Luxury rentals in Vaca Key

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.

Hemingway Oceanfront Luxury: Pool • Marina • Views

Think Hemingway’s Keys spirit, but with a chef’s kitchen, designer interiors, and panoramic Atlantic views. This spacious 5BR waterfront retreat offers nearby marina slips, a resort-style pool, pickleball and generous outdoor living. Enjoy shoreline breezes, middle Keys sunsets, and effortless access to Marathon dining, marinas, and unforgettable ocean adventures throughout your stay. Experience the sun rising over the Atlantic and disappearing over the Gulf, all from one unforgettable location.

Oceanfront Mangrove Manor at SeaGlass Cove FL Keys

Mangrove Manor at SeaGlass Cove is a luxury oceanfront retreat in Marathon, Florida. This modern five-bedroom home features panoramic Atlantic views, refined coastal interiors, and seamless indoor-outdoor living. Sleeps twelve with a chef’s kitchen, ocean-view terrace, and access to resort-style amenities including a pool and pickleball courts. Located near marinas, dining, boating, fishing, and snorkeling, with concierge services for charters and private chefs. Perfect for relaxed Keys escapes.

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 Pearl at SeaGlass Cove Waterfront Luxury Home!

Welcome to The Pearl at SeaGlass Cove, a professionally designed waterfront retreat in Marathon. This modern coastal home features refined interiors, curated finishes, and serene water views throughout. Known as the true gem of the SeaGlass community, it offers seamless indoor outdoor living and elevated comfort in a relaxed island atmosphere. Perfect for families or groups seeking luxury, style, and an unforgettable Florida Keys escape in an exclusive gated oceanfront setting with water views.

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.

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.

The Grand Blue Mansion•120'Dock•4 Bedroom•Htd Pool

Come stay with us! Here you’ll find it all: a fully renovated home just minutes from the beach, a 124-foot canal ready for your yacht, a heated pool, private mini golf, and a game room full of fun. Sun, sea, and unforgettable memories are waiting for you. Book your stay and start living the Key Colony Beach dream!