House in Upper Matecumbe Key, FL
14 guests · 7 bedrooms · 5 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
Spectacular property - two stories of true keys paradise in a relaxed basin-front setting. Newly renovated, the property has 7 bedrooms, 5 baths, 2 living rooms, and a tiki cabana flanking the pool! The house sits on a beautiful basin with deep water that houses many manatees in the heart of the Village of Islamorada! This patch of paradise is less than one minute to open water of the Bayside of Islamorada. Super location – a 1 minute walk to many local restaurants. The island has so much to offer - amazing, galleries, shops, restaurants, aqua blue waters, incredible fishing and boating!
This property offers an exceptional collection of amenities designed for comfort, entertainment, and relaxation. Outside, guests can enjoy a stunning waterfront pool surrounded by a tropical lounge area and a tiki cabana for shaded relaxation. The property features a 35-foot-wide deep-water dock, perfect for accommodating larger boats—an especially valuable feature for Islamorada travelers looking to explore the Keys by water or enjoy world-class fishing and boating. Guests also have access to two paddleboards and two kayaks for on-the-water adventures, as well as ample parking with dedicated boat trailer space. Additional conveniences include laundry facilities, elegant indoor and outdoor dining areas, and thoughtfully designed spaces that blend island charm with elevated comfort.
Islamorada is an absolute paradise - we love the island and are happy to share the vacation house with guests looking to escape to a patch of heaven in the Keys. The property is exclusively offered as a vacation rental - it is exceptionally clean and easy to enjoy. Designed by award winning Hospitality designers, it has many features which not only rival but exceed hotel accommodations.
There are 2 paddle boards and 2 kayaks included for guest use.
There is plenty of parking as well as boat trailer parking onsite.
The restaurants within walking distance: Lorelei Restaurant, Islamorada Beer Company, Morada Bay Beach Café, Pierre's Chef Michael's, Kaiyo Grill, Keys Brewery, Bayside Gourmet, Bayside Gourmet, Bitton Bistro and Mangrove Mike’s.
LICENSE #: 26-0319 - Islamorada. This property has a single Nest camera on the exterior corner facing the street for access security only.
This property offers an exceptional collection of amenities designed for comfort, entertainment, and relaxation. Outside, guests can enjoy a stunning waterfront pool surrounded by a tropical lounge area and a tiki cabana for shaded relaxation. The property features a 35-foot-wide deep-water dock, perfect for accommodating larger boats—an especially valuable feature for Islamorada travelers looking to explore the Keys by water or enjoy world-class fishing and boating. Guests also have access to two paddleboards and two kayaks for on-the-water adventures, as well as ample parking with dedicated boat trailer space. Additional conveniences include laundry facilities, elegant indoor and outdoor dining areas, and thoughtfully designed spaces that blend island charm with elevated comfort.
Islamorada is an absolute paradise - we love the island and are happy to share the vacation house with guests looking to escape to a patch of heaven in the Keys. The property is exclusively offered as a vacation rental - it is exceptionally clean and easy to enjoy. Designed by award winning Hospitality designers, it has many features which not only rival but exceed hotel accommodations.
There are 2 paddle boards and 2 kayaks included for guest use.
There is plenty of parking as well as boat trailer parking onsite.
The restaurants within walking distance: Lorelei Restaurant, Islamorada Beer Company, Morada Bay Beach Café, Pierre's Chef Michael's, Kaiyo Grill, Keys Brewery, Bayside Gourmet, Bayside Gourmet, Bitton Bistro and Mangrove Mike’s.
LICENSE #: 26-0319 - Islamorada. This property has a single Nest camera on the exterior corner facing the street for access security only.
Amenities
Non-smoking
No pets allowed
Family friendly
Map of Upper Matecumbe Key, FL
Ratings and reviews
10 / 10Outstanding·May 2026
We have stayed at VRBO properties all around the USA and this was by far the nicest we have rented. This place was absolutely beautiful, very clean, modern and spacious for our party of 11. The backyard is an oasis with the pool and shaded seating pavillion. The kitchen had every amenity you could ask for. The property listing says there is a drip coffee maker but the kitchen also has a Nesspresso and Keurig machine, that made the coffee lovers in the family quite happy. A manatee came to visit on the first day of the trip. If you're looking for an amazing place to stay in Islamorada then this is the place to book!
10 / 10Outstanding·Apr 2026
Great location! House is awesome, easily host 3 families. We will be back
10 / 10Outstanding·Apr 2026
The property was even better than we thought it would be. Very quiet, yet close to everything. Immaculate and well equipped. The outdoor area is amazing.
10 / 10Outstanding·Mar 2026
We had a wonderful time at this home. Our group of 12 had plenty of space to move around and room for ourselves. The kitchen was very well stocked. All the outdoor areas are amazing to relax. Plenty of sun or shade areas. Some of us used the paddle boards and kayaks. The highlight has to be the many manatee that would swim around the docks. The location is great as well. We were able to walk to a lot of places.
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Top rated by guests
10Outstanding
(68 Ratings)
"We have stayed at VRBO properties all around the USA and this was by far the nicest we have rented. This place was absolutely beautiful, very clean, modern and spacious for our party of 11. The backya..."
Michael C.Don't miss out! Price and availability may change
