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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Bahamian Bamboo $6,413.00 - $13,013.00 Weekly

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

Pilar's Secret $1,056.00 - $3,118.50 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Nightly, Weekly, Monthly
    • 3Bedrooms:
    • 2Baths:
    • 8Sleeps:
    52 people are interested in this property!
  • Description:
    2-Story Private Home with Private Pool off Duval St, 3 Bedrooms, 2 Baths (Sleeps 6-8) Available Nightly, Weekly, Monthly...Read More

The Emerald Orchid $8,552.50 - $22,429.00 Monthly

  • Property Highlights
    Type: House
    Pets Allowed: No
    Neighborhood: Old Town
    Stay Type: Monthly
    • 3Bedrooms:
    • 3.5Baths:
    • 6Sleeps:
    21 people are interested in this property!
  • Description:
    Pristine 3 Bedroom 3.5 Bathrooms Private 2 Story Home W/ Private Pool In Old Town...Read More

Moondance $3,498.00 - $7,876.00 Monthly

  • Property Highlights
    Type: Condominium
    Pets Allowed: Yes
    Neighborhood:
    Stay Type: Monthly
    • 2Bedrooms:
    • 2Baths:
    • 4Sleeps:
    18 people are interested in this property!
  • Description:
    Completely Renovated Elegant Design Condo With Water Views 2 Bedroom 2 Bathrooms. Available Monthly....Read More

That's Amore! $7,001.50 - $18,502.00 Monthly

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

Viva Margarita! $7,260.00 - $17,847.50 Monthly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Monthly
    • 3Bedrooms:
    • 4.5Baths:
    • 8Sleeps:
    22 people are interested in this property!
  • Description:
    Three-Story Private Home in Old Town, 3 Bedrooms, 4.5 Bathrooms (Sleeps 8). Available Monthly....Read More

Spoonbills' Escape $3,102.00 - $8,030.00 Monthly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Key West Golf Club
    Stay Type: Monthly
    • 2Bedrooms:
    • 3Baths:
    • 6Sleeps:
    22 people are interested in this property!
  • Description:
    Two Story Private Home near the Pool at the Key West Golf Club, 2 Bedrooms, 3 Bathrooms. Screened-in patio with serene ...Read More

Flamingo Dreams $6,490.00 - $19,294.00 Monthly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Monthly
    • 3Bedrooms:
    • 2Baths:
    • 6Sleeps:
    26 people are interested in this property!
  • Description:
    2-Story 3BR/2BA Private Home w/ Private Pool in Old Town, First Floor Master, Sleeps 6. Available Monthly....Read More

Villa Bahama $2,887.50 - $6,352.50 Weekly

  • Property Highlights
    Type: Townhouse
    Pets Allowed: No
    Neighborhood: Truman Annex
    Stay Type: Weekly, Monthly
    • 2Bedrooms:
    • 2.5Baths:
    • 6Sleeps:
    32 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

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:
    23 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