Upper Matecumbe Key vacation rentals

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Top-rated vacation rentals in Upper Matecumbe Key

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Top guest favorite

Two bright blue Adirondack chairs and a small table are positioned on a wooden dock overlooking calm water. Lush greenery frames the scene, while a clear blue sky enhances the tranquil atmosphere. The dock offers direct access to the water, inviting relaxation.

Cottage in Islamorada

4.95 out of 5 average rating, 41 reviews

Waterfront Cottage Walk to World Famous Lorelei

Waterfront Conch Cottage with Dockage. Short walk to world famous Lorelei for sunset celebrations. Great location for kayaking & paddleboarding. Custom length of stays can be arranged if booking a sandbar/fishing charter with our family. The fishing cottage built in the 1940s is not fancy, as photos show, but in the heart of Islamorada! Dockage available for additional $50 per night fee not included in nightly rate. Free trailer storage on site. Pet friendly :) 1 pet under 20 lb $150 fee.

Guest favorite

A sunny outdoor space features a palm tree swaying gently in the breeze, with a nearby stone light tower on the left. A large rock structure is visible, and a stone bench offers a view of the calm water and distant boats under a clear blue sky.

Apartment in Islamorada

4.98 out of 5 average rating, 66 reviews

Hidden Gem Islamorada | 1st Floor

This newly renovated unit is truly is a Hidden Gem in the heart of Islamorada! This duplex is nestled in the trees just a few steps from one of the most amazing sunsets in the Upper Keys. Walking distance to all the wonderful shops, restaurants and breweries that Islamorada has to offer. Bikes and Kayaks can be rented steps away from the front door of this unit. Want to find a place that you'll want to return year after year? Look no further! 🌅🌴😎💎 This unique property was originally built

Guest favorite

Condo in Tavernier

4.9 out of 5 average rating, 286 reviews

SPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!

Enjoy a Top Floor condo with stunning ocean views from your living room and balcony. This condo features a King bed in the bedroom, updated kitchen, a queen pull out sofa and a new washer and dryer. Enjoy the wonderful amenities the property offers to include a Large pool/ spa area or relax on the private beach with lounge chairs provided. There are lighted tennis courts, areas to grill out and a small playground. This property sits on 68 acres and one side is surrounded by a nature preserve.

Top guest favorite

A wooden dock extends over calm waters, flanked by posts leading to a serene view of the sky at sunset. Lush palm trees are visible in the background, enhancing the tranquil atmosphere of the canal.

Guest suite in Key Colony Beach

4.99 out of 5 average rating, 108 reviews

Turtle-By-The-Sea: the Best Deal in KCB!

A perfect get-away for couples or budget travelers, Turtle-by-the-Sea is the best priced vacation rental or hotel room in the middle-keys. Together with its prime location and amenities there simply isn’t a better deal to be had! Bursting with Keys charm, this cozy retreat is the perfect place to relax & escape. Owners Mallory & Steve infused their love of the Keys & its surrounding ocean into every aspect of their waterside home. Shoot us a message & start planning your dream Keyscation!

Top guest favorite

A serene outdoor space features a dining table with comfortable green cushions, set against a backdrop of the sunset over the water. Two chaise lounges and a hammock are visible, alongside palm trees, creating a relaxed atmosphere by the waterfront.

Tiny home in Key Largo

4.97 out of 5 average rating, 145 reviews

Oceanfront Lookout Point w/two Kayaks & Deck

Lookout Point is Wide open breathtaking Water View , Amazing Sunrises with a cup of Morning coffee, Refreshing breeze, Sound of water and Rustle of palm trees will start your day… Fishing right from the property, Kayaking. Taking sunbath on Chaise lounges or Reading books or just sitting under Tiki having a nice conversations and enjoying beautiful scenery of the view. You will see fishes jumping out of water, seagulls trying to catch up it , you might see manatee swimming by or dolphins.

Guest favorite

Two wooden lounge chairs, positioned under a large red umbrella, face a serene body of water. A wooden dock extends into the bay, with a colorful sunset reflecting off the water's surface in the background.

Guesthouse in Key Largo

4.87 out of 5 average rating, 443 reviews

Romantic Cabin/Guesthouse, beach Sunsets, fishing.

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"

Top guest favorite

A framed wooden sign hangs on a light-colored wall, featuring the message 'LET THE SEA SET YOU FREE' in large white letters on a soft blue background. The rustic frame is textured with a weathered finish and complemented by a knotted rope for hanging.

Vacation home in Key Largo

4.99 out of 5 average rating, 209 reviews

Waterfront, GROUND LEVEL, Awesome Sunsets!!!

This ground level unique location is close to everything. Walk to some of the most iconic restaurants and bars Key Largo has to offer for fresh seafood and awesome drinks! We Do Not allow fishing on our Property! Dockage Available for additional fee! Enjoy the amazing sunsets over the water from your private porch and dock. John Pennekamp Coral Reef State Park close by. Walk to dolphin research center!! 28 day rental I am a licensed charter boat captain and offer discounts for all guests

Superhost

A modern houseboat is anchored on calm waters during sunset. The structure features large windows and a spacious front deck with a grill station. The warm glow of the setting sun illuminates the exterior, reflecting off the water, creating a serene atmosphere.

Boat in Marathon

4.8 out of 5 average rating, 270 reviews

Paradise awaits on this cozy houseboat!

Our vision is for you to kick back, relax, and find your home away from home! Wether you want to celebrate with your loved one or retreat by yourself this floating home offers comfortable space for 2 adults. Located near the 7 mile bridge in Marathon Florida on the Atlantic Ocean nestled in a quiet, reserved mangrove area. This spot is fantastic because you have unparalleled access to out of this world sunset/sunrise views. Kayak through the mangrove and explore the surrounding areas.

Guest favorite

Bungalow in Islamorada

4.96 out of 5 average rating, 54 reviews

Castaway Island - Pool, Spa, Tiki Bar, Kyaks,Sup’s

Sleeps 4 adults and 1 child. 3rd bed is a full size sofa bed, suitable for a child. Indulge in the ultimate tropical retreat at our captivating bungalow Castaway Island, showcasing over 120 perfect guest reviews across multipl venues. Your hosts' extensive hospitality experience is evident in the restoration and thoughtful amenities, guaranteeing an exceptional vacation experience. Discover your ideal home away from home, where every detail is carefully designed to surpass expectations.

Top guest favorite

A vibrant garden area features colorful picnic tables and chairs arranged under lush greenery. A winding stone pathway leads through the space, surrounded by tropical plants and flowers. The lively atmosphere is enhanced by decorative lighting elements hanging nearby.

Home in Islamorada

4.97 out of 5 average rating, 192 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.

Top guest favorite

A houseboat is anchored in calm waters, surrounded by lush greenery under a soft sunlit sky. The vessel features a roof deck and a solar panel, reflecting a commitment to sustainable living. Gentle ripples on the water create a serene atmosphere.

Boat in Islamorada

4.93 out of 5 average rating, 349 reviews

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.

Guest favorite

An office space is furnished with a modern gray chair and a desk complemented by a printer. A vibrant leafy wallpaper decorates the walls, while a vintage-style bar cart holds various bottles. A round jute rug adds warmth, and natural light filters through a window.

Home in Key Largo

4.94 out of 5 average rating, 128 reviews

Little Cottage on an island

Very nice quiet neighborhood. Clean updated home with new appliances. Owner does live on property. There is a shared washer/dryer outside. The house is fully furnished with a queen bed and pullout sofa bed twin size. The home has a beautiful little office to work in and a full kitchen with all dishes and cooking utensils. Centrally located in Key Largo... 1 mile away from everything you need! There is a 21 yrs and over policy - house does have liquor bar. Thank you! 🏝️😊