Vacation rentals with a firepit in Stock Island

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

Grouper Getaway @ Ocean Isles Fishing Village

Escape to paradise at the Grouper Getaway located at Ocean Isles Fishing Village in Marathon Key, FL. This beautiful brand new fully furnished 1 bed/2 bath studio townhouse, offers a central location and an array of luxurious amenities for a truly unforgettable vacation. Steps away from the the Atlantic Ocean, enjoy the largest pool in Marathon with clear views of the VACA Cut boat traffic and the Sombrero Light House. Enjoy fishing, paddle boarding, kayaking, tiki huts, beach, and grills.

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.

Perfect Paradise

Perfect paradise is located in the heart of marathon. Only 9 minutes away from sombrero beach. Restaurant, supermarkets, ice cream, aquarium, and much more less than 7 minutes away. Public boat ramp is 5 minutes away. The house has plenty of parking spaces in the front to park your boat and cars. The home is fully stocked with everything you will need during your stay. For specific dates please message me first before booking so I may accommodate you to the dates that you would like to book.

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.

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.

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

*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.

2 Bedroom Yellow Cabin

2 Bedroom Cabin located in the Old Wooden Bridge Resort and Marina in Big Pine Key, FL. Guests have access to all Old Wooden Bridge Resortt and Marina's amenities. There is NO Swimming in the Marina Boat Basin. There is a beautiful salt water pool to use for your swimming pleasure. This is a marina with houseboats and rental boats in the slips. There is a pet fee of $15 plus tax per night, per pet, to be paid at check in.

The simple life on Seaplicity!

Come stay on our beautiful & Super Comfy 38 ft Hunter Sailboat at the Perry Hotel & Marina! Start your morning with a fresh cup of coffee on board & "SIMPLIFY" your vacation with unrestricted access to all resort amenities! Two heated salt water pools, gym, laundry, and bathrooms and try one of the great restaurants onsite. Shuttle service takes you to old town Key West, leaving every hour from the hotel lobby.

COZY Family Home- 5 minutes from sombrero beach

⸻ Keep it simple at this peaceful, centrally located getaway. Our Paradise Key sits in the heart of Marathon—close to restaurants, supermarkets, and all the island fun. Sombrero Beach is just 2.5 miles away, and if you’re bringing a boat, the ramp is only 5 minutes from the house. We pride ourselves on spotless spaces, cozy comfort, and happy guests. Our reviews say it all!