Many of Islander Resort’s guests are repeat visitors, and not just once- or twice-return guests, but the year-after-year, generation-after-generation type. And your first impression of the resort — a vintage, larger-than-life sign seen from Overseas Highway — is a testament to those travelers. When you pass the icon to reach Islander Resort, you’ll quickly find that the old(ish) hotel has updated itself, too, adequately blending the best of both worlds.

Many of the hotel’s guests don’t just stay for a few nights or even a week, either; they’re likely to stay for up to a month at a time. Why, you ask? It’s simple. Islamorada is a low-key (no pun intended) Florida Keys island, and much of the area’s ambiance can be experienced right at the Islander Resort. The hotel has a private beach (with spectacular sunset views), two oceanfront swimming pools, a fishing pier and several boat slips. It’s also inhabited by wildlife, which includes large, colorful iguanas, one of which we saw when we visited!

Additionally, it offers basketball, volleyball, shuffleboard, complimentary breakfast and an onsite restaurant. If that’s not enough of a sell, we don’t know what is. But consider that every one of the hotel’s spacious units has a fully equipped kitchen and porch, too, completing its quest to provide everything a family needs — and then some — in Islamorada.

Islander Resort has 114 spacious lanais and villas, housed in several one-level buildings.
Each unit has tiled floors and simple, yet pleasant décor, with pale yellow and cobalt blue pallets, complimented by seashell and floral prints. Townhomes are also available.

The Courtyard Double Lanais are ideal for families, as they provide two double beds, along with a fully equipped kitchen, table with chairs, and a porch with another table and chairs, reachable by sliding doors. Bathrooms, surprisingly small in comparison, have shower and tub combinations.

Courtyard Villas and King Villas, similar to standard suites, are also suitable for families. These units have a king bed in one area, and a sofa bed in another; the two areas are separated by an open passageway. They also have kitchens with tables and chairs inside and outside, as well as work areas. If you want complete privacy, opt for a One-Bedroom Suite, which basically has the same amenities, but with a door to separate the bedroom from the area in which the sofa bed and living area are located.

Bayside Townhomes, ideal for large groups, come in three variations, though each one has two separate bedrooms with queen beds, along with two bathrooms. They also have large living areas with sofa beds. This unit sleeps up to six or seven people (with the use of a rollaway bed or crib, available upon request).

All units have flat-screen TV's, hairdryers, safes, irons and ironing boards. ADA compliant and connecting rooms are also available.

Note: Consider whether you want to be closest to the pool area, ocean or main building, where complimentary breakfast is served, when you reserve your room. The resort's buildings and facilities are pretty spread out.

Islander Resort has a private beach with lounge chairs, and it's one that should not be missed, particularly at sunset when you can enjoy a peaceful stroll and breathtaking views of the Atlantic Ocean.

Still, the hotel's two swimming pools -- both of which are oceanfront and one of which features zero-entry -- reign supreme with families, who spend much of their time there. There's also a hot tub for families to enjoy. Be aware that the pool areas are not manned by lifeguards.

Other offered activities include basketball, volleyball and shuffleboard, along with boat slips and a fishing pier, lighted at night for sea life sightings. You can rent a bike or kayak at the hotel, as well.

Complimentary continental breakfast is offered in a casual dining room adjacent to the lobby, located in the resort's main building. It includes cereal, bagels and other pastries, along with coffee and juice.

The resort's restaurant, Guy's Beachside Bar & Grill, offers alfresco, poolside dining, complete with views of the Atlantic Ocean. Open from 11 a.m. to 10 p.m. daily, it serves lunch, dinner, dessert, snacks and cocktails. It also offers a kid's menu and takeout service, which includes boxed meals, ideal -- though expensive at $22 per person -- for day trips or for a relaxing afternoon or evening in your room.

All kids' meals are $7, and include chicken fingers, hamburgers and grilled cheese sandwiches. Children's side dishes, which are also perfect for poolside snacks, include applesauce, fruit salad, and veggies and dip.

The regular lunch and dinner menus offer an array of small plates, salads, soups and main dishes. For lunch, small plates include conch fritters, tacos and ceviche. Salads are fairly standard, with Caprese and Caesar offered, and main dishes include burgers and sandwiches. The dinner menu is more extensive, offering lobster macaroni and cheese and seared scallops for appetizers, with crab cakes, New York strip steaks and duck for dinner. Albeit the kids' meals, lunch and dinner are sort of pricey here; lunch entrees range from $12 to $18, and dinner entrees range from $25 to $30.

On Saturdays, the hotel hosts a pig roast on the beach at 6 p.m. For $35 per person, you can enjoy sweet, fried plantains, snapper ceviche, and Cuban garlic bread and chicken, along with a selection of desserts. Since the event doesn't include a specific children's menu, we suggest it for a date night or for families with older children (or those who enjoy Cuban cuisine).

Additionally, you'll find grills and picnic tables around the resort. Stop by The Trading Post, just a few minutes away, to buy all the fixings for a family barbecue. Payfair Supermarket, though farther away (eight miles), has a bigger selection of food.

All About the Extras
Free Wi-Fi is available throughout the property, and is included in rates.

The hotel doesn't provide babysitters, but can recommend you to an outside service should you need one.

Pets are welcome to stay at Islander Resort for a $75 non-refundable fee. They are welcome to join you at Guys Beachside Bar & Grille, as well, but are not permitted in the pools.

Guy"s Beachside Bar & Grill offers special meals for Thanksgiving, Christmas and other holidays. These meals can also be boxed if you're on the go.

Islander Resort has a fitness room, and also houses the Florida Keys Conference Center, a fairly new facility that's perfect for weddings, meetings and other events.

Local wildlife includes chickens and roosters, seen in the yards of homes and restaurants throughout the Florida Keys. That said, there's a chance you'll be awakened by a rooster early in the morning, as we were when we stayed in one of the 200-numbered buildings. Our friends in the 300-range building didn't have this problem, but there's no telling when and where this will happen!

The Art of Smart Timing
December through April is peak season in Islamorada, and pretty much all of the Florida Keys; expect to pay premium rates during this time. You'll find cheaper rates May through November, which is a hot, but excellent time to visit the area.

Getting There
If you're traveling to Islamorada by plane, fly into Miami International Airport and rent a car. Reliable, public transportation isn't readily available in this area, so you'll want to drive to the hotel. You'll also need a car to get around Islamorada, where attractions are fairly spread out across the island. Miami International Airport is about an hour from the Islander Resort.

For Mom and Dad
Make a reservation at the Green Turtle Inn, just 5 minutes from the Islander Resort. There, you'll enjoy delicious food in a dimly lit setting that feels casual enough to wear jeans in, but fancy enough for a romantic evening. Try the turtle chowder and lobster macaroni and cheese.

If you can't get away from the hotel, you can still enjoy a quiet stroll along the private beach, followed by or preceding a cocktail at Guy's Beachside Bar & Grill.