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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

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

Gorgeous 4-bedroom home with 8-person hot tub

Mimosa Manor is a stunning newly renovated 4bedroom, 3bath home. Upstairs great room w/ vaulted celling's & plenty ofnatural lighting. The kitchen is a chefs dream. The master BDRM is equipped with an adjustable bed & spacious in suite bathroom. The downstairs, its own private living area w/2 bedrooms, bathroom & kitchenette and its own entrance. The home is equipped w WIFI & TVs in every room. The backyard has an 8-person hot tub, tiki hut and table for six. Cabana Club access included.

Private 4/3 Pool Heater/Dock/Kayaks/Bikes,etc

Wake up to breathtaking water views at our 4-bedroom, 3-bathroom villa. Enjoy the 1800 sq ft layout, fully equipped kitchen w/stainless steel appliances, and granite countertops. Sleeps 10 with memory foam beds. Outside, relax by your private heated pool (winter) and tiki-shaded area. Fish from the 32' dock or use the BBQ gas grill. Includes 2 kayaks, 2 paddleboards, and 4 adult bikes for a 5-minute ride to Sombrero Beach. Exterior cameras for security. Vacation License #VACA-22-40. Book now!

Beautiful Waterfront book now 2026 filling up fast

This property is like having your own private resort. We are on the Gulf of Mexico with a Million-dollar waterfront view & sunsets. 4BR + bonus room w/queen bed & futon. 2 full bathrooms 4 TVs. Pool, Private Dock. Watch the Dolphins daily. We a located next to the World-Famous Dolphin Research Center. House has wrapped around deck plenty of seating inside/out. Large private yard with plenty of room for all your needs. Walking distance to restaurant, marina. Kayaks/Paddleboards mostly available.

Salty Kisses Beach House

Salty kisses is a Modern brand new construction 5/4 beach house with a pool and a dock Salty kisses is a piece of paradise in Marathon. Gorgeous brand new 5 bedrooms,4 bathrooms single family home with open balconies to capture the breeze and enjoy with your family and friends. The space Five bedrooms, Four bathrooms First level has a bathroom/bedroom with the living room, Kitchen and dining room. Second floor The master suite that takes your breath away. The kids bedroom has 2 bulk beds

Blue House - Receive $400 towards a Boat Rental!

Receive a $400 gift certificate towards a boat rental. When you reserve a week for any of the dates and house below. When you book a full week at one of our vacation rental homes staying between the dates of September 1st through Dec 20, 2025. Please reach out before booking for boat availability. Vacation home has a view over Cudjoe Bay to the Atlantic from the common deck and from the private pool deck. 4 bedroom and 2 bathrooms. Large dock with water access for a small boat.

NEW: Vaca Cut with 60' dock, 4br-4ba, 2 kitchens

Boaters and anglers, welcome to paradise! This renovated 4BR/4BA home just off Vaca Cut offers unbeatable Ocean and Bayside access, a 60’ dock, cleaning station, and a dock power station. Relax on the two-story waterfront deck, spot dolphins and manatees, or head out for world-class fishing just minutes away. With two kitchens, two living rooms, 4 bathrooms and plenty of space, it's perfect for families, friends, or couples looking to unwind and explore the best of the Florida Keys!

Angler’s Eden

Amazing get-away in the beautiful Florida Keys! This property (constructed in 2018) is a haven for families seeking to escape to paradise year-round. Situated on a deep water canal with ocean access and enough dock space to park your boat for the week. A floating dock is also provided with kayaks and a paddle-board. Enjoy the large pool or ping pong table, or lounging in the sun! Beautiful Sombrero Beach is within walking distance (approx 1.5 miles) via a paved bike path.

Chick-A-Pea Cottage ~ Enjoy Key West's charisma

This delightful Key West charmer is full of sunshine, modern amenities, and island vibes. In no time you will be unwinding in your private pool and cabana. This home is walkable to several restaurants, shops, and the Southernmost Point. THE PROPERTY: Come enjoy the Key West cottage lifestyle where you can people watch from your front porch or take a dip in your pool. Whether you lounge in the cabana or enjoy dinner under the stars, this home has it all!

Beach House Key West, with a daily rentals license

This listing is one of the very few beach houses with a daily, rental license in the Key West area. A unique island experience awaits you in the spacious and peaceful oceanfront house. The property is perfect for a family or friends gathering. House has a beautiful oceanfront pool, the pool is not heated, big yard, outdoor grill, and barbecue. The dock is is steel dock located in a deep water canal, the control depth is 6' It was recently rebuilt.

Palm Breezes! Room for Everyone on the Ocean.

This 5 bedroom 3 bath house with pool on Ocean front property on Highway 1.. This lovely home has its own huge pool area with full lounge chairs all the way around pool area, the pool is heated. Grill, Jacuzzi. Full WiFi. TVs in every bedroom! Travel down our private dock way to the beautiful Cudjoe Bay, hop one of the many kayaks and take a healthy paddle with your friends/family or just enjoy the breathtaking ocean view while you sit on the porch.