Pet Friendly Key West House Rentals

Pets like vacations too! Key West is the perfect place to bring your fur friends. From pet-friendly restaurants to the Casa Marina dog beach, there are so many places in Key West that your pets can enjoy with you, including some of our rental properties. If you decide to bring a pet along, just know that there is an additional fee, and depending on the length of your stay, you may be subject to a mid-stay clean.

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Sweet Home Angelita $1,116.50 - $3,492.50 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Nightly, Weekly, Monthly
    • 5Bedrooms:
    • 4Baths:
    • 13Sleeps:
    18 people are interested in this property!
  • Description:
    Spacious and Modern 5 Bedroom, 4 Bathroom Home just off Duval Street...Read More

Heart of the Harbor $6,600.00 - $13,123.00 Monthly

  • Property Highlights
    Type: Townhouse
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Monthly
    • 3Bedrooms:
    • 3.5Baths:
    • 8Sleeps:
    11 people are interested in this property!
  • Description:
    Brand New Modern Townhome + Community Pool, 3 Bedrooms, 3.5 Bathrooms (Sleeps 8) Available Monthly....Read More

Havana House $5,500.00 - $13,337.50 Monthly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Monthly
    • 3Bedrooms:
    • 2Baths:
    • 8Sleeps:
    18 people are interested in this property!
  • Description:
    1.5 Story Private Home + Private Pool in Old Town, 3 Bedrooms, 2 Baths, Sleeps 6-8. Available Monthly....Read More

Casa Plumeria $8,882.50 - $18,188.50 Monthly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Monthly
    • 4Bedrooms:
    • 3.5Baths:
    • 10Sleeps:
  • Description:
    2-Story 4BR/3.5BA Private Home with Guest Cottage & Private Pool in Old Town, (Sleeps 8-10) Available Monthly....Read More

Star of the Seaport $1,474.00 - $5,197.50 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Nightly, Weekly, Monthly
    • 5Bedrooms:
    • 5Baths:
    • 12Sleeps:
  • Description:
    Grand Spacious Home + Private Pool & Grounds, 5 Bedrooms, 5 Bathrooms (Sleeps 10) Available Nightly, Weekly, Monthly....Read More

The Smiling Ibis $880.00 - $2,695.00 Nightly

  • Property Highlights
    Type: Townhouse
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Nightly, Weekly, Monthly
    • 3Bedrooms:
    • 3.5Baths:
    • 8Sleeps:
    22 people are interested in this property!
  • Description:
    2-Story 3BR/3.5BA Private Townhome w/ Private Pool in Old Town. Sleeps 6-8. Available Nightly, Weekly, Monthly....Read More

Southernmost Hospitality V $1,941.50 - $3,751.00 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Nightly, Weekly, Monthly
    • 5Bedrooms:
    • 5.5Baths:
    • 12Sleeps:
    13 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

The Contented Crane $880.00 - $2,695.00 Nightly

  • Property Highlights
    Type: Townhouse
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Nightly, Weekly, Monthly
    • 3Bedrooms:
    • 3.5Baths:
    • 8Sleeps:
    13 people are interested in this property!
  • Description:
    2-Story 3BR/3.5BA Private Townhome w/ Private Pool in Old Town. Sleeps 6-8. Available Nightly, Weekly, Monthly....Read More

Conch Casa Grande $9,240.00 - $17,325.00 Weekly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Truman Annex
    Stay Type: Weekly, Monthly
    • 5Bedrooms:
    • 7Baths:
    • 8Sleeps:
  • Description:
    3-Story Large Private 5BR/7BA Home in Truman Annex w/ Private Pool. Sleeps 8. Available Weekly & Monthly....Read More

Keys Kokomo $6,105.00 - $15,152.50 Monthly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Casa Marina & Casa East
    Stay Type: Monthly
    • 3Bedrooms:
    • 2Baths:
    • 6Sleeps:
  • Description:
    1-Story Private Home + Pool & Tiki Hut, 3 Bedrooms, 2 Bathrooms (Sleeps 6-8) Available Monthly....Read More