House in Upper Matecumbe Key, FL
6 guests · 3 bedrooms · 2 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Top-tier experienceA high end property in this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental
About this house rental
Welcome to a one-of-a-kind Florida Keys escape! This unique home, originally used as the Islamorada Courthouse, has been thoughtfully transformed into a stunning waterfront getaway while keeping its historic charm. Located in the heart of Islamorada, this property offers access to what the Keys are known for: the best fishing, dining, and great sunsets.
For the comfort and safety of all guests, our accommodation is designed for guests aged 12 years and older. Pets are not permitted.
Escape to this bright and welcoming 3-bedroom, 2-bathroom home, perfectly designed for relaxation and connection. Located right on the water, this Keys-style getaway blends indoor comfort with unbeatable outdoor living.
Highlights of your stay:
✔ Smoke Free environment
✔ Three comfortable bedrooms with cozy bedding
✔ Two full bathrooms (no ensuite)
✔ A stylish and comfortable living room with ample seating for winding down after a day in the sun
✔ A full kitchen with all the essentials, plus a dining table for six for shared meals and game nights.
✔ A screened in porch overlooking the water.
Step outside to your private waterfront tiki hut, fully outfitted with:
✔ Outdoor TV for game days or movie nights
✔ Refrigerator & ice maker for easy refreshments
✔ Dining and lounge areas ideal for morning coffee, sunset dinners, or just soaking up the breeze.
Our waterfront property offers private boat dockage for vessels up to 30 feet, so feel free to bring your boat and make the most of your stay! From your own backyard, you can easily cruise through the crystal-clear waters of the Florida Keys, discover hidden sandbars, fish in world-class spots, or enjoy stunning sunsets from the water. Whether you're island-hopping or just exploring the beautiful surrounding areas, your adventure starts right here!
The villa is stocked with all the basics you will need to start enjoying your vacation right away without any worries. The villa also boasts amenities like an iron/iron board, a hairdryer, beach towels, umbrella, and beach chairs. To start your day, there is a Keurig duo coffee maker (K-cup and drip), french press, and a kettle.
The design of the villa consists of two separate units — one on the ground floor (yours) and another on the upper floor. Both units have separate entrances and are not connected in any way. All outdoor amenities are exclusive for you and your guests.
Book your stay now and enjoy waterfront living, island breezes, and all the comforts of home—Keys-style!
For the comfort and safety of all guests, our accommodation is designed for guests aged 12 years and older. Pets are not permitted.
Escape to this bright and welcoming 3-bedroom, 2-bathroom home, perfectly designed for relaxation and connection. Located right on the water, this Keys-style getaway blends indoor comfort with unbeatable outdoor living.
Highlights of your stay:
✔ Smoke Free environment
✔ Three comfortable bedrooms with cozy bedding
✔ Two full bathrooms (no ensuite)
✔ A stylish and comfortable living room with ample seating for winding down after a day in the sun
✔ A full kitchen with all the essentials, plus a dining table for six for shared meals and game nights.
✔ A screened in porch overlooking the water.
Step outside to your private waterfront tiki hut, fully outfitted with:
✔ Outdoor TV for game days or movie nights
✔ Refrigerator & ice maker for easy refreshments
✔ Dining and lounge areas ideal for morning coffee, sunset dinners, or just soaking up the breeze.
Our waterfront property offers private boat dockage for vessels up to 30 feet, so feel free to bring your boat and make the most of your stay! From your own backyard, you can easily cruise through the crystal-clear waters of the Florida Keys, discover hidden sandbars, fish in world-class spots, or enjoy stunning sunsets from the water. Whether you're island-hopping or just exploring the beautiful surrounding areas, your adventure starts right here!
The villa is stocked with all the basics you will need to start enjoying your vacation right away without any worries. The villa also boasts amenities like an iron/iron board, a hairdryer, beach towels, umbrella, and beach chairs. To start your day, there is a Keurig duo coffee maker (K-cup and drip), french press, and a kettle.
The design of the villa consists of two separate units — one on the ground floor (yours) and another on the upper floor. Both units have separate entrances and are not connected in any way. All outdoor amenities are exclusive for you and your guests.
Book your stay now and enjoy waterfront living, island breezes, and all the comforts of home—Keys-style!
Amenities at Off The Charts-Waterfront Tiki Bar & Private Dock
Non-smoking
No pets allowed
Family friendly
Map of Upper Matecumbe Key, FL
Ratings and reviews
10 / 10Outstanding·Jul 2026
From the last minute reservation till morning of checkout, everything about this stay was perfect. If you’re looking to escape the new normal sterile keys housing developments and settle into old keys charm, this is the place. Convenient to everything. Water-out your back doorManatee’s- out your back doorYour boat-out your back doorRelaxing tiki- out your back doorGreat restaurant/bar-1/2 a block down the streetPublix-just down the streetI’ve spent the last 20 years pulling my boat down to the keys. Never stayed in the same spot once. That streak ended this year. I will never return to the keys if I can’t return to this beautiful home. Thank you you so much for the stay. Everything was perfect!
10 / 10Outstanding·Jun 2026
This place is exactly as advertised. A great escape from the humdrum of daily ins and outs. Perfectly central to everything good in Islamorada. We spent a lot of our time enjoying the tiki hut in the back. It has a definite vibe that fits perfectly in the keys. The interior is comfortable and decorated very nicely with plenty of island decor. The beds are almost too comfortable lol I could sleep all day. I will definitely be booking again. Thanks to the host's for putting it on the site.
10 / 10Outstanding·Nov 2025
Off the Charts is a wonderful property - perfectly situated in the heart of Islamorada on a peaceful street. The villa is beautifully appointed with thoughtful attention to detail; the host is responsive and welcoming. The kitchen is nicely equipped, the property was spotless with comfortable beds and furnishings throughout. My wife and I have stayed in many, many properties over the years and we can honestly say that Off the Charts is in a class of its own! Thank you Ana & Chris - we will be back :)
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Top rated by guests
10Outstanding
(4 Ratings)
"From the last minute reservation till morning of checkout, everything about this stay was perfect. If you’re looking to escape the new normal sterile keys housing developments and settle into old keys..."
Mike P.Don't miss out! Price and availability may change
