La Siesta Resort in Islamorada: A Family-Friendly Trip in the Florida Keys
Planning a family getaway that balances relaxation and fun can feel like a challenge, but thankfully there are so many incredible destinations within driving distance of Orlando. Islamorada in the upper Florida Keys is one of them.
Located just five hours from Orlando, this serene, tropical retreat combines spacious accommodations, kid-friendly amenities, and outdoor adventures. My family and I had the pleasure of staying for two nights, hosted by La Siesta Resort & VIllas. Here is what we loved, what we would do differently next time and nearby spots for dining with kids.
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La Siesta Resort & Villas in Islamorada with Kids
As a Florida native, I love the perks of being a Floridian, from travel to activities, and it’s such a joy to raise our son here. But like many folks, the Florida Keys generally bring up visions of 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 relaxation and charm, and it is a shorter drive by comparison.
Spacious Accommodations That Feel Like Home
We stayed in a three-bedroom suite at La Siesta Resort & Villas, and it was the perfect fit for our family of three. The master bedroom offered a cozy retreat for us parents, while our six-year-old, loved having his own space to unwind.
The suite’s open-plan living and dining area provided plenty of room for family meals and relaxation. One of our favorite features was the large balcony, where we could enjoy the sunrise together, surrounded by swaying palm trees and lush greenery.
But this gorgeous view also overlooked the pool. You can probably guess what happened anytime our son caught a glimpse of the pool… we ended up poolside a lot!
Poolside Fun and Ocean Views
The resort’s beachfront pool became our go-to spot each afternoon. It is a bit small, no frills aside from being zero-entry, and that suited us just fine.
If you’re looking for Florida resorts with water parks, this is not one of them, but sometimes you just need a calm place to relax.
While our son splashed in the pool, we lounged under the thatched-roof cabanas, sipping cold drinks and soaking in the stunning ocean views. The pool area’s family-friendly atmosphere made it easy to relax while also engaging with our son – and we made friends with other families. We even noticed a thoughtful eco-friendly touch—the resort provides refillable water bottles, reducing single-use plastic waste.
Underwater Adventures and Relaxing Moments at Amara Cay
One of the best features of La Siesta is that it has a sibling resort five minutes down the road, Amara Cay.
On our second day at Islamorada, we ordered breakfast in bed (a service available at La Siesta and Amara Cay). Then we hopped in our family car for a short 3-minute drive to Amara Cay where a hosted snorkel trip with Wild Dolphin Tours awaited.
We arrived in time for a relaxing mid-morning swim in Amara Cay’s pool. Guests of La Siesta have access to Amara Cay’s amenities, including the pool. The poolside bar and dining options are more elaborate at Amara Cay compared to La Siesta, so we made a mental note to grab lunch here after our adventure on the water.
Our snorkel trip and boat tour with Wild Dolphin Tours gave us an up-close look at the vibrant watery world of the Florida Keys. Watching our son’s excitement as he perched at the front of the boat, straw hat and life vest firmly in place, was unforgettable. Captain Kevin made sure to keep a watchful eye while also pointing out some kid-friendly spots.
The calm waters and surrounding mangroves provided a peaceful backdrop for spotting wildlife and exploring the beauty of the Florida Keys. For families with older kids, La Siesta resort also offers paddleboards and kayaks for some on-the-water fun.
After our aquatic escapades, we headed back to Amara Cay Resort. The lush lawn and inviting outdoor dining area were perfect for a leisurely meal. We enjoyed some poolside drinks (I had a mocktail) and we LOVED our lunch served in plastic trays – making it super convenient to dine while lounging in our pool chairs.
Surrounded by swaying palms and the gentle sea breeze, it was the ideal spot to take in the beauty of the Keys while savoring a moment of quiet family time.
Local Dining on Islamorada
When it came to dining, we found plenty of family-friendly options nearby.
At the suggestion of Captain Kevin, we headed ten minutes down the road to Morada Bay Beach Cafe. What a beautiful place for a casual dinner with our toes in the sand. Our son gladly ran around the wide-open sandy area. My husband and I snuck in a few romantic kisses during the gorgeous sunset while our boy enjoyed the extra space.
A visit to the quirky and colorful Midway Cafe was a hit with our trio, thanks to its fun decor and delicious snacks. We walked there on our departure morning – it took just about five minutes to walk from La Siesta.
A variety of breakfast sandwiches and pastries fill the menu alongside specialty coffees. The indoor seating is limited, but there is plenty of outdoor seating. Just be aware it is near two roadways so make sure the kiddos stay safe and away from the street.
We wrapped up our Islamorada trip with a laid-back lunch at the Square Grouper Bar & Grill, where the grouper sandwich and fries were a big hit with the adults. And our son enjoyed walking around the marina while waiting for our food and after our meal. It made for a great way to bid farewell Islamorada and La Siesta Resort.
Our short trip packed in some precious memories and some much needed rest.
La Siesta is Perfect for Families
From spacious suites to kid-approved activities, La Siesta Resort offers everything a family needs for a memorable Florida Keys vacation. The relaxed atmosphere, friendly staff, and convenient location make it an ideal choice for families looking to reconnect and recharge.
La Siesta Resort & Villas
80241 Overseas Hwy, Islamorada, FL 33036
(844) 207-9265
