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

New Luxury Oceanfront House. Hot Tub & Sunset View

Brand new build 2024. This 5 bed/4bath luxury ocean gulf home with boat dock, heated/chilled pool/ spa, paddle boards kayaks, bicycles was meticulously designed and custom built like no other house in Marathon Key. You can see ocean water from every room in the house. and the interior design was chosen to maximize comfort, with a stress-free peaceful setting. Only three homes on this one-acre private ocean gulf lot that has the look and feel of a private island with 400 feet of bulk head

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.

Garden Oasis with Ocean Views | Pool & Beach

Uncover a hidden gem in our charming condo overlooking a tranquil garden with two unexpected side views of the ocean. It’s perfect for couples seeking a value-packed Keys getaway. A peaceful retreat, it is steps from the beach and pool, featuring a king bed, updated decor, and a screened balcony. With a full kitchen, it's your cozy base for exploring Marathon's beauty. Dive into relaxation or adventure, all while enjoying the comforts of our island home. Discover your Marathon haven today!

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.

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

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.

The Roseate House at Grassy Key Lic. #VACA-25-222

Lic. #VACA-25-222: Make The Roseate House at Grassy Key your next get away. 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.