Luxury rentals in Monroe County

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.

View · Decor · Pool · Beach · Hospitality · Indoor spaces · Outdoor spaces · Family · Location

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.

Hospitality · Backyard · Amenities · Layout · Quiet · Indoor spaces · Family · Access · Kitchen

Dolce Vita Estate • Luxury Private Villa • Events

⚜️Welcome to Dolce Vita Estate, a private 5-acre retreat where laid-back luxury meets effortless charm. The space includes a heated pool, 5 beautifully designed bedrooms, a chef’s kitchen, and 3 gardens for reflection, celebration and meditation with serene views in every direction. This is where time slows down. Ideal for intimate escapes or special moments worth celebrating. Step away from the noise and gather with loved ones. Not just a place to stay but a place to experience the Dolce Vita

Hospitality · Family · Outdoor spaces · Location · Cleanliness · Pool · Accuracy · Access · Value · Indoor spaces · Decor · View · Noise · Pets · Comfort · Wifi

Luxury Villa | 5 BR 5 BA | Private Pool & Hot Tub

Proudly vetted as an Airbnb Luxe Home! Experience luxury at Brickell Villa, a beautifully remodeled 5BR/5BA retreat in the heart of Miami. This upscale villa sleeps up to 14 guests and features a heated pool, hot tub, BBQ, dedicated workspace, and parking for 3 cars. Enjoy stylish interiors, seamless indoor-outdoor living, and a private resort-style backyard oasis just minutes from Brickell City Centre, Downtown Miami, beaches, and MIA. Perfect for families, groups, and corporate retreats.

Hospitality · Location · Cleanliness · Pool · Indoor spaces · Comfort · Bathroom · Backyard · Accuracy · Kitchen · Condition · Hot tub · Nearby · Family · Outdoor spaces · Decor · Sleep quality · Amenities · Walkability · Getting around · Check-in · Value · Beach · Grill · Layout · Quiet · Access · Checkout · TV · Long stay · Noise · Air conditioning

47th-Flr Sunset & Skyline Views

Experience luxury in this stunning 47th-floor Miami condo, offering panoramic skyline & ocean views from a private wraparound balcony. This modern 2-bed, 2-bath residence comfortably accommodates up to 6 guests, featuring a fully equipped kitchen, Smart TV, high-speed Wi-Fi, and in-unit laundry. Guests enjoy exclusive access to resort-style building amenities including multiple pools, a state-of-the-art fitness center, yoga studio, and sauna. Perfect for an unforgettable Miami getaway

Hospitality · Location · View · Family · Indoor spaces · Cleanliness · Amenities · Pool · Walkability · Decor · Accuracy · Nearby · TV · Hot tub · Value · Quiet · Comfort · Wifi · Check-in · Parking

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.

Hospitality · Family · Pool · Accuracy · Outdoor spaces · View · Bathroom · Kitchen · Sleep quality · Grill · Quiet · Laundry · Cleanliness

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.

Hospitality · Location · View · Cleanliness · Comfort · Amenities · Nearby · Decor · Indoor spaces · Family · Accuracy · Walkability · Sleep quality · Check-in · Value · Checkout · Bathroom · Parking · Getting around · Pool · Condition · Beach · Access · Kitchen · Quiet · Noise · TV · Heating · Wifi · Long stay

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.

Location · Hospitality · Outdoor spaces · Cleanliness · Pool · Parking · Walkability · Bathroom · Comfort · Indoor spaces · Noise · Check-in · Accuracy · Quiet · Nearby · Amenities · Decor · TV · Pets · Kitchen · Family · Backyard · Condition · View · Beach · Sleep quality · Access · Checkout · Value · Air conditioning

Miami Jungle Retreat | Luxury Wellness Oasis

Welcome to Jungle Book House, a one-of-a-kind luxury wellness retreat just 5 minutes from Downtown Miami. Surrounded by lush gardens, century-old trees, and modern tropical design, this home is made for relaxation and reconnection. Enjoy a steam shower, open living spaces, and a stone Caribbean bench under the stars. Whether for a mindful getaway, romantic escape, or stylish city stay, Jungle Book offers serenity steps from Miami’s vibrant heart.

Hospitality · Location · Decor · Cleanliness · Outdoor spaces · Indoor spaces · Amenities · Bathroom · Kitchen · Layout · Comfort · Nearby · Walkability · Condition · View · Sleep quality · Accuracy · Quiet · Wifi · Access · Air conditioning

Wonderlake 7BR Resort • Pool_BBQ | Luxury Stay

Escape to our newly renovated luxury retreat, boasting 7 bedrooms and 7 bathrooms, ideal for large groups and special occasions. Dive into endless entertainment with a heated pool, oversized chess board, fire pit, basketball half-court, tennis court, mini-golf, playground, ping pong, hammocks, sand volleyball beach, kayaks, lake view and mini soccer field! Whether relaxation or excitement calls, our retreat exceeds expectations at every turn.

Hospitality · Amenities · Family · Outdoor spaces · Accuracy · Pool · Backyard · Cleanliness · Indoor spaces · Location · Bathroom · Hot tub · Comfort · Condition · View · Check-in · Kitchen · Nearby · Laundry · Beach · Getting around · Sleep quality · TV · Parks · Quiet · Parking · Long stay · Checkout

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.

Location · Hospitality · Cleanliness · Pool · Family · Indoor spaces · View · Comfort · Outdoor spaces · Accuracy · Kitchen · Check-in · Amenities · Getting around · Nearby · Condition · Noise · TV · Grill · Quiet · Bathroom · Layout · Backyard · Access · Sleep quality · Checkout · Value · Decor · Pets · Laundry · Walkability

Brickell 6BR Penthouse | Skyline Views

Experience luxury penthouse living in this extraordinary two-story, 7,000 square foot residence. Features 6 bedrooms, 7.5 bathrooms, and panoramic skyline views through dramatic floor-to-ceiling windows. Designed with custom finishes including Spanish white marble and onyx feature walls, the penthouse comfortably accommodates up to 12 guests and offers an unforgettable stay above the city.

Hospitality · View · Location · Cleanliness · Decor · Accuracy · Indoor spaces · Family · Amenities · Sleep quality · Kitchen · Layout · Comfort · Check-in