
House holiday rentals in Lower Matecumbe Key
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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.
LocationBathroomAccess
5.0 out of 5 average rating, 7 reviews
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!
FamilyValueRiver
4.91 out of 5 average rating, 207 reviews
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.
FamilyLocationBeach
4.93 out of 5 average rating, 154 reviews
Life On A Rock Luxury Home in Downtown Islamorada
This Tommy Bahama Inspired Home Located at Mile Marker 81. Restaurants, Bars, Shops, and Beach all Walkable in this location. Located in the Heart of Downtown Islamorada. If you need specific dates please reach out to us. The Home features all Tommy Bahama Furniture, New Tempur-Pedic Breeze Mattresses. If you need specific dates please reach out to us. Room for Boat / Trailer Storage Perfect Biking Location Full Kitchen Washer / Dryer 65 Inch TV in Living Room Wifi Natural Light House
LocationFamilyNearby
5.0 out of 5 average rating, 9 reviews
Largo Getaway: 3 King Suites + In-Law Space
🔑 Managed by KEYLARGOTRAVELS See our profile for all listings. VIRTUAL TOUR: YouTube @Keylargotravels, go to Shorts it is called Mariners 🛏 SLEEPING Bedroom 1 – First Floor In-Law Suite: King bed, en-suite full bathroom with shower, plus a full-size sleeper sofa in the living area Bedroom 2 – Third Floor Master: King bed, en-suite full bathroom, plus a twin floor mattress available if needed Bedroom 3 – Third Floor Guest Suite: King bed plus twin bunk beds, en-suite full bathroom
LocationFamilyGetting around
4.93 out of 5 average rating, 100 reviews
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.
LocationValueNearby
4.97 out of 5 average rating, 220 reviews
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.
LocationValueKitchen
4.99 out of 5 average rating, 159 reviews
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
FamilyLocationView
5.0 out of 5 average rating, 6 reviews
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!!
FamilyLocationHospitality
4.92 out of 5 average rating, 252 reviews
Marathon Oceanfront 4BR Private Pool 60’ Boat Dock
Wake up to open-water views at your private oceanfront retreat in Marathon. Bring the boat, step into your private pool, Perfect for families and boating groups.Your private 60' dock offers direct water access, freshwater for rinsing gear and flushing engines, while parking accommodates up to 4 vehicles. • Direct oceanfront setting • Private swimming pool • Private 60' boat dock • Complimentary kayaks • Sleeps up to 10 • Parking for 4 vehicles • Wi-Fi + dedicated workspace
LocationFamilyPool
5.0 out of 5 average rating, 6 reviews
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!
ValueLocationOutdoor spaces
4.81 out of 5 average rating, 42 reviews
Waterfront Condo | Heart of Islamorada | Boat Slip
Nestled in the sought after Bay Harbour community, this spacious waterfront condo offers everything you need for an unforgettable stay in Islamorada - the Sport fishing capital of the world. Whether you are planning a fishing adventure, family getaway, or relaxing retreat, you'll be minutes from the best dining, sandbars, snorkeling and sunsets the Keys have to offer. Just a few steps away is a pool, hot tub, tennis court, gym and club house available for guests.
FamilyNearbyCleanliness
5.0 out of 5 average rating, 3 reviewsPopular amenities for Lower Matecumbe Key house rentals
House rentals with a pool

4BR 3B, Heated Pool & Spa, 60' Dock
LocationFamilyQuiet
4.95 out of 5 average rating, 108 reviews
OceanView 2/2.5 w Beach Pool & Marina Islamorada
FamilyLocationHeating
5.0 out of 5 average rating, 22 reviews
El Encanto | Private pool & tropical tiki
LocationFamilyAir conditioning
4.96 out of 5 average rating, 24 reviews
Beach House, Private Pool, Dock, Gulf View Sunsets
ValueLocationAir conditioning
4.93 out of 5 average rating, 82 reviews
The Villa by the Bay Pool/Boat Dock, Islamorada Fl
FamilyLocationNearby
5.0 out of 5 average rating, 12 reviews
4-Bedroom Coastal Retreat *Special Fall Rates*
FamilyLocationCleanliness
5.0 out of 5 average rating, 11 reviews
TheSandbar: Partial Ocean view,Pool,Free Dockage
FamilyLocationKitchen
5.0 out of 5 average rating, 27 reviews
Tropical Keys Retreat | Pool | Hot Tub | Cinema
LocationValueKitchen
5.0 out of 5 average rating, 81 reviewsWeekly house rentals

Off The Charts-Waterfront Tiki Bar & Private Dock
LocationFamilyWalkability
5.0 out of 5 average rating, 15 reviews
P31 - 2 bed, 2 bath with Spectacular Open Water on
LocationFamilyNearby
4.92 out of 5 average rating, 24 reviews
The Grand Blue Mansion•120'Dock•4 Bedroom•Htd Pool
FamilyValueHospitality
4.94 out of 5 average rating, 34 reviews
Sunset Catch Gulf Front, Pool, Dock, Kayaks, Fish
FamilyLocationBarbecue
4.92 out of 5 average rating, 49 reviews
Gorgeous Ocean View Home!
FamilyLocationAir conditioning
4.84 out of 5 average rating, 100 reviews
Emerald Palms ~ Waterfront ~ Pool ~ Dock ~ Games
FamilyLocationPool
5.0 out of 5 average rating, 3 reviews
3/2 Home w Dock, lagoon, kayaks!
LocationFamilyBeach
4.86 out of 5 average rating, 14 reviews
Villa del Sol | Waterfront 2BR Villa | Free Kayaks
LocationFamilyQuiet
5.0 out of 5 average rating, 24 reviewsPrivate house rentals

Oceanview Rooftop Retreat 3BR 3BA in Marathon FL
LocationFamilyNearby
4.8 out of 5 average rating, 15 reviews
SAY'S BY THE SEA
FamilyLocationAccess
4.89 out of 5 average rating, 19 reviews
Islamorada Reef Canal & Pool home off Tav Creek-
LocationFamilyKitchen
5.0 out of 5 average rating, 31 reviews
KCB Tropical Escape
FamilyValueComfort
5.0 out of 5 average rating, 17 reviews
Best Location in Marathon & KCB!
FamilyLocationSleep quality
5.0 out of 5 average rating, 18 reviews
Luxury 3/2 Mini-golf, Hot Tub, Kayaks & Pedal boat
ValueLocationQuiet
4.96 out of 5 average rating, 48 reviews
Sunset Key Escape/Pool, Dock, Kayaks & Gulf Access
LocationFamilyAccuracy
4.73 out of 5 average rating, 26 reviews
Waterfront Keys Home | Pool, Hot Tub & 35’ Dock
LocationFamilyLong stay
4.84 out of 5 average rating, 50 reviewsDestinations to explore
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- Everglades National Park
- Sombrero Beach
- John Pennekamp Coral Reef State Park
- Schnebly Redland's Winery & Brewery
- Homestead-Miami Speedway
- 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
- Harry Harris Beach and Park
- Dolphin Research Center
- 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





