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 Joyrise House at Solaire Lunara Bay

Discover elevated island living at Joyrise House at Lunara Bay, an exclusive collection of 26 luxury residences within a private gated waterfront community. This newly built six-bedroom retreat offers the perfect blend of sophistication and relaxation, featuring a private pool, a private boat dock accommodating vessels up to 40 feet, and expansive indoor and outdoor living spaces designed for effortless entertaining. Enjoy complimentary gym access and personalized itineraries curated by our loca

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.

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.

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.

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.

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.

Evershore Estate at Lunara Bay | Wellness Home

Evershore Estate is a waterfront 4-bedroom, 4-bath home at Lunara Bay - a collection of 26 luxury homes in a gated community. Perfect for activity and relaxation, it features a private pool and dock, parking, a pet-friendly gated yard, and fitness amenities including a Peloton, free weights, and yoga mats. Tailored itineraries help you uncover hidden gems and local favorites for an unforgettable Lunara Bay experience.