Accommodations
King Bed · En-Suite Bath · Main Level
The ground-floor primary suite features a king bed, 65" Ultra HDR 4K Smart TV, and private en-suite bathroom. Wake to preserve views through sheer curtains and step directly out to the screened porch.
King Bed · En-Suite Bath · Upper Level
Ascend the spiral staircase to a stunning vaulted loft with exposed wood beams, skylights, and panoramic water and preserve views. The suite includes a king bed, dedicated workspace, en-suite bath, and a sitting area with board games and books.
Bunk Beds with Trundle · Main Level
The versatile guest room features bunk beds with a pull-out trundle plus an additional twin bed, comfortably sleeping up to four. Generously sized with ample closet space, coastal decor, and hardwood floors throughout.
Amenities
Your Hosts
As natives of the Chesapeake Bay area of Virginia, our lives have always been tied to the water. Among all the places we've explored, the Florida Keys hold a special place in our hearts. The unhurried pace, the endless horizon, and the salty breeze spoke to us — so we made it ours.
We've owned this home for over four years and have thoughtfully designed every detail so our guests can experience the Keys the way we do. This isn't just a rental — it's a retreat we cherish and enjoy ourselves. We welcome guests who appreciate the natural beauty of the Lower Keys and the laid-back luxury of coastal living.
We're always available to help with local recommendations, whether it's the best fishing spots, sunset cruise operators, or hidden restaurants the tourists don't know about.
— Josh & Megan
Elevated Stays
For guests who want more than a place to stay, Josh offers a fully guided, full-service experience during your time in the Keys.
Josh prepares every meal using locally sourced seafood and produce from the Keys, alongside curated meat options. From dockside breakfasts to multi-course dinners under the palms.
Explore the surrounding mangrove trails by kayak or paddleboard with Josh as your personal guide. Discover the backcountry waterways that make the Lower Keys unlike anywhere else.
Private designated driving anywhere in the Keys. Enjoy a night out on Duval Street, a sunset dinner in Islamorada, or a day in Key West without the worry of getting home.
Full-service options require a minimum of 5 consecutive nights during your stay. Inquire below for availability and pricing.
Guest Reviews
“We had an amazing stay at Finding Remo in Big Pine Key! The house was peaceful, private, and well stocked, with wonderful neighbors and very responsive hosts. We spent our days boating in both the Gulf and Atlantic, fishing, and lobstering, then came back to relax by the pool — it was perfect. Big Pine Key is such a great area with a laid-back feel, and Finding Remo made the ideal home base for our trip. Highly recommend!”
“This property exceeded our expectations. The layout allowed for privacy with the upstairs loft bedroom/bathroom combination. The screened in wrap around porch was a dream. When the private gate opens you truly feel like you are on your own island. The saltwater pool is heated and the landscaping gave amazing privacy. The beautiful Key Deer welcomed us everyday with a walk by hello. Josh & Megan were incredible hosts. Everything was just magical and we can't wait to return.”
“We’ve rented houses all over the Keys and this was hands down the most memorable. The property itself is stunning — gated, private, the pool is gorgeous, and the dock was our favorite spot every evening. But what set this apart was the concierge experience. Josh cooked for us almost every night and I’m not exaggerating when I say the meals rivaled any restaurant we’ve been to down here. Seared hogfish with mango from the yard, grilled lobster tail he picked up that morning from a local guy — just unreal. One afternoon he took us out on the paddleboards through the mangroves and we saw baby lemon sharks, horseshoe crabs, a massive tarpon just cruising right under us. My husband still talks about it. Josh also took us by boat out to the Content Keys — these pristine uninhabited islands in the backcountry — crystal-clear water, not another soul in sight. Felt like we had our own private island for the afternoon. The property is full of coconut palms and Josh would crack them open with a machete for fresh coconut water anytime we wanted some — little things like that made it feel so special. The house, the food, the personal attention — it’s not a vacation rental, it’s a private resort.”
“From the moment we pulled through the gate we knew this was going to be different. The property is immaculate — the tropical landscaping, the pool, the screened porch where we ate most of our meals. We opted for the full service package and it completely changed how we experienced the Keys. Josh had dinner ready our first night and every meal after that was a highlight. He has a real gift in the kitchen. Fresh grouper, yellowtail, beautiful salads with local produce — everything was thoughtful and delicious. He also took us kayaking through the mangroves one morning and it was pure magic. We floated right over a school of tarpon and spotted nurse sharks resting in the shallows. Carl and I caught a ton of mangrove snapper right off the dock and Josh filleted and cooked them for us that same evening — it doesn’t get fresher than that. One morning a manatee came right up to the dock and we just sat there petting it. Carl and I agreed it was the single best experience of the trip. We’ve already told everyone we know. This is the only way we’ll do the Keys from now on.”
“My husband and I travel quite a bit and rarely feel compelled to write a review, but Finding Remo deserves one. The property is beautiful — the heated pool, the lush grounds, deer wandering through the yard in the mornings. It feels very secluded even though you’re minutes from everything. We did the full service option and Josh absolutely spoiled us. He made the most incredible blackened mahi tacos our second night and followed it up with a stone crab dinner later in the week that I’m still dreaming about. He also grilled the most perfect ribeye one night for Richard — the man knows his way around a steak just as well as he does seafood. He took us paddleboarding one afternoon through these quiet mangrove channels — we saw stingrays gliding underneath us, a huge tarpon, dozens of little horseshoe crabs along the bottom, and even a pair of manatees drifting through one of the channels. It was so peaceful. He also drove us into Key West for dinner one evening which was such a nice touch — no worrying about parking or driving back. Richard said it felt like having a personal concierge at a five-star resort, and honestly that’s exactly what it is.”
"Dine under ceiling fans on the expansive screened porch, with sweeping preserve views and nothing but birdsong and gentle water."
Location
Situated on a serene canal in the heart of the Lower Keys, Finding Remo offers the rare combination of total privacy and effortless access to the best the Florida Keys have to offer.
Things to Do
These are some of our favorite places. From world-class dining on a private island to legendary dive bars, the Lower Keys offer an experience unlike anywhere else in Florida.
A private island accessible only by boat or seaplane. Michelin-recognized fine dining, world-class spa, and thatched-roof bungalows on four pristine acres. One of the most exclusive resorts in the United States — and it's accessible from your dock.
10 minutes by carRanked the #1 beach in America by Dr. Beach. Three pristine beaches with gin-clear water, world-class snorkeling at Looe Key reef, kayak rentals, and the iconic Old Bahia Honda Bridge. A must-visit.
15 minutesEstablished 1931. Walls plastered with over $90,000 in signed dollar bills, legendary pizza, smoked fish dip, and cold beer. A Florida Keys institution just half a mile from Finding Remo. You can't leave without going.
0.5 miles — walking distanceWaterfront beach bar and grille with your feet in the sand. Fresh seafood, craft cocktails, and live music every night. The perfect sunset spot with tiki bar vibes and a raw bar that doesn't quit.
10 minutesA Lower Keys staple known for the freshest local seafood in the area. Consistently rated one of the best restaurants between Key West and Marathon. Don't miss the fresh catch and key lime pie.
10 minutesUpstairs craft cocktail lounge above Square Grouper. Opens at 4:20 pm with artfully made cocktails, raw bar with fresh-shucked oysters, gourmet tapas, and live music nightly. Happy hour is not to be missed.
10 minutesA chain of pristine, uninhabited mangrove islands in the backcountry just offshore. World-class kayaking, paddleboarding, and bonefishing through crystal-clear flats. Accessible directly from your dock — no crowds, no development, just nature.
Direct access from property by boatOne of the most spectacular coral reefs in North America. Over 150 species of tropical fish, elkhorn coral formations, and crystal-clear visibility. A protected sanctuary offering snorkeling and diving experiences that rival the Caribbean — just miles offshore.
Short boat ride from Big Pine KeyJust 30 miles west. Duval Street nightlife, Mallory Square sunset celebrations, world-class dining, historic architecture, water sports, and the Hemingway Home. An easy day trip or evening out from Finding Remo.
30 miles westThe Lower Keys are a fishing and lobstering paradise. Wade the flats for bonefish and permit, cast from your dock for tarpon and snapper, or head offshore for dolphin, tuna, and grouper. During lobster season, head right out from the property to dive for spiny lobster in the surrounding waters. The backcountry channels accessible from your property are teeming with life, and the Gulf Stream is just a short run out. Two of our favorite charter captains:
Rates
Availability
Calendar syncs with Airbnb and VRBO. Select your dates below or book through your preferred platform.
28-night minimum stay per Monroe County ordinance. Calendars open approximately one year in advance. Returning guests have a two-week priority window after their stay to reserve the following year. For dates beyond one year out, please submit an inquiry below.
Reserve
Skip the middleman. We offer direct bookings with our own contract and flexible payment options.
Travel
Big Pine Key sits in the heart of the Lower Keys, with convenient access from several airports.
30 miles west
The closest commercial airport with daily flights from Miami, Atlanta, Charlotte, Dallas, and seasonal routes from major cities nationwide.
35 miles east
Ideal for private aviation. A popular choice for charter and private jet arrivals to the Middle Keys.
130 miles north
Full international service with a scenic 3-hour drive south along the Overseas Highway through the entire island chain.
165 miles north
Often the most affordable option with extensive domestic and international routes. About 3.5 hours by car.