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  Key West vacation 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 Key West rentals are heated in the winter months.

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Cielo Azul $297.00 - $1,045.00 Nightly

  • Property Highlights
    Type: Condominium
    Pets Allowed: No
    Neighborhood: Key West Beach Club
    Stay Type: Weekly, Monthly
    • 2Bedrooms:
    • 2Baths:
    • 6Sleeps:
    14 people are interested in this property!
  • Description:
    Second Floor Oceanfront Condo in Private Gated Community on the Beach, 2 Bedrooms, 2 Bathrooms, Sleeps 4-6. Available We...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

That's Amore! $249.70 - $660.00 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Monthly
    • 3Bedrooms:
    • 3.5Baths:
    • 8Sleeps:
    14 people are interested in this property!
  • Description:
    Stunning 3BR/3.5BA Private Old Town Home & Pool (Sleeps 6-8) Available Monthly....Read More

Keys Kokomo $192.50 - $540.10 Nightly

  • 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

Atlantic Reflections $220.00 - $1,353.00 Nightly

  • Property Highlights
    Type: Condominium
    Pets Allowed: No
    Neighborhood: 1800 Atlantic
    Stay Type: Nightly, Weekly, Monthly
    • 2Bedrooms:
    • 2Baths:
    • 6Sleeps:
    18 people are interested in this property!
  • Description:
    Penthouse Waterfront Condo with Pool + Tennis Court, 2 BR, 2 BA (Sleeps 4-6)...Read More

Moondance $110.00 - $280.50 Nightly

  • Property Highlights
    Type: Condominium
    Pets Allowed: Yes
    Neighborhood:
    Stay Type: Monthly
    • 2Bedrooms:
    • 2Baths:
    • 4Sleeps:
  • Description:
    Completely Renovated Elegant Design Condo With Water Views 2 Bedroom 2 Bathrooms. 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

The Contented Crane $385.00 - $2,398.00 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

Brisa Fresca $495.00 - $2,065.80 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: No
    Neighborhood: Truman Annex
    Stay Type: Weekly, Monthly
    • 3Bedrooms:
    • 3Baths:
    • 8Sleeps:
    14 people are interested in this property!
  • Description:
    2-Story 3BR/3BA Private Home w/ Private Pool in the Truman Annex, Sleeps 6-8. Available Weekly & Monthly....Read More

Walking on Sunshine $122.10 - $330.00 Nightly

  • Property Highlights
    Type: Apartment
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Monthly
    • 2Bedrooms:
    • 1Baths:
    • 4Sleeps:
    13 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