4-5 Bedroom Monthly Rentals

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Casa, Suite Casa $370.70 - $711.70 Nightly

  • 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

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:
    14 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 Vie En Rose $275.00 - $524.70 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Casa Marina & Casa East
    Stay Type: Monthly
    • 4Bedrooms:
    • 4Baths:
    • 10Sleeps:
    11 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

Baileys Mango Mansion $313.50 - $825.00 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Monthly
    • 4Bedrooms:
    • 4Baths:
    • 12Sleeps:
    10 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

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:
  • Description:
    2-Story Private 5BR/5BA Private Home w/ Expansive Private Pool Area in Casa Marina Neighborhood of Old Town. Sleeps 10....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:
    23 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

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:
    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

Heavenly Zen $440.00 - $924.00 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Monthly
    • 4Bedrooms:
    • 3Baths:
    • 8Sleeps:
    16 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

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:
    14 people are interested in this property!
  • Description:
    1-Story Immaculate Estate in Old Town + Private Pool, 4 Bedrooms, 4 Bathrooms (Sleeps 8). Available Monthly....Read More

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