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Oceanfront Cottage with Open Water Views

Oceanview Serenity provides stunning open water views, and a 60 foot seawall for your boat. Comes with paddle board, kayaks, and more. Newly renovated 2BR cottage sleeps MAXIMUM OF FOUR (4) GUESTS, with a King in the Master BR and one Queen size bed Guest BR (both with new JW Marriott mattresses for comfort). All new appliances! Enjoy resort amenities like a pool, hot tub, tennis, and marina store. Just 30 minutes from Key West. One-time $125 RESORT FEE DUE AT CHECK-IN (PER STAY, NOT PER PERSON

Key West Outpost: eco-vacation

The Outpost is a unique experience. This is a place where you can be completely off the grid, but still have all of the amenities. Private conch cottage on the backcountry waters surrounding Key West. Enjoy watching the amazing wildlife from your private deck. You can paddle board, kayak or do some light tackle fishing right off the boat. You can even add eco-tours to enhance the adventure. We will take you out for arrival and bring you back on your departure day, via one of our other boats.

Palm - Beach Houses Key West

If you’re reading this, you’re already on the path to paradise! Thank you for considering us for your dream vacation—we can’t wait to host you. Experience the charm of our recently renovated, one-of-a-kind two-bedroom beach bungalow, nestled right on the shore. Enjoy breathtaking ocean views from your private deck, relax on the sandy beach, and soak in the tropical ambiance. This family-friendly retreat offers the perfect setting to make you feel like you’re on your very own private island.

Family Suite at Sugarloaf Key Hotel (Pet Friendly)

Discover the perfect blend of comfort, relaxation and adventure at the Sugarloaf Key Hotel, nestled within the Sugarloaf Key / Key West KOA Resort campground. Newly built in 2023, this beautiful 6-person pet-friendly vacation suite offers everything you need for a great stay. Nestled amongst gorgeous tropical scenery, this resort includes robust amenities including resort-style pool and hot tub with an adjacent pub, quaint sand beach, marina, water rentals, café, camp store and more!

Waterfront Cozy Cottage with Boat Ramp & Dock!

Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with 250 foot dock, ramp, and basin for your boat. It's a must-see rustic outdoor environment and fishery experience, very typical in the Keys! The property lot is almost an acre with a work section and still very spacious. Stunning panoramic water views, sunrise and sunset. Steps away from ocean water. Bring or rent fishing and snorkel gear nearby to fish right off the dock and enjoy the underwater scenery!

Key West Beach House

Welcome to the Hyatt Beach House, a Hyatt Residence Club, your own private sanctuary in Key West with crystal-clear water views and direct beach access. Enjoy the private beach, furnished with thick-cushioned chairs, picnic tables, barbeque grills and a private dock. Soak up the sun in the zero-entry lagoon shaped pool and hot tub. Walk down stairs and enjoy the complimentary kayaking, gorgeous beach area and pool. Spend a wonderful week in the sunny Florida Keys!

Yellow Home - Receive $400 towards a Boat Rental!

Receive a $400 gift certificate towards a boat rental. When you reserve a week for any of the dates and house below. When you book a full week at one of our homes staying between the dates of Sept 1, 2026 through Dec 19, 2026 Except for Nov 21-28, 2026 Please reach out before booking for boat availability. Beautiful 3 bedroom 2 bath home. Kayaks included. Private heated pool and deck with a view of the Atlantic Ocean. Boat dockage available with parking.

Condo de Paradise/Salt Water Pool/Boat Dock

This is one of the best kept secret locations. Can be a very romantic escape. This is a good place for honeymooners, guys or gals getaway, fishermen/fisherwomen weekend get away or family time. A private unit in paradise in a gated community. Only 10 miles to Duval Street and all that Key West has to offer. There is a dock that can be used to dock up to a 26 foot boat that can be launched at Geiger Key, a mile down the road and they will store your trailer.

3 Bedroom Home - Perfect Location & Private Pool

The historic William Skelton Home is ideally located on Eaton Street in Old Town Key West, steps from Duval Street and all major attractions. This rental listing includes the second and third floors of the home, which features three bedrooms, a private swimming pool, spacious living areas inside and outside, off-street parking, and a newly renovated chef's kitchen to prepare meals. The first story of the home will be left vacant when this listing is rented.

Palm Breezes! Room for Everyone on the Ocean.

This 5 bedroom 3 bath house with pool on Ocean front property on Highway 1.. This lovely home has its own huge pool area with full lounge chairs all the way around pool area, the pool is heated. Grill, Jacuzzi. Full WiFi. TVs in every bedroom! Travel down our private dock way to the beautiful Cudjoe Bay, hop one of the many kayaks and take a healthy paddle with your friends/family or just enjoy the breathtaking ocean view while you sit on the porch.

*Emerald Seas*-Florida Keys Ocean Front Paradise!

Welcome to our Florida Keys Ocean Paradise, Emerald Seas! Truly a special place to get away and relax. Enjoy the crystal-clear waters and amazing views. Bring or rent a boat, look for sea turtles, manatees, dolphins, lobster & tropical fish right from your patio or dock. Take in a glorious sunrise or moonlit night over the water. The amazing, 180 degree panoramic ocean views will take your breath away every moment you are there.

Cottage

Experience island living at Sugarloaf RV Resort's NEW Cottages in the Lower Keys, just 25 minutes from Key West. These Two-Bedroom Cottages sleep up to 4 guests with 2 Queen beds. Features include a kitchenette with double burner stovetop, dorm fridge, microwave, single serve coffee maker, toaster, plus outdoor seating. Coastal charm with keys-style design and a private patio perfect for morning coffee or sunset relaxation.