10 Best Islamorada Resorts: A Detailed Guide

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Source: depositphotos.com

Beautiful Islamorada resorts in the Florida Keys provide guests with an intimate and luxury hideaway halfway down the Overseas Highway. Despite its modest size, this charming haven boasts an excellent blend of art, history, beautiful beaches, and a fantastic range of smaller and opulent resort retreats.

You’ll want to go fishing while in Islamorada resorts, as ‘Islamorada’ is known as the Sportfishing Capital of the World. The numerous attractions in Islamorada resorts keep guests entertained, and the wide range of resorts makes it easy to pick the appropriate spot to stay.

To assist you, there are various fish charters and boat rentals available, some of which are even linked to the best Islamorada resorts, with concierge staff on hand to make arrangements for you throughout your stay.

Top 10 Islamorada Resorts

Whether you’re looking for a family beach vacation where you can build sandcastles and splash around in the emerald waves or a relaxing couple’s beach holiday in a plush hotel with a spa, our list of the top 10 Islamorada resorts has something for everyone.

1. Cheeca Lodge & Spa

Islamorada resorts
Photo by Len Radin from Flickr/ Copyright 2017

Off the pristine, sandy beach at the quaint 4 stars Cheeca Lodge & Spa, a long wooden pier juts into the azure Atlantic waves. It invites visitors to relax and enjoy the tranquility that this beautiful island paradise provides.

The comfortable beds in each spacious guest room and suite, decorated with tropical-themed decor and balconies, include pillow-top mattresses, following a tour of the sprawling 27-acre estate of Islamorada resorts. These rooms provide the ideal setting for unwinding. Don’t worry; bikes are available to help you go from one location to the next.

Three restaurants will satisfy your hunger while providing an ocean view as spectacular as the entries. If you choose to eat somewhere other than the resort, take advantage of the complimentary shuttle service, which will take you anywhere within a two-mile radius. If you go off-site to eat, check out the outstanding Green Turtle Inn, which is known for its delectable seafood chowder.

The resort’s gaming area, Xbox Arcade, heated pools, and family activities, such as beach cruiser bicycle excursions and water sports, will appeal to them. Camp Cheeca will keep kids amused while you relax in the adults-only pool or pamper yourself at Cheeca Lodge’s magnificent Spa.

Use the resort’s many other first-rate amenities while you’re here. Fishing off the pier, playing pickleball, tennis, basketball, or shuffleboard, or trying your hand at making par on the 9-hole golf course, one of only a few in the Keys, are just a few of the activities available.

Location: 81801 Overseas Hwy, Islamorada, FL 33036, United States

Contact number: +1 305-664-4651

2. Islander Resort

It’s simple to see why the 3-star Islander Resort attracts many visitors. This delicious Atlantic-facing site radiates natural beauty in the shape of tall, verdant palm trees and a clean 24 acres white, sandy beach, making it one of the top Florida Keys resorts for families.

The two heated saltwater pools of Islamorada resorts and the on-site splash pad will keep the kids entertained for hours. Go snorkeling, kayaking, paddleboarding, fishing, or bodysurfing at the beach. There are complimentary bike rentals, basketball, volleyball, ping pong, and shuffleboard for land-based entertainment.

When hunger strikes, the property’s two restaurants, Tides Beachside and Elements Lounge & Restaurant, have enough to offer. Go to Tides on a weekend afternoon for live music or on a Thursday at dark for a family movie night. If you need more space, choose a specialty suite with a kitchen that makes feeding little children a breeze. If you do opt to eat out, there are a plethora of excellent eateries around that provide fresh local seafood.

Location: 82100 Overseas Hwy, Islamorada, FL 33036, United States

Contact number: +13056642031

3. Amara Cay Resort

The stunning 3-star Amara Cay Resort also has a pristine private beach, and it’s a sight to behold. Beautiful hammocks line the beach, suspended from swaying palm trees that provide shade from the intense Florida heat. Enjoy stunning views of the Atlantic while relaxing in a thatched hut or swimming in the zero-entry pool of Islamorada resorts.

To soak in the atmosphere at this opulent resort, relax on a swinging chair or gather around an evening fire pit. Have you forgotten your swimsuit? There is no need to be concerned.

Everything from trendy beach attire to gifts is easy to find at the Island Trendz Boutique. The resort cost includes kayak and SUP rentals, beach chairs, towels, lawn games, bicycles, fitness center access, and a free shuttle to attractions within four miles of the hotel.

Relax in a spacious room with a furnished balcony and a peaceful combination of modern and tropical-themed comfort. Eat breakfast in the Dining Room or at Reel burger, or lunch or dinner at Tiki Bar for a poolside break. Reel burger serves dinner on Fridays and Saturdays.

Location: 80001 Overseas Hwy, Islamorada, FL 33036, United States

Contact number: +13056640073

4. The Caribbean Resort

Guests of Upper Mate Cumbe Key’s aptly titled ‘The Caribbean Resort’ stay in one of a range of charming, upmarket residences with a Caribbean flair. The outside grill, in-unit kitchen, and washer dryer make it simple to feel at home in this lovely paradise. Your sole wish will be for more vacation time.

Guests will have full access to the resort’s amenities whether they rent by the day, week, or month. A beautiful pool is kept cool by the surrounding garden, full of palm, pineapple, and banana trees. A hot tub helps tourists relax on chilly nights, while waterfalls provide a sense of overall tranquility.

Stand-up paddleboarding, kayaking, and bicycling are excellent companion activities available at Islamorada resorts. Why not rent a fishing rod and try your luck off the 45-foot pier while there? Catching a large one is best done early in the morning.

Location: Islamorada, FL 33036, United States

Contact number: +18007999175

5. Postcard Inn Beach Resort & Marina

Look no further if you’re looking for a relaxed Florida vacation in an Instagram-worthy setting. The 3-star Postcard Inn Beach Resort & Marina on Holiday Isle has it. The resort’s lovely beach is where visitors spend most of their time, laid out on comfortable loungers on the smooth, golden sand, rising only to cool off in the emerald seas offshore or partake in some water sports.

Beach chairs and towels, bicycle rentals, kayak, paddleboard rentals, snorkeling equipment, and shuttle service within four miles of Islamorada resorts are included in the daily resort fee. Visitors can grab a cup of freshly made coffee at the Starbucks café or a meal from one of the four on-site restaurants. Choose from various clean, island-themed guest rooms or rent a cottage for a more private and spacious getaway.

Guests have access to the resort’s sister properties, La Siesta Resort & Marina, Amara Cay Resort, and Pelican Cove Resort & Marina and its restaurants and amenities. Bring your favorite family members, including your four-legged friends, to join in the excitement.

Location: 84001 Overseas Hwy, Islamorada, FL 33036, United States

Contact number: +13056642321

6. La Siesta Resort & Marina

The accommodations of Islamorada resorts are large and pleasant. They feature large guest rooms, multi-bedroom suites, brightly painted private cottages, and holiday homes with direct beach access and spectacular views of the Atlantic. La Siesta Resort & Marina has a beautiful beachfront pool and a clean private beach.

Breakfast, a shuttle service, and fishing equipment are all included in the daily resort charge. Rentals of bicycles, kayaks, paddleboats, and paddleboards are also free. Guests can also enjoy the facilities of La Siesta’s sibling properties, Postcard Inn, Pelican Cove, and Amara Cay.

The resort’s poolside restaurant, Wild & Lime, serves light meals and afternoon snacks just steps from the beach. Breakfast is available at the Welcome Center, and dinner can be prepared in your cottage kitchen or at one of the sister property’s eateries. The local Indian Key Historic State Park is only a four-minute walk away, and the History of Diving Museum is a little under three miles from the resort.

Location: 80241 Overseas Hwy, Islamorada, FL 33036, United States

Contact number: +13056642132

7. Chesapeake Beach Resort

The views from the Chesapeake Beach Resort of the Atlantic are breathtaking. Sugar white sand, tall, waving palm palms, and green lakes glisten beneath a sky that seemed too fantastic to be accurate. But it’s true. This recently renovated resort, which opened in 2021, is bright, airy, and contemporary.

Fabrics that evoke the area’s history can be found in the guest rooms of this high-quality 3-star resort. Guests can take deep breaths of salty air while being soothed by soothing ocean breezes caressing their cheeks on the furnished balconies.

If you’re traveling with children to Islamorada resorts, a villa is a way to go. You’ll appreciate the increased room as well as the privacy. The resort’s beach is nestled peacefully alongside a calm, protected bay, making it a perfect vacation spot for families with little children. The tranquil, protected waters provide a safer environment for children to enjoy. The two oceanfront pools are ideal for cooling down on a hot day.

Location: 83409 Overseas Hwy, Islamorada, FL 33036, United States

Contact number: +13056644662

8. Pelican Cove Resort & Marina

Islamorada resorts
Photo by _crobin from Flickr/ Copyright 2008

Pelican Cove Resort & Marina provides a wealth of amenities for its visitors. This gorgeous 3-star resort is a sanctuary for anyone wishing to unwind at the seaside, with verdant gardens and a private beach and saltwater lagoon. Take a bite to eat at the Cabana Bar, swim in the freshwater pool, or gaze at the boats in the on-site marina.

Pelican Cove is a smaller resort than its sibling properties, Siesta Resort & Marina, Amara Cay Resort, and Postcard Inn Beach Resort & Marina, with only 63 rooms and suites to select from, making your stay feel more boutiquey and lovely.

The resort price includes breakfast and shuttle service and snorkeling equipment, kayaks, and paddleboard rentals. Register for a ‘Fish Like a Local’ instruction, which takes place every Thursday and Saturday.

Visitors of Islamorada resorts can also use the facilities of the resort’s sibling properties. And Pelican Cove is about as near as you can get to one of the Keys’ most popular attractions, the Theatre of the Sea. This wildlife encounter features must do dolphin swims and is located directly across the street from the resort.

Location: 84457 Overseas Hwy, Islamorada, FL 33036, United States

Contact number: +13056642321

9. Pines & Palms Resort

Islamorada resorts
Photo by Terence Faircloth from Flickr/ Copyright 2013

Pines & Palm Resort is a great place to stay if you’re looking for a bit of additional space during your vacation to Islamorada resorts. The large one, two, and three-bedroom cottages and suites on this five-acre property have a full kitchen.

A heated freshwater pool and a Tiki Bar are also available at the village-style resort. Take a yoga class, go pier fishing, or rent a bicycle, kayak, or paddleboard. Visit the orchid nursery for some peace, and relax on the beach to soak up the rays.

Location: 80401 Old Hwy, Islamorada, FL 33036, United States

Contact number: +18006240964

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10. The Moorings Village

It’s difficult to be anxious at the Atlantic facing Moorings Village, shaded by gigantic palms set back from the silky sand and brilliant blue water, wildly if you’re swinging in an oceanfront hammock. This picturesque area, formerly a coconut farm, is now a natural wonderland with over 800 palm trees, orchid-lined paths, and glistening ocean waves.

The site is peppered with luxury cottages that provide tourists with a luxurious escape from reality. These lovely rooms are open and light, with a kitchenette and a relaxing atmosphere. Kayaks, paddleboards, bikes, a fitness facility, tennis courts, and a swimming pool are all available to guests.

While there are no restaurants on-site, several restaurants are within walking distance, and the staff can make supper arrangements for you. Chef Michael’s seafood restaurant is a short walk away from some Islamorada resorts and serves fresh-caught fish daily.

Location: 123 Beach Rd, Islamorada, FL 33036, United States

Contact number: +13056644708

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