Holiday rentals with a fire pit in Key West

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

Viamarhe House-Private beach, Kayak, yard games

If you are looking to enjoy the natural beauty and the captivating views of the Florida Keys, our charming Oceanfront house is the place for you. Enjoy the breathtaking views of the sunrise and the starry night show over the beautiful Atlantic ocean. You and your family can enjoy the exclusivity this property will give you, Viamarhe is its own little resort, 5 kayak and fishing rods, volleyball, chess and bowling ground, Domino, Billiards, Ping-Pong, and Football. the propane BBQ grill, fire pit

SAY'S BY THE SEA

Oceanfront 2BD/2BA and separate 1BD/1BA pool-side overlooking the Atlantic* Enter your paradise dream home with stunning views and privately nested away from the big city noise. You'll be staying in our large three bedrooms and three baths secluded retreat with a large terra overlooking the Atlantic Ocean. The home's rooftop deck on the third floor offers a panoramic and open observatory which is great for catching rays, watching sunrises, sunsets and shooting stars. RENTAL LICENSE #VACA-22-30

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.

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.

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!

Tiki Time! Private Pool~Tiki Hut~Kayaks~Grill!

Tiki Time ~ your private paradise in beautiful Marathon, heart of the Florida Keys! This is the perfect place for a family vacation or relaxing getaway. Gorgeous 3BR home with your own private salt water pool, Tiki Hut, space to park a 30' boat/trailer, and ocean views from the balcony~Kayaks, grill, beach toys await you for your beautiful day in the Florida Keys! Less than 5 min to Sombrero Beach, Dining & Local Bars! Experience the Florida Keys like a local and book Tiki Time today!

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!

Gorgeous Ocean View Home!

Beautiful family friendly ocean view home centrally located in the heart of Marathon (only 10min from Sombrero Beach) were you’ll be able to do many things like snorkeling, fishing, boating, Scuba, museums, visit the aquarium, and/or the dolphin research center, and even dine on the water with many restaurants selections near by. This property does NOT have dock space for a boat or trailer parking. Licensed and inspected by the city of Marathon Lic.# VACA-23-144

New Waterfront Views | Pool & Tiki Bar

Be our first guest at the MYSTIC MERMAID a brand new built 1BR/1BA Waterfront Villa that sleeps up to 4 guests! This luxury retreat is located on a scenic canal with marina slips right outside its' door! Enjoy amazing resort amenities including a pool, Tiki Bar, restaurant, pickleball & volleyball courts, fitness center, complimentary breakfast & more. Perfectly situated in the middle of the FL Keys making it the ultimate Florida Keys escape!