4-5 Bedroom Key West Vacation Rentals


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La Vie En Rose $8,552.50 - $14,701.50 Monthly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Casa Marina & Casa East
    Stay Type: Monthly
    • 4Bedrooms:
    • 4Baths:
    • 10Sleeps:
  • Description:
    Two Story Private Home Near Beaches + Private Pool, 4 Bedrooms, 4 Bathrooms (Sleeps 10) Available Monthly....Read More

Avalynn House $9,949.50 - $18,150.00 Weekly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Truman Annex
    Stay Type: Weekly, Monthly
    • 5Bedrooms:
    • 3.5Baths:
    • 8Sleeps:
    19 people are interested in this property!
  • Description:
    3-Story 5BR/3.5BA Private Home w/ Private Pool in Truman Annex, Sleeps 10, Available Weekly & Monthly....Read More

Casa Victoria $1,474.00 - $4,537.50 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Nightly, Weekly, Monthly
    • 5Bedrooms:
    • 7Baths:
    • 12Sleeps:
    23 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 Royal Compound $14,998.50 - $31,971.50 Monthly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Monthly
    • 5Bedrooms:
    • 6Baths:
    • 14Sleeps:
    42 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

Americana Tropicale $1,078.00 - $3,465.00 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Nightly, Weekly, Monthly
    • 4Bedrooms:
    • 4.5Baths:
    • 10Sleeps:
    26 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 Vistas $11,000.00 - $18,903.50 Monthly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Monthly
    • 4Bedrooms:
    • 3.5Baths:
    • 8Sleeps:
    11 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

Cielo Tropicale $14,998.50 - $30,316.00 Monthly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Casa Marina & Casa East
    Stay Type: Monthly
    • 5Bedrooms:
    • 5.5Baths:
    • 10Sleeps:
  • Description:
    2-Story Private 5BR/5BA Private Home w/ Expansive Private Pool Area in Casa Marina Neighborhood of Old Town. Sleeps 10....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:
    23 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

Casa, Suite Casa $10,395.00 - $19,954.00 Monthly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Casa Marina & Casa East
    Stay Type: Monthly
    • 4Bedrooms:
    • 5Baths:
    • 10Sleeps:
  • Description:
    3-Story Large 4BR/5BA Private Home w/ Private Pool in Casa Marina Neighborhood. Sleeps 8-9. 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