11 Best Islamorada Hotels with Marina

Just 90 minutes south of Miami, the Six Keys of Islamorada are one of the more upscale regions of the Florida Keys. Famed as the world’s fishing capital, this lovely village is also a hotspot for boating, snorkeling, and diving, making for a luxurious and intimate escape. And even though it was small, we had a ball exploring this pretty paradise and its lovely beaches, history, art, and architecture. So, when it came to looking for places to stay, we went a rather offbeat route – we went looking for an Islamorada hotel with marina. While Islamorada resorts with beachfront locations are equally popular, we wanted access to marinas to explore the turquoise waters around Islamorada easily.

However, the great news is that many of the best places to stay in the village had marina access and complimentary access to kayaks and paddleboards and beachfront with soft white sands. So, what are you waiting for? Pack your best one-piece Amazon swimsuits, sun beach hats, and beach sandals, and check out this detailed guide to Islamorada.

Did you know that the Florida Keys are one of the world’s most spectacular sunset locations? Yes!

Postcard Inn Beach Resort & Marina

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It only makes sense to start a list of excellent Islamorada stays with the Postcard Inn Beach Resort & Marina. The picturesque resort has an Instagram-worthy setting, and the beach is where we’d spend half our time, sprawled across the comfy loungers on the golden sand. The other half of the time, we’d enjoy a day out on the water, thanks to the resort’s fishing and tour fleet. From venturing offshore to indulging in a thrilling sandbar adventure, the Postcard Marina boasts a fleet of seasoned captains who ensured that we had a fantastic time out on the water.

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On the days that we didn’t venture out, the two crystalline pools were where we’d be. Since the daily resort fee included beach chairs and towels, and even paddleboards, kayaks, and snorkeling equipment, we didn’t have to worry about renting stuff to enjoy the water or the amenities. As for the food, how incredible was the terrace bar, which had fire pit tables and ocean views. And when we were hungry, the Italian restaurant satiated our hunger pangs, accompanied by live shows! Did you know that the resort even has a Starbucks and a complimentary shuttle (included in the resort fee), which we could use to travel within four miles in any direction? Yep.

We had the choice of many crisp, island-themed rooms and even cottages for a roomier and more exclusive escape. Notwithstanding the type of digs, all accommodations featured a subtle nautical theme, while the best, including our oceanfront cottage, even had private balconies with views of the Atlantic.

Caloosa Cove Resort

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Best value for money. We were a large group of friends who were looking for a good value place to stay in Islamorada, and the Caloosa Cove Resort perfectly fit the bill. This slice of heaven is famed for its fishing activities and is home to a full-service marina. The marina cove sits next to the famed Channels 2 and 5 bridges, offering some of the best tarpon fishing in the Keys. So, it wasn’t a surprise that we could indulge in everything from in-shore and offshore to backcountry fishing and deep-sea fishing from this marina. In fact, it’s a protected marina with 32 slips, so we even saw travelers dock their own boats here – what fun!

Aside from the marina, the property even had a gorgeous beach area with sun loungers and beach umbrellas for when we wanted to lounge after a swim in the sea. Back at the resort, there was a fabulous outdoor pool, one of the best in the region, as well as a sun terrace right by the poolside. What’s more, the resort fee includes daily shuttles to some of the locations around and a hearty complimentary breakfast. So, we’d be fueled up right at the beginning of the day, especially if we were headed out to explore Islamorada on the Multi-Activity Private Boat Charter. Plus, the onsite restaurant served delicious meals.

What we loved about the units at this hotel was that they all came with balconies with sweeping ocean views! What’s more, all had flatscreen TVs and fully-equipped kitchens where we could whip up meals when we didn’t want to eat outside. Plus, units ranged from studios to two-bedroom apartments.

The Caribbean Resort

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Caribbean charm comes to Islamorada in the form of the Caribbean Resort in Upper Matecumbe Key. The resort is aptly named as the choice of stays we had here were adorable, upscale-chic homes full of Caribbean charm – think brightly colored fabrics and mahogany and teak furniture. Since it has just 22 “luxury homes,” it didn’t really feel like a hotel. What’s more, they had furnished porches, which only added to the island feel. Plus, we had modern comforts like washer-dryers, kitchens, and outdoor grills, making our week-long stay more comfortable than we could have ever thought of.

Whether one chose to rent the homes by the day, week, or month, everyone had full access to the resort’s amenities. The highlight here is the gorgeous pool, which was cool even in the humid months due to the lush gardens of banana, pineapple, and palm trees and flowering shrubs surrounding it. On cooler nights, a luxurious soak in the bubbling waters of the hot tub helped take the edge off.

That didn’t mean that we didn’t have a thrilling time here. Despite being a secluded place, this Islamorada hotel has a boat dock and marina and also has free ka use. In fact, we indulged in a host of complimentary activities like kayaking and stand-up paddleboarding. Besides the 45-ft long pier, the marina had a gentle-slope boat ramp to easily launch boats, especially for travelers who had their own boats. That, along with comfy chairs, lounges, and shaded Tiki huts, certainly made even marina activities very enjoyable. Did we mention the off-shore diving and fishing on offer here? That’s what made it so hard to leave this place!

Amara Cay Resort

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If your idea of an Islamorada vacation is to simply chill but with access to a beach and marina, then look no further than the gorgeous Amara Cay Resort. The pristine private beach boasts picturesque hammocks hanging from palm trees, thatched huts for lounging, and wonderful views of the Atlantic. When we wanted to get moving, we were thrilled by the onsite marina that partners with Islamorada Spearfishing Adventures and Wild Dolphin Tours. So, we could indulge in all kinds of water adventures right off the resort’s dock, and we especially love our tropical excursion touring the Islamorada Sandbar. Since the resort’s daily fee included access to SUPs and kayak rentals as well as towels and beach chairs, our water activities here were an absolute breeze. It’s one of the best Islamorada oceanfront hotels for the same reason.

Back at the resort, we’d head straight to the sparkling oceanfront pool, where we’d swim laps and retire to the daybeds for some unwinding accompanied by cocktails from the poolside Tiki Bar. When the hunger pangs came calling, we had two options of restaurants to eat from. Evenings were reserved for relaxing in the swinging chairs, followed by some lawn games and a session at the fire pit for an alfresco dinner under the stars. Since the resort fee even gave us access to bike rentals and a free shuttle, we’d even head out to explore the neighborhood.

Finally, we come to the digs at this resort, all of which feature a relaxing mix of tropical- and modern-themed luxury. The furnished balcony was a highlight, and since ours was an oceanfront room, we were treated to stellar views of the Atlantic.

La Siesta Resort & Villas

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Nestled on a postcard-perfect private beach in Islamorada, La Siesta Resort & Villas was just the laid-back resort we were looking for. Not only was it home to a pristine private beach, but it even had a palm-lined marina, which was perfect for our offshore excursion on a small boat. And when we wanted the quintessential Keys experience of reeling in a fresh catch, we simply booked an excursion from the marina at the sister property of Postcard Inn Beach Resort. In fact, the daily resort fee even included fishing equipment, kayaks, paddleboards, and paddle boats, which meant that all our water excursions were taken care of.

There was a lot to back at the resort, even when we weren’t doing anything! Our days began with a complimentary breakfast (included in the resort fee), after which we’d mostly be swimming in or sprawled by the gorgeous outdoor heated oceanfront pool. Since the resort fee also included a shuttle service and bicycle rentals, we got to explore the neighborhood and surrounding region in comfort too. Plus, the poolside restaurant served everything from light lunches to afternoon snacks. Did you know that we also had access to the amenities at sister resorts Amara Cay and Postcard Inn? Yes!

We had the choice of many plush and spacious accommodations, including rooms, multi-bedroom suites, and even brightly painted private cottages, which is where we were. Our one-bedroom oceanfront cottage even boasted direct beach access and breathtaking sea views. And finally, thanks to the kitchen, we’d always be able to whip up food on the fly.

Fisher Inn Resort & Marina

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Best fishing hotel. Rustic fishing holidays on Islamorada are best done at the Fisher Inn Resort & Marina, which is one of the only Islamorada digs with a boat ramp and parking!

Since we were bringing our own rental boat, it was ideal and rather hassle-free to stay here. After coming back from a successful fishing expedition, we even had a place to cook our catch – the fish cleaning stations and barbeque grills right at the hotel! In fact, there were many restaurants offering “cook your catch” menus nearby, which the staff was more than happy to recommend. When we weren’t fishing, we’d grab the kayaks and paddleboards to explore the waters. Back at the hotel, the outdoor pool and waterfront with daybeds were the perfect places to unwind with a beer or a drink. And thanks to the launderette, we were ensured of clean clothes everyday! Outdoor games and free Wi-fi wrap up the amenities here.

Free Wi-fi even extended to the accommodations, which ranged from the luxurious seaside villas to the modern rooms. Our seaside villa had mod-cons like plush beds, cable TVs, and even a kitchenette, as we love cooking our own food!

Cheeca Lodge & Spa

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Best family resort. We were looking for an Islamorada resort that offered water activities, something for the kids, and some serious R&R for us. Of them all, the four-star lush island haven of Cheeca Lodge & Spa fit the bill perfectly.

The first thing that impressed us was the long wooden pier that jutted into the azure Atlantic waters right off the pristine white-sand beach. Did you know that it’s been dubbed the Florida Keys’ longest fishing pier? We indulged in fishing and snorkeling tours and private excursions thanks to the watersports facility on the property. Since floats, paddleboards, snorkel gear, and even beverages were included in our resort fee, we adults and the kids had a gala time, especially since we also did the world-famous sandbar excursion!

Thanks to the bikes, we could get around easily within this sprawling resort. Camp Cheeca, with its games room, Xbox Arcade, and activities, kept the kids busy as we spent time at the adults-only pool and spoilt ourselves silly at the luxurious spa. It was followed by a sunset cruise trip – again, thanks to the resort! Later, we indulged in family time at the huge outdoor heated pool, played shuffleboard and pickleball, went on bicycle rides and beach cruiser rides, and dug into delicious meals at not one but three restaurants. Did you know that the 9-hole golf course on the property is one of only a handful of greens in the Keys? We were impressed, too.

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After spending time on our feet at this sprawling property, the spacious rooms with their tropical decor, pillow-top mattresses, and oceanfront views from the balconies were the cherry on top.

Islander Resort

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Staying away from the crowd is easy at the fabulous Islander Resort, which sits on 24 acres of luscious verdure and white sands in a prime Atlantic-facing spot in Upper Matecumbe Key. This casual, easygoing, and idyllic resort was perfect for us t-shirt-and-flip-flop-wearing travelers. Of course, this resort attracted us also due to its local experts who offer guided whole-craft tours, visiting everywhere from the Islamorada sandbar to various snorkeling sites. Heck, they even offered Gulfside slips for those travelers who came with their own boats! The icing on the cake is their partnership with Clearly Unique Watersports, which allowed us to go on a sandbar swim and a sunset cruise, too.

Back at the resort, two heated saltwater pools awaited us, as did the perfect beach, where we swam, lounged, and played beach volleyball. Apart from the many activities the concierge can arrange, there are many other activities, including family movie nights, kids’ crafts for travelers with children, and even yoga on the beach. When hunger struck, we found plenty to tempt our palates at the two eateries, the lounge and restaurant, and the beachside one. Plus, taking long walks in the landscaped native gardens was a favorite activity to do.

The accommodations didn’t fail to impress us either. Stunning water views and colorful artwork abound, but the decor is sleek and minimalistic. For extra space, the specialty suites with living rooms and kitchens are great. Of course, even we couples loved the extra space and the views of the ocean from our seaside patios, which led directly to the sandy beach.

Casa Morada

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Chilled outdoor activities are the name of the game at Casa Morada, a boutique island oasis on Islamorada. And when that oasis sat on acres of tropical land and included its own watersports and marina, then we knew we were in holiday heaven. The outdoor pool and the marina were the highlights of the gorgeous manmade island, complete with hammocks, sun loungers, and a gazebo. We indulged in boat tours, snorkeling trips, and even a sunset cruise onboard the restored 1917-built wooden boat, aptly called Blue Mist. Since we’re the chilled adventuring kind, we loved the varied complimentary amenities, which included paddleboarding, kayaking, cycling, and even yoga classes. The best bit? The daily resort fee even included bicycle rentals and a delicious breakfast spread. Check out the resort’s water life.

Tucked off the beaten track in Upper Matecumbe Key, this “cultivated wild” place was part of the 1950s Sunset Inn. Today, it’s hard not to feel blissed out here, as the almost adults-only resort (16 years and above only) has a free-wheeling, secluded, barefoot luxury vibe. What’s more, it had just 16 individual suites, so staying here felt very intimate. They’re set amongst lush natural gardens, with the curving white-sand paths leading from the rooms to the seafront. We had the choice of both garden and sea views, and we opted for the latter. Notwithstanding the view, all rooms came with deep soaking bathtubs and private terraces, and ours came with a panoramic sea view, of course.

Did you know that the hotel even offered a limited room service menu in the afternoons? Furthermore, they were even kind enough to arrange for in-room massage treatments. Sigh.

Pines & Palms Resort

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We wanted to live like locals in Islamorada, and we got to do so at the gorgeous five-acre Pines & Palms Resort. Outdoor water activities abound at this village-like resort, which also has a fantastic pier where we could enjoy a spot of fishing. We had a wonderful chat with the onsite fishing guides, Captains Jacob Hill and Chris Hanbury, who organized fantastic fishing adventures for us in the backcountry of Everglades National Park and even out at sea. In fact, we saw many people arrive by boat here, docking it for free – how cool was that! Moreover, we even borrowed paddleboards and kayaks and enjoyed exploring the waters off the shore of the resort.

Back on land, we had a lot of things to look forward to, too. The heated freshwater pool was our favorite haunt, and after a swim, we’d lounge on the daybeds or the palm-shaded hammocks. Plus, we’d even order cocktails and snacks from the Tiki Bar, which would also offer daily entertainment.

The spacious oceanfront cottages at this self-catering resort are peppered with palm trees, making for a tropical village-like vibe. What’s more, we had the choice of one-, two-, and three-bedroom suites and cottages, all of which feature a full kitchen. So, we could cook meals whenever we felt or didn’t feel like stepping outside to eat.

The Islands of Islamorada

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Most romantic. Nestled right on the Atlantic, the luxury club resort of The Islands of Islamorada boasted an awe-inspiring beach setting that was perfect for the two of us. With just 22 waterfront suites and villas occupying 600 ft of private shoreline, staying here was as romantic as it could get. We went for the spacious one-bedroom oceanview villa, which boasted spectacular sea views from everywhere. Besides the large living spaces, the villa also had bespoke bath products in a luxe bathroom, a cable flat-screen TV, a coffee/tea maker, and even alfresco daybed seating on the terrace facing the seafront.

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“We couldn’t have found a more romantic yet adventurous spot for our Islamorada sojourn.”

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When we did get out of the room, and we did, we headed straight to the private marina. Not only did it offer dockage space for travelers bringing their own boats, but we could even easily book fishing expeditions, snorkeling tours, and even romantic cruises during our stay. And we didn’t have to travel anywhere to do so! When it comes to the other amenities, we loved the sea-facing saltwater pool. We enjoyed a luxurious swim before settling into one of the cabanas for a lounge with drinks and snacks. The beachside fire pit was a great place to begin our evening revelries, especially since we could also mingle with the other guests. And since it was our anniversary, the hotel even arranged for a special seafood dinner on the beach! After dinner, we even played corn hole and Scrabble.

Our Verdict!

Islamorada and its amazing waterfront stays and accommodations have our hearts, especially since the best of them even come with their own docks and marinas. That said, here are the best of the lot:

• Best value for money: Caloosa Cove Resort
• Best fishing hotel: Fisher Inn Resort & Marina
• Best family resort: Cheeca Lodge & Spa
• Most romantic: The Islands Of Islamorada

Where to Stay in Islamorada?

Islamorada sits right in the heart of the Florida Keys. With warm weather throughout the year, it was the perfect base for us to explore this stunning region. So, which are the best neighborhoods in this village, tiny as it is?

We begin with Upper Matecumbe Key, which is nestled right in the heart of Islamorada and is perfect for those who are visiting this region for the first time. Not only does it have a bustling entertainment district, but it also boasts peaceful spots with marvelous views perfect for a romantic dinner out. Secondly, there’s Lower Matecumbe Key, which is the final island within the Islamorada chain. It’s the most peaceful of all islands in Islamorada and is known for its adult-friendly stays and activities more than the other villages. Finally, there’s Plantation Key, the region’s largest island, which is also very family-friendly. In fact, the island’s southern part is home to the local creative commune of the Rain Barrel Village, which is a haven for artsy types.

Interesting trivia: The main highway running through Islamorada is an extension of the famed Overseas Highway that connects the Florida mainland to the Keys. It’s one of the world’s most scenic drives.

What is Islamorada best known for?

Islamorada plays host to the largest fishing fleet (per sq. mile) in the world and is known as the “Sportfishing Capital of the World.”

Do you need a car in Islamorada, Florida?

Yes, staying anywhere in the Keys outside of Key West will require travelers to have automotive transportation. Crossing it on foot isn’t advisable since everything is close to the extremely busy highway.

Is Islamorada worth a visit?

If you have time just for a weekend, then the colorful Islamorada is the place where you should be.