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Sleeps 8 | Sunset + Boat Basin | Islamorada

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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

10 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)
  • First aid kit
  • Fire extinguisher

General

  • Garden
  • Unit size: 1,200 square feet

Similar properties

Policies

Check-in

Check-in time starts at 4:00 PM

Minimum check-in age - 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

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
View more Holiday homes in Islamorada
Map
Islamorada, FL

What's nearby

  • Florida Keys Brewing Co.
    Florida Keys Brewing Co.
    1 min drive - 1.7 km
  • Islamorada_BudnMarysDiveCenter_6069243-0004
    Bud n' Mary's Dive Center
    4 min drive - 5.0 km
  • Anne's Beach
    Anne's Beach
    14 min drive - 17.9 km
  • Islamorada Brewery & Distillery
    1 min walk - 0.1 km
  • Robbie’s of Islamorada
    7 min drive - 10.0 km

Getting around

  • Marathon, FL (MTH-Florida Keys Marathon)
    39 min drive

Restaurants

  • Lorelei Restaurant & Cabana Bar
    10 min walk
  • Wahoo's Bar & Grill
    2 min drive
  • Wendy's
    6 min walk
  • Islamorada Fish Company
    2 min drive
  • Bayside Gourmet of Islamorada
    6 min walk

Frequently asked questions

Is Sleeps 8 | Sunset + Boat Basin | Islamorada pet-friendly?

No, pets are not allowed at this property.

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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Sleeps 8 | Sunset + Boat Basin | Islamorada Reviews

Reviews

Exceptional

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.
More informationOpens in a new window
Rating 10 - Excellent. 11 out of 11 reviews
Rating 8 - Good. 0 out of 11 reviews
Rating 6 - Okay. 0 out of 11 reviews
Rating 4 - Poor. 0 out of 11 reviews
Rating 2 - Terrible. 0 out of 11 reviews

10

Cleanliness

10

Location

Reviews

Verified

10/10 Excellent

claire c.

Liked: Cleanliness, check-in, communication, location, listing accuracy
the units were spotless, the beds are comfy, the kitchen has everything if you were to cook.the outside was perfect to sit around and chat .
Stayed 3 nights in Oct 2025
Verified

10/10 Excellent

Mark J.

Liked: Cleanliness, check-in, communication, location, listing accuracy

50th Birthday fishing and fun

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.
Stayed 3 nights in Nov 2023
Verified

10/10 Excellent

Steve S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing Condos

The property is amazing, excellent renovation, the condos are so nice, clean, new, very comfortable. Very unique and quaint property. We would definitely return.
Stayed 4 nights in Nov 2023
Verified

10/10 Excellent

Jackie R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fantastic place with an awesome location!

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!
Stayed 3 nights in Oct 2024
Verified

10/10 Excellent

John F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fantastic Week

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.
Stayed 5 nights in Aug 2023
Verified

10/10 Excellent

Emily B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Good for a group

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.
Stayed 4 nights in Dec 2024
Verified

10/10 Excellent

ronda g.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Six Chicks Trip

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.
Stayed 3 nights in Oct 2023
Verified

10/10 Excellent

Gina W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Location!

Everything about this property was amazing! We can’t wait to return!
Stayed 4 nights in Jun 2025
Verified

10/10 Excellent

Mark S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Hidden Gem

We had a great experience with this property. Great location, checkin process was fantastic. I’d stay there again
Stayed 3 nights in Mar 2023
Verified

10/10 Excellent

Jeffrey F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Hidden Gem it is!

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
Stayed 3 nights in Mar 2023
Verified

10/10 Excellent

Jessica B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect location

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.
Stayed 4 nights in Aug 2022