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

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.

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.

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.

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.

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.

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.

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.

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.