Vacation rentals in Monroe County

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Top-rated vacation rentals in Monroe County

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite

An aerial view showcases a modern house situated near a tranquil canal. Lush green lawns and palm trees surround the property, with kayaks resting on a concrete area by the water's edge. The clear blue sky enhances the peaceful ambiance of the neighborhood.

Home in Miami

Enjoy our Beautiful Home on a Fun Canal! Hot tub!

Beautiful & Modern 4/3 Canal House! completely renovated. Go Kayaking through the Canals.. Enjoy the views of the backyard and canal with jumping fish all day, House is in a centric and quiet neighborhood. Amazing backyard & terrace with a BBQ, 2 Kayaks provided for Guest. Home is near nice restaurants and close to main Highways.. ✔️15min from Miami International airport ✔️25min - Downtown Miami ✔️ 30min - Miami Beach ✔️10-15min - Dadeland Mall & Merrick Park Come Relax at our Paradise Home!

4.93 out of 5 average rating, 247 reviews

Top guest favorite

A covered Tiki Hut is featured at the waterfront, furnished with comfortable seating arrangements. Views of the water and dock are visible beyond the structure, framed by lush greenery and palm trees. The space is designed for relaxation and enjoyment of the serene surroundings.

Home in Key Colony Beach

Captain’s Quarters Ahoy Mateys! Florida, Keys

This is located at the Florida Keys in Key Colony, Marathon. It is a spacious two bedroom, two bathroom duplex surrounded by water. It is a renovated beauty and close to the best restaurants and the tranquility of this city. It is the perfect getaway where you can recharge your exhausted batteries. Captain’s Quarters is a clean and spacious base camp location for the many adventures that await you in this amazing location. Water views and the accessibility to the best fishing in the world.

4.93 out of 5 average rating, 151 reviews

Superhost

Houseboat in Marathon

Tiny Home Aqua Lodges 2/1

This memorable place is anything but ordinary. Stay in our fully equipped aqua lodge with private surroundings. This lodge has 1 queen bed, 1 full bed, a sofa sleeper full size on the main floor, and 1 twin in the loft. It has a full kitchen, mini split ac, and full bathroom with hot water. This location has great sunset views and private BBQ waterfront area. All lodges have all bedding and dishes and cooking utensils. You will also have access to the Cabana Club located in Key Colony Beach.

4.77 out of 5 average rating, 148 reviews

Guest favorite

The outdoor space features a tropical-inspired saltwater pool with a unique shape, surrounded by natural stone decking. A thatched-roof tiki hut is visible nearby, along with a dining table and lounge chairs, creating an inviting area for relaxation and leisure.

Home in Homestead

Private Paradise between Miami & the Keys

My 4/3 home is in the area known as the "Gateway to the Keys". Enjoy a comfortable stay for 10 people in 4 bed rooms. Great place for families & travelers. Very comfy home, & the back yard has the feel of a true tropical paradise. Good WIFI. NO ADDITIONAL GUESTS & NO DJs. NO PARTIES. I RESERVE THE RIGHT TO ENTER THE HOME IF I FEEL THERE IS AN UNAUTHORIZED PARTY/EVENT. FINES WILL BE APPLIED FOR NOISE VIOLATIONS. We do not allow parties. UNAUTHORIZED parties can/will result in a $500 fine.

4.93 out of 5 average rating, 455 reviews

Top guest favorite

A modern living room showcases marble accents and a large wall-mounted flat screen TV. A plush sectional sofa with bold black and white patterns is arranged around a decorative coffee table. Natural light filters through the window with minimalistic blinds.

Home in Miami

| LuxeLanding | Pool+Lounge+Chess+BBQ+Golf+Airport

Discover the magic of Miami at our stunning 4BR/3BA modern retreat in vibrant Little Havana’s west side! This spacious, open-concept home sleeps up to 11 and features a sleek living room, fully stocked kitchen with stainless steel appliances, dinnerware, wine/shot glasses, cookware, tabletop appliances & complimentary coffee. The highlight? A resort-style backyard with a pool, mini golf, life-size chess, cornhole, Connect Four, outdoor pool table, a covered gazebo & deluxe grill/hibachi!

4.95 out of 5 average rating, 119 reviews

Top guest favorite

A sunset view is captured from a covered outdoor seating area, showcasing a tranquil waterway. Silhouettes of kayaks and a table are visible, while the setting sun creates a warm glow across the horizon. Natural textures are evident in the thatched roof above.

Tiny home in Key Largo

My Little Oasis2 Waterfront Retreat, Key Largo

Million Dollar view at a fraction of the price! This property is on the water with amazing bay views. It includes one kayak for 2 people, paddle board, fishing rod, washer and dryer, kitchen with all cooking utensils. Note: The upstairs room is not comfortable for seniors or adults, the ceiling height is 4 feet (an adult has to walk on his knees). The property is located on a residential island, restaurants, bars, stores and grocery stores are within a 15 minute drive from the property.

4.97 out of 5 average rating, 231 reviews

Top guest favorite

A spacious backyard is showcased, featuring a clean saltwater pool surrounded by lounge chairs and tropical landscaping. A covered patio area is visible, with a stone countertop and decorative plants. The bright blue sky complements the serene outdoor setting.

Home in Fountainebleau

Miami Sanctuary | Heated Saltwater Pool & BBQ

Come and create unforgettable memories in this modernly designed single-family home with a spacious layout and a range of comfortable bedrooms. It features two king-size beds, one queen-size bed, and a twin fold-up bed, as well as an Italian queen-size sofa bed. The house is bathed in natural light and boasts modern amenities that cater to your convenience. Located in a prime location, this house is close to all the tourist areas!! The pool is salt water with heater, Also a grill area

5.0 out of 5 average rating, 486 reviews

Top guest favorite

A solar and wind powered houseboat is moored on calm waters, featuring bright yellow shutters and a roof deck. Wind turbines and an American flag adorn the top, contrasting with the soothing blue sky and fluffy clouds in the background.

Boat in Islamorada

360 DEGREE WATERVIEW HOUSEBOAT

IMPORTANT Enjoy your own private retreat aboard a solar and wind powered houseboat moored 1/2 mile from land in the beautiful Islamorada Please do not arrive after dark and NO night riding. Need experience with hand pull outboard motors a 12 foot skiff with a 6hp outboard motor is provided reliable to go back and forth from shore NOT reliable for exploring No hot water on shower, heat water in Tpots or Solar bags. Please shave before arriving No suitcases, least amount of cloths.

4.93 out of 5 average rating, 391 reviews

Superhost

Home in Marathon

Marathon Oceanfront 4BR Private Pool 60’ Boat Dock

Wake up to open-water views at your private oceanfront retreat in Marathon. Bring the boat, step into your private pool, Perfect for families and boating groups.Your private 60' dock offers direct water access, freshwater for rinsing gear and flushing engines, while parking accommodates up to 4 vehicles. • Direct oceanfront setting • Private swimming pool • Private 60' boat dock • Complimentary kayaks • Sleeps up to 10 • Parking for 4 vehicles • Wi-Fi + dedicated workspace

5.0 out of 5 average rating, 4 reviews

Guest favorite

An aerial view showcases a coastal community with a spacious beach area, palm trees, and turquoise waters. The two-story unit features a large balcony above the entrance, with the surrounding buildings and lagoon clearly visible, highlighting the vibrant landscape of the area.

Home in Cudjoe Key

Cudjoe Key Home with a View

We are so excited to share our little piece of paradise with you! Our unit is located a short walk away from all the amenities the Venture Out community has to offer such as a pool, hot tub, lagoon, bocce ball, tennis courts, playground and boat marina. On the property we have a 2-person hybrid kayak for your enjoyment. We also provide table games (we love a game night) as well as the equipment to play bocce ball and darts which can be played in the recreation center.

4.96 out of 5 average rating, 209 reviews

Guest favorite

A scenic waterfront area is depicted with vibrant green lounge chairs positioned on a sandy peninsula. Surrounding waters provide a tranquil blue hue. Wooden docks extend into the bay, complemented by lush palm trees and colorful buildings in the background.

Home in Summerland Key

Waterfront Anchor House with Boat Basin & Ramp!

Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with boat basin and ramp for your boat. The property lot is almost an acre with another rental home and still very spacious (search for Haven House to reserve both homes if available). Stunning panoramic water views, sunrise and sunset. Steps away from ocean water. Bring or rent fishing and snorkel gear nearby to fish right off the point and enjoy the underwater scenery!

4.95 out of 5 average rating, 116 reviews

Top guest favorite

Lounge chairs with blue umbrellas surround a sandy beach area, providing a relaxed setting by the water. Steps lead down to the shoreline, where vibrant greenery and palm trees offer a natural frame against the bright blue sky and turquoise sea.

Home in Summerland Key

Ocean front classic keys cottage

This classic keys cottage is tucked among the palm trees on the open water of Niles Channel. Enjoy the breathtaking sunrises and romantic moonrises, seabirds,dolphins, and a nearly south-easterly breeze. This lovely hideaway is next to last home on dead end street, this 3 BRs, 2 baths ground level home has a large kitchen and Master suite. this location is only 30 minutes from the historic key west, close to restaurants and a nearby marina.

4.95 out of 5 average rating, 20 reviews