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:
Unique, 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. Walk to top restaurants, breweries, and shops, then return to a peaceful, tucked-away setting. This first-floor unit offers easy access, fast WiFi, and everything you need for a comfortable Keys getaway! 🌅🌴😎💎
The Space:
● 2 bedrooms / 2 bathrooms (620 sq ft)
● Primary: Queen bed + en suite bathroom
● Guest room: King bed + separate bathroom
● Open living area + small kitchen
● Courtyard-facing (quiet, tucked-away setting)
Note: no closets or dressers—luggage racks and hanging space provided
This unit is part of a unique, private, wooded waterfront property spanning the bay side of the Florida Keys. While the unit 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 unit, 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 upstairs unit. 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, flexible arrival.
The Neighborhood:
Located at Mile Marker 82.5 in the heart of Islamorada, this retreat is in one of the most 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
Unique, 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. Walk to top restaurants, breweries, and shops, then return to a peaceful, tucked-away setting. This first-floor unit offers easy access, fast WiFi, and everything you need for a comfortable Keys getaway! 🌅🌴😎💎
The Space:
● 2 bedrooms / 2 bathrooms (620 sq ft)
● Primary: Queen bed + en suite bathroom
● Guest room: King bed + separate bathroom
● Open living area + small kitchen
● Courtyard-facing (quiet, tucked-away setting)
Note: no closets or dressers—luggage racks and hanging space provided
This unit is part of a unique, private, wooded waterfront property spanning the bay side of the Florida Keys. While the unit 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 unit, 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 upstairs unit. 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, flexible arrival.
The Neighborhood:
Located at Mile Marker 82.5 in the heart of Islamorada, this retreat is in one of the most 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·May 2026
Please was great, I would recommend it
10 / 10Outstanding·Apr 2026
We had a fantastic stay! The house was great. The patio area is a total dream for morning coffee. Check-in was a breeze, and the host was very responsive. We will be back!
10 / 10Outstanding·Sep 2025
This property was terrific! It is clean and well-maintained. Access to the water and walkable to food and shopping. We had a wonderful stay.
10 / 10Outstanding·Jun 2025
We stayed at the Hidden Gem; a 2 bdrms, 2 baths cute unit. We loved the entire place and it's subtle quaint atmosphere. A very short walk to the water had a stunning view. We will definitely be back.
$$$$
Top rated by guests
9.8Outstanding
(48 Ratings)
"Please was great, I would recommend it"
Roxana T.Don't miss out! Price and availability may change
