House holiday rentals in Lower Matecumbe Key

Sea Ray Cove w/ Pool, Beach, 80' Dock & Tiki hut

2025 - New concrete dock, fenders & fish filet table. This ground level waterfront home has received a new face lift. Completely remodeled 3 bedroom with bonus room in the well known Sombrero Beach neighborhood. Just a short block walk to the sandy beach shore. Home has an open floor plan overlooking the in-ground pool deck and new tiki hut. Enjoy your morning coffee and happy hour in the screened-in porch with views of the wide lagoon. Come and create your family memories in the fabulous Keys.

Waterfront House with 37 ft Dock & Cabana Club

Right in the middle of the action between Miami and Key West. This 2/2 house has been nicely renovated and furnished with new stainless kitchen appliances and a gorgeous granite countertop. Comfortable outside/inside living space perfect for a getaway in paradise. Walk out to the porch and backyard, and you will be engulfed by the beauty of the sunset views while lying on the cozy hammock. It features lots of outdoor entertaining: fishing, paddling, BBQ or just plain hanging out in the shade.

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.

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!! Enjoy the sunsets from your private porch. Easy access to Atlantic Ocean. We Do Not Allow Fishing on our Property! 28 day I am a licensed charter captain and offer discounts to guests! Fishing, Sandbar or a Sunset Cruise!!!

Florida Keys Cottage with Pool - Hawks Cay Resort

Welcome to our tropical Conch Cottage, a lovely place to create memories on your idyllic Florida Keys vacation in paradise. Our stylish waterfront villa sits alongside a clear turquoise canal on picturesque Duck Key, inside the Hawk's Cay resort, and just 10 minutes from busy Marathon. Get involved in on-site activities like snorkeling, scuba diving, fishing, boating and dolphin encounters—or simply lay out on the coral stone patio, soak up the sun, and slide into your private plunge pool.

Flakey's

Flakeys, short for Florida Keys is everything you would expect to find on the small Caribbean island. Its paradise! Located in the heart of Islamorada there is no need for a car. You can walk or bike to the best restaurants, bars, beaches and shops this island has to offer. On Morada Way in the middle of the Art and Culture district. Everything at Flakeys is brand NEW! All new appliances, furniture and decor. Shabby Island Chic! Affordable, super clean and you can't beat the location.

Islamorada Home 5/3 Private Beach! freshly updated

Relax in Islamorada, Enjoy the day deep sea fishing, and watch the sunset at our private beach. Our 5/3 House is freshly updated. Master has a king bed and the two others have full beds with trundles underneath to sleep 3 or 4 kids, 2 more bedrooms downstairs with 1 king size bed, and 1 king and twin bed, Freshly furnished, and the bathrooms are freshly updated as well. The boat dock can hold up to a 40 ft boat with power and water at the dock there is a lot to do and see in the keys!

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.

Key Largo Waterfront Retreat | Tiki, Dock & Pool

This waterfront retreat is perfect for couples, families, or boaters looking to explore the best of the Keys. Snorkel right from the dock, paddle through mangroves with the included kayak, or relax with a drink while the sun sets over the canal. Steps from two heated pools, a playground, and a sandy beach, plus only 0.3 miles from groceries and restaurants. Whether you’re fishing, diving famous reefs, or just unwinding under the tiki, this home puts paradise at your doorstep.

Oceanfront Tiny Villa in the Heart of the FL Keys

Welcome to your happy place in the beautiful Florida Keys! Our oceanfront villa is located on Duck Key right outside of Marathon and next to the world famous Hawks Cay Resort. Halfway between Key Largo and Key West, it’s the perfect location to explore all our island paradise has to offer. Enjoy world class fishing, diving and snorkeling or kick back with a cold beverage and enjoy a stunning sunset on one of our covered porches. And always remember…it’s 5 o’clock somewhere!!

Anglers Terrace, Condé Nast Traveler's Best Airbnb

As published in Condé Nast Traveler, this is one of the best Airbnb's in Florida. Newly Built two story Tropical Oasis with pool has been thought-out meticulously. An open, very light & spacious floor plan, carefully appointed furnishings, and great location provide the perfect surroundings. Decorated with a Zen sensibility, It’s outdoor Patio deck and Rooftop Terrace extends your living space into the private quiet ocean setting with panoramic views

Waterfront Cozy Modern Retreat w/Deep Canal

Welcome to our beautiful waterfront home in Marathon! Our smoke-free property is modern, clean and features a 37ft long concrete dock, perfect for boating and fishing enthusiasts. With easy access to the movie theater, Sombrero Beach, Turtle Hospital, Publix, Walgreens, and delicious restaurants, you'll have everything you need right at your fingertips. We can't wait for you to experience the peacefulness and convenience of our lovely home.