House in Upper Matecumbe Key, FL
10 guests · 5 bedrooms · 4 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Top-tier experienceA high end property in this area
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About this house rental
Deep water dockage & heated pool!
Modern, clean & fresh interiors make this rental perfect.
Manatees visit the dock daily - they are sweet, gentle giants!
Dock is about 75’ long on and located on a protected, deep water basin seconds from open water. 2 paddle boards & 2 kayaks for guest use.
This Bayside house with a gorgeous heated pool and deep water is centrally located in the heart of the Village of Islamorada. The house is walking distance to the most of what makes Islamorada so special. It is only a 1/2 block from famous Lorelei Cabana Bar & Restaurant and 1/2 block from the Casa Morada Hotel. Large open living/dining/ kitchen area overlooking a partial view of open ocean on Bayside. Back Country Fishing is minutes away as the house sits only one property from open ocean. It has 3 master suites with king each, 1 king bedroom and 1 additional bedroom with twin beds.
Modern, clean & fresh interiors make this rental perfect.
Manatees visit the dock daily - they are sweet, gentle giants!
Dock is about 75’ long on and located on a protected, deep water basin seconds from open water. 2 paddle boards & 2 kayaks for guest use. The waterfront pool is heated to 86 degrees.
Plenty of boat trailer parking onsite.
THIS PROPERTY RENTS SATURDAY TO SATURDAY - we might make exceptions but during high season we have Saturday to Saturday bookings only.
Islamorarda has so much to offer, amazing restaurants, aqua blue waters, incredible fishing and boating!
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.
About the owner: Islamorada is absolute paradise - we love the island and happy to share the vacation house with guests looking to escape to a patch of paradise in the Keys. The is property is exclusively offered as a vacation rental so it is similar to staying at a hotel ; it is exceptionally clean and easy to enjoy.
We privately own a total of 5 boutique vacation rentals in Islamorada:
VRBO listing #1576833 (5 bedroom)
VRBO listing #1054019 (5 bedroom)
VRBO listing #1977457 (7 bedroom)
VRBO listing #689629 (5 bedroom)
LICENSE #: 26-0278 - Islamorada
Modern, clean & fresh interiors make this rental perfect.
Manatees visit the dock daily - they are sweet, gentle giants!
Dock is about 75’ long on and located on a protected, deep water basin seconds from open water. 2 paddle boards & 2 kayaks for guest use.
This Bayside house with a gorgeous heated pool and deep water is centrally located in the heart of the Village of Islamorada. The house is walking distance to the most of what makes Islamorada so special. It is only a 1/2 block from famous Lorelei Cabana Bar & Restaurant and 1/2 block from the Casa Morada Hotel. Large open living/dining/ kitchen area overlooking a partial view of open ocean on Bayside. Back Country Fishing is minutes away as the house sits only one property from open ocean. It has 3 master suites with king each, 1 king bedroom and 1 additional bedroom with twin beds.
Modern, clean & fresh interiors make this rental perfect.
Manatees visit the dock daily - they are sweet, gentle giants!
Dock is about 75’ long on and located on a protected, deep water basin seconds from open water. 2 paddle boards & 2 kayaks for guest use. The waterfront pool is heated to 86 degrees.
Plenty of boat trailer parking onsite.
THIS PROPERTY RENTS SATURDAY TO SATURDAY - we might make exceptions but during high season we have Saturday to Saturday bookings only.
Islamorarda has so much to offer, amazing restaurants, aqua blue waters, incredible fishing and boating!
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.
About the owner: Islamorada is absolute paradise - we love the island and happy to share the vacation house with guests looking to escape to a patch of paradise in the Keys. The is property is exclusively offered as a vacation rental so it is similar to staying at a hotel ; it is exceptionally clean and easy to enjoy.
We privately own a total of 5 boutique vacation rentals in Islamorada:
VRBO listing #1576833 (5 bedroom)
VRBO listing #1054019 (5 bedroom)
VRBO listing #1977457 (7 bedroom)
VRBO listing #689629 (5 bedroom)
LICENSE #: 26-0278 - Islamorada
Amenities
Non-smoking
No pets allowed
Family friendly
Map of Upper Matecumbe Key, FL
Ratings and reviews
10 / 10Outstanding·Mar 2026
⸻We had an amazing week at this property! The house and grounds were exactly as described—clean, well-maintained, and beautifully situated with stunning bay views.The heated pool was perfect, and the kayaks and fire pit were a huge hit with our group. We especially loved being able to fish right off the dock, and it was incredibly easy getting our rental boat in and out.The location couldn’t have been better—close to great restaurants, a brewery, and Publix—yet still quiet and private. It truly offered the best of both convenience and relaxation.We thoroughly enjoyed our stay and are already looking forward to renting again!
10 / 10Outstanding·Jan 2026
We stayed at this property over the Christmas holidays (2025) and cannot say how happy we were with the house, owner, and location.Location: We explored other Keys but found this location to be perfect. Near Publix, restaurants (although we ate in most nights), Lorelei was just down the block, and less than a two hour drive from Miami International. House: very clean and spacious. Plenty of bedrooms that fit our family (my wife and I, four grown children and two significant others). The kitchen was well equipped (with additional items added by the owner after we inquired). We used the pool everyday and our kids fished off the dock everyday (and we also saw a mother and baby manatee).Owner: Chausey was great. She was extremely responsive and added items upon inquiry (Christmas tree, roasting pan). Thanks Chausey!It was such a hit with our family, we hope to stay here again next year!
10 / 10Outstanding·Nov 2025
We loved everything about our stay, especially the details our host Chausey helped us with. The pool was cozy warm for old and young, our kids fished off the dock of plenty. Groupers, angel fish, nurse sharks, mud sharks, they just kept coming. The local shopping, music, bars, just the best location! Chausey made sure our group had enough paddle boards and kayaks. We made alot of good memories!
10 / 10Outstanding·Nov 2025
We had an amazing stay in the House. Everything was perfect, the owner was very nice and helpful.
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Top rated by guests
10Outstanding
(132 Ratings)
"⸻We had an amazing week at this property! The house and grounds were exactly as described—clean, well-maintained, and beautifully situated with stunning bay views.The heated pool was perfect, and the ..."
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