Luxury rentals in Marathon

New Waterfront Luxe: Pool-Spa-Dock-Beach-Gulf View

The Gulfside Retreat is the perfect tropical luxury location to unwind in the sun, enjoy endless activities, and stay a while. This 4-bedroom, 5-bathroom 1.5 acre Gulf-front home offers the ideal private resort experience. Our home features an open layout with massive outdoor space and amazing Gulf views. You will have your own private beach, boat dockage, protected lagoon, and a long private pier to enjoy the gulf breezes. Plus, easy access to the oceanside in minutes by boat via the Vaca Cut.

Private Beach / Pickleball Court and Tiki Bar

Hidden in the heart of Islamorada, this oceanfront villa offers an unmatched privilege of a secluded private beach—an experience few can claim. Expansive terraces stretch across both levels, framing ocean views. This haven's open design and spacious rooms blend seamlessly with serene surroundings. A lush tropical yard meets the oceanfront, where swaying palms and vibrant greenery create a private oasis, crafting a retreat as rare as it is extraordinary. Enhanced cleaning practices implemented.

The Sea Glass House~LUXoceanfront Pool~Dock~Views

The Sea Glass House is a Luxury Exclusive Oceanfront Treasure with more than 100’ of dock and stunning ocean views from virtually every room. Located perfectly in the Middle Keys with direct access to the Atlantic Ocean and the Gulf of Mexico. With unlimited supplies provided, it can’t get easier. This Estate has it all! Saltwater pool with wading area, spa, 100 ft of dock, fire table, summer kitchen and grill, bicycles, ping pong table, kayaks and SUP boards, more! ​​ Come escape to luxury.

Ocean Palms Luxury Oceanfront SeaGlass Cove FLKeys

Welcome to Ocean Palms, a private oceanfront retreat in SeaGlass Cove on Grassy Key in Marathon, the Heart of the Florida Keys. This exclusive end unit features a rare resort style private pool, elevated privacy, and sweeping Atlantic views. Enjoy sunrise coffee, poolside lounging, and seamless indoor outdoor living with modern coastal design. Ideal for families or couples seeking luxury, space, and a true Keys escape. Experience unmatched ocean views, privacy, and comfort daily in paradise.

Private Beach & Dock / Heated Pool / Dolphin Key

Relish ocean serenity in this villa set directly on a secluded beach, where an open-concept design seamlessly merges the living area and gourmet kitchen with a grand terrace, all framed by uninterrupted Ocean views. Bask in the heated pool, unwind on the covered patio or tiki lounge, or step onto your private dock for a true waterfront escape. With a pristine stretch of sand and loungers reserved just for you, this is coastal living at its finest. Enhanced cleaning practices implemented.

P97 - Premier 5 bedroom, 3.5 bath waterfront home

Brand New in our inventory. A premier waterfront property offering luxurious living in the heart of the Florida Keys! This home includes 5 spacious bedrooms and 3.5 bathrooms and abundant living space for family and friends. Guests are delighted with this home’s private heat optional pool and spectacular views of Boot Key Harbor. Boating guests are especially pleased to find 50 feet of deep-water dockage, with additional amenities including a fish cleaning station and bait freezer.

Private beach / Heated Pool / volleyball / Orchid

Immerse yourself in captivating tranquility and sweeping ocean views from the expansive private beach, every corner of the estate, infinity heated pool, and hot tub. Designed for effortless gathering, the central villa boasts open-concept living and dining alongside a chef’s kitchen and family room. Retreat to the privacy of the primary suite villa and separate guest suite wing. Serene escapism at its finest in a private tropical oasis. Enhanced cleaning practices implemented.

Peninsula Villa | Boat Dock | Heated Pool | Sunset

This grand peninsula retreat, embraced by the Ocean and lush mangroves offering utmost privacy, has been designed for ultimate vacationing. Nestled along the tranquil shores of Florida Bay, its array of indoor & outdoor living and lounge areas, heated pool with a tiki bar, expansive sandy playgrounds, dock with ocean-access canal, gazebo boasting sunset views make this magical oasis ideal for serene escapes or vibrant family gatherings. Enhanced cleaning practices implemented.

Casa Dos Hondos II

Escape to this laid-back, oceanfront townhouse in Angler’s Reef, where coastal vibes and easy living come together in the perfect Keys getaway. With three bedrooms, three baths, and plenty of charm, this spot is all about kicking back and enjoying the island life. Whether you’re here with family or friends, this laid-back spot in Angler’s Reef has all the comforts you need for a relaxing, sun-soaked escape.

4 Bedroom Oceanfront Accessible Villa – Capacity 8

Spacious and fully accessible, this 3,100+ sq ft villa spans three stories with elevator access and ADA-compliant features. Three en-suite king bedrooms plus a twin room sleep up to eight. A full kitchen, dining room, and ground-floor loggia set a relaxed pace, while private balconies, laundry, and a two-car garage round out the experience.

Oceanview 4BR Family Villa + Resort Perks | Bunks

Experience expansive living with breathtaking Atlantic Ocean views and blend into the natural surroundings with indoor-outdoor living. Each 3,100-square-foot Villa features three ensuite king-bed bedrooms, a bunk room, a full kitchen, dining room, laundry room, and balconies. Additionally, the Villas offer a two-car garage.

Oceanfront + Resort Perks | 4BR Villa (Sleeps 8)

Experience expansive living with breathtaking Atlantic Ocean views and blend into the natural surroundings with indoor-outdoor living. Each 3,100-square-foot Villa features three ensuite king-bed bedrooms, a twin room, a full kitchen, dining room, laundry room, and balconies. Additionally, the Villas offer a two-car garage.