Homes with Pools for Sale in Monroe County, FL

Home with a Pool for sale in Monroe County, FL:

This 4-unit tropical compound spans nearly 9,500 sq. ft. and includes a spacious 3BD/3.5BA main home plus three charming 1BD/1BA cottages. Enjoy resort-style living with a pool, tiki bar, and lush outdoor space. This property offers flexibility for employee housing, long-term rentals, or a 'Key West Melrose Place'-style retreat. Centrally located near beaches, dining, and Old Town—live and earn in paradise!

Home with a Pool for sale in Monroe County, FL:

A rare architectural masterpiece by renowned architect Max Strang, this modern coastal estate in Port Antigua, Islamorada, redefines luxury waterfront living. Set on a private sandy beach, the residence offers 5 bedrooms, 6 full baths and 2 half baths across 6,367 SF of interior space and 10,483 total SF. Strang’s signature tropical modernist design showcases natural materials, clean lines, and expansive glass walls framing panoramic ocean views. Amenities include a gym, golf simulator room, movie theater living area and a spectacular summer kitchen for entertaining. Outdoor living shines with a resort-style pool, spacious terraces and direct beach access. Every detail embodies refine

Home with a Pool for sale in Monroe County, FL:

2019 2BR/1B 36.5 ft RV on a concrete slab with pavers. The lot has an insulated aluminum roof/patio, outdoor kitchen, TV, and a large awning with pavers. Use it as a weekend get-a-way and or a short-term rental property. Calusa is one of the few communities in the Florida Keys that allow short term nightly rentals. Just an hour's drive from Miami and you are in paradise. Calusa has many amenities like a marina/boat ramp, temporary dockage, boat storage, 24-hour security, tennis/pickleball, basketball court, playground, onsite laundry, pool and recreational hall. Additionally, the property is located close to world class fishing/diving, Miami International Airport, amazing local attractions/

Home with a Pool for sale in Monroe County, FL:

SeaGlass Cove is an exclusive gated community nestled in the heart of the Florida Keys. This rare enclave features 14 brand-new luxury residences, each offering sweeping views of the Atlantic Ocean. This unit features 5 bedrooms and 4.5 baths. Residents will enjoy world-class amenities, including a resort-style pool, pickleball court, sandy beach, and the convenience of flexible weekly rentals. The first level features a private two-car garage and a covered cabana with generous outdoor living areas that flow seamlessly to the beach & pool deck. Upstairs, an open-concept layout connects the gourmet kitchen, dining area, and great room—all oriented toward breathtaking ocean views.