Luxury rentals in Key West

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Top-rated luxury vacation rentals in Key West

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Luxe
A modern two-story home is displayed, featuring a light-colored exterior with black-framed windows. A well-maintained lawn surrounds the property, complemented by tropical plants. An outdoor seating area with four chairs and a table is visible, alongside a pool area, enhancing the outdoor living space.
Home in Key Haven
5 out of 5 average rating, 4 reviews

The Shellstone House at Solaire Lunara Bay

Discover an exquisite new build featuring eight spacious bedrooms and a private pool. This remarkable home boasts premium amenities, including complimentary gym access and ample living spaces designed for relaxation and entertainment. With a contemporary design and luxurious finishes, this property caters to those who value comfort and style. Embrace a new level of living that effortlessly combines elegance and convenience in this extraordinary residence. Prepare to enhance your lifestyle in a h

Luxe
A spacious outdoor area showcases a gleaming pool with separate hot tub, surrounded by elegant paver stones. Two covered lounge areas are present, featuring comfortable seating under shaded structures. Lush palm trees frame the scene, while a modern two-story home provides a stylish backdrop.
Home in Marathon
5 out of 5 average rating, 3 reviews

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.

Luxe
The exterior of the new build is showcased with a light-colored façade, framed by tall palm trees. A spacious front porch is visible, with white railings and multiple large windows allowing natural light. The inviting entrance is designed for seamless access to the interior.
Home in Key Haven
5 out of 5 average rating, 3 reviews

The Dreamside House at Lunara Bay

Discover a luxurious new waterfront home, 8 spacious bedrooms and a private pool. 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! Elevate your visit with our Private Chauffeur Service for effortless tran

Luxe
An aerial view of a modern two-story home is showcased, featuring a private pool surrounded by lounge chairs. Large glass doors open to the outdoor area, with palm trees lining the property. The serene waterfront is visible in the background, enhancing the tranquil atmosphere.
Home in Key Haven

The Fairhaven House at Solaire Lunara Bay

Explore a luxurious new build 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. Discover a new standard of living where elegance meets convenience in an exceptional setting. Get ready to elevate your lifestyle in a

Luxe
Home in Key West

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,

Luxe
A modern two-story house is showcased in the background, overlooking a private pool surrounded by lush green grass. Several lounge chairs are neatly arranged near the pool, and a barbecue grill is positioned nearby, inviting relaxation and outdoor gatherings.
Home in Key Haven
5 out of 5 average rating, 4 reviews

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.

Luxe
An aerial view of a modern home reveals a private pool surrounded by palm trees and outdoor seating. The sun sets in the background, casting warm light over the property. Nearby greenery and landscaped paths add to the inviting ambiance of the space.
Home in Key Haven

The Joyrise House at Solaire Lunara Bay

Discover a luxurious new build at the Joyrise House, featuring six spacious bedrooms and a private pool. This stunning home offers exceptional amenities, including free gym access, boat docking for up to 40’, ample living space perfect for relaxation and entertainment and curated itineraries from our local guest experience team. Extend your stay 7+ nights for 10% off your entire stay! Elevate your visit with our Private Chauffeur Service for effortless transportation.

Luxe
An aerial view captures the vibrant rooftops of Old Town Key West, with colorful buildings lining the bustling Duval Street below. A private rooftop deck is visible, featuring seating and outdoor decor, with glimpses of the ocean and a lighthouse in the distance.
Condo in Key West
4.9 out of 5 average rating, 21 reviews

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.

Luxe
The exterior of a modern multi-story home is presented with large windows and a sleek white facade. A spacious yard features lush greenery and lounge chairs near a private pool. An inviting hammock rests between two palm trees, creating a relaxing outdoor space.
Home in Key Haven
5 out of 5 average rating, 8 reviews

The Sunray Home at Lunara Bay

Discover a luxurious new build featuring waterfront views, a private dock, eight spacious bedrooms and a private pool. This stunning home offers exceptional amenities, including free gym access and ample living space perfect for relaxation and entertainment. With modern design and high-end finishes, this property is ideal for those seeking comfort and style. Experience a new level of living that combines elegance and convenience in this remarkable home.

Luxe
A modern waterfront home is set against a clear blue sky, featuring multiple levels and large windows. A private pool is visible in front of the house, surrounded by lush green landscaping and loungers. A pathway leads from the dock to the entrance of the home.
Home in Key Haven
4.6 out of 5 average rating, 5 reviews

Tidelands House at Lunara Bay

Discover a luxurious new build featuring waterfront views, boat docking, eight spacious bedrooms and a private pool. This stunning home offers exceptional amenities, including free gym access and ample living space perfect for relaxation and entertainment. With modern design and high-end finishes, this property is ideal for those seeking comfort and style. Experience a new level of living that combines elegance and convenience in this remarkable home.

Luxe
Home in Key West
5 out of 5 average rating, 16 reviews

Pool & Parking, & Near Duval - The Rigby House

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.

Luxe
The living area features large windows allowing natural light to fill the space. A comfortable sofa and two armchairs are arranged around a wooden coffee table. A flat-screen TV is positioned on a sideboard, with decorative items adding a touch of style.
Home in Key West
4.86 out of 5 average rating, 7 reviews

Truman's Trove at The Annex

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. ** Hunting for the perfect Key West vacation home can feel like a daunting task. However, once you discover TRUMAN’S TROVE, you’ll know that you’ve struck gold! This two-story private home has been beautifully furnished and designed to the highest standard.

Popular amenities for Key West luxury vacation rentals

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