4-5 Bedroom Key West Vacation Rentals


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Southernmost Comfort $660.00 - $3,540.90 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Truman Annex
    Stay Type: Weekly, Monthly
    • 4Bedrooms:
    • 4Baths:
    • 8Sleeps:
    13 people are interested in this property!
  • Description:
    3-Story 4BR/4BA Private Home w/ Private Pool & Fully Fenced Yard in Truman Annex. Sleeps 10. Available Weekly & Monthl...Read More

Iguana Getaway $157.30 - $392.70 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Key West Golf Club
    Stay Type: Monthly
    • 4Bedrooms:
    • 3Baths:
    • 10Sleeps:
    14 people are interested in this property!
  • Description:
    Serene Two-Story Private Home in the Key West Golf Club Gated Community, 4 Bedrooms, 3 Bathrooms, Sleeps 8-10. Available...Read More

Conch Casa Grande $550.00 - $2,750.00 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Truman Annex
    Stay Type: Weekly, Monthly
    • 5Bedrooms:
    • 5.5Baths:
    • 8Sleeps:
    17 people are interested in this property!
  • Description:
    Large Private 5BR/5.5BA Home in Truman Annex w/ Private Pool. Sleeps 8. Available Weekly & Monthly....Read More

Rhapsody In Paradise $313.50 - $674.30 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Casa Marina & Casa East
    Stay Type: Monthly
    • 4Bedrooms:
    • 4.5Baths:
    • 8Sleeps:
    16 people are interested in this property!
  • Description:
    2-Story Private Home w/ Private Pool, Guest House & Widows Walk Near Beaches, Sleeps 8, Avail Monthly....Read More

Casa Victoria $770.00 - $4,537.50 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Nightly, Weekly, Monthly
    • 5Bedrooms:
    • 7Baths:
    • 12Sleeps:
    39 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

Paradise Perfected $176.00 - $581.90 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Casa Marina & Casa East
    Stay Type: Monthly
    • 4Bedrooms:
    • 2Baths:
    • 10Sleeps:
    15 people are interested in this property!
  • Description:
    1-Story 4BR/2BA Private Home + Office & Private Pool w/ Fully Fenced Yard Near Smathers Beach. (Sleeps 6-8) Available Mo...Read More

La Grande Reunion $392.70 - $897.60 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Monthly
    • 5Bedrooms:
    • 5.5Baths:
    • 10Sleeps:
    16 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

Southern Star $370.70 - $711.70 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Monthly
    • 4Bedrooms:
    • 3.5Baths:
    • 8Sleeps:
    12 people are interested in this property!
  • Description:
    2-Story Private Home in Old Town + Private Pool, 4 Bedrooms, 3.5 Bathrooms (Sleeps 8). Available Monthly....Read More

Southernmost Hospitality V $880.00 - $4,394.50 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Nightly, Weekly, Monthly
    • 5Bedrooms:
    • 5.5Baths:
    • 12Sleeps:
    25 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

Endless Summer $550.00 - $3,300.00 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Nightly, Weekly, Monthly
    • 5Bedrooms:
    • 5Baths:
    • 12Sleeps:
    66 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