Moonlit Bay
10 guests
4 bedrooms
Key Haven, Key West
Just beyond the buzz of Key West, this waterfront villa offers easy-going luxury in a gated community. Outside you can relax in the private pool, fire up the barbecue, or jet off from the private slip.
The Pearl of Key West
16 guests
6 bedrooms
Key Haven, Key West
Spend your days soaking up the island breeze at this laid-back retreat just outside Key West. Tucked inside a quiet gated community, this spacious six-bedroom home is made for group getaways, with a private boat slip, breezy balconies, and enough room for everyone to spread out.
Six Leaves Left
4 guests
2 bedrooms
South Middle River, Fort Lauderdale
Kids and pets will appreciate the large outdoor space at this two-bed home in Fort Lauderdale – perfect for water fights, playing catch or just lying in the hot tub beneath the lush, shady trees. There’s also a heated pool for an invigorating early morning swim.
Naples Aglow
8 guests
4 bedrooms
Old Naples, Naples
You’ll find this modern, adult-only home in Old Naples, a short walk from Fifth Avenue with its plethora of delicious eateries and trendy shops. Comfortable for eight, each bedroom boasts an ensuite and with two separate living areas, there’s plenty of room for guests to spread out here.
Explore the 672 most perfect homes in our collection
All Plum Guide homes in Key West, Monroe County, Florida, United States have been tested and approved by our team of independent home critics. These meticulous beings inspect everything –from the convenience of each house’s location right down to the art on the walls– so what you see really is what you get. Worried about thin curtains? Accessibility? Maybe wifi speed is your biggest concern? Rest assured, we obsessively check each home in Key West, Monroe County, Florida, United States before approving it, so you can book with peace of mind.
