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10 Best Resorts on Islamorada, FL

Written by Shandley McMurray
Apr 2, 2021

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Beautiful Islamorada offers visitors an intimate and luxurious escape halfway along the Overseas Highway in the Florida Keys. Although small (it's only about seven square miles in size), this pretty paradise boasts an impressive mix of art, history, and lovely beaches.

Islamorada's extensive selection of fun attractions keep visitors occupied, and the large variety of resorts make it easy to find the perfect place to stay. Islamorada is known as the sportfishing capital of the world, so you'll want to get in some angling while you're here.

Whether you're hoping to build sandcastles and splash in the emerald waters with your kids, or you want to enjoy a tranquil beach vacation in a plush hotel with a spa, you'll find an ideal spot to rest your head in Islamorada.

Use our list of the best resorts on Islamorada to help you choose the right accommodations for your trip.

Note: Some businesses may be temporarily closed due to recent global health and safety issues.

1. Islander Resort

Photo Source: Islander Resort
Photo Source: Islander Resort

It's easy to see why so many guests fall in love with the Islander Resort. One of the best Florida Keys resorts for families, this luscious spot oozes natural beauty in the form of tall, verdant palm trees and a pristine 24 acres including white, sandy beach.

Kids will love jumping about in the two heated saltwater pools and running around the on-site splash pad. Head to the beach for some snorkeling, kayaking, paddleboarding, fishing, or bodysurfing - the possibilities are endless. Complimentary bike rentals, basketball, volleyball, ping pong, and shuffleboard are also available for land-based fun.

When hunger strikes, you'll find plenty to tempt your palate at the property's two eateries: Tides Beachside and Elements Lounge & Restaurant. Insider's tip: Visit Tides on a weekend afternoon for live entertainment or on a Thursday at dusk for family movie night.

If you're looking for extra space, choose a specialty suite; they include a kitchen, which makes feeding little ones a cinch.

Address: 82100 Overseas Highway, Islamorada, FL

Accommodation: Islander Resort

2. Cheeca Lodge & Spa

Photo Source: Cheeca Lodge & Spa
Photo Source: Cheeca Lodge & Spa

A long wooden pier juts into the azure Atlantic waters off the white, sandy beach at Cheeca Lodge & Spa. It welcomes guests (which have included presidents and celebs) to bask in the peaceful bliss enveloping this lush island haven.

Pillow-top mattresses adorn the comfy beds of each spacious guest room and suite, which are adorned with tropical-themed décor and balconies. After wandering around the extensive 27-acre property, these rooms offer the ideal environment to unwind. Don't worry, there are bikes on hand to make it easier to get from one spot to the next.

Three restaurants will curb your cravings as you gorge yourselves on an ocean vista as phenomenal as the entrées. If you choose to dine off-site, make use of the free shuttle service, which drops guests anywhere within a two-mile radius of the resort.

Bring the kids along. They'll love the games room, Xbox Arcade, heated pools, and family-based activities, including beach cruiser bicycle rides and water sports. Camp Cheeca will keep them occupied while you spend time in the adults-only pool, or spoil yourself in the luxurious Spa at Cheeca Lodge.

While you're here, take advantage of the other lush amenities: fish off the pier; play a game of pickleball, tennis, basketball, or shuffleboard; or try your hand at making par on the 9-hole golf course.

Address: 81801 Overseas Highway, Islamorada, FL

Accommodation: Cheeca Lodge & Spa

3. Amara Cay Resort

Photo Source: Amara Cay Resort
Photo Source: Amara Cay Resort

The gorgeous Amara Cay Resort is also home to a pristine private beach, and boy is it a beauty! Picturesque hammocks pepper the sandy shore, hanging from swaying palm trees that offer shade from the hot, Floridian sun. Lounge in a thatched hut or take a dip in the zero-entry pool.

Relax in a swinging chair or gather around an evening fire pit to soak up the ambience at this luxe resort. Forgot your swimsuit? No worries. The Island Trendz Boutique makes it easy to shop for everything from stylish beach wear to souvenirs.

The resort fee includes water sport rentals such as kayaks and SUPs, as well as beach chairs, towels, lawn games, bicycles, fitness center access, and a free shuttle to places that lie within four miles of the hotel.

Kick back in a large room featuring a relaxing mix of modern- and tropical-themed luxury, complete with a furnished balcony. Grab breakfast in the Dining Room or at Reelburger or munch on lunch or dinner at Tiki Bar for a poolside respite. Insider's tip: Dinner is served on Reelburger on Fridays and Saturdays.

Address: 80001 Overseas Highway, Islamorada, FL

Accommodation: Amara Cay Resort

4. The Caribbean Resort

Photo Source: The Caribbean Resort
Photo Source: The Caribbean Resort

Guests of the aptly named The Caribbean Resort stay in one of a variety of adorable, upscale homes rich in Caribbean charm (we're talking teak and mahogany furniture and brightly colored fabrics). Furnished porches only add to the island feel, while the outdoor grill, in-unit kitchen, and washer-dryer make it easy to feel truly at home in this pretty paradise. The only thing you'll wish for is more vacation time!

Whether guests choose to rent by the day, week, or month, they will have full access to the resort's amenities. These include a gorgeous pool kept cool by the surrounding garden bursting with palm, pineapple, and banana trees. A hot tub helps take the edge off cool nights, while waterfalls lull visitors into a sense of overall calm.

Activities like stand up paddleboarding, kayaking, and bicycling are also complimentary. While you're at it, why not borrow a fishing rod and try your luck off the 45-foot pier? Insider's tip: dawn is the optimal time for reeling in a big one.

Address: 117 South Carroll Street, Islamorada, FL

Accommodation: The Caribbean Resort

5. Postcard Inn Beach Resort & Marina

Photo Source: Postcard Inn Beach Resort & Marina
Photo Source: Postcard Inn Beach Resort & Marina

Looking for a relaxing Florida vacay in an Instagram-worthy setting? You'll find it at Postcard Inn Beach Resort & Marina. The picturesque beach is where guests spend most of their time, lying sprawled upon comfy loungers on the soft, golden sand, rising only to cool off in the emerald waves offshore or take a dip in one of the two crystalline pools.

The daily resort fee includes beach chairs and towels, bicycle rentals, use of kayaks and paddleboards, as well as snorkeling equipment and a shuttle that travels within four miles of the resort. As for food, visitors can enjoy a freshly brewed coffee at the Starbucks café or a meal at one of the four on-site eateries.

As for your nightly retreat, choose from the many crisp, island-themed guest rooms, or rent a cottage for a more exclusive and roomy escape.

Guests are also granted access to the restaurants and amenities at the resort's sister properties: La Siesta Resort & Marina, Amara Cay Resort, and the Pelican Cove Resort & Marina. Bring your favorite family members to join in the fun - four-legged pals included.

Address: 84001 Overseas Highway, Islamorada, FL

Accommodation: Postcard Inn Beach Resort & Marina

6. La Siesta Resort & Marina

Photo Source: La Siesta Resort & marina
Photo Source: La Siesta Resort & marina

Like other hotels on this list, La Siesta Resort & Marina is home to a pristine private beach and a gorgeous oceanfront pool (heated, of course). Accommodations here are vast and lush. They include spacious guest rooms, multi-bedroom suites, private cottages, and vacation homes with beach access and breathtaking views. Not too shabby!

The daily resort fee includes breakfast, a shuttle service, and fishing equipment. Bicycle, kayak, paddle boat, and paddleboard rentals are also complimentary. Another plus, guests can use the amenities at La Siesta's sister resorts (Postcard Inn, Pelican Cove, and Amara Cay).

Wild & Lime is the resort's poolside restaurant, offering light lunches and afternoon snacks mere steps from the beach. Breakfast is served at the Welcome Center, and dinner can be found at an eatery on one of the sister properties or cooked in your cottage kitchen.

An easy, four-minute walk takes guests to the nearby Indian Key Historic State Park and the History of Diving Museum is located just under three miles from the resort.

Address: 80241 Overseas Highway, Islamorada, FL

Accommodation: La Siesta Resort & Marina

7. Chesapeake Beach Resort

Photo Source: Chesapeake Beach Resort
Photo Source: Chesapeake Beach Resort

The view from the Chesapeake Beach Resort is the stuff of dreams. Sugar-white sand; tall, waving palm trees; and emerald waters dance below a sky so blue, it looks fake. Renovated in 2021, this newly revamped resort is bright, airy, and contemporary.

Guest rooms feature fabrics that evoke the area's remarkable natural landscape and furnished balconies that allow guests to inhale deep breaths of salty air while being calmed by soft ocean breezes caressing their cheeks. If you're traveling with kids, opt for a villa. You'll be thankful for the extra space, as well as the exclusivity.

The resort's private beach is set serenely beside the quiet, protected bay, making this an ideal vacation destination for families with young children. The calm, protected waters make it safer for little ones to enjoy. Two oceanfront pools are the prime place to cool off on a warm day.

Address: 83409 Overseas Highway, Islamorada, FL

Accommodation: Chesapeake Beach Resort

8. Pelican Cove Resort & Marina

Photo Source: Pelican Cove Resort & Marina
Photo Source: Pelican Cove Resort & Marina

Pelican Cove Resort & Marina has a lot to offer its guests. Surrounded by verdant gardens and featuring a private beach and saltwater lagoon (complete with a giant water trampoline), this lovely spot is a haven for those looking to relax beachside. Grab a bite at the Cabana Bar & Café, dip your toes in the freshwater swimming pool, or ogle the boats at the on-site marina.

Smaller than its sister resorts (Siesta Resort & Marina, Amara Cay Resort, and Postcard Inn Resort & Marina), there are only 63 rooms and suites to choose from, which makes your stay feel more intimate and charming.

Breakfast and use of the shuttle service are included with the resort fee, as are rentals of snorkel equipment, kayaks, and paddleboards. Sign up for a Fish-Like-a-Local lesson offered each Thursday and Saturday. Visitors are also granted access to the amenities on offer at its sister resorts.

Address: 84457 Overseas Highway, Islamorada, FL

Accommodation: Pelican Cove Resort & Marina

9. Pines & Palms Resort

Photo Source: Pines & Palms Resort
Photo Source: Pines & Palms Resort

Who wants to be stuffed into a tiny hotel room when they're on vacation? Not us. If you're someone who appreciates a little extra space with your holiday, you'll be happy to stay at Pines & Palms Resort, especially if you have kids in tow.

This five-acre resort boasts spacious one-, two-, and three-bedroom cottages and suites, which feature a full kitchen. The village-like resort is also home to a heated freshwater pool and Tiki Bar. Book a yoga class, enjoy fishing off the pier, or borrow a bicycle, kayak, or paddleboard. Visit the orchid nursery for a little serenity, and lounge beachside to soak up the rays.

Arriving by boat? You can dock it for free at the resort.

Address: 80401 Old Highway, Islamorada, FL

Accommodation: Pines & Palms Resort

10. The Moorings Village

Photo Source: The Moorings Village
Photo Source: The Moorings Village

Shaded by giant palms set back from the silky sand and vibrant blue water, it's hard to feel stressed at Moorings Village, especially if you're swinging in an oceanfront hammock. Once a coconut plantation, this idyllic spot is a natural wonderland bursting with beauty in the form of more than 800 palm trees, pathways lined with orchids, and sparkling ocean waves.

Luxury cottages are spotted throughout the property, offering visitors a luscious retreat from reality. Open and bright, these gorgeous accommodations come with kitchens and a very welcome air of relaxation.

While there are no restaurants on-site, many eateries are reachable within minutes, and the staff can easily book dinner reservations on your behalf. A stay here includes access to kayaks, paddleboards, bikes, a fitness room, tennis courts, and a swimming pool.

Address: 123 Beach Road, Islamorada, FL

Accommodation: The Moorings Village

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