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KW CanalFront 3BR: Htd Pool, Boat Tie-Up, Pet OK

Your own private Key West hideaway awaits. Surrounded by lush tropical landscaping, this peaceful home offers a large pool, outdoor shower, grill, and fire pit — perfect for relaxing days and starlit evenings. Enjoy complete privacy indoors and out, with three comfortable bedrooms, a fully equipped kitchen, washer/dryer, and 66' of canal frontage- bring your own boat or ask one of our favorite captains to pick you up! Whether out on the town or relaxing in your own home, you will love it here!

Amazing Location Harbor Key West- 2BD/2BA

As our guest, you’ll have exclusive access to our amazing 2BD/3BA Suite that sleeps 6. Centrally located overlooking the Harbor in Key West. Walk out your front door to all that Key West has to offer with restaurants and shopping. You will feel right at home as you sleep comfortably in the plush king size bed and queen bed. Everyone in your party will enjoy the open layout with living area, dining, and fully equipped kitchen. You will be amazed at water views from all parts of the property.

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.

Sentient Waters: 63’ Boat With Full Amenities

Welcome aboard Sentient, your own private 63’ boat in Key West! We're thrilled to have you & hope you enjoy every moment of your stay. Whether you're relaxing on deck, enjoying the sway of the water, or soaking in the sunset, we want you to experience the tropical island vibes with all the comforts of home mixed in. Aboard you will find 2 full beds & baths, a full pull out, a full kitchen & coffee bar, snorkel gear, comfortable seating & more! Step aboard & enjoy your own tropical paradise!

Oceanside home 109, dock,kayaks,bikes,pool,fishing

This luxurious home overlooking the Atlantic Ocean is part of Sunrise Beach Resort, an exclusive gated community built in 2007 with only 10 other homes. This is #109 and I also rent adjacent homes 111 and 107 in case you need more than one. We are 80 feet from the water's edge facing Southwest. Lounge in your private hammock or enjoy the gorgeous tropical landscaping and cool breezes on the balconies or poolside, where you can sun, fish or boat from the docks. Key West is 17 miles away.

Tropical Paradise

Oceanfront home with private pool, boat dock, kayaks, and private beach Tropical Paradise has been a popular and romantic vacation rental getaway since 2003. There are kayaks for adventures, a dipping pool and private beach for relaxation, a floating dock for fishing and docking a boat, (up to 24' boat allowed) screened in porch for dining There are 2 king bedrooms, 3rd bedroom has a queen with trundle 2 1/2 bath. This home has an open floor plan and recently remodeled kitchen.

43' Classic Yacht Views, Pools, Duval Shuttle

Create unforgettable Key West memories while staying on our long time charming liveaboard 43' Trawler. This 2 bedroom 1.5 Bath mini yacht will be the perfect home base for your adventures around town or to just sit and enjoy the incredible views and nature. Being at the award winning Perry Marina gives you all the amenities of a 5 star resort. 2 Pools, 3 Restaurants on site, free shuttle to town, hotel gym, laundry and all the charter and adventure options you could ever ask for.

Luxury Boat Stay | Resort Amenities

A Whim isn’t just a place to sleep - it’s permission to unplug and let vacation unfold naturally. Docked at the exclusive Perry Hotel & marina, this 40 ft 2-bed luxury boat with island bright touches is tucked away from the crowds in a resort style marina while being just minutes from downtown Key West. Featuring indoor and outdoor spaces for living, dining, and relaxing, as well as hotel amenities such as a pool, 3 bars and restaurants, and a gym. Vacation differently on A Whim.

Waterfront Sanctuary in the Keys!

Your WATERFRONT Keys getaway!! Updated appliances & fixtures, this 2BR/2BA elevated property won’t disappoint! Fully stocked kitchen/bathrooms. Never ending activities for your group at the Venture Out Resort- a gated community with oversized pool, hot tub, pickle ball/tennis/basketball courts, fishing, lobstering, biking, kayaking, boating! Launch your boat from the private ramp and tie it up on our 35’ seawall! Situated between Key West & Marathon, this property is THE PLACE!

Luxurious 40' Sailing Yacht!

Enjoy exclusive use of this 40-foot yacht all to yourselves, with the opportunity to get close to ocean life. This yacht is docked at the Perry Hotel & Marina, with free access to two stunning waterfront swimming pools, live music, three restaurants, complimentary shuttle service, & more. Come and go on the yacht anytime, day or night. Participating in an ocean excursion on this yacht is mandatory & comes at an extra charge. Inquire here about our other yachts in our fleet

Key West Oasis:Charming Retreat

Escape to our charming Key West houseboat, a serene oasis docked in a vibrant marina. This cozy retreat sleeps 4, featuring a comfy queen bed, a pull-out sofa, and a modern bathroom. Enjoy a fully equipped kitchen, Wi-Fi, and AC. Sway gently on the water, soak in stunning sunsets, or explore nearby Duval Street, just a short trip away. Perfect for couples or small families seeking a unique island adventure. Relax on the deck in paradise. Your Key West dream awaits!

Lakefront Bungalow

Welcome to our King Bed Bungalows — your bright little island retreat designed for pure relaxation🌿✨ Each bungalow features a king-size bed, coffee station, mini fridge, toaster, and the couch includes a convenient pull-out bed, ideal for kids or additional guests. Open layout room windows invite in beautiful natural light. Please note: our bungalows do not include a kitchen — just the essentials for comfort, connection, and carefree island living.🌴