Luxury rentals in Monroe County

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.

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.

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.

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.

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.

New Waterfront Estate - The Sunray Home

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.

4 Bedroom Oceanview Villa with Bunkbeds

Experience expansive living with breathtaking Atlantic Ocean views and blend into the natural surroundings with indoor-outdoor living. Each 3,100-square-foot Villa features three ensuite king-bed bedrooms, a bunk room, a full kitchen, dining room, laundry room, and balconies. Additionally, the Villas offer a two-car garage. *A 5% Monroe county tourism tax will be collected at check in, as Airbnb does not include this tax in there bookings*

Villa Celine

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.

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.