4-5 Bedroom Key West Vacation Rentals


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Villa Olivietta $334.40 - $577.50 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Monthly
    • 4Bedrooms:
    • 5Baths:
    • 8Sleeps:
  • Description:
    Private Home with Private Resort-Style Pool, 4 Bedrooms, 5 Baths (Sleeps 8) Available Monthly....Read More

Cielo Tropicale $440.00 - $1,082.40 Nightly

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

La Vie En Rose $304.70 - $524.70 Nightly

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

Avalynn House $863.50 - $3,300.00 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Truman Annex
    Stay Type: Weekly, Monthly
    • 5Bedrooms:
    • 3.5Baths:
    • 8Sleeps:
    16 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

Plantation Tropicale $1,222.10 - $4,400.00 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Truman Annex
    Stay Type: Weekly, Monthly
    • 5Bedrooms:
    • 4Baths:
    • 8Sleeps:
    23 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

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:
    11 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

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:
    12 people are interested in this property!
  • Description:
    Historic Truman Annex Home + Guest House & Private Pool, 5 Bedrooms, 5.5 Bathrooms. Available Monthly....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:
    21 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

Heavenly Zen $440.00 - $924.00 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Monthly
    • 4Bedrooms:
    • 3Baths:
    • 8Sleeps:
    19 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

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 10-14) Available Monthly....Read More