The Best Hotels to Book in Islamorada, Florida for Every Traveler

Headed to the stunning landscapes of Islamorada in Florida? Enjoy a stay at the stunning Casa Morada
Headed to the stunning landscapes of Islamorada in Florida? Enjoy a stay at the stunning Casa Morada | Courtesy of Casa Morada / Expedia
Photo of Mandi Keighran
27 January 2022
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Just 90 minutes south of Miami, the village of Islamorada covers six of the Florida Keys and is known as the fishing capital of the world – as well as a hotspot for diving, snorkeling and boating in the Sunshine State. From luxurious family getaways to romantic tropical resorts, we’ve curated the best hotels, inns and resorts in Islamorada, Florida – bookable on Culture Trip.

Postcard Inn Beach Resort and Marina, for seaside lazing

The glamorous seaview deck at Postcard Inn at night, dotted with candles, outdoor seating and a large firepit
Courtesy of Postcard Inn / Booking.com

You don’t need to be a beach bum to stay at Postcard Inn, but we have a feeling you’ll become one by the time you check out of this Islamorada hotel. Make like a piece of driftwood and spend all day washed up on the sugar-white sand. You’re welcome to wade back into your cottage at any time to snooze among the nautical decor, or simply sit for a spell on your private balcony. All it will take is a sip of a Rum Runner to send you back to your spot in the sand.

Drop Anchor Beach Lodge, for easy living

The pastel toned exterior of the Drop Anchor Lodge with outdoor seating on the sand
Courtesy of Drop Anchor / Expedia

You’re welcome to drop anchor – figuratively or literally – at Drop Anchor. A night in one of these easy-breezy rooms is one of the best ways to break up the long drive or sail down to Key West. Get introduced to the Florida island lifestyle in the oceanfront trailer, complete with your own kitchenette and wooden deck. They’ll supply the sunrise – all you need to bring is a pair of shades, a pair of sandals and a pair of mimosas.

Casa Morada, for private island luxury

An aerial overhead shot of Casa Morada on the ocean with multiple jetties and boats
Courtesy of Casa Morada / Expedia

When a hotel in Islamorada has its own private island, you know you’ve found a literal slice of paradise. Casa Morada is a quiet haven where complimentary yoga classes will forever change your wake-up routine. You’re free to glide around their island on kayaks or paddleboards – if you can find the willpower to remove yourself from your suite’s soaking tub, that is. Resist the urge by reserving a garden suite instead where its private outdoor shower will rain over you with serenity.

Islander Resort, for family-friendly fun

Upscale modern king bedroom with green tufted headboard, light tile floors and chandelier over seating area at Islander Resort
Courtesy of Islander Resort / Expedia

Looking for a luxurious family getaway? The Islander Resort offers plenty of family-friendly activities and accommodations over 24 acres (10ha) of oceanfront property, including three pools, landscaped native gardens and beach volleyball. There’s yoga, kids’ crafts and family movie nights and the friendly concierge service can organize other activities such as fishing, snorkeling, or a romantic eco-tour sunset cruise. Feeling hungry? Opt for a casual pizza or tacos at Tides Beachside Bar and Grill or indulge in fresh local seafood at Elements Lounge and Restaurant.

Fisher Inn Resort and Marina, for rustic fishing holidays

Outdoor seating area at Fisher Inn Resort and Marina with string lights and palm trees
Courtesy of Fisher Inn Resort and Marina / Expedia

This boutique inn is one of the only hotels in Islamorada with boat parking and a boat ramp – making it the ideal place to stay if you’re bringing your own boat. Looking for somewhere to cook your catch? Use the hotel’s fish cleaning stations and BBQ grills to cook it yourself, or get a recommendation from the hotel staff for a nearby restaurant offering a “cook your catch” menu. Accommodation ranges from the luxurious Seaside Villa Deluxe – just steps from the ocean, to the modern Tarpon Rooms – which feature two queen beds. Plus, guests have use of the hotel paddleboards and kayaks free of charge.

Pines and Palms Resort, for easy self-catering

Double room with seaview terrace at Pines and Palms Resort with rattan furniture
Courtesy of Pines and Palms Resort / Expedia

Live like a local at this self-catering resort set over five acres (2ha), with oceanfront cottages and suites arranged amongst more than 100 coconut palm trees to create a tropical, village-like vibe. There are a variety of accommodation types to suit families, couples and groups of all sizes – ranging from one to three bedrooms. There’s also an oceanfront freshwater pool complete with a poolside Tiki bar offering daily entertainment. Chat with the on-site fishing guides, Captain Chris Hanbury and Captain Jacob Hill, to organize a fishing adventure out at sea or in the backcountry of Everglades National Park.

The Sunset Inn, for chilled outdoor activities

Outdoor grounds at the Sunset Inn with hanging egg chairs and large trees
Courtesy of Sunset Inn / Expedia

This modern inn is a celebration of the Floridian inns of yesteryear – with a quintessential climate-controlled pool featuring bright orange umbrellas and cabanas, as well as an oversized chessboard, Jenga and a ping-pong table that channel fun 60s vibes. Cook up a feast on the BBQs, explore the surrounding area on a beach cruiser, or indulge in a sundowner in one of the hanging egg chairs in the garden. The simple rooms feature comfy beds with chic neutral bedding – while the walls are adorned with vintage photographs of the Florida Keys from the Matecumbe Historical Trust.

Cheeca Lodge and Spa, for options for everyone

Doube bedroom at Cheeca Lodge and Spa with white linen and balcony overlooking ocean
Courtesy of Cheeca Lodge and Spa / Expedia

Serious anglers and casual fishermen will love this tropical resort set over 27-acres (11ha) by the sea. There are more than 500 species of fish within minutes of the shore and a 525ft (160m) pier – the longest in the entire Florida Keys. Not into fishing? Head to the spa to enjoy treatments inspired by lush tropical vegetation in the gardens, like the Sea Breeze Swedish-inspired massage, or dine at one of the three on-site restaurants. Think mojito lime snapper at Atlantic’s Edge, Neapolitan pizza at Mia Cucina and handmade sushi and bento boxes at Nikai Sushi.

Amara Cay Resort, for evenings spent fireside

Covered deck with sun beds overlooking pontoon and ocean at Amara Cay Resort
Courtesy of Amara Cay Resort / Expedia

Immerse yourself in the tropical surroundings of Islamorada at this luxurious resort: relax in a hammock on the private beach lined with swaying palm trees or swim laps in a sparkling oceanfront pool. Enjoy fresh fish tacos in the Tiki Bar in the evening, before relaxing around a beachside fire pit. The affordable resort fee includes the use of beach chairs, lawn games, bicycles, kayaks, paddleboards and a Mercedes van to shuttle guests within a 4mi (6.4km) radius.

Nick Dauk contributed additional reporting to this article.

These recommendations were updated on January 27, 2022 to keep your travel plans fresh.

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