Villa holiday rentals in Monroe County

4.98 out of 5 average rating, 187 reviews

An outdoor space is highlighted by a wooden picnic table and a cozy sofa underneath a large umbrella. String lights are illuminated above, creating a warm ambiance. Stepping stones set in dark rocks lead through the greenery, providing a tranquil setting for relaxation.

Villa in Homestead

The Pass Through - Brand New 2 | 1 Modern Villa

The Pass-Through is a cozy home located off of Florida’s Turnpike. Perfect if you’re looking for a pit stop when headed down to the Florida Keys or if you want to stay for a few days to explore Miami. Only a few minutes from Black Point Marina, where you can enjoy waterfront ambiance with outdoor seating, food, drinks, live band, and take your boat out for a ride to Biscayne Nat'l Park or Everglades Nat'l Park.Close to Florida’s Outlet Mall, authentic restaurants, wineries, freshfarms, and more.

Top guest favourite

A private heated pool is surrounded by a spacious patio with laid brick flooring. Palm trees frame the scene, while a vibrant sunset casts warm colors across the sky. Lounge chairs are positioned by the pool, inviting relaxation by the serene water view.

4.95 out of 5 average rating, 155 reviews

Private 4/3 Pool Heater/Dock/Kayaks/Bikes,etc

Wake up to breathtaking water views at our 4-bedroom, 3-bathroom villa. Enjoy the 1800 sq ft layout, fully equipped kitchen w/stainless steel appliances, and granite countertops. Sleeps 10 with memory foam beds. Outside, relax by your private heated pool (winter) and tiki-shaded area. Fish from the 32' dock or use the BBQ gas grill. Includes 2 kayaks, 2 paddleboards, and 4 adult bikes for a 5-minute ride to Sombrero Beach. Exterior cameras for security. Vacation License #VACA-22-40. Book now!

A private pool is positioned in the foreground, featuring crystal clear water and blue mosaic tiles. In the background, a covered patio area furnished with outdoor seating and blooming plants creates a relaxing environment. Sun loungers are arranged around the pool on a grassy area.

4.91 out of 5 average rating, 117 reviews

D'Mauchi House/Coral Gables/Miami/Pool/Beach20min

Welcome to D' Mauchi House our family-friendly property. An unforgettable tropical vacation awaits you in the center of Coral Gables, Miami. The property is just 20 minutes from the nearest beach, 10 minutes from Miami airport and Little Havana, Downtown, and 25 minutes to South Beach. Luxury for large groups is central to most tourist spots in the city. The home comprises 4 spacious bedrooms and 3 bathrooms, providing plenty of privacy while still allowing you to congregate as one large group.

4.93 out of 5 average rating, 123 reviews

A serene beachfront area is presented with several white lounge chairs facing the tranquil blue waters. Rocky shoreline and greenery outline the space, creating a peaceful environment for relaxation.

Villa in Key Largo

Kawama Yacht Club and Molasses Reef Marine

Vacation in paradise. Beautiful sunsets. Swim at the salt water lagoon or at the beach plus two pools. Our villa is fully equipped, 3 bedrooms wish tv and 3 full baths First floor: garage, 1 bedroom, full bathroom, game room, pool table, bar, family room with TV, and terrace with barbecue and swing. Second floor 2 bedrooms and 2 full bathrooms, fully equipped kitchen and living a big TV, outside balcony with outdoor furniture . Tennis courts available. Optional 24' ft boat slip available.

Top guest favourite

A spacious outdoor porch features a round dining table surrounded by four chairs. A kayak is positioned nearby, and lush greenery and water views are visible in the background, enhancing the inviting outdoor space.

Villa in Duck Key

4.96 out of 5 average rating, 184 reviews

Beach House Getaway - Free Kayaks 2/2.5

Welcome to Beach House Getaway, a charming villa tucked away on the serene island of Duck Key and perfectly situated in the heart of the Florida Keys. Nestled between Key Largo and Key West, Duck Key serves as a peaceful yet convenient base for your island getaway. Its central location means you’re just a short drive from some of the most iconic destinations in the Keys, including the natural wonders of Bahia Honda State Park, the famous waters around Islamorada, and the lively Key West.

An outdoor patio area features comfortable seating arrangements under a shaded pergola, overlooking a large swimming pool. The vibrant green lawn is bordered by palm trees, while the sunset colors softly illuminate the sky in the background.

4.88 out of 5 average rating, 190 reviews

NEW! "Villa Paradise" ~ Luxury Gem ~ Pool ~ Game Room

Bring your family to the luxurious 3BR 2Bath Villa Paradise in the tranquil and friendly neighborhood in southern Miami, FL. Visit the exciting attractions, natural landmarks, restaurants, shops, and much more, and then retreat to the lavish oasis that will leave you in awe with its stylish design, private backyard, and rich amenity list. ✔ 3 Comfortable BRs ✔ Open Design Living ✔ Fully Equipped Kitchen ✔ Heated Pool ✔ Game Room ✔ Smart TVs ✔ Smart House ✔ High-Speed Wi-Fi ✔ Free Parking

4.91 out of 5 average rating, 158 reviews

One Of A Kind Smart Villa - Pool/Spa/Gym/BBQ/Vibes

🎨 House of Art Miami — where design becomes the experience 🎨 This art-forward smart villa blends resort-style amenities with the comfort, privacy, and freedom of a home. Designed for groups to relax, connect, and enjoy Miami together — without feeling rushed or crowded. 🔥 Heated pool, jacuzzi, fire pit & BBQ 🏀 Mini golf, ping pong & basketball 🖼️ Curated art + immersive sound indoors & out 📍 Minutes from beaches, dining & nightlife More than a stay. An experience. @BeyondTheBNB

A welcoming living area features a cozy sofa and two wooden chairs arranged around a decorative coffee table. A round mirror is mounted above a fireplace, complemented by indoor plants. Soft lighting enhances the warm atmosphere, and a bright red front door is visible in the background.

4.96 out of 5 average rating, 142 reviews

Stylish villa in heart of Miami

Get away from the day to day and enjoy a great book on the hammock as your friends/family gather around the patio to plan your near by Miami adventures. Located close to Brickell/Miami Beach/Wynwood/Little Havana & Key Biscayne. Minutes from high end restaurants, beaches, state parks, etc... Fully stocked kitchen w/ cozy dining room; tv room includes large flat screen TV. Enjoy morning coffee walking out of French doors to inviting patio. Dedicated work space away from main home.

Three modern Aqua Lodges are positioned on water, featuring white exteriors and blue roofs. Each lodge has a furnished deck with chairs, providing relaxed seating options. A smooth, concrete path runs alongside the lodges, leading to a marina setting with sailboats in the background.

4.88 out of 5 average rating, 560 reviews

New Aqua Lodge 2Beds 1 Bath with Full Kitchens

This hip spot is the new thing in lodging. Aqua Lodge is all the modern amenities while being on the water. Full kitchens, flat screen tv's, wi-fi , pool, bikes, sunset beach. We have it all right at your finger tips. You can sleep up to 5 people comfortably. We have great air conditioning and big showers. The deck is furnished with a dining table for those romantic outdoor dinners in the moonlight. We also have a sunset beach area for the best sunsets in the Florida keys!

4.83 out of 5 average rating, 117 reviews

A large lagoon-style pool is surrounded by lush tropical landscaping and palm trees. The clear water reflects the blue sky, while sun loungers are positioned around the pool. The elegant white buildings of the resort are visible in the background.

Villa in Key Largo

Oceanfront Resort W/Indoor Pickleball - Speakeasy!

An island paradise situated in the heart of Key Largo, adjacent to John Pennekamp Coral Reef State Park and Molasses Reef. This 3/3.5 villa is located in Key Largo's most upscale oceanfront resort. The area has the distinction of being Key Largos newest oceanfront gated destination, with some of the most unique amenities in all of the keys. It caters to those who simply desire the very best in luxury accommodations. Unique amenities include a Speakeasy Themed Rec. Area.

A circular table is positioned on a covered deck, accompanied by four lounge chairs. The view extends to the calm waters beyond, framed by green trees on the coastline, under a clear blue sky. Ceiling fans hang above, providing a cooling breeze.

4.82 out of 5 average rating, 109 reviews

Villa 5023 on Duck Key BOAT SLIP available

Boat slip available for additional $100 a night. Ask for availability. This villa boasts breathtaking sunsets, close to watersports, charter fishing, restaurants while being surrounded by one of the most exclusive island neighborhoods with lush landscaping. Duck Key is family-friendly, or it can be a serene couples retreat. Dine with Sunsets on the rear deck, or explore the world-class restaurants of the middle keys. Please NO Smoking indoors and NO pets.

An outdoor lounge area features a private spa pool surrounded by tropical plants and seating. Soft lighting creates a welcoming atmosphere, while the vibrant sunset sky adds a colorful backdrop. Sliding doors connect the space to the interior of the villa.