House holiday rentals in Monroe County

4.98 out of 5 average rating, 220 reviews

A serene waterfront scene captures a vibrant sunset reflecting off calm waters. Multiple boats are docked along the marina, with silhouettes of masts against the colorful sky, creating a peaceful atmosphere ideal for relaxation.

Home in Key Largo

Waterfront Sunsets, Great Price, Relaxing Spot!!!

Beautiful Waterfront, Modern Coastal Décor, Spacious !! Enjoy your vacation in this beautiful recently renovated home. Views from almost every window and door of the harbor. Walk to many local restaurants and bars for fresh local seafood and a cold draft beer!! 28 day rental. Enjoy sunsets from your private porch. Easy access to Atlantic Ocean. We Do Not Allow Fishing on our Property! I am a licensed charter captain and offer discounts to guests! Fishing, Sandbar or a Sunset Cruise!!!

4.97 out of 5 average rating, 289 reviews

Home in Key West

Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!

Historic Harrison's Hideaway is in an 1880's Cigar Maker's cottage renovated in 2010. It features a K size Pottery Barn memory foam bed, custom made full sleeper sofa, renovated kitchen with granite counter tops, 2 burner stove, under counter fridge/freezer, dishwasher, microwave, air fryer/oven tumbled marble 2 person shower, private front deck with seating for 4, 2 person Solana spa. Perfect for a couple or a family with children. Freshly painted a Caribbean blue with plantation shutters.

4.93 out of 5 average rating, 124 reviews

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.

The exterior of the home features a clean, modern façade with large windows allowing for ample natural light. Lush greenery and two palm trees frame the entrance, creating a welcoming approach. The pathway leads to a well-defined entryway with a minimalist railing on either side.

4.9 out of 5 average rating, 115 reviews

Modern Miami Home 2BR 1BA Free Parking

Centrally located and newly renovated, this 2 bedroom 1 bathroom home offers a king size bed in one bedroom and a queen size bed in the second bedroom. Perfect for 4 guests. The open layout provides natural light, a full sized kitchen with new stainless steel appliances and a living room with an HD Smart TV. Located in a quiet neighborhood just minutes from Coconut Grove & Coral Gables. It's a quick 15-20 min drive to Brickell, Wynwood, Key Biscayne, South Beach and other Miami hot spots.

4.99 out of 5 average rating, 111 reviews

A spacious living area features a comfortable sectional sofa adorned with pillows and a coffee table. A large television is positioned on a cream-colored console, with light filtering through a nearby window. The open design connects to a dining space and kitchen, enhancing the layout.

Home in Coral Gables

Modern-Miami charming bungalow home, pet friendly*

Charming bungalow home near the heart of Coral Gables. Designer decor, nicely appointed with confort in mind. Lush landscaping, pet friendly*,fenced back yard with gas propane grill and parking for 4 cars, RV or boat. Great location, 5 minutes from historic downtown Coral Gables, (Miracle Mile). A short 10 minute drive to Coconut Grove, Shops at Merrick, and 15 mins to Downtown-Miami/ Brickell, Edgewater, Midtown (Wynwood). Also, 10 mins from Miami MIA airport and 20 minutes to South Beach.

A light-filled living area features a soft beige leather couch and armchairs arranged around a wooden coffee table. A decorative wall mirror and a potted plant add to the space. A television is mounted on the wall, and light drapes cover the windows.

4.93 out of 5 average rating, 402 reviews

Private duplex in the center of Miami.

1 bed/1bath Duplex located in the heart of Miami. Outdoor space is communal with free street parking. 2 minute WALK to Magic City Casino, 5 minutes away from Miami international airport, 5 minutes from restaurants and nightlife in Coral Gables & calle ocho, 10 minutes from downtown Miami, bayside, etc. Perfect for anyone with long layover at Miami Int Airport, or awaiting a cruise departure from port of Miami (Port of Miami is 10 minutes away). FREE wifi & cable included during your stay.

4.95 out of 5 average rating, 133 reviews

A paved outdoor patio features two lounge chairs and a small round table, surrounded by tropical plants and palms. The tranquil canal is visible in the background, offering a serene waterfront view.

Home in Key Colony Beach

Waterfront Home 37.5-ft dock, Cabana Club Included

Bright, Open Floor Plan with new floors & kitchen. East facing for sunny mornings and shady afternoons on the great screened porch. Two roomy bedrooms and 2 full baths. Plenty of parking on the paved driveway. Perfectly located with the boater and angler in mind on a 37. 5 ft concrete dock, on deep & wide canal. Here on Key Colony Beach you can walk or bike the entire city to the marina, Sunset Park, 3 restaurants, play golf, tennis, pickle ball, bocce ball, horseshoes & basketball.

Home in Upper Sugarloaf Key

The bungalow stands illuminated against a night sky, surrounded by swaying palm trees. Soft reflections shimmer on the water's surface, while the sandy beach extends along the shoreline. The structure features large windows, showcasing a welcoming interior visible from outdoors.

4.94 out of 5 average rating, 109 reviews

The Lighthouse - Beach Houses Key West

If you’re reading this, you’re already one step closer to paradise. Thank you for considering us for your getaway. Our charming Lighthouse Bungalow is a 2-bedroom, 1-bath loft-style retreat located just steps from our private beach. The master bedroom loft, accessed by a spiral staircase, offers a stunning bird’s-eye view of the Atlantic Ocean. The nautical-inspired living area opens to an exterior deck overlooking the beach—an ideal spot for peaceful mornings and ocean breezes.

4.94 out of 5 average rating, 159 reviews

A welcoming living area features a brown leather sofa paired with a round coffee table on a light rug. Wall art adorns the beige walls, and a ceiling fan provides airflow. A dining area is visible in the background, complemented by indoor plants.

Home in Homestead

CozyHome Near National Parks Between Miami & Keys

This cozy, family friendly, 3 bedroom 2 bathroom house is located in Historic Downtown Homestead. It is in close proximity to two National Parks (Everglades & Biscayne) in addition to other local attractions such as the Florida Keys Outlet Mall, Homestead-Miami Speedway, Fruit and Spice Park, and more. In only an 9 minute walk away, you can also enjoy movies, bowling and an arcade at Hooky Entertainment or the performance arts at the Historic Seminole Theatre.

4.89 out of 5 average rating, 160 reviews

The exterior of the house features a lush garden area with tall palm trees and vibrant greenery, providing a sense of privacy. A small green gate is visible, leading to the house, with a clear view of the peaceful street lined with residential homes.

Home in Coral Gables

Luxury Guayabita’s House

Luxury Guayabitas House is a spacious single-family house located in the prestigious Coral Gables neighborhood, 9.6 km from downtown Miami and 5 km from the international airport. It offers a spacious living room with a flat-screen TV, one bedrooms, an equipped kitchen with a dining area, and a bathroom with free toiletries and a hairdryer. The garden area has an area to enjoy a nice snack surrounded by nature with access to private parking.

A spacious pool area is surrounded by vibrant greenery and palm trees. Seating arrangements with cushions are positioned near the water, complemented by a shaded area under an umbrella. The pool features a rock formation and is accented by colorful lounge chairs.

4.97 out of 5 average rating, 396 reviews

The Miracle Cottage & Pool on Acre Miami Florida

Beautiful, brand new PRIVATE cottage on an acre property situated in million dollar neighborhood. Perfect place to relax and enjoy the Miami sun. This is a little piece of heaven in the heart of a magical city. Come & enjoy your best vacation. Charming , peaceful & comfortable . Cottage is a completely separate building from the main house. It’s 900 sf of living area. Cleaning & Decontamination as per CDC guidelines before every check in.

Superhost

A spacious bed is centered in a bright room, adorned with crisp white linens and decorative pillows. Two bedside lamps sit on either side, illuminating the space. A framed cityscape artwork hangs above the bed, complementing the serene and clean aesthetic.