82236 Overseas Highway, Islamorada, Florida 33036, United States
Sleeps 8 | Sunset + Boat Basin | Islamorada
- 8 Sleeps
- 4 bedrooms
- 4 bathrooms
- 4 Beds
Overview
Unique property in the heart of Islamorada, ideal for groups and families traveling together. Enjoy rare access to a private boat basin and fishing jetty just steps away—perfect for sunset views and relaxing by the water. Two separate living spaces offer privacy and flexibility while still staying connected. Walk to restaurants, shops, and breweries, then unwind in a peaceful setting.
Amenities
What this place offers
- Accessible-height bed
- Accessible-height toilet
- Air conditioning
- BBQ grill
- Baking sheet
- Barbeque utensils
- Beach essentials
- Bed linens
- Blender
- Boat slip
- Body soap
- Ceiling fan
- Cleaning Disinfection
- Cleaning products
- Coffee maker
- Conditioner
- Cookware
- Dishes and silverware
- Dishwasher
- Dryer
- Dryer in common space
- Emergency exit
- Enhanced cleaning practices
- Essentials
- Family/kid friendly
- Fire extinguisher
- First aid kit
- Fishing
- Free parking on premises
- Free parking on street
- Garden or backyard
- Hair dryer
- Hangers
- Heating
- Hot water
- Internet
- Iron
- Kettle
- Kitchen
- Laptop friendly workspace
- Long term stays allowed
- Microwave
- Near Ocean
- Outdoor seating (furniture)
- Oven
- Path to entrance lit at night
- Patio or balcony
- Private entrance
- Refrigerator
- Room-darkening shades
- Shampoo
- Shower gel
- Smoke detector
- Step-free access
- Stove
- Suitable for children (2-12 years)
- Suitable for infants (under 2 years)
- TV
- Toaster
- Towels provided
- Washer
- Washer in common space
- Waterfront
- Wine glasses
- Wireless Internet
- Drying rack for clothing
Availability
$ 598
/ nightReviews
42 Reviews
Very nice, comfortable place conveniently located for Islamorada activities.
What a very charming, delightful & spacious place. It was perfect for my parents to have a separate easy entry access for themselves and have ultimate privacy upon our stay. We enjoyed the private beach access and picnic area everyday to watch the sunset and soak in our awesome adventure. Sean was most attentive and responsive to any questions. We look forward to the next time we visit the Keys and get the chance to stay at one of these wonderfully curated & exceptional places. What a treat! Thank you!
Sean’s place was just as advertised and was the perfect set up for 4 couples. We had both units allowing for 2 couples upstairs and 2 downstairs with each level having 2 bathrooms and a kitchen. The main outside area was a great gathering spot for morning coffee, afternoon happy hour and evening games. We did not use the grill or laundry room but they would have been great options had we been there a little longer. Sean was a great communicator and gave great instructions about locating the Hidden Gem as it is tucked in a bit off the Main Street. The Hidden Gem is walkable to a couple of local shops, a local outfitter, a breakfast spot and a brewery. A little farther but walkable is a CVS. Everything on the key is within a short drive of the Hidden Gem making it a great location to take in everything Islamorada has to offer. Should our travels find us back on the key we would definitely stay at one of Sean’s properties again!
Maddy Meyer
April 22-2026 5.00Love love love this place! Definitely would like to come back
Things to know
Space
This rental includes two separate, fully private living spaces—one upstairs and one downstairs—with separate entrances and no interior connection. It’s ideal for groups and families who want to stay together while still having their own space. Upstairs (second floor): ● 2 bedrooms / 2 bathrooms ● Both bedrooms feature King beds ● Full kitchen + living area Downstairs (first floor): ● 2 bedrooms / 2 bathrooms ● Primary: Queen bed + en suite bathroom ● Guest room: King bed + separate bathroom ● Full kitchen + living area Note: no closets or dressers—luggage racks and hanging space provided Guests also enjoy a private courtyard with seating, grill, and private laundry for your group’s use. This duplex is part of a quiet, wooded waterfront property spanning the bay side of the Florida Keys. While the spaces are courtyard-facing (no direct ocean 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.
Access
Guests have full access to both the upstairs and downstairs units. The courtyard, grill, and laundry area are private to your group and shared only between the two spaces. The remaining property grounds—including the boat basin, fishing jetty, and waterfront areas—are shared with a small number of other units on the property. Parking is available on-site for up to 4 vehicles. Self check-in is provided via a keypad for a smooth and flexible arrival.
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
Neighborhood
Located at Mile Marker 82.5 in the heart of Islamorada, this property 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.
Transit
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.
Notes
● Maximum occupancy: 8 guests ● Two separate units (upstairs + downstairs) with NO interior connection ● Parking available for up to 4 vehicles ● COURTYARD VIEW (no direct ocean view), with full access to the boat basin and fishing jetty Boat Basin Access (Optional) ● Dockage available for up to TWO vessels 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.
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