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

The Roseate House at Grassy Key

DUE TO AIRBNB'S ANTI HOST ENVIRONMENT, I WILL NO LONGER USE THEIR PLATFORM. PLEASE LOOK FOR US ACROSS OUR OTHER PLATFORMS. Relax, fish, swim and explore at your own personal resort. The home is perfect for couples, family or girls retreat. Families return year after year to create their memories. Honeymooners appreciate the privacy as well as the attention to detail. Come live among the treetops in this vintage conch Key West style cottage situated half way between Key Largo and Key West.

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.

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.

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!

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!

Viamarhe Cabin-Private beach, Kayak, yard games

If you are looking to enjoy the natural beauty, and romantic stay in a rear cabin with complete bath and kitchen independent of the main house but with a patio that shares the amenities of games and entertainment of a mini resort our Oceanfront small apartment is the place for you. You and your couple can enjoy the exclusivity this property will give you, like the 5 kayak and fishing rods, volleyball, chess, bowling, carbon and propane BBQ grill, and a fire pit.

2br/1ba w heated pool, 1 mile to robbies marina

Your slice of Islamorada awaits at the Key Lime Cottage! Step inside this charming 2 bedroom cottage and you will instantly feel at home. Located in the heart of the Florida Keys yet nestled in a serene neighborhood, it offers the perfect blend of comfort and relaxation. With a full kitchen, access to a gorgeous pool shared with only 6 other homes, outside seating with grill and a fire pit, beach chairs and key lime treats - there is something for everyone!

Lux Waterfront: Dock, Volleyball, Putt Putt, More

Pescayo Pointe Welcome to your modern Florida Keys escape—an upscale 4-bedroom, 3-bath canal-front home designed for comfort, entertainment, and effortless access to the ocean. This newly built property blends tropical elegance with resort-style amenities, making it perfect for families, couples, and avid boaters. Step into a bright and inviting living space adorned with coastal accents and designer touches. 4 bedrooms | 6 beds | 3 bathrooms