
House holiday rentals in Lower Matecumbe Key
Find and book unique houses on Airbnb
Top-rated house rentals in Lower Matecumbe Key
Guests agree: These houses are highly rated for location, cleanliness and more.

Waterfront / Ocean Access Canal / Kamp Key
This quaint Keys-style home offers timeless charm in a premier waterfront setting on an ocean-access canal. The open-concept living, kitchen, and dining area flows effortlessly through the terrace to the backyard, where a private dock invites boating and fishing, and an outdoor bar and dining area offer an effortless al fresco setting. Savor serene nights in lighter-than-cotton bedsheets, bath rituals with natural Pure Fiji products and opulent towels. Enhanced cleaning practices implemented.

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.

Luxury Heated Pool/Jacuzzi, Games & Nice Backyard.
✨Bring the whole family to this great located house with a nice pool with spa, combo game table and lots of room for fun, and enjoy the beach, restaurants and entertainments around the area. ✨5BRs with smart TVs and comfortable mattresses and pillows. 3BR upstairs/2BR downstairs. ✨3 bathrooms, 1BR downstairs/2BR upstairs. ✨2 kitchens fully equipped with everything you may need. ✨Nice and quite neighborhood. ✨Sunsets are amazing at The Florida Keys. ✨Guest are always our priority.

75130 Overseas Highway- VR 24-0415
Great house in Lower Matecumbe (south side of Islamorada) at the 75 mile marker on the bayside. This house has fabulous sunset views in a nice quiet part of town. There is a small beach area in the back with palm trees giving you a little more privacy. A screened in porch with tables and chairs makes for a great sunset watching area. The house has a deck on the roof that allows for you to see both sides of the island! (This home does not have dockage for a boat.) WEEKLY RENTAL

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!

Angler's Eden
Amazing get-away in the beautiful Florida Keys! This property (constructed in 2018) is a haven for families seeking to escape to paradise year-round. Situated on a deep water canal with ocean access and enough dock space to park your boat for the week. A floating dock is also provided with kayaks. Enjoy the large pool or ping pong table, or lounging in the sun! Beautiful Sombrero Beach is within walking distance (approx 1.5 miles) via a paved bike path.

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.

4BR 3B, Heated Pool & Spa, 60' Dock
Enjoy breathtaking views of the Gulf and Ocean from the screened in patio of this beautiful 4 BEDROOM/3 BATH canal front home. Bring your boat to the 60' dock on a 200' wide canal just 10' away from the Ocean. Relax by the pool/spa area after a day of fishing. A pool heater is offered as an option for your convenience. Please inquire about water heater fee and operating instructions before booking. (VR Lic # PLR2020-00104)

Coco Plum Waterfront Hideaway Home in Marathon
This Coco Plum home is the ultimate family getaway! With four bedrooms, two bathrooms, a modern living room with a 4K TV and surround sound, and an outdoor area that includes a fire pit, outdoor dining, and outdoor living space. The boat dock and breathtaking sunset views make this the perfect home for your fishing adventures. Beautiful Coco Plum beach is just a ten minute walk away. Make this home your next island adventure.
Popular amenities for Lower Matecumbe Key house rentals
House rentals with a pool

Waterfront House with 37 ft Dock & Cabana Club

El Encanto | Private pool & tropical tiki

Marathon Oceanfront 4BR Private Pool 60’ Boat Dock

OceanView 2/2.5 w Beach Pool & Marina Islamorada

Beach House, Private Pool, Dock, Gulf View Sunsets

Ocean’s Fourteen: Direct Ocean View- Htd Pool

NEW!The Hideaway~Pool~Pickleball~Putt-Putt~Kayaks!

Sunset Catch Gulf Front, Pool, Dock, Kayaks, Fish
Weekly house rentals

Life On A Rock Luxury Home in Downtown Islamorada

Off The Charts-Waterfront Tiki Bar & Private Dock

Sleeps 8 | Sunset + Boat Basin | Islamorada

Luxury 3/2 Mini-golf, Hot Tub, Kayaks & Pedal boat

Waterfront Pool Home w/ Private Dock, Tiki Hut & B

Entire private two family water front home.

Villa del Sol | Waterfront 2BR Villa | Free Kayaks

Waterfront Keys Home | Pool, Hot Tub & 35’ Dock
Private house rentals

Pristine Islamorada Pool Home with Ocean View and

Mariners Club Resort, Best in the Upper Keys!

Ocean view, seaside paradise with golf cart.

Luxury 5Bdrm/6bath New in 2024

Kingsail Resort Home

Largo Getaway: 3 King Suites + In-Law Space

Boating Paradise Villa rental Lic# VACA-25-124

Sunset Key Escape/Pool, Dock, Kayaks & Gulf Access
Destinations to explore
- Miami Holiday rentals
- Four Corners Holiday rentals
- Miami Beach Holiday rentals
- Orlando Holiday rentals
- Fort Lauderdale Holiday rentals
- Tampa Holiday rentals
- Hollywood Holiday rentals
- Kissimmee Holiday rentals
- Key West Holiday rentals
- Cape Coral Holiday rentals
- Nassau Holiday rentals
- St. Petersburg Holiday rentals
- Pet-friendly rentals Lower Matecumbe Key
- Rentals with a hot tub Lower Matecumbe Key
- Family-friendly rentals Lower Matecumbe Key
- Rentals with beach access Lower Matecumbe Key
- Beachfront rentals Lower Matecumbe Key
- Waterfront rentals Lower Matecumbe Key
- Luxury rentals Lower Matecumbe Key
- Rentals with pools Lower Matecumbe Key
- Condo rentals Lower Matecumbe Key
- Rentals with a kayak Lower Matecumbe Key
- House rentals Monroe County
- House rentals Florida
- House rentals United States
- Everglades National Park
- Sombrero Beach
- John Pennekamp Coral Reef State Park
- Homestead-Miami Speedway
- Schnebly Redland's Winery & Brewery
- Coral Castle
- Bahia Honda State Park
- Seven Mile Bridge
- Robbies Marina Of Islamorada
- Everglades Alligator Farm
- Key Largo Kampground And Marina
- Theater of the Sea
- Ernest F. Coe Visitor Center
- Florida Keys Aquarium Encounters
- Dolphin Research Center
- Harry Harris Beach and Park
- Founder's Park
- History Of Diving Museum
- Homestead Bayfront Park
- Calusa Campground
- Conch Key
- Fruit & Spice Park
- Curry Hammock State Park
- The Rain Barrel Village





