As we pulled into La Siesta Resort & Marina, the welcoming sign, framed by swaying palms and lush greenery, instantly set the mood for our mini escape. Just five hours from Orlando, Islamorada felt worlds away, with its tranquil ambiance and the promise of a peaceful, tropical retreat.
As a Florida native, I love the perks of being a Floridian and I am no stranger to the Florida Keys. Except, like most folks, I have spent the most time at Key West. I am happy to report that the upper keys, which are closer to Orlando than the lower keys like Key West, are full of romance and charm, and it is a shorter drive by comparison.
Our two nights there refreshed my husband and me, (though a few more nights would be even better.) Here is what to expect on your very own romantic getaway to Islamorada. Plus, highlights from our hosted stay at La Siesta Resort & Villas.
Road Trip from Orlando to Islamorada: Where to Stay, Eat, and Relax
Drivng to Islamorada
La Siesta Resort is located in Islamorada, Florida Keys, and it is very easy to get to. This beachside resort offers a tranquil and romantic escape ideal for couples seeking a quick getaway from Orlando. Approximately a five-hour drive from Orlando, the resort provides a serene atmosphere complemented by the natural beauty of Islamorada.
During our five hour drive I cranked up my vacation playlist full of Jimmy Buffett, Zac Brown Band, Irration, The Hip Abduction, and the like. I love road trips with my husband, sitting side by side, stealing the occasional quick kiss. Five hours from Orlando is just enough to feel like a real, true getaway without it being a grueling drive.
Tropical Hideaway with Plenty of Space
We checked into a spacious three-bedroom suite, which in this case rests just above the resort's office and front desk. La Siesta is an all-suite resort, meaning every single room type is a suite.
The living room and dining area were open, airy, and tastefully decorated in soothing tones, with plenty of seating for everyone. With our six-year-old in tow, the ample space made it easy to feel at home. He loved darting back and forth between rooms, and we appreciated the cozy yet modern furnishings that gave us space to unwind.
Sliding glass doors led out to a large balcony, where each morning we watched the sunrise while sipping our coffee and soaking in the beauty of the resort’s tropical landscaping. The master bedroom, with its large windows and plush bed, felt like a private oasis—a peaceful hideaway perfect for a quick romantic recharge.
Of course, since our large balcony faced the sparkling pool, our son requested that we spend every moment we could splashing there.
Relaxing by the Pool and Eco-Friendly Touches
One of our first stops was the resort's beachfront pool. Surrounded by thatched huts and string lights, it had an idyllic tropical vibe that encouraged us to slip right into vacation mode. As the day went on more guests arrived at the pool. Soon an unspoken rule seemed to be in effect as couples migrated to the deep end and families stayed near the zero-entry shallow side.
The resort even provided refillable water bottles—a small but appreciated eco-friendly touch that reminded us of La Siesta's commitment to sustainability. As luck would have it, our suite had a refillable water bottle station just outside our entrance steps, making it easy to stay hydrated as the Florida Keys sun beamed down on us.
I lounged by the pool with a cold drink (a mocktail margarita), watching the waves in the distance, while my husband splashed around with our son. It was easy to imagine this spot as perfect for couples alone, but it worked well with our family dynamic.
Beachfront Cottages
We also spent some time around La Siesta resort’s colorful beachfront cottages, where vibrant pink and green exteriors made the cottages feel like playful little beachside escapes.
These cottages offer couples a private, charming spot to stay if they’re looking for something cozier. There are only a handful of these cottages and they book quickly. And although it could be easy to feel some FOMO, rest assured the resort's regular suites are just as charming and well appointed.
Exploring Local Dining and Cozy Cafes
If you're anything like me, you feel compelled to get out and explore the local dining scene anytime on vacation or a quick getaway. With that in mind, there are lots of local dining options near La Siesta and a few small attractions and museums too.
Along the way to La Siesta the sign for Square Grouper Bar & Grill caught my husband's eye. We savored a mouth-watering grouper sandwich and fries, while overlooking the bustling marina. The fresh, local flavors hit the spot and added a taste of the Florida Keys to our trip.
And on our second night, and therefore our final night in Islamorada, we headed ten minutes down the road to Morada Bay Beach Cafe. Here we literally dined with our toes in the sand as Mother Nature treated us to a dazzling pink and purple sunset.
To ease the pain of having to depart, we ventured to the Midway Cafe on the morning of our check-out. This colorful and quirky spot is just around the corner from La Siesta. We walked there using the sidewalk just outside the resort and it took us less than ten minutes.
The bright walls and mismatched furniture added a touch of charm, and it was the perfect place for a quick breakfast before hitting the road. In fact, the name “Midway Cafe” comes from the fact that this gem is midway between Miami and Key West.
Adventure on the Water at Amara Cay
A real highlight was our boat trip with Wild Dolphin Tours. After our arrival day and enjoying the resort we woke up the next day to the sunrise over the water and ordered breakfast delivered to our suite. Truly a special moment.
Once we finished our glorious in-suite breakfast we headed half a mile down the road to Amara Cay, the sister resort to La Siesta. As guests of La Siesta, you have access to the amenities at both resorts. This means you can relax by the pool at both La Siesta and Amarta Cay too! There is even a complimentary shuttle van to take you between the two resorts (a five minute drive) as well as other local spots nearby.
Wild Dolphin Tours works with La Siesta and Amara Cay, having the ability to dock at the marina at either resort to give guests the ability to head out on the water and explore.
We briefly browsed the Amara Cay lobby we relaxed by the pool and ordered lunch at the tiki bar. We could see the marina, as we enjoyed the pool before our adventure on the ocean. Lunch at Amara Cay exceeded my expectations and the presentation made it easy to dine poolside, reclined in our lounge chairs.
After fueling up we grabbed our beach bags and walked out on the dock to meet our boat captain with Wild Dolphin Tours.
Out on the ocean, with our son bundled up in his life vest and sporting a straw hat to match his dad’s, we felt connected to the beauty of the surrounding islands and the endless blue water. Even as storm clouds gathered on the horizon it was easy to relax and appreciate this moment.
There’s something special about being on the water in Islamorada—it’s serene yet full of life, and it felt like a breath of fresh air for all of us. Even though we were there as a family, there were quiet, romantic moments to share as we drifted, surrounded by the peacefulness of the Keys.
Our phenomenal boat captain with Wild Dolphin Adventure Tours navigated the waters and took us to a favorite shallow spot for some snorkeling. The nearby storms caused the water to be a bit murky, still we caught sight of some small fish and aquatic life. The snorkel gear provided to us, included in the tour, surpassed any snorkel equipment I've used before – great quality!
After a three hour adventure on the water we returned to Amara Cay's marina. We soon returned back to La Siesta and pay homage to the resort's namesake, taking a siesta of our own in our spacious suite.
Paddleboard Adventures
Just a few steps away, the resort’s beach had paddleboards ready for us—perfect for a bit of adventure. There are multiple amenities included in your stay, including the use of paddleboards and kayaks. We watched other couples try it out, gliding over the clear, calm water, and had our own mini adventure on the water too.
The next morning was much windier and the activities cabana closed off the water activities as a safety precaution. Still, the beach at La Siesta is quite wide and large, offering plenty of space to enjoy the sand, with lounge chairs and beachside games.
Final Reflections
As we wrapped up our stay, we felt relaxed, rejuvenated, and grateful for our time in Islamorada. La Siesta Resort & Marina offers the perfect blend of peaceful seclusion and island charm, ideal for Orlando couples looking to escape the hustle and bustle.
Even with our son by our side, we found moments of romance and tranquility. Whether you’re drawn to the bright beach cottages, the inviting pool, or the local dining, La Siesta is a wonderful choice for a quick getaway in the Florida Keys—a place that makes you feel both far from home and completely at ease.
Important note: Our two night stay as well as dining credits and the boat tour were provided to us at no cost. Some purchases we made on our own at both La Siesta and Amara Cay, and we paid our own way at all dining outside the resort. We also paid for our travel to and from the resort.
La Siesta Resort & Marina
80241 Overseas Hwy, Islamorada, FL 33036
1 (888) 313-6200
$59 nightly resort fee includes Rum Runner water taxi, local shuttle service between MM77-MM85, daily bicycle rental, daily paddleboard and kayak rentals, enhanced Wi-Fi, complimentary coffee in the lobby 7:30 am – 11 am, one reusable water bottle (per guest per stay), self-parking, and beach and pool chaise lounges and umbrellas.
