Apartment in Upper Matecumbe Key, FL
4 guests · 2 bedrooms · 2 baths
Reasons to book
Guests love it hereGuests give this property a top rating
High-end valueWell priced for 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 apartment rental
Summary:
Elevated, thoughtfully updated retreat in the heart of Islamorada with rare access to a private boat basin and fishing jetty—perfect for sunset views and relaxing by the water. Set above the trees for a more open, airy feel, yet tucked into a peaceful setting. Enjoy walkable access to restaurants, shops, and breweries, plus fast WiFi and everything needed for a comfortable Keys getaway 🌴
The Space:
● 2 bedrooms / 2 bathrooms (620 sq ft)
● Primary: King bed + en suite bathroom
● Guest room: King bed + separate bathroom
● Open living area + small kitchen
● Second-floor setting with a more open, airy feel
● Courtyard-facing (quiet, tucked-away setting)
● Shared external laundry room
Note: no closets or dressers—luggage racks and hanging space provided
This retreat is part of a unique, private, wooded waterfront property spanning the bay side of the Florida Keys. While the space does not have direct water views, guests have full access to the property, including a boat basin and fishing jetty just a short walk away—perfect for sunsets and relaxing by the water.
Guest Access:
Guests have full access to the entire space, as well as the shared property grounds. This includes the boat basin, fishing jetty, and waterfront areas—perfect for relaxing and enjoying sunset views.
The courtyard and outdoor areas are shared with the downstairs space. A shared laundry area is also available on-site.
Parking is available on-site for your convenience. Self check-in is provided via a keypad for a smooth and flexible arrival.
The Neighborhood:
Located at Mile Marker 82.5 in the heart of Islamorada, this home is in one of the more walkable areas in the Upper Keys. You’re just steps from local shops and a short walk to popular restaurants, bars, and the well-known Islamorada Beer Company.
Despite being close to everything, the property itself is tucked away in a quiet, wooded setting—offering a more relaxed and private feel than most nearby stays.
A detailed guestbook is provided with our favorite recommendations for dining, drinks, and local activities.
Getting Around:
While this area of Islamorada is more walkable than most in the Keys, we recommend having a vehicle to fully explore nearby attractions, beaches, and surrounding areas.
For shorter trips, many restaurants, shops, and local spots—including Islamorada Beer Company—are within walking distance. Biking is also a great option, and rentals are available nearby.
Other Things to Note:
● Maximum occupancy: 4 guests
● SHARED courtyard, grill, and laundry with the upstairs unit
● COURTYARD VIEW (no direct ocean view), with full access to the boat basin and fishing jetty
Boat Basin Access (Optional)
● Dockage available for ONE vessel up to 24’ MAX (with engine)
● Space is shared and not assigned (placement may vary)
● Boat ramp available for vessels up to 20’ MAX
● Larger boats cannot be accommodated
● Marina waiver required prior to arrival
● Trailer parking available on-site
● NO JET SKIS
Cancellation Policy
● 100% refund: 60+ days before check-in
● 50% refund: 30–60 days before check-in
● No refunds within 30 days
Travel insurance is strongly recommended.
Interaction with Guests:
We provide self check-in for a smooth and flexible arrival, but we’re always available if you need anything during your stay. We’re local and happy to help with recommendations, questions, or anything that comes up. - Sean
Elevated, thoughtfully updated retreat in the heart of Islamorada with rare access to a private boat basin and fishing jetty—perfect for sunset views and relaxing by the water. Set above the trees for a more open, airy feel, yet tucked into a peaceful setting. Enjoy walkable access to restaurants, shops, and breweries, plus fast WiFi and everything needed for a comfortable Keys getaway 🌴
The Space:
● 2 bedrooms / 2 bathrooms (620 sq ft)
● Primary: King bed + en suite bathroom
● Guest room: King bed + separate bathroom
● Open living area + small kitchen
● Second-floor setting with a more open, airy feel
● Courtyard-facing (quiet, tucked-away setting)
● Shared external laundry room
Note: no closets or dressers—luggage racks and hanging space provided
This retreat is part of a unique, private, wooded waterfront property spanning the bay side of the Florida Keys. While the space does not have direct water views, guests have full access to the property, including a boat basin and fishing jetty just a short walk away—perfect for sunsets and relaxing by the water.
Guest Access:
Guests have full access to the entire space, as well as the shared property grounds. This includes the boat basin, fishing jetty, and waterfront areas—perfect for relaxing and enjoying sunset views.
The courtyard and outdoor areas are shared with the downstairs space. A shared laundry area is also available on-site.
Parking is available on-site for your convenience. Self check-in is provided via a keypad for a smooth and flexible arrival.
The Neighborhood:
Located at Mile Marker 82.5 in the heart of Islamorada, this home is in one of the more walkable areas in the Upper Keys. You’re just steps from local shops and a short walk to popular restaurants, bars, and the well-known Islamorada Beer Company.
Despite being close to everything, the property itself is tucked away in a quiet, wooded setting—offering a more relaxed and private feel than most nearby stays.
A detailed guestbook is provided with our favorite recommendations for dining, drinks, and local activities.
Getting Around:
While this area of Islamorada is more walkable than most in the Keys, we recommend having a vehicle to fully explore nearby attractions, beaches, and surrounding areas.
For shorter trips, many restaurants, shops, and local spots—including Islamorada Beer Company—are within walking distance. Biking is also a great option, and rentals are available nearby.
Other Things to Note:
● Maximum occupancy: 4 guests
● SHARED courtyard, grill, and laundry with the upstairs unit
● COURTYARD VIEW (no direct ocean view), with full access to the boat basin and fishing jetty
Boat Basin Access (Optional)
● Dockage available for ONE vessel up to 24’ MAX (with engine)
● Space is shared and not assigned (placement may vary)
● Boat ramp available for vessels up to 20’ MAX
● Larger boats cannot be accommodated
● Marina waiver required prior to arrival
● Trailer parking available on-site
● NO JET SKIS
Cancellation Policy
● 100% refund: 60+ days before check-in
● 50% refund: 30–60 days before check-in
● No refunds within 30 days
Travel insurance is strongly recommended.
Interaction with Guests:
We provide self check-in for a smooth and flexible arrival, but we’re always available if you need anything during your stay. We’re local and happy to help with recommendations, questions, or anything that comes up. - Sean
Amenities
Non-smoking
No pets allowed
Family friendly
Map of Upper Matecumbe Key, FL
Ratings and reviews
10 / 10Outstanding·Jan 2026
The unit was nicely decorated and very clean. The kitchen and bathrooms had everything we needed. The showers were large and the water pressure was good. The host checked on us to make sure everything was OK. I recommend this rental and would stay there again.
10 / 10Outstanding·Oct 2025
Great location. Lovely property. It’s the second time staying here and will not be the last!
10 / 10Outstanding·Sep 2025
This place has is all!!! Location couldn’t have been any better. We were there to boat and fish during Labor Day weekend and this place was absolutely perfect!!! Sean was so great and incredible helpful. It was seamless and easy to locate the property, check- in and launch the boat. The marina is smaller than it looks in the photos but it was manageable with our Key West. Two couples stayed very comfortably and we had some good luck fishing right there at the back of the property. The courtyard directly behind Hidden Gem is very nice. I sat out there and drank my coffee a few mornings. It was beautiful with orchids and tropical vegetation…very relaxing. I highly recommend this place!!!
10 / 10Outstanding·Jun 2025
Great as always. Location, clean and great property manager.
$$$$
Top rated by guests
9.9Outstanding
(36 Ratings)
"The unit was nicely decorated and very clean. The kitchen and bathrooms had everything we needed. The showers were large and the water pressure was good. The host checked on us to make sure everything..."
Charlene W.Don't miss out! Price and availability may change
