Key West Homes with Pool View

Key West Homes with Pool View

Welcome to Key West, Florida—a tropical paradise that boasts stunning sunsets, vibrant culture, and a laid-back lifestyle that draws visitors and residents alike. Nestled in Monroe County, Key West is the southernmost point of the continental United States, offering a unique blend of history, adventure, and relaxation. With its charming architecture, lush gardens, and beautiful beaches, this island city is a dream destination for those seeking a slice of paradise.

One of the most coveted features of Key West homes is the breathtaking pool view. Imagine waking up each morning to the gentle sound of water lapping against the pool’s edge, surrounded by swaying palm trees and the vibrant colors of tropical flora. Homes with pool views in Key West offer an oasis of tranquility, perfect for unwinding after a day of exploring the island's eclectic shops, lively bars, and world-class dining options.

Whether you're lounging by your private pool or entertaining friends in your outdoor space, these homes provide a perfect backdrop for both relaxation and enjoyment. The warm, sunny climate allows for year-round outdoor living, making your poolside retreat an integral part of your Key West lifestyle.

From charming cottages to luxurious estates, the real estate market in Key West offers a variety of options for those looking to make this enchanting city their home. Discover the magic of Key West living, where every day feels like a vacation, and let the allure of homes with pool views sweep you off your feet.

Newest Key West Homes with Pool View

735 50 Street Unit Gulf, Marathon, Key West
$5,495,000
5 Beds ⋅ 6 Baths ⋅ A12064822 MLS
!!!NEW CONSTRUCTION IN MARATHON!!!This beautiful property is brand new and tastefully furnished. “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
2601 S Roosevelt Boulevard Unit 103C, Key West
$889,000
3 Beds ⋅ 2 Baths ⋅ A12064540 MLS ⋅ C BLDG.
This ground-floor unit was thoughtfully converted from three bedrooms into a spacious two-bedroom, two-bath residence -- each with its own ensuite -- plus an open dining room and wet bar built for Keys-style living: relaxed, social, and always ready for company. Kitchen and bathrooms are fully renovated. Marble floors throughout. Soundproof impact doors and windows. Dual-zone split A/C systems mean cool bedrooms and comfortable common areas -- no compromises in the tropics.Hurricane-rated glass doors frame a lush garden view and open directly to the resort-style pool -- engineered for outward visibility with true privacy from outside. An elevated private patio puts the pool, tennis courts, and tropical grounds steps away.HOA includes cable, security, building insurance, exterior maintenance, and exterminating -- predictable carrying costs, no surprise weekends managing a property.In 50 years since 1974, Key West by the Sea has never flooded through a single named storm. The City and State recently completed a raised stormwater system and elevated South Roosevelt -- infrastructure built for the next 50 years.Old Town, Duval Street, the Historic Seaport, Mallory Square -- all a short bike ride away. You're connected to everything Key West is, and then you come home to a quiet, gated community that feels a world apart.Full-time residence, mainland escape, or the life you've been working toward, #103C is ready. Key West isn't accidental. You choose it. Choose this.

2601 S Roosevelt Boulevard Unit 103C, Key West
1011 Simonton Street Unit 1, 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
508 Grinnell Street, 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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