Key West Homes with Pool

Key West Homes with Pool

Welcome to the enchanting island paradise of Key West, Florida, where sun-kissed beaches, vibrant culture, and a laid-back lifestyle converge to create an idyllic living experience. Nestled in Monroe County, Key West is renowned for its stunning sunsets, historic architecture, and a rich tapestry of local traditions that make it a truly unique destination. With its charming streets lined with colorful conch houses and lush tropical landscapes, life here feels like a permanent vacation.

For those dreaming of a home that embodies the essence of island living, Key West offers an array of stunning properties, many of which boast private pools. Imagine stepping out into your own backyard oasis, where you can soak up the sun, host gatherings with friends, or enjoy tranquil evenings under the stars. Homes with pools in Key West are not just residences; they are gateways to a lifestyle filled with relaxation and leisure.

Whether you’re seeking a cozy cottage or a luxurious estate, the real estate market here caters to a diverse range of preferences and budgets. With the Atlantic Ocean as your backdrop, each day promises new adventures—from sailing and snorkeling to exploring the vibrant nightlife and culinary delights that Key West has to offer.

Living in Key West means embracing a community that values art, history, and the great outdoors. With an average temperature of 75°F and an abundance of sunshine, you’ll find that every day is an opportunity to enjoy the beauty of island life. Come discover your dream home with a pool in this tropical haven, where every moment is a celebration of paradise!

Newest Key West Homes with Pool

$5,495,000
5 Beds ⋅ 6 Baths ⋅ A12064822 MLS
“Discover Sunset Paradise – a stunning new construction Gulf-front retreat built in 2023 in the heart of Marathon, Florida Keys. This turnkey, fully furnished single-family home offers approximately 3,219 square feet of luxurious living space on a spacious 0.43-acre lot with direct open-water Gulf access.Boasting 5 bedrooms and 4.5 bathrooms (main house plus a separate guest cabana with A/C), this property sleeps up to 12 and is ideal for large families, multi-generational getaways, or premium vacation rentals. Built with durable concrete construction (CBS), it features bright, coastal-inspired interiors with panoramic Gulf views, a gourmet kitchen, and expansive living areas that flow seamlessly to outdoor entertainment spaces. It also includes a 4-car garage.Step outside to your private waterfront oasis: enjoy a beautiful heated pool with jacuzzi (perfect for year-round use, including winter), covered decks, and a massive 74-foot concrete dock ideal for boating, fishing, kayaking, or simply relaxing by the water. Additional highlights include a pergola, fish-cleaning station, bait freezer, and ample room for boat trailer storage.This home is a proven income producer with an active short-term rental license and established bookings through VRBO, Airbnb, and the highly regarded local management company Florida Keys Vacation Rentals. It is sold fully furnished and turnkey – ready for immediate enjoyment or continued rental success.

735 50 Street Unit Gulf, Marathon, Key West
$899,000
3 Beds ⋅ 2 Baths ⋅ A11989717 MLS
olid CBS construction home with a durable metal roof, ideally located within walking distance to marinas, restaurants, and local shops. This 3-bedroom, 2-bathroom property offers an elevated position with glimpses of the water from one side.Enjoy a spacious backyard perfect for entertaining, complete with an above-ground pool and plenty of room to relax or expand. The property also features off-street parking ideal for an RV or boat, plus ample street parking for guests.A great opportunity to own a well-built home in a prime Key West location with both convenience and lifestyle at your doorstep.

2311 Patterson Avenue, Key West
$2,685,000
4 Beds ⋅ 5 Baths ⋅ B26044978 MLS
Brand-new construction in one of Key West's most desirable residential neighborhoods, the Casa Marina area of Old Town, just blocks from upper Duval Street and four blocks from the beach. This 4 bedroom, 4.5 bath single-family home blends modern durability with relaxed island living, offering the ease of low-maintenance ownership in the highly sought-after X flood zone. Built in 2026 to Florida's toughest standards, the home features concrete board siding, impact doors and windows, and an elevated first floor. The construction is designed to withstand winds up to 180 MPH. Inside, spacious living areas with high ceilings flow comfortably to a private outdoor retreat with an inground pool and water features. All bedrooms are en-suite, with one located on the first floor. A $15,000 builder appliance credit allows you to choose the finishes and appliance brands, at cost, that best suit your lifestyle. Off-street parking adds everyday convenience, while reclaimed wood accents from the historic schooner Western Union bring a meaningful connection to Key West history into the architecture. Quiet, private, and close to everything, this home offers luxury, walkability, and the best of Key West living.

1316 Royal Street Unit 6, Key West
$4,375,000
5 Beds ⋅ 6 Baths ⋅ R11113482 MLS ⋅ The Seven Palms - A Key West Oasis BLDG.
Welcome home to an exceptional new-construction residence in a private, gated community offering resort-style amenities, a boat slip and nightly rental opportunities. Conveniently located next to Summerland Key Airport, this fully upgraded home features a private elevator, a stunning infinity pool overlooking the water and an expansive rooftop deck perfect for enjoying breathtaking Florida Keys sunsets. Only have two homes remaining.

231 E Shore Drive Unit Unit 6, Key West
$1,799,000
3 Beds ⋅ 3 Baths ⋅ R11007158 MLS
Excellent opportunity whether looking for a private residence or an investment. This condo will not disappoint. Artfully renovated very spacious three story . Plenty of outside area including private courtyard with a heated pool. Walk out the front door and just steps away from Duval st. and everything Key West has to offer. This is maintenance free living while it gives the feeling of a private residence. Assigned off street parking right in front of the unit. This property is being offered turnkey. Vacation Rental history available .This home has all hurricane impact windows and doors. making the unit noiseless.

1011 Simonton Street Unit 1, Key West
$2,595,000
3 Beds ⋅ 3 Baths ⋅ R11067758 MLS
Traditional key West home impeccably maintained, boasts three bedrooms, three full baths with plenty of closets throughout the home. Large private lot with a heated pool featuring a waterfall. Nice size cabana room that has a/c and heat with ample closet space can be a fourth bedroom. This home has large rooms for entertaining, quaint front porch and off street parking. A true treasure.

508 Grinnell Street, Key West
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