House holiday rentals in Islamorada

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!!!

Tiny Home on Waterfront | Bay Views | Deck | Pool

Down by the waters of Manatee Bay, you’ll find this idyllic tiny home for 6. With a full kitchen, three comfy beds,and access to a community pool, this is a prime location to enjoy the best of Key Largo. Sit on the deck and dip your toes in the water or explore the bay using the available kayaks and paddle boards. 10 Min Drive to the Gilbert’s Resort 15 Min Drive to John Pennekamp Coral Reef State Park 22 Min Drive to African Queen Canal Cruise Experience Key Largo With Us & Learn More Below!

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.

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.

Off The Charts-Waterfront Tiki Bar & Private Dock

Welcome to a one-of-a-kind Florida Keys escape! This unique home, originally used as the Islamorada Courthouse, has been thoughtfully transformed into a stunning waterfront getaway while keeping its historic charm. Located in the heart of Islamorada, this property offers access to what the Keys are known for: the best fishing, dining, and great sunsets. For the comfort and safety of all guests, our accommodation is designed for guests aged 12 years and older. Pets are not permitted.

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!!

Islamorada Bungalow # 5

Bring the whole family to this great place with lots of room for fun.Escape to our charming 2-bedroom, 1-bathroom bungalow in Islamorada, FL, where luxury and convenience await! Relax on the spacious patio and take a refreshing dip in the pool, perfect for unwinding after a day of exploring nearby attractions. You're just moments away from pristine beaches, world-class fishing. Whether you seek adventure or relaxation. Secure your stay now for an unforgettable experience!

Private Pool Tropical Oasis - Centrally Located

Centrally located in the Florida keys, this beautiful three-bedroom home is steps away from fishing, restaurants, boat rentals and water sports. The property features a private and lush backyard filled with your own private pool, loungers and outdoor games. In the evening, unwind with a refreshing drink under the outdoor lighting or in the heated pool. The villa includes a high chair, pack and play, bed rails, booster seat, baby gate and kids dishware.

Angler’s Terrace Conde 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

Lakefront pool house, jacuzzi Beachfront

Serene Lakefront Retreat – Your Perfect Getaway! Escape to paradise in this beautiful lakefront home , offering breathtaking water views, and a relaxing atmosphere. Nestled in a tranquil neighborhood, this home is perfect for families, couples, or friends looking to unwind and enjoy Florida’s natural beauty. Whether you're seeking a peaceful retreat or an adventure-filled getaway, this lake house provides the best of both worlds.

NEW! Private Pool, 50’ Dock, Kayaks, Waterfront

Slack Tide Cove Welcome to Slack Tide Cove, a stunning 3-bedroom, 2-bathroom waterfront retreat in the heart of Marathon, FL. This brand-new construction is chicly decorated with a coastal theme, offering the perfect blend of luxury and relaxation. Take in breathtaking views of Boot Key Harbor from the pool or balcony, and enjoy 50 feet of deep-water dockage with a fish cleaning station for your day’s catch.

Luxury Treehouse | Spacious Parking |

Escape to a charming treehouse-style retreat in Tavernier, perfect for 28+ night stays. Handcrafted by a master carpenter, this unique home offers privacy, warmth, and authentic Florida Keys charm. Surrounded by lush tropical greenery, it feels like a hidden retreat, yet it’s minutes from world-class fishing, diving, marinas, and great dining. Ideal for a peaceful extended stay.