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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Southernmost Palms $220.00 - $1,245.20 Nightly

  • Property Highlights
    Type: Townhouse
    Pets Allowed: No
    Neighborhood: Truman Annex
    Stay Type: Weekly, Monthly
    • 2Bedrooms:
    • 2.5Baths:
    • 6Sleeps:
    18 people are interested in this property!
  • Description:
    3-Story 2BR/2.5BA Townhome in Truman Annex w/ Pool Access. Sleeps 4-6. Available Weekly & Monthly....Read More

Maison Tropicale $206.80 - $688.60 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Monthly
    • 3Bedrooms:
    • 3Baths:
    • 8Sleeps:
  • Description:
    2-Story 3BR/3BA Private Home w/ Private Pool in Old Town. Sleeps 8. Available Monthly....Read More

Americana Tropicale $550.00 - $3,300.00 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Nightly, Weekly, Monthly
    • 4Bedrooms:
    • 4.5Baths:
    • 10Sleeps:
    22 people are interested in this property!
  • Description:
    2-Story Private Home in Old Town with Private Pool, 4 Bedrooms, 4.5 Bathrooms (Sleeps 8-10) Available Nightly, Weekly, M...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:
    16 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

La Provence Tropicale $122.10 - $330.00 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Key West Golf Club
    Stay Type: Monthly
    • 2Bedrooms:
    • 3Baths:
    • 6Sleeps:
    19 people are interested in this property!
  • Description:
    2-Story 2BR/3BA Private Home w/ Private Spa at Key West Golf Club on Stock Island. (Sleeps 4-6) Available Monthly....Read More

2 Cool Fish $220.00 - $1,061.50 Nightly

  • Property Highlights
    Type: Townhouse
    Pets Allowed: No
    Neighborhood: Truman Annex
    Stay Type: Weekly, Monthly
    • 2Bedrooms:
    • 1.5Baths:
    • 4Sleeps:
    19 people are interested in this property!
  • Description:
    2-Story 2BR/1.5BA Townhome in Truman Annex w/ Community Pool Access. Sleeps 4. Available Weekly & Monthly....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

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

Cayo Calypso $195.80 - $581.90 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Casa Marina & Casa East
    Stay Type: Monthly
    • 3Bedrooms:
    • 3Baths:
    • 8Sleeps:
    12 people are interested in this property!
  • Description:
    2-Story Private Home + Private Pool, 3 Bedrooms, 3 Baths (Sleeps 6-7) Available Monthly....Read More

Casa Serendipity $330.00 - $2,011.90 Nightly

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