Luxury rentals in Monroe County

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Top-rated luxury vacation rentals in Monroe County

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Luxe

An expansive terrace showcases a sleek pool with a bubbling hot tub illuminated in vibrant colors. Modern lounge furniture is arranged around the pool, set against a backdrop of palm trees and a contemporary building featuring tall windows.

Villa in Miami

Dreamvilla in Pinecrest by Jatina Group

Towering palms and animal-shaped hedges greet you at this Miami escape. Sliding glass doors create an effortless transition from the sleek interior to the sprawling terrace. Work up a sweat in the in-house gym before plunging into the pool. At night, the bubbling hot tub transforms with a variety of vivid hues. There is a golf course nearby as well as plenty of parks and scenic beaches to wander. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Primary: King size bed, Ensuite bathroom with stand-alone shower, Walk-in closet, Television, Safe, Terrace • Bedroom 2: Queen size bed, Ensuite bathroom with stand-alone shower, Television, Safe, Terrace • Bedroom 3: 2 Queen size beds, Ensuite bathroom with stand-alone shower, Television, Safe • Bedroom 4: 2 Queen size beds, Ensuite bathroom with stand-alone shower, Television, Safe • Bedroom 5: Queen size bed, Ensuite bathroom with stand-alone shower, Television, Safe • Bedroom 6: Twin size bed, Ensuite bathroom with stand-alone shower, Television OUTDOOR FEATURES • Terrace

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

A private beach is framed by lush palm trees and vibrant foliage. The coastline is met by calm waters, with a seaplane visible in the distance. A blue surface can be seen in the foreground, suggesting recreational space, while serene skies add to the tranquil atmosphere.

Home in Islamorada

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.

Luxe

An aerial view captures the expansive tropical retreat surrounded by Florida Bay and lush mangroves. A heated pool and tiki bar are visible within the vibrant garden area, along with a dock extending towards the water, ideal for fishing or boating activities.

Home in Islamorada

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.

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 West

5 out of 5 average rating, 3 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

A modern living area features a large flat-screen TV mounted on a light wood panel. Soft seating in deep blue surrounds a unique coffee table made of natural wood. Dining space is visible in the background, showcasing a table set for six, with sunlight streaming through large windows.

Apartment in Miami

4.99 out of 5 average rating, 76 reviews

2-Story 3BD Brickell Penthouse | Heated Pool | Gym

This incredible penthouse offers the premium amenities and service of a luxury hotel, combined with the space and value of a vacation rental. Enjoy sweeping views of Brickell and Biscayne Bay from the top 2 floors of the building. The first floor has floor-to-ceiling windows, flooding the space with natural light, along with a balcony and the 1st bedroom. The second floor has 2 bedrooms as well as a dedicated work space. The property is located in the heart of Brickell.

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 West

5 out of 5 average rating, 7 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

Home in Key West

5 out of 5 average rating, 15 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 outdoor area features a lagoon-style pool surrounded by lounge chairs and tropical landscaping. The two-story residence displays expansive windows reflecting evening light, while palm trees provide shade. An umbrella is positioned over the pool, and a relaxing atmosphere is enhanced by soft illumination from the house.

Apartment in Islamorada

Maison Residences, 8 Bedroom oceanfront w Pool

Escape to a laid-back paradise at this 8-bedroom Islamorada residence, where two sprawling units are rented as one. The terrace boasts ocean views while soaring windows drench the interior in ribbons of natural light. Tropical palms sway in the balmy breeze as you stroll to the beach. Take a dip in the pool, try snorkeling through the coral reefs, or grab a bite to eat at a local restaurant. Copyright © Luxury Retreats. All rights reserved.

Luxe

The outdoor space features a serene pool surrounded by palm trees, with lounge chairs positioned along the poolside. Lush green grass enhances the tropical ambiance, while the vibrant sky adds a soft glow to the scene.

Villa in Miami

Dream Villa in Coral Gables by Jatina Group

This unique villa showcases Miami modern and Caribbean flair featuring 5 en-suite bedrooms and six baths surrounded by lush tropical rectangular grounds canopied by majestic trees. 5 Bedrooms 6 Bathrooms 5,000 Interior Sq Ft Resort Style Pool & Jacuzzi Pool table / Ping-Pong / Game Room The entertainment continues inside in the Game Room where you can have your hand at billiards, ping-pong, arcades or just lounge and watch the fun ensue.

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.