4-5 Bedroom Key West Vacation Rentals


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The Commodore's Manor $825.00 - $3,778.50 Nightly

  • Property Highlights
    Type: Townhouse
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Nightly, Weekly, Monthly
    • 5Bedrooms:
    • 4Baths:
    • 14Sleeps:
    25 people are interested in this property!
  • Description:
    3-Story 5BR/4BA Waterfront Home w/ Private Pool & Boat Slip on Garrison Bight in Old Town. Sleeps 14. Available Nightly...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:
    18 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

Baileys Mango Mansion $313.50 - $825.00 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Monthly
    • 4Bedrooms:
    • 4Baths:
    • 12Sleeps:
    14 people are interested in this property!
  • Description:
    3-Story Private Home in Old Town + Private Saltwater Pool, 4 Bedrooms, 4 Bathrooms (Sleeps 10-12) Available Monthly....Read More

Good Vibrations $687.50 - $3,333.00 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Nightly, Weekly, Monthly
    • 4Bedrooms:
    • 4.5Baths:
    • 10Sleeps:
    25 people are interested in this property!
  • Description:
    2-Story Private Home with Heated Pool, 4 Bedrooms, 4.5 Baths (Sleeps 8-10) Available Nightly, Weekly, Monthly....Read More

Southernmost Comfort $770.00 - $3,540.90 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Truman Annex
    Stay Type: Weekly, Monthly
    • 4Bedrooms:
    • 4Baths:
    • 8Sleeps:
    17 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

The Admiral's Estate $535.70 - $1,375.00 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: No
    Neighborhood: Truman Annex
    Stay Type: Monthly
    • 5Bedrooms:
    • 5.5Baths:
    • 8Sleeps:
    11 people are interested in this property!
  • Description:
    Historic Truman Annex Home + Guest House & Private Pool, 5 Bedrooms, 5.5 Bathrooms. Available Monthly....Read More

The Artists' Muse $464.20 - $825.00 Nightly

Historic Florida Keys Foundation Award Winner
  • Property Highlights
    Type: House
    Pets Allowed: No
    Neighborhood: Old Town
    Stay Type: Monthly
    • 4Bedrooms:
    • 4Baths:
    • 8Sleeps:
  • Description:
    1-Story Immaculate Estate in Old Town + Private Pool, 4 Bedrooms, 4 Bathrooms (Sleeps 8). Available Monthly....Read More

Avalynn House $715.00 - $3,300.00 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Truman Annex
    Stay Type: Weekly, Monthly
    • 5Bedrooms:
    • 3.5Baths:
    • 8Sleeps:
    21 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

The Royal Compound $392.70 - $1,141.80 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Monthly
    • 5Bedrooms:
    • 6Baths:
    • 14Sleeps:
    13 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

Plantation Tropicale $1,100.00 - $4,400.00 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Truman Annex
    Stay Type: Weekly, Monthly
    • 5Bedrooms:
    • 4Baths:
    • 8Sleeps:
    32 people are interested in this property!
  • Description:
    Two Story Private Home + Two Guest Houses & Large Private Pool, 5 Bedrooms, 4 Bathrooms, Available Weekly & Monthly....Read More