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Oceanfront Rooftop Views w/ 75ft of Dockage

Welcome aboard Captains Rooftop, Your 4BR Rooftop Deck Hot Tub Oasis on a direct ocean access canal with 75ft of dockage. This three story stilted rooftop home provides a unique unforgettable Florida Keys experience for your entire family. 🏊‍♂️ 2 Luxury jet Hot Tubs (One on the roof, one in the backyard) ⛵ Private 75ft dock surrounded by a mangrove jungle 🕹️ Foosball Table 🍳 Rooftop patio with BBQ grill & open ocean view dining 💻 High-speed Wi-Fi for streaming & remote work 🛏️ Comfortable

Sailboat Stay + Resort Amenities

Unplug and unwind aboard The Dream, your own sailboat in Key West, Florida! This is not your typical Airbnb — it's a floating escape on a beautiful 1-bedroom, 2-bathroom 42 foot sailboat docked at the exclusive Perry Hotel & Marina (just minutes from downtown!) Enjoy a queen bed in the spacious Captain’s suite, 2 full-sized paddle boards, snorkel gear, private Wi-Fi, and more. With tropical vibes, luxury touches, and the comforts of home, this is where island adventure meets peaceful retreat.

Oceanfront . 5br Luxury . Hot tub. January Special

Escape to this new stunning waterfront pool home. Enjoy panoramic ocean views, a private boat dock, with , fishing area, snorkeling, kayaks, paddle boards, bicycles and more.... The spacious, modern interior features a fully equipped kitchen, cozy bedrooms, and an open living area perfect for relaxation. Step outside to a beautiful patio or two balconies with seating to take in the views. Ideal for multiple couples, big families, or friends looking to explore the best of the Marathon key.

Resort chic on the water!

Enjoy the sights and sounds of nature while you stay on this 42' roomy sailboat. The cockpit has a small table and is very spacious. There is 6' 8" headroom and lots of light down below. The boat is docked at the Perry Hotel, one of the finest resort locations in the world. There are 2 pools, 3 restaurants and a 24 hour gym on sight. The concierge can arrange trips for you, and a shuttle will take you to downtown every hour until 10:30 pm. The lobby is a great place to relax and mingle.

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.

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.

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!

P30 - Charming 2 bed, 2 bath home with stunning Bo

New on the rental market! This 2 bedroom, 2.5 bath home is stunning! The water views of Boot Key Harbor are breath taking! This home boasts an open floor plan and private heat optional pool and ample dockage. - Maximum Occupancy: 4 guest (includes adults and children of any age) (*children of any age, including infants, count toward occupancy) - No day guests or visitors allowed above the advertised max. occupancy. - Parking: 2 vehicle max

*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.

Dream Catamaran

🌴 Welcome Aboard SeaJaz — Your Private 42’ Catamaran Getaway at the Perry Hotel & Marina You’ll love this unique, romantic, tropical escape aboard SeaJaz, a 3-bedroom Owner’s Version 42’ Manta sailing catamaran. It's cozy, intimate, and one of the most memorable places you can stay in Key West. Ever dream of staying on a catamaran in the Caribbean? Now is your chance — at a steep discount compared to traditional charters.