Villa holiday rentals in Monroe County

4.83 out of 5 average rating, 101 reviews

An aerial view captures a row of white-roofed villas along a turquoise lagoon, surrounded by lush greenery. The serene waters extend towards the horizon, with a distant shoreline visible, creating a tranquil and spacious atmosphere.

Villa in Duck Key

Villa 5034 on Duck Key BOAT SLIP available

Boat slip available for an additional $100 per night. Ask about availability. This villa boasts breathtaking sunsets and is just minutes from watersports, charter fishing, waterfront restaurants, and local attractions, all while being surrounded by one of Duck Key’s most exclusive island neighborhoods with lush tropical landscaping. Duck Key is perfect for families or a serene couples retreat. Dine while watching spectacular sunsets from the rear deck, or explore the Middle Keys. No smoking/Pet

4.89 out of 5 average rating, 116 reviews

A bright and spacious living area features a large dining table with wooden chairs and a central coffee table. Soft seating is arranged around a sliding glass door that opens to the outdoor patio. Decorative curtains frame the windows, enhancing natural light.

Villa in Duck Key

Waterfront Island Escape with Private Plunge Pool

Come and relax in your own private plunge pool that overlooks a turquoise canal on the beautiful Duck Key. The outdoor living space is quiet and serene, making it a perfect place to unwind. Families and honeymooners alike can enjoy this island oasis. Centrally located at Mile Marker 61, Duck Key is just a short drive to Key West. Explore everything the Florida Keys have to offer or stay locally to enjoy world-renowned restaurants, fishing, snorkeling, and diving. The opportunities are endless.

4.86 out of 5 average rating, 181 reviews

Lakefront Luxury Resort • Entertainment | Pool_BBQ

Welcome to a newly renovated tropical retreat designed for relaxation and fun. This private home features a heated pool, Jacuzzi, lakefront views, and a custom private beach. Enjoy on-site basketball, kayaking, nearby golf courses, or unwind by the water. Perfect for families, groups, or remote work with fast WiFi. Cook and dine outdoors using the BBQ area under the stars. Whether you’re here to relax or explore, this home offers the perfect balance of comfort, privacy, and memorable experiences

4.98 out of 5 average rating, 194 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.

Villa in Marathon

4.95 out of 5 average rating, 159 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!

4.91 out of 5 average rating, 123 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.

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, 188 reviews

Beach House Getaway - Free Kayaks 2/2.5 Villa

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.

4.86 out of 5 average rating, 196 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

A serene pool area is framed by lush greenery and palm trees, with a softly shaped pool surrounded by a light-colored stone deck. The outdoor seating area features a table and chairs, offering a perfect spot for relaxation.

4.84 out of 5 average rating, 99 reviews

Tropical MIAMI Oasis BBQ/ Pool/Games and More

Kick back and relax in this calm, stylish space. This elegant home will leave you speechless from the moment you walk in. Enjoy breeze and sun from your private Pool . Close to nearby Restaurants Metro Zoo Miami 2.2 miles away Bayside market place mall 19 miles away . Little Havana visitor center 17 miles Versailles Cuban cuisine 15 miles away Lincoln road mall 22 miles away Everglades national park 34 miles away Miami international airport 16 miles away . South beach 22 miles away

4.91 out of 5 average rating, 163 reviews

Ritz Resort | Pool/Spa/Gym/BBQ/Golf/FirePit/Arcade

🎨 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, 148 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.