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.

Map All Results

Villa Cubana $220.00 - $880.00 Nightly

  • Property Highlights
    Type: Townhouse
    Pets Allowed: No
    Neighborhood: Old Town
    Stay Type: Weekly, Monthly
    • 2Bedrooms:
    • 2Baths:
    • 4Sleeps:
    19 people are interested in this property!
  • Description:
    Two Story Tropical Cottage in Gated Community Near Duval Street, 2 Bedrooms, 2 Bathrooms, Sleeps 4. Available Weekly & ...Read More

The Lilac Cottage $161.70 - $501.60 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Monthly
    • 2Bedrooms:
    • 2Baths:
    • 7Sleeps:
    13 people are interested in this property!
  • Description:
    2-Story 2BR/2BA Private Home + Private Pool & Large Fenced Yard in Old Town. Sleeps 4-6. Available Monthly....Read More

The Emerald Orchid $304.70 - $800.80 Nightly

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

Windswept Palms $522.50 - $2,211.00 Nightly

  • Property Highlights
    Type: Condominium
    Pets Allowed: No
    Neighborhood: 1800 Atlantic
    Stay Type: Nightly, Weekly, Monthly
    • 3Bedrooms:
    • 2Baths:
    • 6Sleeps:
    22 people are interested in this property!
  • Description:
    3rd Floor Oceanfront Condominium, 3 Bedrooms, 2 Bathrooms, Sleeps 6. Available Nightly, Weekly, Monthly....Read More

Puerta Coralina $275.00 - $1,650.00 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Nightly, Weekly, Monthly
    • 2Bedrooms:
    • 3Baths:
    • 6Sleeps:
    23 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

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

The Smiling Ibis $385.00 - $2,486.00 Nightly

  • Property Highlights
    Type: Townhouse
    Pets Allowed: Yes
    Neighborhood: Old Town
    Stay Type: Nightly, Weekly, Monthly
    • 3Bedrooms:
    • 3.5Baths:
    • 8Sleeps:
    27 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

Sea Captain's Haven $209.00 - $1,072.50 Nightly

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

Here Comes The Sun $176.00 - $411.40 Nightly

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

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:
    25 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