type: Monthly
    • 3Bedrooms:
    • 3.5Baths:
    • 6Sleeps:
  • Description:
    Pristine 3 Bedroom 3.5 Bathrooms Private 2 Story Home W/ Private Pool In Old Town...Read More

Villa Cubana $1,963.50 - $4,966.50 Weekly

  • Property Highlights
    Type: Townhouse
    Pets Allowed: No
    Neighborhood: Old Town
    Stay Type: Weekly, Monthly
    • 2Bedrooms:
    • 2Baths:
    • 4Sleeps:
    15 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

La Casita En Cima $4,669.50 - $11,132.00 Monthly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Monthly
    • 2Bedrooms:
    • 2Baths:
    • 6Sleeps:
    11 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

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:
  • Description:
    3-Story Private Home with Private Pool in Old Town, 5 Bedrooms, 5.5 Bathrooms, Sleeps 10. Available Monthly....Read More

The Contented Crane $880.00 - $2,695.00 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