Key West Rentals with Pool

While in paradise, why not have some fun in the sun? Being able to enjoy a pool while on vacation is crucial. We have numerous rentals with pools throughout Key West, both of the private and community variety. In the warmer months, having access to a pool is perfect for cooling off after a long walk or bike ride around the island. In the cooler months, pool heat is recommended.

Renting a home with a private pool is great for families and groups that are looking for a more intimate vacation setting. If you're coming for a month or longer, pool heat is included with your rental. For stays of less than a month, pool heat is optional for a minimal fee and can be added to your reservation at checkout.

Many of our condos and apartments offer access to large on-site community pools. This is a great way to interact with other vacationers or locals staying in your area. All of the community pools that are offered with our rentals are heated in the winter months.

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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

La Vie En Rose $8,552.50 - $14,701.50 Monthly

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

Walking on Sunshine $3,432.00 - $9,262.00 Monthly

  • Property Highlights
    Type: Apartment
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Monthly
    • 2Bedrooms:
    • 1Baths:
    • 4Sleeps:
    10 people are interested in this property!
  • Description:
    Chic 2nd-floor Apartment in Old Town, 2 BR/1 BA (Sleeps 4-6) Available Monthly...Read More

The Coral Frog $4,994.00 - $14,052.50 Monthly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Casa Marina & Casa East
    Stay Type: Monthly
    • 2Bedrooms:
    • 2Baths:
    • 6Sleeps:
  • Description:
    One-Story Private Home with Private Pool in Casa Marina Neighborhood, 2 Bedrooms, 2 Bathrooms, Sleeps 4-6, Available Mon...Read More

The Artists' Muse $13,002.00 - $23,100.00 Monthly

Historic Florida Keys Foundation Award Winner
  • Property Highlights
    Type: House
    Pets Allowed: No
    Neighborhood: Old Town
    Stay Type: Monthly
    • 4Bedrooms:
    • 4Baths:
    • 8Sleeps:
    21 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

Casa Oliviana $9,900.00 - $33,000.00 Monthly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Monthly
    • 6Bedrooms:
    • 6Baths:
    • 12Sleeps:
    11 people are interested in this property!
  • Description:
    3-Story Large Private 6BR/6BA Home w/ Private Resort-Style Pool in Old Town. Sleeps 12. Available Monthly. Also Availa...Read More

Plantation Tropicale $13,321.00 - $27,720.00 Weekly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Truman Annex
    Stay Type: Weekly, Monthly
    • 5Bedrooms:
    • 4Baths:
    • 8Sleeps:
    19 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

Villa Olivietta $9,350.00 - $16,170.00 Monthly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Monthly
    • 4Bedrooms:
    • 5Baths:
    • 8Sleeps:
    14 people are interested in this property!
  • Description:
    Private Home with Private Resort-Style Pool, 4 Bedrooms, 5 Baths (Sleeps 8) Available 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

Puerta Coralina $544.50 - $1,732.50 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Nightly, Weekly, Monthly
    • 2Bedrooms:
    • 3Baths:
    • 6Sleeps:
    22 people are interested in this property!
  • Description:
    2-Story Private Home in Old Town, 2 Bedrooms + Sleeper Sofa, 3 Baths, Private Pool (Sleeps 4-6) Available Nightly, Weekl...Read More