Luxury Poolside Retreat with Dock in Florida KeysN°001
Florida Keys, USA
Key Colony Beach
Private poolSea viewWaterfront
From $8,043 per week · $1,149 per night
Photo by Baron Alloway on UnsplashThe Florida Keys are a string of subtropical islands curving from the southern tip of mainland Florida toward Key West. Renting a luxury villa here puts a private pool, waterfront dock and concierge service within reach of turquoise shallows, world-class diving and the only living coral reef in the continental United States.
Updated October 2026
- Waterfront luxury villas with private pools and boat docks
- Snorkelling and diving on the Florida Reef at John Pennekamp and Looe Key
- Sport fishing in the Gulf, Atlantic and the famed backcountry flats
- Sunset culture and historic charm in Key West
- Easy island-hopping along the scenic Overseas Highway
Known forCoral reef diving, sport fishing, turquoise flats and laid-back island living along the Overseas Highway
Best time to visitDecember to April for warm, dry weather and calm seas; spring offers fine fishing
Nearest airportKey West International (EYW); Miami International (MIA) serves the Upper Keys
Ideal forCouples, families and groups seeking waterfront villas, diving, fishing and relaxed luxury
Beachfront Penthouse with Ocean Views in OrlandoN°002
Florida Keys, USA
Islamorada
Sea viewWaterfront
Nov 25 – Dec 2 · $5,506 for 7 nights
2homes available
3–4bedrooms
up to 10guests
1with a pool
1book instantly →Florida Keys in pictures
What's on in Florida Keys
- Late October
Fantasy Fest
Ten days of costumed parades and street parties consume Key West in the islands' most exuberant event. Book villas well ahead, or time a quieter stay around it.
- April
Seven Mile Bridge Run
Runners cross the famous Seven Mile Bridge near Marathon with open water on both sides, one of America's most scenic and sought-after race entries.
- Early May
Key West Songwriters Festival
Nashville's leading songwriters play intimate sets in bars and theatres across Key West over five days, the largest festival of its kind.
- July
Hemingway Days
Key West celebrates its most famous resident with the look-alike contest at Sloppy Joe's, readings and a marlin tournament around his July birthday.
Florida Keys through the seasons
- Winter (December – February)
Peak season in the tropics
Dry, warm and reliably sunny while the mainland shivers: prime months for sailing, flats fishing and sunset cocktails from a private waterfront villa.
- Spring (March – May)
Calm seas and clear water
Superb visibility for diving and snorkelling the continental United States' only living coral barrier reef, with tarpon season drawing anglers to the flats.
- Summer (June – August)
Warm-water diving and lobster season
Bath-warm seas, long days on the water and the start of spiny lobster season. Afternoon storms pass quickly, and villa pools take the edge off the heat.
- Autumn (September – November)
Quiet keys and value season
The islands at their most local: uncrowded reefs, easy restaurant tables and Fantasy Fest's late-October crescendo before winter visitors return.
All 2 villas in Florida Keys
Every home in Florida Keys that can be booked with Smiling House, as a plain list.
Smiling House also offers a concierge for private chefs, transfers, ski instructors, yachts and cars, a VIP Club with first access to new residences and member rates, chalets for sale in the Gstaad region through its real estate division and instantly bookable homes with live availability.
The Area
The Florida Keys stretch roughly 120 miles from Key Largo through Islamorada, Marathon and the Lower Keys to Key West, linked by the Overseas Highway and its celebrated Seven Mile Bridge. Each island has its own character, from the diving capital of Key Largo to the artistic, historic streets of Key West. The archipelago is bounded by the Atlantic on one side and the Gulf of Mexico on the other, with shallow turquoise flats, mangrove islets and the protected Florida Reef offshore. A luxury villa in the Keys typically means open water views, a private dock and that unhurried, sun-soaked rhythm that defines island life in this corner of the United States.
Where to Stay
Choice of island shapes the holiday. Key Largo and Islamorada in the Upper Keys suit divers, anglers and families wanting space and easy reach of Miami. Marathon sits midway, a relaxed base near the Seven Mile Bridge. The Lower Keys and Key West reward those after nightlife, dining and historic atmosphere. Key Haven, a quiet residential island just outside Key West, offers waterfront villas with the city minutes away yet a calmer setting. Across these areas Smiling House presents a curated collection of luxury villas, many with private pools, docks and direct access to the water, supported throughout by concierge service.
Things to Do
Water defines life in the Keys. Snorkel or dive the coral gardens of John Pennekamp Coral Reef State Park, Looe Key and the wrecks scattered along the reef line. The flats around Islamorada are legendary for bonefish, tarpon and permit, while offshore charters chase sailfish, mahi-mahi and grouper. Paddle the mangrove channels by kayak, visit the Dolphin Research Center near Marathon, or watch the famous sunset gathering at Mallory Square in Key West. Quieter pleasures include Bahia Honda State Park's beaches and slow days spent on a private dock with the boat ready and the water glassy at dawn.
Dining & Nightlife
The Keys serve fresh-off-the-boat seafood with a Caribbean and Cuban accent. Local stone crab, pink shrimp, hogfish and the inescapable key lime pie appear on menus from waterfront fish shacks to polished restaurants. Islamorada and Key Largo offer relaxed dockside dining where you can eat what the day's charter landed. Key West is the social heart, its Duval Street lined with bars, live music and conch fritters, balanced by quieter courtyard restaurants tucked among the old town's lanes. Villa guests can also have a private chef arranged through concierge, turning the day's catch into dinner at home.
When to Visit
The dry season from December to April brings warm days, low humidity and the calmest seas, making it the prime window for diving, boating and beach time. Spring is excellent for fishing, with tarpon running through the flats. Summer is hotter and more humid with afternoon showers, but water visibility for diving is often superb and the islands quieter. Hurricane season runs June through November, peaking in late summer and early autumn, so flexibility helps if travelling then. Whenever you come, a waterfront villa with a pool keeps the heat at bay and the ocean always within reach.
Getting There
Most visitors fly into Key West International Airport for the Lower Keys or Miami International for the Upper Keys, then drive south on the Overseas Highway, US Route 1, the single road that threads the entire archipelago. The scenic drive from Miami to Key West takes around three to four hours, passing over dozens of bridges and open water. A hire car is the most practical way to explore island to island. Smiling House concierge can arrange airport transfers, car hire and a boat charter so the journey from runway to villa dock is seamless.