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

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

Brickell Miami Lux Villa | 5 Suites Pool & Hot Tub
Experience luxury at Brickell Villa, a beautifully remodeled 5BR/5BA retreat in the heart of Miami. Proudly vetted as an Airbnb Luxe Home, 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.

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.

47th-Floor High-Rise w/ 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-bedroom, 2-bathroom residence comfortably sleeps 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.

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.

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.

Wonderlake 7BR Resort – Luxury Stay | Pool_BBQ
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.

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.

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 holiday rentals
Other great luxury holiday rentals in Monroe County

The Shellstone House at Solaire Lunara Bay

Floralee House at Lunara Bay

7BR Villa with Pool, Jacuzzi, Pickleball / Bball

New Luxury estate, Pool / Jacuzzi / GYM

Brand new Villa with Pool/Jacuzzi/GameRoom

Modern waterfront Villa w/ Pool and Gym, Sleeps 8.

The Pearl at SeaGlass Cove Waterfront Luxury Home!

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




