The #1 most common question asked, by those ready to take on Key West is undoubtedly,
“Where is the best place to stay?”.
With good reason. This southernmost island in the continental USA may only be 4 miles long by 3 miles wide, but there are boundless options for travelers when choosing accommodations.
The first question you need to ask yourself is, “What location appeals to me?”. Location is extremely important in Key West, and we’ll delve into that first, below.
The second question you should ask is, “What type of lodging am I looking for?”. Of course, your answer will depend on your party. Are you coming as a couple? Or how about a family with kids, a large group, or a girl’s weekend?
Furthermore, worth noting is that it’s important for you to plan in advance. Key West has seen an enormous spike in tourism and options for accommodations are more difficult to come by, the closer to your trip you wait.
Location
First, let’s examine the most important of these two. Location, location, location, location, location, location. Yes, it really is that important.
Key West can simply be divided into two sections: Old Town and New Town. For all night partying, lots of activities and restaurants, ease of walking anywhere you want to go, you’ll want to stay in Old Town. Old Town houses the most well known street on the island (Duval St), where you can find nearly all night libations, shops, restaurants and other entertainments.
For resorts with larger beaches, where it’s more quiet and low key but not as easy to get to the hustle and bustle of activities, you should choose New Town. If you plan on hitting up Duval St., doing some sightseeing, and checking out other areas of the island, you’ll need to rent bicycles, golf carts, a car or Uber to Old Town. However, please note that bicycling from New Town to Old Town can be dangerous because of traffic in New Town.
In general, you’ll find that most people coming to Key West, choose Old Town. This is because you are walking distance from anything you will want to see, eat or do.
The map below depicts the difference between Old Town and New Town. You’ll see the middle section, aptly termed “Mid Town” but for our purposes here, we’ll consider that to be New Town as well.
Types of Accommodations
Large Resorts:
A plethora of incredibly large and lavish resorts lie on Key West and are perfect for honeymooners, traveling couples or a girl’s trip. If having a spot right on the beach is a must, then you will need to book a stay at a resort. Most of the resorts on the island do have an on-site beach, albeit some of them are fairly small. You can also find an on-site restaurant, some of them have on-site spa services and of course, bars for the hotel guests.
Some of the best resorts on the island are:
However, the downside of booking stays at any KW resort now is that most of them are running at least $500 per night. Yes, you read that right. $500 per night for a hotel room. Why, you ask? Well, Key West tourism is positively booming. I believe that with COVID still on the forefront of people’s minds, they are foregoing international travel. And if you’re going to be doing some domestic travel, Key West is as good as any!
All of the resorts listed are located in the Old Town part of the island, so you’ll be close to other activities.
Additionally, not only are the resorts able to charge premium fees right now, be aware of the added fees they will likely try to hit you with. “Resort fees”, “Parking fees”, “Technology fees”, you name it.
In February 2021, myself and a small group of girlfriends stayed at Opal Key Resort. Not only was the swimming pool way too small to accommodate the amount of people staying at the resort, the resort fee was $40 each person, per day to use the pool. We opted out of the pool (you’re in Key West, is there really a need?) and we’re glad we did. Most of our time was spent lounging on Key West sand.
Boutique Hotels/Bed & Breakfasts
Key West is packed with some of the absolute best boutique hotels you’ll likely ever find. This is my favorite accommodation of them all. Most of the boutique hotels are tucked quaintly away under lush Key West tropical landscapes, just barely off the well-trodden path.
Most boutique hotels have swimming pools and hot tubs and a hot breakfast. You can choose to stay in Old Town, where all the action is, or in New Town, where it’s a little more quiet and low key.
The competition for snagging travelers is at an all-time high right now so you won’t find a bad place to stay.
Boutique hotels are my favorite way to stay in Key West because they’re small enough that you don’t feel like just another guest, another number. The staff greet you and provide exceptional service and hospitality. I love the gardens that most of them sit among. There’s no better way to enjoy a morning than having a cup of coffee among all the greenery and colorful flowers.
Some of my personal favorites and ones highly recommended by other travelers are:
4. Curry Mansion Inn (beautiful grounds)
5. The Banyan Resort (great location)
9. The Mermaid and the Alligator
Vacation Rentals
The company I have used for years is Vacation Homes of Key West. I simply let them know how big of a place we need, the times we’re looking at coming, and they send me what they have available. They’ve always been extremely responsive, and booking has been easy peasy.
Of course, you can always source properties yourself on VRBO or Airbnb or something similar. I have found that the offerings on these sites are minimal, as most owners in Key West utilize the local rental companies and those companies are moving away from listing on the big-name sites.
Adding yourself on the Key West Facebook Group page is always helpful as well. You can post there with what you’re looking for and any “Mom & Pop” rentals are quick to let you know what they have available.
Truman Annex is a great place to stay and there are lots of vacation rentals available there. Suzie Rodnon is also a great resource for booking lodging and you can contact her here.
Quantities of Vacation Rentals are Limited
It’s helpful to understand that because the island has a finite amount of housing, years ago, the government began taking steps to ensure the residents have enough housing as well. In an effort to make sure houses all over the island aren’t being used as nightly rentals, the city put a ban on the number of homes that qualify to hold a “transient license”. Therefore, any home that doesn’t have the license, isn’t able to rent for less than 28 to 30 consecutive days at a time.
Because of this, the offerings of rentals on the island can be limited so if you’re planning on reserving an entire place for your stay, make sure and complete your rental reservation as quickly as possible.
Motels
Any other place, you likely wouldn’t catch me dead, staying in a motel for vacation. However, the hospitality bar in KW has been set so high, that any of these smaller motels are poised to give you a phenomenal experience. Motels can still offer you a warm breakfast, lush landscapes, a cozy bed and a pool.
When you see “Best Western” on my list, don’t scoff. Seriously, check out the pictures at their website. Cute as can be!
2. Tropical Inn
3. Duval Inn
5. Best Western Hibiscus Motel
I hope you have found this helpful to planning your Key West vacation. For more help in planning, feel free to contact me by commenting below.
If you have other advice that would be helpful for fellow travelers, please include that in the comments below. Sharing is caring, friends!
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