Nestled in the heart of Islamorada, this charming Hidden Gem offers a tranquil retreat with a private courtyard featuring a grill and seating area. Take advantage of bikes and kayaks rentals nearby or stroll to local shops, restaurants, and breweries. With two separate units boasting full kitchens and comfortable beds, this property is ideal for large groups and families.
Reviews
1010 out of 10
Exceptional
Entire home
4 bedrooms4 bathroomsSleeps 8112 sq m
Popular amenities
Kitchen
Washing machine
Dryer
Air-conditioning
Outdoor space
Parking available
Add dates for prices
About this property
Sleeps 8 | Sunset + Boat Basin | Islamorada
Summary:
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.
The 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.
Guest 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.
The 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.
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: 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.
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
Property amenities
Internet
Available in the house: WiFi
Parking and transport
Parking on site
Kitchen
Blender
Coffee/tea maker
Cookware, dishware, and utensils
Dishwasher
Electric kettle
Hob
Microwave
Oven
Refrigerator
Toaster
Bedrooms
4 bedrooms
Bedsheets provided
Bathroom
4 bathrooms
Hair dryer
Shampoo
Shower
Towels provided
Entertainment
TV
Outdoor areas
Balcony
Barbecue grill
Garden
Laundry
Laundry facilities
Washing machine
Work spaces
Office
Comfort
Air conditioning
Heating
Pets
No pets allowed
Suitability/Accessibility
Smoke-free property
Services and conveniences
Iron/ironing board
Location highlights
Near the sea
On the waterfront
Things to do
Boat
Fishing nearby
Safety features
Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
Smoke detector (host has indicated there is a smoke detector on the property)
You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools
Rules
- No Smoking
- No Pets
- No Parties
- No outside noises after 10pm
Pets
Pets not allowed
Children and extra beds
Children are welcome
Events
No events allowed
Smoking
Smoking is not permitted
Important information
You need to know
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
This property accepts cash
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
About the area
Located on the waterfront, this holiday home is in Matecumbe, a neighbourhood in Islamorada. Keys History & Discovery Center and History of Diving Museum are cultural highlights, and some of the area's landmarks include Hurricane Monument and Indian Key Historic State Park. Take the opportunity to explore the area for water adventures such as fishing. Visit our Islamorada travel guide
How much is parking at Sleeps 8 | Sunset + Boat Basin | Islamorada?
On-site parking is available at the property.
What time is check-in at Sleeps 8 | Sunset + Boat Basin | Islamorada?
Check-in begins at 4:00 PM.
What time is check-out at Sleeps 8 | Sunset + Boat Basin | Islamorada?
Checkout is at 10:00 AM.
Where is Sleeps 8 | Sunset + Boat Basin | Islamorada located?
Located in Matecumbe, this holiday home is within a 15-minute walk of Islamorada Brewery & Distillery, Keys History & Discovery Center and History of Diving Museum. Matecumbe United Methodist Church and Florida Keys Brewing Co. are also within 1 mile (2 km).
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All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
This is a great location to all the marinas for fishing. Beautiful sunsets right from your back yard. Great place for a small boat and/or kayaks. Look forward to booking here again.
The property is amazing, excellent renovation, the condos are so nice, clean, new, very comfortable. Very unique and quaint property. We would definitely return.
We were a group of 4 couples celebrating 50th bdays. The place was fantastic! Loved sitting by the water in the morning. Loved the walk ability to shops, breweries, and restaurants. Host was the quickest and most responsive that I have had. We will definitely be booking in the future!
The property was exactly the hidden gem that it was described to be. Sean was often in touch to make sure everything was great. The detail regarding restaurants and activities was extremely helpful.
We had a multigenerational family group and booked both the upstairs and downstairs units. This gave us enough space and we appreciated the designated parking. The outdoor spaces were great for hanging out & enjoying the sunset/sunrise views. We used the boat slip area to have photos taken. The location was central/convenient is Islamorada. The host was very responsive.
The property was PERFECT in every way! Actually all was better than what we expected. The grounds were just beautiful and a great location. Walking distance to plenty of stuff and a little strip of Atlantic beach less than a 5 minute walk away. Sean was always very responsive and accommodating. The “retro” groove was so cute with all modern conveniences! If I could give it 10 stars I would.
Great place, serene and tranquill on the Gulf side with magnificent sunsets, great guests in other units and a property manager that kept us well informed and eager to assist if needed. You'd never know that US 1 was there but it was very convenient and walkable to a good number of bars and restaurants
We went to Islamorada to go scuba diving. All the dive shops we had booked were within a few minutes. The outside patio was perfect for eating al fresco and sitting around talking. The host was attentive and quick to answer questions. I would definitely recommend staying here. And if I ever come back to the Keys , I would stay here again.