Key West Insider Tips: Best Places to Stay

Table of Contents 

• Staying in the Keys: 101 
• Best Hotels in Key West: Top 5
• Best Resorts in Key West: Top 5 

Key Takeaways 

For an island that’s only one mile wide and four miles long, Key West sure has a lot going on! That’s why having access to Key West insider tips is so important when planning activities, deciding where to eat, and figuring out where to stay in Key West. Whether you’re looking for Key West luxury resorts, the best place to stay in Key West for couples, or quaint hotels, Key West has something for everyone. 

Staying In The Keys: 101 

What area of Key West is best to stay in? Well, Key West is small enough that where you stay doesn’t dictate where you spend most of your time. Take these things into consideration when deciding where to stay when visiting our little piece of tropical heaven: 

• What’s your budget? They Keys cater to a wide range of budgets, from those pinching pennies or ready to splurge on an island vacay. 
• Who are you traveling with? There are Key West accommodations for every type of traveler. Whether you’re full-on family adventuring or seeking a honeymoon getaway, Key West is the place to be. 
• What type of vacation are you going for? Is it better to stay in New Town or Old Town Key West? That depends entirely on what you’re looking for! New Town has the feel of an accessible tourist town. Old Town is quintessential Key West, with close proximity to restaurants, activities, and all the things that make Key West unique. Keep in mind, we’re a pretty small spec of sand, so whether you choose to stay in Old or New, you’ll be able to easily visit either. 
• Which is the best Key to stay on? Oof, this one is hard. We’re partial to Key West, but each Key has its own perks. Islamorada is artsy, Key Largo is laid-back, Marathon is pretty family-oriented – the list goes on! 

Best Hotels In Key West: Top 5  

1. Casablanca Key West is located in Key West’s Old Town neighborhood and prides themselves on providing an inviting and tranquil space. They’re a boutique hotel with a pool, and offer a special with champagne and chocolate covered strawberries – this is what honeymoon dreams are made of. 
2. The Perry Hotel and Marina offers hourly shuttle service to Old Town, a pristine view of boats bobbing around the marina, and a drink of the day – making this retreat more adult-centric. A unique feature of The Perry is that they’re exceptionally pet friendly and have two on-site dog parks. If you prefer to travel with your furry friend(s), this hotel is the place for you.  
3. The Gardens Hotel has private cottages. Need we say more? They have a cabaret and award-winning Wine Gallery. They offer bicycle parking and on-site ponds to stroll around, making their property the best getaway if you’re seeking respite from the crowds of Key West. The Gardens Hotel requires guests to be at least 16 years of age. 
4. The Capitana has rooms with bunkbeds, making it an ideal spot for families. Their cottages offer views of the canal and are more elevated than other Key West options. If you’re craving a more modern feel without sacrificing quintessential Key West vibes, The Capitana is a great choice. 
5. Casa Marina specializes in hosting weddings and special events, but don’t miss out on their gorgeous rooms. They have two oceanfront pools, a spa, pickleball courts, and are located on a private beach. 

Best Resorts In Key West: Top 5

1. Parrot Key Hotel and Villas is classified as a boutique island hotel. They offer villas with water views and specialize in family-centered accommodations. They have three bedroom villa options, making Parrot Key an optimal choice for traveling families. 
2. The Hyatt Centric Key West Resort and Spa is waterfront and offers charter boats from the hotel’s dock! The Hyatt offers Sunday morning yoga and sunset dinners. (Psst! If you aren’t at the Hyatt, check out Danger Charters – they depart from two convenient locations.)
3. Opal Key Resort and Marina is located on the waterfront of Old Town and their rooms make you feel like you’re in an oceanic dream. They have three waterfront restaurants offering unique cocktails and truly unmatched waterfront views. 
4. Southernmost Beach Resort and Guesthouses has a spa, fitness center, and three pools. They offer yoga classes, private cabanas, and an ideal location at the tip-top of Duval Street. 
5. Ocean Key Resort and Spa boasts a stacked events calendar and resort-exclusive excursions. Their famous ‘sunset pier’ is 4,000 square feet of pure bliss! Watching the sunset sparkle across the water while sipping a piña colada and snacking on some conch has never been easier. 

We would like to note that there are an array of Airbnb’s and VRBO’s in Key West if you’re looking for a more private stay! And remember our island is only four square miles … so wherever you stay, you’ll be close to Skydive Key West *wink wink*. We would love for you to make a tandem skydive with us while visiting the Keys – book your jump today!