5 Florida Keys Waterfront Retreats with Pool, Docks, and Acreage

Along the waterfront in Marathon, this furnished retreat pairs modern upgrades with an easy, boating-forward lifestyle. Outside, 60 feet of dockage makes time on the water feel effortless, while a heated pool and a charming tiki hut set the scene for slow afternoons and sunset swims. Indoors, tile floors and tasteful nautical décor keep the atmosphere bright and relaxed. The living area is outfitted for everyday comfort with a leather sofa and loveseat, a 55-inch smart TV, and free WiFi. In the kitchen, granite countertops, stainless steel appliances, and a farm sink anchor a well-equipped workspace, complemented by an island with seating for four. Nearby, the dining area seats six for casual dinners after a day on the water, letting the home shift seamlessly from getaway to everyday.

Steps from the shoreline in Key Largo Ocean Resort, this modern multilevel home pairs an open-ocean setting with the ease of a vibrant, gated community. With no neighbor behind, it offers a welcome sense of breathing room, plus two entrances to the car porch and ample covered space downstairs for a boat, golf cart, and outdoor toys. Inside, an open floor plan is finished with porcelain plank flooring, quartz kitchen countertops, stainless steel appliances, and marble bathrooms, complemented by hurricane impact windows and doors and underground utilities. The home is offered exquisitely furnished, making day-to-day living feel effortless. Just outside, resort amenities include a clubhouse, pool, playground, gym, modern fitness center, tennis and basketball, and a full working marina with a private concrete boat ramp and fueling station. Sunrise views from the pier become part of the routine.

Along the water’s edge in Little Torch Key, this three-bedroom, two-bath home is designed for easy indoor-outdoor living. Multiple porches create a natural rhythm to the day, including a screened porch that invites lingering mornings and breezy evenings. For boaters, the setting shines with excellent oceanside boat access, complemented by 60 feet of water frontage and a composite dock ready for life on the water. After a day outside, an outdoor shower offers a simple, coastal ritual before heading in. Practical touches include a garage and a fenced back yard, while tropical landscaping brings a sense of privacy and softness to the outdoor spaces. It’s a relaxed waterfront retreat where porches, dock, and garden frame everyday living.

Set on 4.75 acres in Homestead, this private retreat pairs an open, high-ceilinged interior with the easy rhythm of country living. Tile floors, blinds, and ceiling fans run throughout, while the spacious kitchen is designed for everyday ease with an eat-at island, stainless steel appliances, and a pantry. French doors in the family room extend the living space outdoors, creating a natural flow for quiet mornings or relaxed gatherings. A flex room/office adds versatility, and the primary suite offers a serene reset with dual sinks and a tub/shower. Practical comforts are thoughtfully covered, from the laundry room with washer and dryer to whole-home water filtration, a propane fireplace, and a generator with tank. Outside, a covered patio looks out to a pond, tropical fruit trees, an old chicken coop, plus a detached 2-car garage and carport.

Along the water’s edge in Little Torch Key’s Jolly Rogers subdivision, this three-bedroom, two-bath retreat is oriented to life on the canal, with a deep flow-through waterway and quick boating access. A Trex dock is paired with a 15,000 lb boat lift and a permitted cargo lift, while impact windows and doors, Hardie board siding, aluminum railings, low-maintenance Trex decking, and a standing seam metal roof underscore durability. Indoors, vaulted wood ceilings bring warmth and volume, and the spacious upstairs primary suite includes his-and-her walk-in closets plus vaulted ceilings in both the bedroom and bath. The updated 2025 kitchen centers on granite countertops, a deep stainless sink, and new dishwasher, refrigerator, and microwave. Wraparound front and rear porches—and a screened front porch with fans, Coolaroo shades, and a vaulted ceiling—extend the day outdoors.