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.

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 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.

The Dreamside House at Lunara Bay

Discover a luxurious new waterfront home, 8 spacious bedrooms and a private pool at Lunara Bay - a collection of 26 Luxury homes in a gated community! . This stunning home offers exceptional amenities, including free gym access and ample living space perfect for relaxation and entertainment. Dock boats up to 40’ at private slips, relax in your private pool, access the FYT gym, and enjoy itineraries from our local guest experience team. Extend your stay 7+ nights for 10% off your entire stay!

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 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.

Ebberly & Windrose Estates at Lunara Bay

Discover your dream Key West getaway at Lunara Bay—a collection of 26 luxury homes in a gated community. Ebberly Estate & Windrose Estate are two 6BR, 6.5BA pet-friendly homes blending island charm with modern elegance, just minutes from downtown. Dock boats up to 40’ at private slips, relax by your two private pools, enjoy complimentary FYT gym access, and take advantage of curated itineraries from our local guest experience team.

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.

Larkshine House at Lunara Bay

Larkshine House is an 8-bedroom, 8.5-bath home at Lunara Bay - a collection of 26 luxury homes in a gated community! Perfect for families and large groups, it features a large pool, beautifully designed interiors, lush outdoor spaces, and a prime location near Key West attractions. Dock at the exclusive marina for boats up to 40’. Relax or explore - Larkshine House is your ideal base for an unforgettable getaway.