Sleeps 8 | Sunset + Boat Basin | Islamorada

★ 4.8 (39 reviews) · 8 guests Islamorada, FL

Sleeps 8 | Sunset + Boat Basin | Islamorada

8 guests · 4 bedroom · 4 bath

About this home

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.

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.

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.

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.

Stay details

Check-in 4:00 PM
Check-out 11:00 AM
Minimum stay 3 nights
Pets Not allowed
Smoking Not allowed
Parties/events Not allowed

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 products
Coffee maker
Conditioner
Cookware
Dishes and silverware
Dishwasher
Dryer
Dryer in common space
Drying rack for clothing
Emergency exit
Essentials
Family/kid friendly
Fire extinguisher
First aid kit
Fishing
Free parking on premises
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
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

Availability

★★★★★ 4.8 / 5 · 39 reviews

Guest

Oct 2026
★★★★☆

We quickly learned that the Hidden Gem lives up to its name. We loved that it’s minutes away from everything we needed. We appreciated the privacy from the road and from the other units that share the property. The outdoor living spaces were great places to sit, relax, and enjoy the mild Florida Keys weather. But the boat basin and ramp stood out the most to us. We loved the privacy and convenience of being able to launch and dock our boats right there on the property.

Guest

Sep 2026
★★★★★

We had a great stay at the Hidden Gem! It was perfect for our family of 7! This Airbnb is in a great location and we loved the jetty and the comfortable and relaxing environment. Sean responded to texts promptly and was very helpful.

Guest

Aug 2026
★★★★★

We had an amazing stay in Islamorada! The Airbnb was exactly what we were hoping for clean, comfortable, beautiful, and in a great location. The host was absolutely awesome. Friendly, responsive, accommodating, and made everything easy from start to finish. We had a great time making memories with friends and family, and this was the perfect home base for our Florida Keys trip. We would definitely stay here again and highly recommend it to anyone visiting Islamorada. Thanks for helping make our trip such a great one!

Guest

Jul 2026
★★★★★

This house was perfect for our family trip. Being able to keep our boat in the basin made it easy and convenient.

Guest

Jun 2026
★★★★★

We loved the house and the property. It was essentially two 2 bedroom units, which was great for traveling with adult children. The water access was nice for fishing and swimming/snorkeling or relaxing. We saw lots of fish and sea live and caught some small ones. The mosquitoes were pretty bad in morning and evening hours so mosquito spray was a must but overall great experience.

Guest

Jun 2026
★★★★★

Thank you for providing such a beautiful space, which actually fit our family of 8, and for being so communicative. I felt a lot of pressure getting my family to the Keys for the first time, since I spent my childhood summers there but haven't been back in decades, so thank you for all of your support and recommendations. Everyone was comfortable, all of the promised amenities allowed us to pack lightly for our long drive and the house had everything we needed. We had such a relaxing time watching sunsets, swimming and kayaking. We ended up leaving the house for a snorkel tour with the recommended tour guide, which was really great for the kids, but we could have just stayed at the property for the entire time (and mostly did). The house was just gorgeous, and the Keys are just how I remembered--we can't wait to go back.

Where you'll be

Islamorada, FL

Policies & Rules

House Rules

Property-specific house rules are confirmed before booking and included in the rental agreement when one is required.

Booking Policy

Minimum stay: 3 nights

Cancellation Policy

Please review the booking terms before confirming your reservation. Cancellation terms may vary by property and stay dates.

Amenities

Bedroom & Laundry

  • Accessible-height bed
  • Bed linens
  • Dishwasher
  • Dryer
  • Dryer in common space
  • Hangers
  • Iron
  • Washer
  • Washer in common space

Bathroom

  • Accessible-height toilet
  • Hair dryer
  • Shampoo
  • Shower gel

Heating & Cooling

  • Air conditioning
  • Ceiling fan
  • Heating
  • Suitable for infants (under 2 years)

General

  • BBQ grill
  • Baking sheet
  • Barbeque utensils
  • Blender
  • Body soap
  • Cleaning products
  • Conditioner
  • Drying rack for clothing
  • Emergency exit
  • Essentials
  • Family/kid friendly
  • Fishing
  • Garden or backyard
  • Kettle
  • Long term stays allowed
  • Path to entrance lit at night
  • Private entrance
  • Room-darkening shades
  • Suitable for children (2-12 years)
  • Toaster
  • Towels provided
  • Wine glasses

Outdoor & Features

  • Beach essentials
  • Boat slip
  • Hot water
  • Near Ocean
  • Outdoor seating (furniture)
  • Patio or balcony
  • Waterfront

Kitchen & Dining

  • Coffee maker
  • Cookware
  • Dishes and silverware
  • Kitchen
  • Microwave
  • Oven
  • Refrigerator
  • Stove

Home Safety & Access

  • Fire extinguisher
  • First aid kit
  • Smoke detector

Parking & Facilities

  • Free parking on premises

Internet & Office

  • Internet
  • Laptop friendly workspace
  • Wireless Internet

Entertainment

  • TV

Guest

Oct 2026
★★★★☆

We quickly learned that the Hidden Gem lives up to its name. We loved that it’s minutes away from everything we needed. We appreciated the privacy from the road and from the other units that share the property. The outdoor living spaces were great places to sit, relax, and enjoy the mild Florida Keys weather. But the boat basin and ramp stood out the most to us. We loved the privacy and convenience of being able to launch and dock our boats right there on the property.

Guest

Sep 2026
★★★★★

We had a great stay at the Hidden Gem! It was perfect for our family of 7! This Airbnb is in a great location and we loved the jetty and the comfortable and relaxing environment. Sean responded to texts promptly and was very helpful.

Guest

Aug 2026
★★★★★

We had an amazing stay in Islamorada! The Airbnb was exactly what we were hoping for clean, comfortable, beautiful, and in a great location. The host was absolutely awesome. Friendly, responsive, accommodating, and made everything easy from start to finish. We had a great time making memories with friends and family, and this was the perfect home base for our Florida Keys trip. We would definitely stay here again and highly recommend it to anyone visiting Islamorada. Thanks for helping make our trip such a great one!

Guest

Jul 2026
★★★★★

This house was perfect for our family trip. Being able to keep our boat in the basin made it easy and convenient.

Guest

Jun 2026
★★★★★

We loved the house and the property. It was essentially two 2 bedroom units, which was great for traveling with adult children. The water access was nice for fishing and swimming/snorkeling or relaxing. We saw lots of fish and sea live and caught some small ones. The mosquitoes were pretty bad in morning and evening hours so mosquito spray was a must but overall great experience.

Guest

Jun 2026
★★★★★

Thank you for providing such a beautiful space, which actually fit our family of 8, and for being so communicative. I felt a lot of pressure getting my family to the Keys for the first time, since I spent my childhood summers there but haven't been back in decades, so thank you for all of your support and recommendations. Everyone was comfortable, all of the promised amenities allowed us to pack lightly for our long drive and the house had everything we needed. We had such a relaxing time watching sunsets, swimming and kayaking. We ended up leaving the house for a snorkel tour with the recommended tour guide, which was really great for the kids, but we could have just stayed at the property for the entire time (and mostly did). The house was just gorgeous, and the Keys are just how I remembered--we can't wait to go back.

Guest

Jun 2026
★★★★★

We had a great stay in Sean’s place. Definitely recommend if you will stay at Islamorada for a few days.

Guest

May 2026
★★★★★

Very nice, comfortable place conveniently located for Islamorada activities.

Guest

May 2026
★★★★★

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!

Guest

Apr 2026
★★★★★

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!

Guest

Apr 2026
★★★★★

Love love love this place! Definitely would like to come back

Guest

Jan 2026
★★★★★

The Hidden Gem was a very nice place for our family to stay while we were in town for a wedding. Sean was easy to get in touch with when we had questions or needed help with something, quickly took care of anything that came up, and kept in touch with us. The rooms were clean, we had everything we needed. We would definitely stay here again, if we find ourselves in town. Thank you!

Guest

Jan 2026
★★★☆☆

Great location, clean and orderly space but we did have some issues with Wi-Fi. Pricing is getting close to full service hotels nearby with more amenities. Was satisfactory overall.

Guest

Dec 2025
★★★★★

Wonderful accommodation in a central location. Our group rented both the upstairs and downstairs units, which worked perfectly for our week-long stay over Christmas. We especially enjoyed the outdoor space and spent time fishing from the dock as well.

Guest

Dec 2025
★★★★★

Wonderful place, great location! We could walk to many restaurants and things to do. Units are well stocked and super clean! Love the marina for launching kayaks and fish watching. Would love to come back!

Guest

Nov 2025
★★★★★

The space was perfect. Sean was a very attentive and thoughtful host. I give the whole experience a 10 out of 10.

Guest

Nov 2025
★★★★★

This was one of my favorite places to stay! There were six of us in total and everyone raved about it. It was walking distances to shops and restraunts. Spectacular place and can’t wait to go back!!

Guest

Nov 2025
★★★★★

Sean was awesome. Never more than 5 minutes to respond to text messages. The homes were well equipped and comfortable. Loved the location and the privacy. Would 100% recommend!

Guest

Oct 2025
★★★★★

Great place to stay especially if you’re wanting easy access to the water/boat basin. We would highly recommend this spot!

Guest

Sep 2025
★★★★★

Our family had a wonderful time together at Sean’s property! The area was amazing and beautiful. We would definitely recommend staying here!!

Guest

Sep 2025
★★★★★

The title says it all, a true Hidden Gem! We celebrated my husband’s birthday with friends and two boats. The two units are well thought out and clean. The location is walkable to so much. The boat basin was really convenient. One boat we dropped in using their ramp but navigating getting the trailer in and out was a bit tight. The other was too big so we took it to Founder’s Park which is a 10 minute drive (20-30 minute boat ride) north and charged $25 each use. Trailer parking on-site is tight as well so you have to know what you’re doing. But having all of that available to you is incredible! Overall we had an exceptional time! Everyone plus a few others who stayed nearby all said the same thing, that it was perfect. I know we will be back.

Guest

Sep 2025
★★★★★

We had such fun! A great location to explore the keys from.

Guest

Aug 2025
★★★★★

Sean's place is truly a gem in the middle of Islamorada. The units are very nicely outfitted, the location is fantastic right on florida bay, and the short walk to the attached Marina with fresh water and power is easily the nicest we have stayed at. I'd highly recommend it to anyone looking for a great Airbnb in Islamorada with water access.

Guest

Aug 2025
★★★★★

Such an amazing spot with a perfect setup for families. We came with our kids and my parents for a lobster diving trip and Sean's place checked all of our boxes. We will definitely come back!

Guest

Nov 2024
★★★★☆

Great value spot for a big group- we rented out both units for 8 of us and it worked very well. Proximity to the water is fabulous!

Guest

Oct 2024
★★★★★

This unit is near the desirable mile markers in Islamorada. Very close to the best restaurants and across the street from Islamorada Brewing Co. We also walked to Mangrove Mikes Diner for a genuine keys breakfast. Easy walk to the gulfside amenity area.

Guest

Sep 2024
★★★★★

We had an amazing time! Hidden Gem is a perfect getaway destination and had everything we needed! The location was close to all our activities and restaurants with easy access to the water.

Guest

Aug 2024
★★★★★

What a great spot for a family get away. Clean , quiet and the boat dock area is fabulous. Snorkeling , swimming and fishing from the dock are wonderful for the kids ( and adults).

Guest

Jul 2024
★★★☆☆

We woke up after our first night mishap (son fell down the outside stairs in the rain) looking forward to a great week. It started with a gurgling noise coming from both downstairs bathrooms. Within minutes sewage was backing up into both showers and filling the unit with an un-pleasant smell. We contacted the mgmt group and had a plumber and cleaners come and resolve whatever issues were going on. It’s un-fortunate but this overshadowed events for the remainder of the week, wondering if it would return and it we would be in the shower when it decided to do so. The mgmt group was prompt in cleaning things up but has yet to make an attempt to make things right. As for the fall down the stairs. We found a sign at the top left of the stairs cautioning about the danger. I would not recommend the top unit for anyone with disabilities or someone elderly.

Guest

Jul 2024
★★★★★

We had a fabulous time at Hidden Gem. It was a long awaited get together of our adult children after learning that I (Cristi) is dealing with a medical situation. We needed the time and it was wonderful. Everyone comments about such close proximity to restaurants. We had a an issue with a breaker. Sean responded immediately to our text message and it was corrected minutes later. Thank you for providing such warm and amazing place for our family to reconnect. We have made fabulous memories at Hidden Gem

Guest

May 2024
★★★★★

Great location, amazing property, fantastic host. Will book again.

Guest

Apr 2024
★★★★★

This place was amazing and perfect for two families as it had both an upstairs and downstairs private kitchen. We travelled with a toddler and the family stayed upstairs, while others enjoyed downstairs. Beautiful surroundings! Comfortable beds, bathrooms, and all! I would totally come back! Great location for anything you want to do!!! HIGHLY RECOMMEND!

Guest

Apr 2024
★★★★☆

This place was great for families. We rented both units, so it worked out wonderfully. The only thing I will say is, this is not central heat and AC, although cold, the place, both units, especially upstairs was extremely musky and not that we used a boat slip, I expected to see the water from the location and it isn’t water front or view at all, just a small area for your boat. However, when renting both unit as a family, I highly recommend!!! It was spotless and allows for two living areas and some privacy. The places were both very comfortable. Although musky, we found the upstairs to feel cooler. I would absolutely recommend this if you are renting both units. Renting 1, it would have been a little odd with a shared courtyard and no privacy. Overall, I really enjoyed the stay.

Guest

Jan 2024
★★★★★

Sean was super communicative, flexible with our needs, and the place was even cuter in person! Walking distance to plenty of spots and you can view the bayside or Oceanside in two short walks. Everyone was happy our accommodations and I’d definitely recommend it to others. Thanks for a special Christmas vacation!

Guest

Nov 2023
★★★★★

Great place! Looking forward to staying again sometime. Beautiful location and property.

Guest

Oct 2023
★★★★★

Beautiful and well kept house, Sean is very easy to get a hold of and was extremely helpful

Guest

Aug 2023
★★★★★

10/10

Guest

Jan 2023
★★★★★

Cette maison était au delà de nos espérances , belle architecture , très confortable et belle décoration . 2 familles peuvent chacune dans un appartement. Situation idéale dans une végétation luxuriante près du bord de mer . Apéritif au coucher de soleil était sublime. En résumé un séjour paradisiaque avec la famille ( 7 personnes ) pour fêter mon anniversaire. En conclusion : Parfait

Guest

Jan 2023
★★★★★

Superfriendly host, answered quickly, asked if everything was ok. The apartments were clean, tidy and the beds were comfy. The outside area was really nice, and even had a cute cat that hung around during our stay. We rented a kayak from the business next door. Some of us saw both manatees and dolphins, and lots of birds and colorful fish when out with the kayaks. Would definitely recommend!