Vacation rentals in Lower Matecumbe Key

Islamorada bungalow 2 bed & pool

Welcome to paradise! Completely remodeled and immaculately maintained, Bungalow Blue is nestled away in the quiet quaint Shady Palms community of 7 cottages in Islamorada, MM 76. Ideally situated next to the community heated pool, down the street from private boat ramp. If you're looking to relax and unwind while also being close to all that Islamorada has to offer, this is the place for you. Enjoy the FL Keys lifestyle in your private backyard, take a bike ride to World Famous Robbie's Marina

Value · Family · Amenities

Beach House, Private Pool, Dock, Gulf View Sunsets

You don’t come to the islands to stay in a town—you come to slow down. Welcome to our tropical keys beach home, tucked away from the traffic and noise of US Hwy #1. Sway with the palms on the wraparound deck, soak in wide-open panoramic bay views, and catch fiery sunsets right off your dock. Fire up the BBQ, brew a Keurig, float in the private pool, or cast a line from the 300’ private pier/dock. Easy going island living with ocean / gulf breezes, comfy beds, quality linens, Wi-Fi, and cable TV.

Location · Value · Getting around

The Nest Villa & Marina in the heart of Islamorada

You will fall in love with the "Nest", a unique and peaceful villa in the heart of Islamorada with private sun terrace & stunning water views of Florida Bay. If you are seeking an unforgettable Keys getaway this is it! Bring your boat (or rent locally). Dock in our protected marina with launch ramp & on site trailer parking. Swim, snorkel & paddle in crystal waters directly from our jetty. World-class fishing and diving only minutes away. Take a short stroll to shops restaurants & a brewery!

Family · Location · Comfort

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

Family · Location · Decor

Tiny Home Aqua Lodges 2/1

This memorable place is anything but ordinary. Stay in our fully equipped aqua lodge with private surroundings. This lodge has 1 queen bed, 1 full bed, a sofa sleeper full size on the main floor, and 1 twin in the loft. It has a full kitchen, mini split ac, and full bathroom with hot water. This location has great sunset views and private BBQ waterfront area. All lodges have all bedding and dishes and cooking utensils. You will also have access to the Cabana Club located in Key Colony Beach.

Value · Family · Bathroom

Perfect escape to the ocean

Enjoy the sounds of nature when you stay in this unique place. What awaits you is fun filled days living and exploring out on the fabulous florida keys waters in your own private floating paradise that is completely solar powered and all the amenities run 24/7! This fabulous floating home was build in 2025 and very nice, update and comfortable, it is 100% solar powered and eco friendly All the amenities run off batteries and solar power so you'll be able to enjoy cold ac, fridge, tv , 24/7

Value · Family · View

Luxury condo with boat slip overlooking the bay

Bay Harbour Starfish is a luxury condo overlooking a large boat basin with views of the Atlantic Ocean. This very spacious 3 bedroom, 2 and half bath condo has been decorated in Tommy Bahama style with a large living and dining area, including a wet bar. The Master suite is very roomy and in suite bath with large jetted soaking tub and seperate shower and walkin closet. Two guest bedrooms have Queen sized beds. There is a 30' boat slip included with electric and fresh water. 7 day minimum.

Family · Location · Checkout

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.

Family · Location · Hot tub

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.

Location · Family · Checkout

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

Family · Location · Hospitality

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

Location · Family · Indoor spaces

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!

Location · Value · Comfort