Townhome holiday rentals in Monroe County

A serene sunset view showcases a circle of white Adirondack chairs positioned around a fire pit. The calm waters reflect vibrant hues of orange and purple from the sky, creating a peaceful atmosphere.

4.87 out of 5 average rating, 181 reviews

Sunrise Escape - Ocean Front Villa - Sleeps 10

Wake up to the sunrise over the ocean and unwind with sunset views from your private jetty. This marina-front, ocean-view townhouse in Kawama Yacht Club puts you steps from kayaking, snorkeling, and the best of the Keys. Spacious, stylish, and designed for unforgettable family and friend getaways. Breathtaking sunrises from one of two private terraces, coffee in hand, overlooking the marina and the Atlantic Ocean. Located in an exclusive, quiet section of Kawama Yacht Club, this beautifully po

4.93 out of 5 average rating, 131 reviews

The rooftop terrace displays a cozy seating area with comfortable couches and vibrant decorations. A large TV is mounted on a stone accent wall, while ambient lighting enhances the atmosphere. A BBQ grill and outdoor sink are located in the space, surrounded by greenery.

Townhouse in Naranja

Vacay Spot Experience Luna Sky! BAR,BBQ,go FL Keys

Luna Sky offers modern upgrades w/ an EV Charger/ Shower Massage jets. This 4-bed, 3.5-bath haven boasts All beds Luxury Sealy Posturepedic comfortSense memory foam mattresses for a restful sleep. 6-Function Shower Massage jets, Bluetooth speakers LED lighting. 1st level master-room/bath King bed and walk-in closet. Enjoy Sky Roof w/ two Terraces 65" TV, BAR, BBQ, comfy seating, 12 chairs, 2 tables to eat together/ dominoes table gaming area. Ambient rooftop lighting creates a unique atmosphere.

4.96 out of 5 average rating, 201 reviews

The charming cottage displays a pastel-colored exterior with a triangular roof and white trim. A small front porch is set above the entrance, flanked by two sets of French doors. Lush greenery and a white picket fence enhance the welcoming entryway.

Townhouse in Duck Key

3Bd 3Ba Cottage/Village at Hawks Cay/Ocean Views

Our Cottage is located between Islamorada and Marathon Key on Duck Key at the Village of Hawks Cay; one of the most desirable locations in the Florida Keys. This is at Mile Marker 61. With ocean views, high end finishes, comfy beds and plenty to do in the surrounding areas, the Cottage offers something for everyone. The outdoor green space overlooking the water is gorgeous. Sunsets are amazing right off the screened in lanai. We hope to host you as our guest in the beautiful Florida Keys.

Townhouse in Key Colony Beach

4.91 out of 5 average rating, 106 reviews

The Palm House in Key Colony Beach, Florida Keys

3/2 Duplex 37.5' dockage on canal in Key Colony Beach. The property's private (fenced in) back patio has a BBQ, couches and dining table/umbrella facing Eastward with morning sunshine and afternoon shade. Property includes usage of the Cabana Club, a large heated/cooled pool, hot tub, Atlantic Ocean beach and drinks/hot food just a 5 minute walk away. The concrete/wood dock has a fish cleaning station, bait freezer, water hose and gated access for the your boat. Welcome back to paradise !

4.81 out of 5 average rating, 235 reviews

A shaded outdoor porch features four blue adirondack chairs arranged around a round table, overlooking tranquil water views. The surrounding area is adorned with lush greenery and distant views of a bridge, creating a serene space for relaxation.

Townhouse in Duck Key

Vibrant Beachfront Villa

Welcome to Beachfront Villa that has recently been renovated. The 2 bedroom 1.5 bath luxury villa is located in the popular area of Duck key alongside of Hawks Cay Resort. Duck Key marina is located across the street where you can dock your boat or charter a boat for the day. Enjoy stunning sunset views from the back porch. Kitchen includes all amenities including silverware ,plates , cups , and pots. Linens and towels provided. *** Pets welcome with host approval and pet fee. ****

A spacious living room features a large sectional sofa facing a mounted flat-screen TV displaying a beach scene. A natural wood coffee table sits at the center, complemented by a decorative area rug. Large windows provide ample natural light and views of the surrounding greenery.

4.87 out of 5 average rating, 104 reviews

Kawama L1 Relaxing Lagoon View free bikes & kayaks

Explore the Florida Keys in this central location and have fun with the whole family at this stylish place. Kawama Yacht Club - Private community with 24 hr security. Amenities include: Salt water lagoon, 2 heated pools, Kids playground, Tennis courts, Marina boat ramp, boat parking, Jetty, 2Kayaks and 2 bikes. Don't wait any longer to experience the ultimate Florida Keys vacation in this luxurious and convenient location. Book now and get ready for the vacation of a lifetime!

4.98 out of 5 average rating, 118 reviews

Fun the Keys! Pool, Marina, Clubhouse, Fishing & m

Escape to paradise on the bayside of Key Largo, where legendary sunsets end every perfect day! This gorgeous, pristine retreat features 2 spacious master suites with private en-suite bathrooms, just steps from a heated swimming pool and kiddie pool. Walk to vibrant waterfront dining or dive into world-class fishing, snorkeling, kayaking, and paddleboarding. Fully equipped with every amenity you need for the ultimate island getaway—unpack, relax, and start enjoying your stay!

4.97 out of 5 average rating, 101 reviews

An open-concept living area is showcased with a light grey sofa and an ottoman situated on a plush white rug. Recessed lighting and pendant lamps highlight the space, which flows into a dining area furnished with a wooden table and chairs, framed by large windows.

Townhouse in Miami

The Sunflower Inn

Our Sunflower Inn is a perfect destination for your getaway in Miami! With close proximity to Miami International Airport, the Everglades, the Florida Keys and more, our space has all of your desired needs. Our townhouse features an open spacious natural living room and dining room area, a fully equipped kitchen, two bedrooms, and amenities such as a tennis court and pool readily available for your use! Come and enjoy our Sunflower Inn! **We are pet-friendly**

4.88 out of 5 average rating, 265 reviews

A tranquil outdoor pool is surrounded by palm trees, with lounge chairs and tables positioned for relaxation. Umbrellas provide shade near the water, while a charming cottage can be seen in the background under a clear blue sky.

Townhouse in Key West

Poolside Cottage #412

Welcome! This beautiful cottage is located in the Coconut Mallory Resort & Marina on the eastern end of KW. This secluded, waterfront oasis includes outdoor pools, hot tub, on-site marina and dock. There's also a new bar & grill, Gumbo's, in the resort. When you want to get out and explore KW, you're only minutes from beaches, the seaport and world famous Duval Street! Bikes, golf carts, kayaks, stand-up paddleboards and other watercraft can all be rented locally!

A spacious living area features a large sectional sofa in a soft gray hue, complemented by a glass coffee table. A modern light fixture hangs overhead, while a decorative plant adds a touch of greenery. Large sliding doors provide an outdoor view, enhancing the bright atmosphere.

4.93 out of 5 average rating, 177 reviews

Kawama N2 Relaxing Lagoon View free bikes & kayaks

Relax and enjoy our family friendly 3 bedroom/3 bathroom Villa Lago in Key Largo! Salt water swimming lagoon, Pools, the Ocean, fishing pier, Marina, Tennis, Bikes, fire pit and playground. Enjoy resort like amenities in the comfort of a home. This beautifully decorated villa sleeps 8 and is conveniently located in a very central location in Key Largo. Close to some great restaurants, diving, fishing, boat tours, State Park. Kawama is fun for all ages.

A serene sunset casts warm orange and purple hues across the calm water, reflecting the fading light. Silhouetted trees and land are visible along the horizon, enhancing the tranquil ambiance of the tropical surroundings.

4.89 out of 5 average rating, 159 reviews

Key Largo House

Casa Key Largo has contemporary elegance in a tropical paradise, a laid back island vibe with all the amenities. We have stocked the home with everything you need and more. Restaurants, boating, fishing, swimming, snorkeling, scuba diving, shopping, and John Pennekamp Coral Reef State Park are all within minutes. It is a great central location for day trips to Key West, Marathon, Miami Beach, and the Everglades.