4-5 Bedroom Monthly Rentals

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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:
    17 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

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:
  • Description:
    1-Story 4BR/2BA Private Home + Office & Private Pool w/ Fully Fenced Yard Near Smathers Beach. (Sleeps 6-8) Available Mo...Read More

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:
    10 people are interested in this property!
  • Description:
    3-Story Large 4BR/5BA Private Home w/ Private Pool in Casa Marina Neighborhood. Sleeps 8-9. Available 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:
  • Description:
    Historic Truman Annex Home + Guest House & Private Pool, 5 Bedrooms, 5.5 Bathrooms. 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:
    14 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

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:
    14 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 Polynesian House $427.90 - $1,017.50 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: No
    Neighborhood: Casa Marina & Casa East
    Stay Type: Monthly
    • 4Bedrooms:
    • 4.5Baths:
    • 10Sleeps:
    16 people are interested in this property!
  • Description:
    Immaculate Island Estate + Private Pool & Jacuzzi, 4 Bedrooms + Yoga Studio, 4.5 Bathrooms. 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

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

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