
Beachfront holiday rentals in Lower Matecumbe Key
Find and book unique beachfront homes on Airbnb
Top-rated beachfront rentals in Lower Matecumbe Key
Guests agree: these beachfront homes are highly rated for location, cleanliness and more.

Villa 5027 on Duck Key BOAT SLIP available
Boat slip available for additional $100 a night. Largest boat that can fit is 33 ft. Ask for availability. This villa boasts breathtaking sunsets, close to watersports, charter fishing, restaurants while being surrounded by one of the most exclusive island neighborhoods with lush landscaping. Duck Key is family-friendly, or it can be a serene couples retreat. Dine with Sunsets on the rear deck, or explore the world-class restaurants of the middle keys. Please NO Smoking indoors and NO pets.

Best View Ocean Pointe Pool Beach King Bed, Gated
***IMPORTANT*** The pictures you see here are of OUR unit. What you see is what YOU GET. No surprise when you arrive at Ocean Pointe. NO bait and switch. We own in the Prominent Building #3 just steps from the Pool & Jacuzzi. Wireless Internet Netflix & Cable TV, XBOX ONE. ***Most of our guests (99%) claim this is the cleanest Airbnb they have ever stayed in.*** You will get a TRUE UNIMPEDED OCEAN VIEW in our unit. Read our reviews, our past guests tell it all. ⭐ 5 STAR ⭐ Get what you pay for.

Romantic cozy peaceful Guesthouse beach Sunsets.
Private Romantic Bayside Cabin/Guesthouse, peaceful settings, lovely sunsets, beach, fishing pier, lush gardens surrounded by nature and wildlife, birds, iguanas, manatees, dolphin’s, eagles, the beach is just a short walk away from the Guesthouse enjoying a cocktail, fishing, boats cruising by, kayaking, snorkeling or an amazing sunset. *This Guesthouse is on bayside not Bayfront ! Same property but private from the residence! "No pets, Airbnb-granted pets Exemption cus allergies reasons"

Kawama Yacht Club and Molasses Reef Marine
Vacation in paradise. Beautiful sunsets. Swim at the salt water lagoon or at the beach plus two pools. Our villa is fully equipped, 3 bedrooms wish tv and 3 full baths First floor: garage, 1 bedroom, full bathroom, game room, pool table, bar, family room with TV, and terrace with barbecue and swing. Second floor 2 bedrooms and 2 full bathrooms, fully equipped kitchen and living a big TV, outside balcony with outdoor furniture . Tennis courts available. Optional 24' ft boat slip available.

NEW! CASA AZUL - Golf Cart, 2 Kings, Pool, Kayaks
NO RESORT, GUEST OR MANAGEMENT FEES WHEN BOOKING MY HOMES! Welcome to your Key Largo vacation rental. This oceanside villa is family friendly and filled with amenities, including a private Golf Cart, pools, one adult kayak, and three kids, kayaks, pickleball and tennis courts, and a unique swimming lagoon. Spend your days kayaking, fishing, boating, snorkeling, or visit the beach at John Pennekamp. Our villa has earned hundreds of 5-star reviews on all major platforms. No Hidden Fees!

Oasis2 in Key Largo With a million dollar view
Million Dollar view at a fraction of the price! This property is on the water with amazing bay views. It includes one kayak for 2 people, paddle board, fishing rod, washer and dryer, kitchen with all cooking utensils. Note: The upstairs room is not comfortable for seniors or adults, the ceiling height is 4 feet (an adult has to walk on his knees). The property is located on a residential island, restaurants, bars, stores and grocery stores are within a 15 minute drive from the property.

360 DEGREE WATERVIEW HOUSEBOAT
IMPORTANT Enjoy your own private retreat aboard a solar and wind powered houseboat moored 1/2 mile from land in the beautiful Islamorada Please do not arrive after dark and NO night riding. Need experience with hand pull outboard motors a 12 foot skiff with a 6hp outboard motor is provided reliable to go back and forth from shore NOT reliable for exploring No hot water on shower, heat water in Tpots or Solar bags. Please shave before arriving No suitcases, least amount of cloths.

Turtle Nest 1 Private beach,Pool, 2bed 2bath
Ocean Pointe Suite is located on the Atlantic. Featuring ocean views from living room, master bedroom and balconies. King bed in master bedroom, Queen bed in guest bedroom, pull out queen sofa, 2 bathrooms, Smart TV's with cable WIFI. Completely stocked kitchen with all appliances. Amenities include heated swimming pool, private beach, marina with boat launch & dockage for extra fee book through marine info in pictures. Tennis courts, gazebo, located on 60 tropical acres.

Oceanfront Condo w/Lake, Kayak, Paddleboard & Bike
Enjoy a Key Largo adventure in our deluxe oceanfront condo WHICH INCLUDES 2 KAYAKS, 2 PADDLEBOARDS, 2 BIKES, TENNIS RACKETS/BALLS AND FISHING GEAR in a private beach resort community with a fishing jetty, a 24/7 boat ramp & a 3-acre salt-water lagoon for swimming, snorkeling, kayaking & paddleboarding. The condo sleeps 6 & is in the gated Kawama Community of Key Largo, surrounded by JOHN PENNEKAMP CORAL REEF STATE PARK. Marina boat slips may be available for rent.

Ocean views at “Sangria Sunrise” 10% off Charters
Welcome to Sangria Sunrise at Ocean Pointe Suites in the beautiful Tavernier Key Florida. Relax and enjoy all of the options offered such as Jr. Olympic sized pool, beach, marina, kayak rentals, tennis courts, and so much more! We invite you to come stay at this cozy and updated one bedroom and one bathroom top floor condo with the most amazing ocean views. We offer a very comfortable queen sized bed and also a queen sleeper sofa that's equally as comfortable.

Beachside Unit 12- Pool, Private Beach & Tiki Huts
Unit 12 Details: Second Floor Unit, Tub with shower, Two Queen Beds, Maximum Occupancy 4 Guests. No elevator on site and Not Handicapped Accessible. A registration and liability waiver form signature will be required as part of your reservation. Our oceanfront property includes a private heated pool and private beach retreat on the Atlantic Ocean. Welcome to Continental Inn Condominiums in Key Colony Beach, Florida known as “The gem of the Florida Keys.”

Houseboat Getaway In Marathon
Get ready to indulge in a relaxing and unforgettable experience at the first overwater houseboat getaway in Marathon, Florida! 🌴🌊 What awaits you is - fun filled days living and exploring out on the fabulous florida keys waters in your own private aqualodge, breathtaking sunsets, and a private sanctuary perched above the sea. 😍 Don't miss out on this one-of-a-kind experience! Book your stay now and create memories that will last a lifetime.
Popular amenities for beachfront rentals in Lower Matecumbe Key
Pet-friendly beachfront home rentals

Beach Home and Boater’s Paradise Sombrero

2 bedroom & 25' Boat Dock Waterfront Atlantic Side

Coco Plum Beach Paradise w Heated Pool & Boat Slip

Sale! Lux Home, Walk to Beach, 90' Dock, Pool

RV In The Keys | Tropical Retreat

Mermaid's Paradise ~ Pool ~ Dock ~ Games ~ Views!

Relaxing Town home with great water views

Brand New 2025 RV 2BR + 2 Lofts, 2BA Pool & Marina
Beachfront home rentals with a pool

Deluxe Oceanfront 1/1 sleeps 4. Cafe & Pool Bar.

Grouper Getaway @ Ocean Isles Fishing Village

Reel Large END Unit in Ocean Point Suites

2BR - Key Largo Sunshine Getaway

(# 6)Waterfront Beautiful 4 Bed 3 Bath Pool Home

P01 - New 3 bed, 3 bath with private pool

Panoramic Ocean Views, Ocean Pointe Condo

Canal/Dock - Cabana Club - Pickleball - Remodeled
Private beachfront home rentals

Spectacular 2BR Oceanfront Dog Friendly | Dock

BayFront Cottage,Bay Front Porch,Central AC,Beach

Oceanfront oasis beach views heated pool U34

Treetops Apt.Sleep1-4 Beach Steps Away

Bayside Townhome in Islamorada with Boat Slip

Islamorada Oceanfront 2 bdrm, 2 bath, View, Pool

SeaEsta! Bring your boat & 1 block to the beach!

Vibrant Beachfront Villa
Destinations to explore
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- Beachfront rentals Monroe County
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- Everglades National Park
- Sombrero Beach
- John Pennekamp Coral Reef State Park
- Calusa Beach & Loggerhead Beach
- Coral Castle
- Sea Oats Beach
- Schnebly Redland's Winery & Brewery
- Long Beach
- Bahia Honda State Park
- Conch Key
- Theater of the Sea
- Everglades Alligator Farm
- Homestead-Miami Speedway
- Key Largo Kampground And Marina
- Seven Mile Bridge
- Sunset Park
- Dolphin Research Center
- Calusa Campground
- Robbies Marina Of Islamorada
- Florida Keys Aquarium Encounters
- Founder's Park
- The Turtle Hospital
- History Of Diving Museum
- Harry Harris Beach and Park




