Explore Oasis

305-684-3397 rentals@oasisfloridakeys.com

Elevated Retreat | Sunset Access + Boat Basin

★ 5.0 (50 reviews) · 4 guests Islamorada, FL

Elevated Retreat | Sunset Access + Boat Basin

4 guests · 2 bedroom · 2 bath

About this home

Elevated, 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. Set above the trees for a more open, airy feel, yet tucked into a peaceful setting. Enjoy walkable access to restaurants, shops, and breweries, plus fast WiFi and everything needed for a comfortable Keys getaway 🌴

● 2 bedrooms / 2 bathrooms (620 sq ft) ● Primary: King bed + en suite bathroom ● Guest room: King bed + separate bathroom ● Open living area + small kitchen ● Second-floor setting with a more open, airy feel ● Courtyard-facing (quiet, tucked-away setting) ● Shared external laundry room

Note: no closets or dressers—luggage racks and hanging space provided

This retreat is part of a unique, private, wooded waterfront property spanning the bay side of the Florida Keys. While the space 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.

Guests have full access to the entire space, 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 downstairs space. 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 and flexible arrival.

Located at Mile Marker 82.5 in the heart of Islamorada, this home 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
Barbeque utensils
Beach essentials
Bed linens
Blender
Boat slip
Body soap
Ceiling fan
Cleaning products
Coffee maker
Conditioner
Cookware
Dishes and silverware
Dishwasher
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
Kitchen
Microwave
Near Ocean
Outdoor seating (furniture)
Oven
Pack ’n Play/travel crib
Path to entrance lit at night
Patio or balcony
Private entrance
Refrigerator
Shampoo
Shower gel
Smoke detector
Stove
Suitable for children (2-12 years)
Suitable for infants (under 2 years)
TV
Toaster
Towels provided
Washer in common space
Waterfront
Wine glasses
Wireless Internet

Availability

★★★★★ 5 / 5 · 50 reviews

Guest

Oct 2026
★★★★★

Very comfortable place, clean and well maintained. Would certainly stay again.

Guest

Oct 2026
★★★★★

It was a great place to stay. I would definately stay there again. Great hospitality.

Guest

Sep 2026
★★★★★

The two bedroom apartment was beautiful with full kitchen, lots of light, and air conditioning worked great. The beds were very comfortable and everything was very clean. The location is what made this space special being part of a small multi unit setting with common area for grilling and gathering. You could not see the water from the windows but it was only a short walk to the water with awesome sun set views. There is a protected basin for driving your boat right up and keeping boat close while you stay any the property. Also walkable to the Islamorada Brewery.

Guest

Sep 2026
★★★★★

We had a wonderful stay at Sean’s Airbnb! The place was comfortable, welcoming, and perfect for our family. We had an amazing time and truly enjoyed our visit. Thank you so much, Sean, for hosting us and making us feel welcome. We would definitely stay again!

Guest

Jul 2026
★★★★★

Sean was great host! His instructions were very clear and concise. When we had questions, we messaged him and he responded quickly. The laundry room on site came in handy. Would definitely come back to this Airbnb. Convenient location, close to grocery store, launch ramps and attractions.

Guest

Jun 2026
★★★★★

The location is convenient to Islamorada, fishing, and good restaurants. The rental was as described and had the items described in the listing. It is an upstairs unit.

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 in common space
  • Hangers
  • Iron
  • 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
  • Barbeque utensils
  • Blender
  • Body soap
  • Cleaning products
  • Conditioner
  • Drying rack for clothing
  • Emergency exit
  • Essentials
  • Family/kid friendly
  • Fishing
  • Garden or backyard
  • Pack ’n Play/travel crib
  • Path to entrance lit at night
  • Private entrance
  • 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
  • Wireless Internet

Entertainment

  • TV

Guest

Oct 2026
★★★★★

Very comfortable place, clean and well maintained. Would certainly stay again.

Guest

Oct 2026
★★★★★

It was a great place to stay. I would definately stay there again. Great hospitality.

Guest

Sep 2026
★★★★★

The two bedroom apartment was beautiful with full kitchen, lots of light, and air conditioning worked great. The beds were very comfortable and everything was very clean. The location is what made this space special being part of a small multi unit setting with common area for grilling and gathering. You could not see the water from the windows but it was only a short walk to the water with awesome sun set views. There is a protected basin for driving your boat right up and keeping boat close while you stay any the property. Also walkable to the Islamorada Brewery.

Guest

Sep 2026
★★★★★

We had a wonderful stay at Sean’s Airbnb! The place was comfortable, welcoming, and perfect for our family. We had an amazing time and truly enjoyed our visit. Thank you so much, Sean, for hosting us and making us feel welcome. We would definitely stay again!

Guest

Jul 2026
★★★★★

Sean was great host! His instructions were very clear and concise. When we had questions, we messaged him and he responded quickly. The laundry room on site came in handy. Would definitely come back to this Airbnb. Convenient location, close to grocery store, launch ramps and attractions.

Guest

Jun 2026
★★★★★

The location is convenient to Islamorada, fishing, and good restaurants. The rental was as described and had the items described in the listing. It is an upstairs unit.

Guest

Jun 2026
★★★★★

Sean was fantastic and very personable. We appreciate the recommendations provided via app chat and the binder they provide in their air B&B. We used the binder a lot! The place was clean, cozy and the location was great. Highly recommend, you won’t regret it!

Guest

Jun 2026
★★★★★

Great place, would definitely stay there again!

Guest

May 2026
★★★★★

This was a great little place for a quick getaway.

Guest

Apr 2026
★★★★★

We LOVED our stay in Hidden Gem! The setting is lovely. Just a short, private walk to a beautiful spot on the water. Sunsets were glorious! The apartment was perfect for us -- a couple traveling with our grown daughter. We used the kitchen (so well-stocked!) and the outdoor BBQ every night for dinner, which we enjoyed outdoors on the patio. Everything was clean and fresh. The location is convenient to spots both north and south along the Keys. Sean was a pleasure to deal with - quick, friendly responses. We would love to return. Highly recommend!

Guest

Apr 2026
★★★★★

This place was great. The location was perfect for us because we chartered a boat for fishing close by. And it was close to restaurants. The place was squeaky clean and very cutely decorated with retro style appliances in the kitchen which added to the charm. The only downside is there isn't a ton of communal space inside the apartment. But there are plenty of tables downstairs in the shared patio space to hang out and play games. Would definitely stay here again!

Guest

Apr 2026
★★★★★

Sean is a great, attentive host. Makes sure your stay is perfect. Hidden Gem is an amazing place.

Guest

Apr 2026
★★★★★

Our favorite location and stay during our travel from Key West to Miami. Condo was spotless and communication was excellent. Local book and recommendations were a plus. Only 6 units in total share this same location, very private and loved the water access, ramp, and dock. Everyone we spoke to seemed to be coming here for years. Excellent local food, lots to do, and great private sunsets each night.

Guest

Apr 2026
★★★★★

Sadly, we only had two nights at Hidden Gem Islamorada! Sean's place was such a delight in every possible way. Charming spot, lovingly decorated, and totally immaculate. The 2BR/2BA space was the perfect size and layout for our party (my husband, me & two teen girls). The communication from Sean from the outset was most appreciated--the property is "tucked away" from the road, but we had no problem finding it with his proactive instructions. We arrived a little ahead of schedule and he was gracious enough to let us check in early. Property access was easy, and the guidebook provided many wonderful local suggestions for restaurants (with spectacular food/sunsets!) One of the things we loved most was the semi-private access to the kayak ramp. We rented kayaks from Backcountry Cowboy (next door, at the suggestion of Sean). They delivered our kayaks to us and we enjoyed exploring the bay on our own time. The girls cite this as the highlight of our trip! Love this place!!

Guest

Apr 2026
★★★★★

We loved our stay here and would definitely stay again.

Guest

Jan 2026
★★★★★

This place was perfect for two couples to meet for a long weekend getaway. The beds are very, very comfortable. Sean's recommendations for restaurants and activities were superb. Highly recommend!!

Guest

Jan 2026
★★★★★

Hidden Gem was as shown in pictures, clean and modern looking. The outfitters right next door was so convenient for bike and kayak rentals, and the area was also very walkable to bars and restaurants. You can view beautiful sunsets at the boat launch area on the property and beautiful sunrises, just across Hwy 1 (end of Dogwood street next to the Islamorada Brewery). Locals are so friendly, and we very much enjoyed our stay.

Guest

Jan 2026
★★★★★

This is the place to stay. Perfect location. Perfect set up. Wonderful to work with. I would highly recommend.

Guest

Jan 2026
★★★★★

Sean and team made this experience very memorable. The space was immaculate and very peaceful. Highly recommend!

Guest

Dec 2025
★★★★★

Excellent host and property. Great directions for finding a hidden property, easy check in, very clean. Would gladly stay again in the future.

Guest

Nov 2025
★★★★★

Clean property exactly as described, with cute décor and everything you need—bath supplies, kitchen essentials, ice, and plenty of towels, including beach towels. The bathroom was stocked with shampoo, conditioner, and soap. Fans and a well-working AC kept the place cool and comfortable. The unit sits on a quiet cove perfect for taking out kayaks and paddleboards, with a rental shop right next door so you can walk them over and head straight to the beach. The bay was calm and enjoyable, making it easy to spend the day on the water. We were pleasantly surprised by how walkable the area was—restaurants, breakfast spots, coffee, and shopping were all close by. The host was excellent: attentive, responsive, and helpful. There was ample parking, and the location was peaceful. Islamorada was truly a joy to experience.

Guest

Nov 2025
★★★★★

We had a nice stay. Sean was very helpful when I had questions. Would stay again

Guest

Nov 2025
★★★★★

Place was just as described. Sean was very active with sending out all notifications and not having to ask for information. Would definitely stay here again.

Guest

Nov 2025
★★★★★

My family stayed at the Hidden Gem last weekend, it truly lives up to its name! The location was excellent, walked to a few places for food and drinks. The area outside of the rental house was great, really enjoyed sitting out near the marina. Definitely a place that I would rent in the future! Sean is a great host, very responsive and helpful

Guest

Oct 2025
★★★★★

The perfect Gem, love the location and everything is quality , beds linen , kitchen and all the nice thing even a fresh orange juice crush lol, this place has all the toys bells and whistles. The perfect vacay

Guest

Sep 2025
★★★★★

Amazing place to stay! Boat slip was perfect! Absolutely BEAUTIFUL place!

Guest

Aug 2025
★★★★★

It really is a Hidden Gem with convenient access to a boat ramp. Loved it.

Guest

Jul 2025
★★★★★

Very responsive. Very clean place. The air conditioning worked great on very hot days. Very happy with our stay there.

Guest

Jul 2025
★★★★★

Fantástico alojamiento, de los mejores que hemos estado en Florida y en el mundo (y hemos estado en unos cuantos!!), el cleaning crew hace un impecable trabajo. El apartamento se mantiene tal y como se ve en las fotos. Echamos de menos haber reservado más días aquí porque realmente fue maravilloso. Las recomendaciones locales de Sean igual de estupendas!

Guest

Jun 2025
★★★★★

We stayed at Hidden Gem for a long weekend. The location is fantastic as you are walking/bike riding distance to plenty of shops and restaurants. The unit was adorable and was perfect for 2 couples. We had everything we needed to cook meals and grill out. Onsite trailer parking and assigned unit parking spots was a plus! The boat basin is very protected and the bay is perfect for a swim. We will definitely stay again.

Guest

May 2025
★★★★★

I had a wonderful stay at Sean’s place! The home was absolutely beautiful—clean, comfortable, and exactly as described. Sean was a fantastic host: responsive, welcoming, and made everything super easy from check-in to check-out. I would absolutely stay here again and highly recommend it to anyone looking for a relaxing and well-kept spot in the Florida Keys.

Guest

Apr 2025
★★★★★

Came here for my fiancés birthday and it was such an excellent place to stay. It was clean, comfy, and had an excellent location. Will absolutely be back!

Guest

Apr 2025
★★★★★

Truly hidden gem. Super host. Wish I could've stayed longer.

Guest

Feb 2025
★★★★★

This place truly is a hidden gem. Just steps from the water and close to many other attractions, it's a wonderful place to vacation. The unit is lovely, comfortable, spotless, and well-appointed, and the patio is gorgeous. Plus, Sean and his wife couldn't have been more responsive, helpful, and gracious.

Guest

Jan 2025
★★★★☆

We were satisfied with our stay, but it wasn’t perfect. Positives… The location is excellent, close to many restaurants and destinations. The decor is very cute, immaculate beach-house vibes. Kitchen is well stocked, big TV works well in guest mode, and the AC is powerful and very quiet. But, a few cautions too… It was a bit hard to find the place initially, especially if you arrive after dark. We found there were a lot of bugs — maybe the walls or foundation don’t seal totally. This was annoying, we were cleaning up dead bugs every day. And the showers didn’t drain super well. Overall, for the steep price, we felt this was satisfactory but not amazing. 4/5

Guest

Nov 2024
★★★★★

This literal Hidden Gem was everything and more! We struggled to find it at dark but that made it so much better because it was off a main road and hidden for privacy. The view by the water turned out to be our favorite spot to hangout. Unit was fully stocked with everything we needed. Such cute places around that are easily walkable. Lots of wildlife and very fun kitty hung out with us. We are already contemplating coming back.

Guest

Nov 2024
★★★★★

Incredible spot and incredible host. Truly a “hidden gem”. 10/10 would recommend staying here!!

Guest

Oct 2024
★★★★★

Perfect space in a beautiful location! The home accommodated two couples perfectly with two private bedrooms and two bathrooms and a comfortable living area, all decorated with a tasteful eye (just look at the photos; this place is adorable!). The location is so peaceful, too! Just a short walk to the water, it’s the perfect spot to start your day with a cup of coffee or wind down in the evening after a day of adventure. Situated in Islamorada, it’s a perfect halfway point between Miami and Key West. There are a handful of cafes/restaurants/bars within walking distance and many others within a short drive. The host is attentive and affable. 100% recommend! Book your stay here - you will not be disappointed!

Guest

Sep 2024
★★★★★

Very clean and tidy spot; had everything ready for a vacation on the water. Very responsive host and friendly neighbors.

Guest

Jun 2024
★★★★★

Wir haben uns als vierköpfige Familie sehr wohl in dieser Unterkunft gefühlt und würden jederzeit wiederkommen oder die Unterkunft an Freunde und Bekannte empfehlen. Besonders war die kleine Badestelle gegenüber hinter der Brewery - sie ist wunderschön und hat uns ebenso gefallen wie die Unterkunft an sich. Sie Kommunikation war jederzeit freundlich, hilfsbereit und schnell. Vielen Dank für die schöne Zeit!

Guest

Jun 2024
★★★★★

Great location in Islamorada - we could walk to the Lorelei restaurant or take in the sunset from the private dock and pier. The rental was beautiful and clean and as described. Would highly recommend!

Guest

May 2024
★★★★★

Place was clean, beds comfy no complaints here.

Guest

Apr 2024
★★★★★

This place is awesome. It's exactly what my family (3 people) needed during our trip to the Keys. The beds are great, plenty of amenities, close proximity to a ton of outdoor activities (snorkeling, kayaking, etc.), etc. We would definitely stay here on our next trip to this part of the world.

Guest

Mar 2024
★★★★★

Sean's place in Islamorada was amazing! Very well equipped with everything you need to feel right at home. Beds were extremely comfortable, the grounds were beautiful and that patio on the water!!! We spent several days out there lying in the sun, reading and just relaxing. The location was very walkable to several local restaurants and breweries. When we didn't walk we just called for a ride using the Freebee app which serves the local Islamorada area. Only thing we wished we had was a boat to explore the local area - and if we did, the dock space that comes with your lodging was a true gem. If we come back to the area we will be sure to stay here again.

Guest

Mar 2024
★★★★★

We loved our stay in this house in Islamorada! The house is very well decorated and is great for 4 people. The location is amazing! We enjoyed many sunsets as the house has an easy access to the water. We are looking forward to being back!

Guest

Jan 2024
★★★★★

This property is an excellent find in Islamorada! Super convenient and walkable to many things. Clean and updated space. The beautiful Gulf views and boat slip access are a wonderful bonus. I would highly recommend to anyone looking for a home base in Islamorada.

Guest

Dec 2023
★★★★★

Truly a gem! Thank you Sean will be back!

Guest

May 2023
★★★★★

This place was absolutely perfect for me and my husband. Its a quaint little place beautifully decorated and in prime location with great access to the water for kayaking and paddle boarding. Very convenient to almost anything from shops, restaurants, coffee shop, trails, beaches and more. Some were walkable as well. It’s small but all we needed since we only spent time in the house to shower and sleep. Easy check in and out process. No complaints! Would highly recommend and stay there again!

Guest

Mar 2023
★★★★★

We met Sean the first day we arrived because he was replacing a sun shade that had torn in the back yard. He was very friendly and helpful, providing us recommendations about where we could get something to eat and watch March Madness. He was spot on. The property was beautifully landscaped and a short walk to the water where we enjoyed our coffee in the morning and a glass of wine at sunset. We’ll be back!

Guest

Jan 2023
★★★★★

This was our first trip to the Florida Keys - The Airbnb was perfect for our needs! Two couples meeting up for a little vacation. The two bedrooms/two bathrooms situation worked out nicely for us. The place was super clean and the beds were comfy! Sean was a great host - He checked on us to make sure we had everything we needed. I highly recommend!