Rentals on Duval Street

Every major destination has a “main street.”  In Key West, our hub of activity, attractions, restaurants, shopping and nightlife is Duval Street.  Because it is only a two-mile road stretching from the Southernmost part of the island to the Cruise Ship port, Duval Street can be walked end-to-end in an afternoon, but it is nearly impossible to experience all that Duval Street has to offer in a day, or even a week.  Key West Foodies will find a never-ending array of dining options, from small walk-up bodegas to upscale restaurants touting competitive accolades.  From street performers to real estate offices, t-shirt shops to upscale boutiques, Duval Street is a magical mix of culture and life that is the island of Key West. 

Although Key West is a small island, and getting around by bicycle, electric car, taxi, or your own car is not difficult, many visitors prefer the luxury of simply walking to all of their favorite spots.  Many of our rental homes are located within walking distance of Duval Street, with several located right on Duval itself.  Although a Duval Street location does come with heavier foot traffic passing by and the chance for a bit more noise outside, staying right in the center of the action is sure to create an experience to remember.

For those ready for the center of action, here is a list of our hmes located on Duval Street.

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Sweet Home Angelita $1,017.50 - $3,327.50 Nightly

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

Americana Tropicale $979.00 - $3,300.00 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Nightly, Weekly, Monthly
    • 4Bedrooms:
    • 4.5Baths:
    • 10Sleeps:
    22 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

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:
    26 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

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:
    18 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

Villa Cubana $1,787.50 - $4,730.00 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 Grande Reunion $11,000.00 - $26,543.00 Monthly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Monthly
    • 5Bedrooms:
    • 6Baths:
    • 10Sleeps:
    19 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

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

Villa Angelita $522.50 - $1,815.00 Nightly

  • Property Highlights
    Type: Condominium
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Nightly, Weekly, Monthly
    • 3Bedrooms:
    • 2Baths:
    • 7Sleeps:
    17 people are interested in this property!
  • Description:
    Fully Renovated 2nd Floor 3 Bedroom, 2 Bathroom Condo just off Duval Street, Available Nightly, Weekly, Monthly....Read More

Papa's Casita $6,875.00 - $18,870.50 Monthly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Monthly
    • 3Bedrooms:
    • 3Baths:
    • 8Sleeps:
  • Description:
    2-Story Private Home with Private Pool in Old Town, 3 Bedrooms, 3 Bathrooms, Sleeps 6-8. Available Monthly....Read More

Smooth Sailing $5,049.00 - $11,709.50 Monthly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Monthly
    • 3Bedrooms:
    • 2.5Baths:
    • 6Sleeps:
    12 people are interested in this property!
  • Description:
    2-Story 3BR/2.5BA Old Town Home + Private Pool (Sleeps 6) Available Monthly...Read More