10 Best Resorts on Islamorada, FL | Vestasoft

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 hotels extensive selection of fun attractions keep visitors occupied, hotels and the large variety of resorts make hotels it easy to find the perfect place to stay. Islamorada is hotels 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 hotels build sandcastles and splash in the emerald waters with your kids, or you want to enjoy a tranquil beach vacation in a plush hotel hotels with a spa, you’ll find hotels an ideal spot to rest your head in Islamorada.

Use our list of the best resorts hotels 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 human side

Photo Source: Islander Resort

It’s easy to see why so many guests fall in love with the Islander Resort.islamorada 

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.islamorada 

Kids will love jumping about in hotels 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. islamorada 

Complimentary bike rentals, basketball, volleyball, ping pong, and shuffleboard are also available for land-based fun.islamorada 

When hunger strikes, you’ll find islamorada 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 hotels afternoon for live entertainment or on a hotels Thursday at dusk for family movie night.islamorada 

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

Address: 82100 Overseas Highway, Islamorada, FL islamorada 

Accommodation: Islander Resort islamorada 

2. Cheeca Lodge & Spa resorts

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

A long wooden pier juts into the azure islamorada Atlantic waters off the white, sandy beach at Cheeca Lodge & Spa. pool

It welcomes guests (which have included presidents and celebs) to bask in the hotels peaceful bliss enveloping this lush island haven.islamorada 

Pillow-top mattresses adorn the beach comfy beds of each spacious guest room and suite, which are adorned with tropical-themed décor and balconies. islamorada 

After wandering beach around the extensive 27-acre property, islamorada these rooms offer the ideal environment to unwind. Don’t worry, beach there are bikes on hand to make it easier to get from one spot to the next.islamorada 

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

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

While you’re here, islamorada take advantage of the other lush amenities: fish off the pier; play a game of pickleball, tennis, basketball, hotels 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 us

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

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

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

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

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

Address: 80001 hotels 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 hotel Resort stay in one of a variety of adorable, hotel upscale homes rich in Caribbean charm (we’re talking teak and mahogany furniture and brightly colored fabrics). hotel

Furnished porches hotel only add to the island feel, while the hotel outdoor grill, in-unit kitchen, and washer-dryer make it easy to feel truly at home in this pretty paradise. hotel

The only thing you’ll hotel wish for is more vacation time!hotel 

Whether guests choose hotel to rent by the day, week, or month, they will have full access to the resort’s amenities. islamorada 

These include a gorgeous florida pool kept cool by the surrounding garden bursting with palm, pineapple, hotel and banana trees. A hot tub helps beach take the edge off cool nights, while waterfalls lull visitors into a sense of overall calm.islamorada 

Activities like stand up paddleboarding, kayaking, florida and bicycling are also complimentary. islamorada 

While you’re at it, why not borrow pool 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.islamorada 

Address: 117 South Carroll Street, Islamorada, FL islamorada 

Accommodation: The Caribbean Resort islamorada 

5. Postcard Inn Beach Resort & Marina

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

Looking for a relaxing hotel Florida vacay in an Instagram-worthy setting? You’ll find it at Postcard Inn Beach Resort & Marina. islamorada 

The picturesque beach is hotel where guests spend most of their time, lying sprawled upon comfy loungers on the soft, golden sand, bot rising only to cool off in the emerald waves photo offshore or take a dip in one of the two crystalline pools.islamorada 

The daily resort fee includes beach hotel chairs and towels, bicycle rentals, use of kayaks and paddleboards, as well as snorkeling equipment and a shuttle free that travels within four miles of the resort.islamorada 

As for food, visitors can enjoy pool a freshly brewed coffee at the Starbucks café or a meal at one of the four on-site eateries.islamorada 

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

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

Address: 84001 Overseas Highway, Islamorada, FL islamorada 

Accommodation: Postcard Inn Beach Resort & Marina islamorada 

6. La Siesta Resort & Marina

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

Like other hotels on this list, best La Siesta Resort & Marina is home to a pristine private beach and a gorgeous oceanfront pool (heated, of course). Accommodations best here are vast and lush. islamorada 

They include spacious guest rooms, best multi-bedroom suites, private cottages, and vacation homes with beach access and breathtaking views. Not too shabby!islamorada 

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

Wild & Lime is the resort’s poolside restaurant, pool offering light lunches and afternoon snacks mere steps from the beach. marina

Breakfast is served at the Welcome Center, marina and dinner can be found at an eatery on one of the sister properties or cooked in your cottage kitchen.islamorada 

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

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

Guest rooms key feature fabrics that evoke the area’s remarkable key natural landscape and furnished balconies that key allow guests to inhale deep breaths of salty air while being calmed by soft ocean breezes caressing their cheeks.islamorada 

If you’re traveling with kids, key opt for a villa. You’ll be thankful for the extra space,key as well as the exclusivity. islamorada 

The resort’s private beach is set serenely key beside the quiet, protected bay, making this an ideal vacation destination for families with young children. The calm, key protected waters make it key safer for little ones to enjoy. marina

Two oceanfront pools are the prime place to cool off on a warm day.islamorada 

Address: 83409 Overseas Highway, Islamorada, FL star hotel

Accommodation: Chesapeake Beach Resort  per night 

8. Pelican Cove Resort & Marina

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

Pelican Cove Resort & Marina resort has a lot to offer its guests. Surrounded by resort verdant gardens and featuring a private beach resort and saltwater lagoon (complete with a giant water trampoline), resort this lovely spot is a haven for those looking to relax beachside. resort

Grab a bite at the Cabana Bar & Café, resort dip your toes in the freshwater swimming pool, or ogle the boats at the on-site marina.resort 

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

Breakfast and use of resort the shuttle service are included with the resort fee, as are rentals of snorkel equipment, kayaks, and paddleboards. islamorada hotels

Sign up for resort a Fish-Like-a-Local lesson offered each Thursday and Saturday. Visitors are also granted access to the amenities on resort offer at its sister resorts. reviews deals rooms 

Address: 84457 Overseas Highway, Islamorada, FL free wi-fi pool

Accommodation: Pelican Cove Resort & Marina  view deal booking

9. Pines & Palms Resort

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

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

This five-acre resort resort boasts spacious one-, two-, and three-bedroom cottages and suites, which feature a full kitchen. The village-like resort resort is also home to a heated freshwater pool and Tiki Bar.view full profile

Book a yoga class,resort enjoy fishing off the pier, or borrow a bicycle, kayak, or paddleboard. Visit the orchid nursery for a little serenity, resort and lounge beachside to soak up the rays.

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

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 marina palms set back from the silky sand and vibrant blue water,marina it’s hard to feel stressed at Moorings Village, resorts especially if you’re swinging in an oceanfront hammock.marina

Once a star coconut plantation, this idyllic spot is a natural wonderland bursting with beauty in the form of more than 800 palm trees, resorts pathways lined with orchids, marina and sparkling ocean waves.overview reviews deals 

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

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

Address: 123 Beach Road, Islamorada, FL

Accommodation: The Moorings Village

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