
Luxury rentals in Monroe County
Find and book unique accommodations on Airbnb
Top-rated luxury vacation rentals in Monroe County
Guests agree: these stays are highly rated for location, cleanliness, and more.

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.

Oceanfront Mangrove Manor at SeaGlass Cove FL Keys
Mangrove Manor at SeaGlass Cove is a luxury oceanfront retreat in Marathon, Florida. This modern five-bedroom home features panoramic Atlantic views, refined coastal interiors, and seamless indoor-outdoor living. Sleeps twelve with a chef’s kitchen, ocean-view terrace, and access to resort-style amenities including a pool and pickleball courts. Located near marinas, dining, boating, fishing, and snorkeling, with concierge services for charters and private chefs. Perfect for relaxed Keys escapes.

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

Luxury Penthouse in Brickell • 6 Bedrooms
Experience Penthouse luxury like never before. Featuring 5 ensuite bedrooms spanning over 7000 sq ft across two levels. Immerse yourself in unparalleled design with soaring 20-foot ceilings; adorned with opulent accents including Spanish white marble and meticulously crafted onyx walls. This penthouse is a true masterpiece, showcasing custom design and finished throughout. Admire unobstructed breathtaking views from the top of the Miami skyline, leaving you awe-inspired and speechless.

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.

47th-Floor High-Rise w/ Sunset & Skyline Views
Wake up on the 47th floor to panoramic sunset views over the Miami skyline, visible from the private wraparound balcony and master bedroom. Floor-to-ceiling windows fill this modern 2BR/2BA condo with natural light, creating an open, elevated space above the city. The condo features a full kitchen with stainless steel appliances, smart TV, high-speed Wi-Fi, central A/C, and in-unit washer/dryer. Sleeps up to 6 with a king, queen, and sofa bed. Crib available upon request

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.

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.

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.

Casa Dos Hondos II
Escape to this laid-back, oceanfront townhouse in Angler’s Reef, where coastal vibes and easy living come together in the perfect Keys getaway. With three bedrooms, three baths, and plenty of charm, this spot is all about kicking back and enjoying the island life. Whether you’re here with family or friends, this laid-back spot in Angler’s Reef has all the comforts you need for a relaxing, sun-soaked escape.

Gables Getaway | Pool | Putting Green | Pro Gym
Experience modern luxury at this brand-new Coral Gables home with 3 king bedrooms, ensuite spa-style baths, a private pool, gym, Sonos sound, putting green, and designer interiors throughout. Soaring ceilings, chef’s kitchen, and sleek living spaces make this the ultimate Miami escape. Relax, recharge, and play—all just minutes from Miracle Mile, Coconut Grove, and top dining.
Popular amenities for Monroe County luxury vacation rentals
Other great luxury vacation rentals in Monroe County

Spindrift House at Lunara Bay

Crestwood House at Lunara Bay

Floralee House at Lunara Bay

The Ebberly Estate at Lunara Bay

The Sunray Home at Lunara Bay

Palmgale Estate at Lunara Bay

The Seagate Estate at Lunara Bay

The Windrose Estate at Lunara Bay
Destinations to explore
- Rentals with a hot tub Monroe County
- Pet-friendly rentals Monroe County
- Private suite rentals Monroe County
- Rentals with a patio Monroe County
- Villa rentals Monroe County
- House rentals Monroe County
- Rentals with an accessible height toilet Monroe County
- Fitness-friendly rentals Monroe County
- Rentals with a washer and dryer Monroe County
- Condo rentals Monroe County
- Farmstay rentals Monroe County
- Boat rentals Monroe County
- Guesthouse rentals Monroe County
- Hotel rooms Monroe County
- Rentals with beach access Monroe County
- Townhouse rentals Monroe County
- Rentals with pools Monroe County
- Family-friendly rentals Monroe County
- Bungalow rentals Monroe County
- Tiny house rentals Monroe County
- Rentals with breakfast Monroe County
- Aparthotel rentals Monroe County
- Rentals with outdoor seating Monroe County
- Cottage rentals Monroe County
- Waterfront rentals Monroe County
- Rentals with a home theater Monroe County
- Resort rentals Monroe County
- Apartment rentals Monroe County
- Rentals with a fireplace Monroe County
- Ski-in/ski-out rentals Monroe County
- Rentals with a sauna Monroe County
- Houseboat rentals Monroe County
- Beachfront rentals Monroe County
- Smoking-friendly rentals Monroe County
- Rentals with an accessible height bed Monroe County
- Rentals with a kayak Monroe County
- Rentals with lake access Monroe County
- Boutique hotels Monroe County
- Serviced apartment rentals Monroe County
- Campsite rentals Monroe County
- Loft rentals Monroe County
- RV rentals Monroe County
- Vacation home rentals Monroe County
- Bed and breakfasts Monroe County
- Rentals with an EV charger Monroe County
- Rentals with a fire pit Monroe County
- Luxury rentals Florida
- Luxury rentals United States
- Everglades National Park
- Sombrero Beach
- Zoo Miami
- John Pennekamp Coral Reef State Park
- Coral Castle
- Schnebly Redland's Winery & Brewery
- Homestead-Miami Speedway
- Bahia Honda State Park
- Theater of the Sea
- Everglades Alligator Farm
- Calusa Campground
- Seven Mile Bridge
- The Turtle Hospital
- Robbies Marina Of Islamorada
- Monkey Jungle
- Florida Keys Aquarium Encounters
- Dolphin Research Center
- Homestead Bayfront Park
- Founder's Park
- Ernest F. Coe Visitor Center
- History Of Diving Museum
- Harry Harris Beach and Park
- Everglades Safari Park
- Fruit & Spice Park
- Things to do Monroe County
- Art and culture Monroe County
- Sports activities Monroe County
- Entertainment Monroe County
- Food and drink Monroe County
- Tours Monroe County
- Sightseeing Monroe County
- Nature and outdoors Monroe County
- Things to do Florida
- Tours Florida
- Art and culture Florida
- Sports activities Florida
- Nature and outdoors Florida
- Wellness Florida
- Food and drink Florida
- Sightseeing Florida
- Entertainment Florida
- Things to do United States
- Tours United States
- Sightseeing United States
- Art and culture United States
- Wellness United States
- Food and drink United States
- Nature and outdoors United States
- Entertainment United States
- Sports activities United States




