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

A welcoming porch area is presented, featuring a light blue exterior and white railings. Two chairs are set beside the entrance, which includes a round window and a decorative welcome mat. Lush greenery enhances the inviting space.

Home in Key West

5 out of 5 average rating, 11 reviews

Key Lime Retreat

Weekly Treat! Downtown vacation experience for entire family. Located in the hearth of Historic Seaport location in Key West. Conveniently walking distance to Duval St shopping, offices, entertainment, restaurants, bars, and everything Key West has to offer. There is not much to say about this condo, The location talks for itself! It’s a must have Key West experience on a quite gated community just steps away from Duval St. It’s a true Gem to experience the Key West living to the fullest extend.

Top guest favorite

Apartment in Marathon

5 out of 5 average rating, 5 reviews

Ocean Side Paradise Awaits!

This gated oceanfront property spans over 7 acres and boasts an Olympic size pool overlooking the mesmerizing Atlantic Ocean. Take advantage of the many tiki huts, fishing dock, air-conditioned clubhouse, and grilling station to cook up your fresh catch. Our turnkey townhouse is perfect for a short vacation or a longer-term stay. Everything in the complex, from the facilities to the furnishings, is brand new. Don't miss the opportunity to experience paradise at its finest. Book your stay now!

Guest favorite

A serene aquatic scene showcases crystal-clear turquoise waters stretching to the horizon. Small boats are seen floating on the surface, with a few partially submerged. Fluffy white clouds drift across a deep blue sky, enhancing the tranquil environment.

Vacation home in Key Largo

4.93 out of 5 average rating, 118 reviews

Ocean Shores Villa 3 with pool and boat slip

This centrally located boater's paradise is the perfect place to relax. Walk to restaurants, cook in kitchen or grill downstairs. With only 4 units in the building the guests have half an acre of waterfront entertainment (boat slip, Kayaks, Bikes, Hammock and Pool). 32ft Dock Slip and Trailer Parking are included in the rental. Relaxing Balcony that looks down the Ocean Canal is the perfect place to have your morning coffee. Conveniently located near Sandbars, State parks and many attractions.

Guest favorite

A modern living area features a spacious white sectional sofa adorned with blue and green decorative pillows. A wooden dining table with white chairs is positioned nearby. Above, a stylish fan circulates air while artwork in calming hues decorates the walls, complementing the light wood flooring.

Home in Key Largo

4.91 out of 5 average rating, 101 reviews

New Oceanside Casa Azul! Voted #1! Golf Cart-Beach

No hidden fees! Casa Azul blends luxury and laid-back island vibes in the heart of Key Largo. With Superhost status and hundreds of 5-star reviews, a perfect escape. Voted the #1 Vacation Rental in Key Largo, it’s ideal for families, couples, and groups alike. Enjoy a free golf cart, fast Wi-Fi, 2 pools, private beach, saltwater lagoon, kayaks, tennis and pickleball courts with gear, marina access, boat ramp, trailer parking, and optional slip rentals. Salt Life meets luxury - this is the one.

Guest favorite

A serene waterway is framed by lush greenery, with the calm surface reflecting the surrounding trees and structures. Boats are docked at a well-maintained pier, with the gentle morning light casting a warm glow on the scene.

Apartment in Key Largo

4.93 out of 5 average rating, 156 reviews

2/1 Oceanfront Apartment with Dockage

The Seaside Vista is a luxurious ocean front retreat located in Key Largo. Only 1 hour from Miami International Airport, we are located in the heart of the fishing and diving areas of the Florida Keys. From great dining, to water sports, to eco tours, to parasail, to museums, shopping and beaches, allow us to be your base for all of your Florida Keys activities. Freshly remodeled , enjoy our little piece of paradise...minutes from all that the Upper Keys has to offer. MC Permit #: 21302180

Guest favorite

Condo in Tavernier

4.99 out of 5 average rating, 106 reviews

Modern and Coastal Ocean Pointe 2307

Are you looking for a Caribbean Vacation in a tropical resort without leaving the USA? Look no further than our Ocean view 2 bedroom and 2 bath condo at Ocean Pointe Suites! Our property offers: 24 hour front gate security, Heated Junior Olympic Pool with 15 person hot tub, tropical Beach, Marina, Tennis/Pickle ball courts. Enjoy our newly re opened ISLAND GRILL pool bar! We are located 60 miles from Miami International Airport and 90 miles from Fort Lauderdale International Airport.

Guest favorite

A heated pool is framed by two thatched umbrellas, offering shade and relaxation. Surrounding the pool are several wooden lounge chairs, inviting comfort in the sun. Lush greenery is visible in the background, enhancing the serene ambiance of the outdoor space.

Home in Marathon

5 out of 5 average rating, 34 reviews

Waterfront Escape -VACA-23-408

Come stay at this brand new home construction on a deep and wide canal leading to the ocean with pool and exotic decor. 75 foot dock with water and electric. Top of the line appliances with a fully stocked kitchen. Spa style showers with high end decor. Luxury at its best. Heated pool with sundeck and lots of seating around the edges. (Pool heater is an additional $100 per stay). Ground level cooking and dining for those beautiful days after boating or while laying around in the pool.

Guest favorite

A spacious outdoor dining area features a glass-top table with several red chairs, set against a vibrant backdrop of greenery and water. The view of the calm sea and fluffy clouds can be seen in the distance, enhancing the tranquil setting.

Home in Cudjoe Key

4.83 out of 5 average rating, 30 reviews

Yellow Home Free Pontoon Rental! See details

If you book your stay for the days shown below May 10th - May 23rd, 2025 May 26th - June 7th, 2025 July 5th - July 26th, 2025 Receive a free 2 day boat rental for a week reservation, 1 day for a 3 days or more reservation. Please reach out before booking for boat availability. Beautiful 3 bedroom 2 bath home nestled off of US 1. Kayaks included with the rental. Private heated pool and deck with a view of the Atlantic Ocean. Boat dockage available with parking.

Superhost

A serene waterfront scene features calm turquoise waters with gentle waves. A thatched-roof gazebo extends over the water's edge, providing a shaded area. In the background, a row of palm trees sways slightly under the bright blue sky, adding to the tranquil atmosphere.

Cottage in Cudjoe Key

4.64 out of 5 average rating, 111 reviews

VO Community 501 Midrise 2Bd/1.5Ba Large Open Deck

This mid-rise home is fully furnished with high ceilings throughout! The living room offers a flat screen television with sleeper sofa. Master bedroom features a queen bed with full bathroom and flat screen television. Guest bedroom features a full size bed and half bath. Additional amenities include large open porch with table and chairs, gas grill and central air conditioning and heat. Free WiFi offered in unit and in Community Recreation Center.

Superhost

A relaxing outdoor seating area is surrounded by vibrant blue chairs facing a calm waterway. A central table features a fire pit, and string lights hang above. Lush greenery can be seen along the shoreline, creating a tranquil atmosphere.

Camper/RV in Key Largo

4.78 out of 5 average rating, 18 reviews

A motorhome in paradise

This place is truly unique. Beautiful cozy has everything you need to have a good vacation pool Marine park Rest area By the sea beautiful views of the sunfall Area to wash up near supermarkets and restaurants definitely a beautiful place It is a TRAILER FIELD surrounded by nature it is not a 5-star hotel or anything like it If you really like adventure and feeling nature air sea beautiful views this is a perfect place No pet

Superhost

Townhouse in Key Largo

4.82 out of 5 average rating, 110 reviews

Oceanfront Resort W/Indoor Pickleball - Spacious!

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.

Superhost

Condo in Tavernier

4.76 out of 5 average rating, 365 reviews

Florida Keys Getaway - Slps 4 - Ocean View

Check out this recently remodeled 1-bedroom condo with relaxing and tasteful beach decor - perfect for your Keys Getaway. Ideally located between Key Largo and Islamorada, it offers the best of both worlds! Ocean Pointe is an oceanfront condo property that's just steps away from all the Keys have to offer - the world's best fishing, diving, snorkeling, paddle boarding, and kayaking.