Luxury rentals in Key West

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.

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.

Floralee House at Lunara Bay

Discover your dream Key West getaway at Lunara Bay - a collection of 26 Luxury homes in a gated community! Floralee House is a 6BR, 6.5BA luxury waterfront estate that seamlessly blends high-end finishes with modern elegance, just minutes from downtown. Dock your boat right in the backyard, unwind in your pool, enjoy complimentary gym access, and enjoy curated itineraries from our local guest experience team. Elevate your visit with our Private Chauffeur Service for effortless transportation.

House of the Royal Palms in Old Town

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! ** Last Key Realty requires a credit card on file for all reservations. ** Key West is known for having amazing properties, but one home stands tall above the rest with its six majestic Royal Palm trees. HOUSE OF THE ROYAL PALMS features a spacious exterior that will make even the most high-end influencer envious. You’ll be spoiled with multiple seating areas, an oversized covered porch,

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.

The Starboard House at Solaire Lunara Bay

Explore a stunning new build with eight generous bedrooms and a private pool. This exceptional home offers top-tier amenities, including free gym access and expansive living areas perfect for unwinding and entertaining. With its modern design and upscale finishes, this property is ideal for those who appreciate comfort and style. Experience a new standard of living that seamlessly blends elegance and convenience in this remarkable residence. Get ready to elevate your lifestyle.

Maya's Secret Treasure at Duval - Unique Condo

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! ** Last Key Realty requires a credit card on file for all reservations. ** Walking along Duval Street dreaming of the ideal Key West vacation destination, scanning the rooftops for possibilities, at first you’ll miss this hidden gem completely…but once you discover MAYA’S SECRET TREASURE, you will know you have found the ultimate home base to enjoy Key West.

Altair House at Lunara Bay

Discover your dream Key West vacation at Lunara Bay - a collection of 26 Luxury homes in a gated community!! Altair House is a 6BR, 6.5BA pet-friendly estate blending island charm with modern elegance, just minutes from downtown. Dock boats up to 40’ at private slips, relax in your private pool, enjoy free access to FYT gym, and curated itineraries from our local guest experience team. Extend your stay 7+ nights for 10% off your entire stay!

The Fairhaven House at Solaire Lunara Bay

Explore the Fairhaven House, a new build at Lunara Bay - a collection of 26 luxury homes in a gated community! Featuring eight spacious bedrooms and a private pool. This stunning home offers top-tier amenities, including complimentary gym access and expansive living areas perfect for both relaxation and entertaining. Boasting a modern design and high-end finishes, this property is ideal for those seeking a perfect blend of comfort and style.

The Rigby House - Pool, One block from Duval St

Escape to paradise with this stunning 6-bedroom, 6.5 bathroom home nestled in the heart of historic Key West. Walking distance to everything, this home is ideal for families or large groups, this spacious retreat offers the perfect blend of modern amenities and tropical charm. Enjoy your own oasis with a sparkling private pool, surrounded by ample lounging space. Perfect for refreshing dips under the sun or evening cocktails under the stars.