Holiday houses in Long Key

Beach House, Private Pool, Dock, Gulf View Sunsets

You don’t come to the islands to stay in a town—you come to slow down. Welcome to our tropical keys beach home, tucked away from the traffic and noise of US Hwy #1. Sway with the palms on the wraparound deck, soak in wide-open panoramic bay views, and catch fiery sunsets right off your dock. Fire up the BBQ, brew a Keurig, float in the private pool, or cast a line from the 300’ private pier/dock. Easy going island living with ocean / gulf breezes, comfy beds, quality linens, Wi-Fi, and cable TV.

Villa del Sol - Free Kayaks 2/2.5

Welcome to Paradise in the Florida Keys! Relax and recharge at Villa del Sol, a charming, totally renovated, waterfront retreat, offering breathtaking sunset views and endless vistas of the amazing turquoise waters. Whether you're sipping coffee at sunrise or enjoying a cocktail at dusk, the ocean is always your backdrop. Conveniently located between Key Largo & Key West, Duck Key serves as the perfect place for your island getaway, just a short drive from all iconic destinations in the Keys.

Captain’s Quarters Ahoy Mateys! Florida, Keys

This is located at the Florida Keys in Key Colony, Marathon. It is a spacious two bedroom, two bathroom duplex surrounded by water. It is a renovated beauty and close to the best restaurants and the tranquility of this city. It is the perfect getaway where you can recharge your exhausted batteries. Captain’s Quarters is a clean and spacious base camp location for the many adventures that await you in this amazing location. Water views and the accessibility to the best fishing in the world.

Keys Getaway- 2 bedrooms w/Boat Dock, Pet Friendly

Put your feet up & relax on the patio. Enjoy the sea breeze and sunset over the Florida Bay. The basin is full of sea life: tarpons, tropical fishes, snapper, and a variety of sea birds. You are conviently located at the marina so take advantage of the bait shop with current fishing reports. If you did not bring your own boat, rent one from us. Our location gives easy access to the Atlantic ocean & Florida Bay. Make some memories at this unique and family-friendly place. You are on Keyz time.

Villa 5087 on Duck Key BOAT SLIP available

Enjoy a Fully Renovated Villa on Duck Key. This villa boasts breathtaking sunsets, close to watersports, charter fishing, restaurants while being surrounded by one of the most exclusive island neighborhoods with lush landscaping. Duck Key is family-friendly, or it can be a serene couples retreat. Dine with Sunsets on the rear deck, or explore the world-class restaurants of the middle keys. Please NO Smoking indoors, NO pets. Please do not take any items from the Villa. No pool access

My Little Oasis2 Waterfront Retreat, Key Largo

Million Dollar view at a fraction of the price! This property is on the water with amazing bay views. It includes one kayak for 2 people, paddle board, fishing rod, washer and dryer, kitchen with all cooking utensils. Note: The upstairs room is not comfortable for seniors or adults, the ceiling height is 4 feet (an adult has to walk on his knees). The property is located on a residential island, restaurants, bars, stores and grocery stores are within a 15 minute drive from the property.

360 DEGREE WATERVIEW HOUSEBOAT

IMPORTANT Enjoy your own private retreat aboard a solar and wind powered houseboat moored 1/2 mile from land in the beautiful Islamorada Please do not arrive after dark and NO night riding. Need experience with hand pull outboard motors a 12 foot skiff with a 6hp outboard motor is provided reliable to go back and forth from shore NOT reliable for exploring No hot water on shower, heat water in Tpots or Solar bags. Please shave before arriving No suitcases, least amount of cloths.

Islamorada Bungalow # 5

Bring the whole family to this great place with lots of room for fun.Escape to our charming 2-bedroom, 1-bathroom bungalow in Islamorada, FL, where luxury and convenience await! Relax on the spacious patio and take a refreshing dip in the pool, perfect for unwinding after a day of exploring nearby attractions. You're just moments away from pristine beaches, world-class fishing. Whether you seek adventure or relaxation. Secure your stay now for an unforgettable experience!

Castaway Island - Pool, Spa, Tiki Bar, Kyaks,Sup’s

Sleeps 5 adults. 3rd bed is si sofa bed with a queen mattress. Indulge in the ultimate tropical retreat at our captivating bungalow Castaway Island, showcasing over 120 perfect guest reviews across multipl venues. Your hosts' extensive hospitality experience is evident in the restoration and thoughtful amenities, guaranteeing an exceptional vacation experience. Discover your ideal home away from home, where every detail is carefully designed to surpass expectations.

Oceanfront w/ Dock, Kayaks, Hot Tub & Secluded

Buchanan Keys Cottage Take a step back into “Old Keys” living. Once Upon A Tide; there was a sense of tranquility & peacefulness found throughout the Keys, like the one you will uncover when choosing to stay at this private, serene, 1/1 oceanfront cottage. Located on Grassy Key, this beautiful home is just 10 minutes from the City of Marathon. Far enough to be away from the hustle & bustle, but close enough to make a grocery/store run a “Keys breeze”.

Private Pool Tropical Oasis - Centrally Located

Centrally located in the Florida keys, this beautiful three-bedroom home is steps away from fishing, restaurants, boat rentals and water sports. The property features a private and lush backyard filled with your own private pool, loungers and outdoor games. In the evening, unwind with a refreshing drink under the outdoor lighting or in the heated pool. The villa includes a high chair, pack and play, bed rails, booster seat, baby gate and kids dishware.

Premium Floating Bungalow by Stay Ombi

Welcome to Stay Ombi, a fully off-grid escape on the gentle waters of Buttonwood Sound in the Florida Keys. Ombi offers three bungalows, crafted to immerse you in nature - without compromising on comfort. Guests are transported to the bungalow by boat (10-minute trip), which will be pre-stocked with all of your requested comforts. Our concierge team will work with you upon booking to plan one of the most unique experiences in the Keys.