Where to Stay in Key West, FL

key west old town

There is nothing better than visiting an island destination with the never-ending sunshine and waters so clear you can see the fish swimming by without a care in the world, but what many people may not know is that it is an island of its own and only connected to the other keys and the mainland via an overseas highway.

Because it is so quaint this could easily be a destination stop to explore for the day and evening for local cuisine before heading back home or to your next pit stop, or enjoy a cozy getaway that is away from the jam-packed tourist spots but close enough to venture there for the day if need be.

Staying in Key West is certainly going to be an eye-opener, and immersing yourself in the goodness that is the culture and the community is the perfect chance to learn new words, try new dishes, and even make new friends. The welcoming atmosphere of the island people is what draws tourists in and then they don’t want to leave. Paradise is just a drive away.

Best Area to Stay in Key West

There are so many factors that determine where you stay from budget to interests, and also depending on the demographic of your traveling party, so we will have options of everything ranging from locations starting at the top of the island, down the mainland and central, and out towards the edge. There will certainly be something for everyone to consider, and we will take a quick browse at:

  • Big Pine Lower Keys – This is a more out-of-the-way, off-the-beaten-track area, but perfect for some tranquility and is significantly less touristy.
  • Bahama Village – In the mix of things and very popular for first-time visitors
  • Outside the City; sugarloaf key – Still in the center and middle region but not as densely populated
  • Old Town – An on-the-edge, endless ocean view spot to rest your head and clear your mind

The Keys always have something amazing going on but be sure to check the weather conditions and times when you are thinking about going because they do have a hurricane season, and although they are not always devastating, you won’t want your holiday spent cooped up indoors because outside is blowing a gale.

Now you have decided where you want to stay, all you have to do is get there, and crossing the 113-mile, the 42-bridge overseas highway is one of the most magical drives you will ever experience. Seeing the vast ocean on both sides as you head to your holiday, gets you in the mood, the variation of blue hues brings on a sense of calm, and you just know this trip is going to be unforgettable.

Big Pine and Lower Keys

big pine key
Big Pine Key

Home to the National Key Deer Refuge Big Pine Key residents and community have taken many precautions to protect this endangered species.

This is more of a secluded area and the main reason why people who enjoy a holiday trip without all the madness and partying prefer this spot for some peace. A tranquil oasis not too far off the beaten track that a simple drive couldn’t complete, but a quiet spot to enjoy water activities for the first time with great snorkeling excursions and adventures.

And if you have kids then thinking about where to stay in Key West with family may have you considering this stop as they can enjoy the water sports, more than likely for the first time, in uncrowded waters which could leave them feeling overwhelmed.

Top Sights: Rated must-see by travelers

  • Florida Keys Nature and History Tour from Key West – A very popular attraction so early booking is essential before it sells out. Everything you want to know about the island’s wildlife, seeing the animals up close and personal with stops along the route for scenic photo opportunities, and a great way to spend half a day. Family-friendly for all ages.
  • Private Looe Key Snorkel from Big Pine – The ultimate way to see the ocean floor and its rainbow-colored marine life. Great for kids to try snorkeling for the first time, head out on the boat, and even try your hand at a bit of fishing. A perfect day out trip and the photos you can take are out of this world.

Top Excursions: Rated by hands-on experience

  • Full-day Tour of Florida Keys with Aquarium Encounters – Seeing the natural wildlife both on land and in the waters doesn’t get better than this. You have a chance to swim with the stingrays, see sharks, and touch the species in the rock pools. A fun trip that includes a picnic stop with food and drink, and then you are off to see the deer that makes the island so special.
  • Self-Guided Audio Tour in the Florida Keys – One of the best ways to see sights and the island at your leisure. Based on your GPS the trips are customizable by you and your interests and suggests stop and sights along the route that the guided tours don’t have the luxury of time to visit. Hidden gems of spots make it worth trying this new experience.

Top Accommodation: Rated by lowest stars and pricing for a more budget-friendly option (where to stay in Key West on a budget)

  • Sunshine Key King Travel Trailer 4 (3 stars, 8.9 fabulous ratings, 9.4 for location) – The perfect spot close to amenities, services, and attractions, but not within earshot of noise and the city hustling and bustling. Spacious for a couple looking for some quality time, and sleeps a family of 4 comfortably. Even your furry family member can vacation with you as they allow pets on request.
  • The Barnacle B&B (3 stars, 8.8 fabulous ratings, 9.3 for location) – If you wanted a spot of heaven this would be it, right on the water’s edge with outdoor dining in the sand while listening to the lapping waves on the shore edge. Breakfast daily and quirky décor, a perfect place to rest your head in the quiet of nature.

Bahama Village

bahama village

The original area was where, in the 19th century, the original black Bahamian settlers arrived. If you want a Caribbean experience rich in culture make this a stop on your tour. The area is teeming with quaint shops for bespoke handmade pieces and souvenirs to take home with you to remember the trip by, eateries filled with sweet delicacies and savories to fill the gap while out exploring.

The outdoor market is a must-visit for premium local products, artisan items that are one of a kind, and gorgeous island memorabilia.

Top Sights: Rated for being fun and charming

  • Perfect Pedi cab – When the day has been long and you just need a moment to catch your breath but don’t want to miss seeing more of the area, the Pedi cab is just what you need. Rest your feet and legs while being pedaled around the area and told stories or tales, and informed of the history of specific spots. A great adventure during the day and equally as great at night.
  • Dog Tired Studio and Gallery – Browse the art and souvenirs in this quaint shop filled with exquisite art pieces, the gallery owner is an avid dog and animal lover as seen in many of his works. Support by purchasing a great piece to take home to hang on the wall, or even the famous t-shirt. We could all use a helping hand in business, and when it comes to the talent to match why wouldn’t you?

Top Excursions: Rated by cultural and immersive

  • Bahama village walking tour – Travelers have commented this may be even better than the driven tours with a locally guided tour operator, embark on the walk around the island while listening to thrilling stories and quirky comments. The best way to hear insider jokes and be right in the heart of the island action.
  • Bahama Village, Hemmingway Home, and Southernmost Point Private Walking tour – A raved-about tour to enjoy with a highly knowledgeable 5th generation tour guide. The tour guide has been going on tours with her grandfather since she was a kid so if you want to know all there is about the African-Caribbean culture, this is the trip to take. Learning so much in only 2 hours is more than worth it.

Top Accommodation: Rated by highest stars and more luxury stays (where to stay in Key West on the beach)

  • The Reach Key West, Curio Collection by Hilton (5 stars, 7.3 good ratings, 9.0 for location) – Waking up to the sound of the ocean is exactly what you‘ll get here, the view from the rooms is unbeatable and you have a mere 5 minutes walk to the beach. If you have had enough on the sands the property has an onsite pool and fully fitted restaurant and fitness center facilities.
  • Casa Marina Key West, Curio Collection by Hilton (5 stars, 6.2 pleasant ratings, 8.5 for location) – Pure luxury at its finest. Oceanfront pools, massage services on the beach, full American continental and buffet breakfast daily, and a private beach just for guests. Start the day with a good workout in the gym, or make a day of it on the golf course off-site booked through the hotel.

Outside the city; Sugarloaf Key

sugarloaf key

The backcountry as they like to call is home to the water adventuring of kayaking, and if you visit this quiet spot it is a must to venture out onto the water in a kayak to explore.

Mangroves in the area make for great nature walks, helicopter tours to see the island from the sky, and even fishing charter tours for a hands-on experience of deep-sea fishing. There is something everyone can enjoy and take part in, and perfect for outdoor enthusiasts.

Top Sightseeing: Rated by uniqueness

  • American Shoal Lighthouse – An amazing sight you can see from far, set against the horizon and elevated on scaffolding so you see clearly through the lower level and embrace the lighthouse and the sea for all that it is.  When you get up close to it you see the intricate steel architecture and design, a must-do trip out by boat.
  • Capt. Clint Moore – Winner of a TripAdvisor Travelers Award 2022 and once you read the reviews and try it for yourself you will see why. A great day out on the water with the friendliest guide you could want, and enjoying snorkeling and marine sightseeing makes this day trip unforgettable.

Top Excursions: Rated by a great day out

  • Back Country Boat Rentals – Having your own boat for the day sounds too good to be true but you can in Sugarloaf Key, and some are kitted out with slides on board so once you are out on the water the kids can fly into the sea, swim back to the boat and do it all again. Thrilling and perfect for family days out. Take your own food and drink and dine out on the ocean, amazing and truly an experience the children will not forget.
  •  Get up and Go Kayaking – If there is only one thing you do while out on the island make sure it is kayaking. These transparent kayaks are something else, and seeing to the bottom of the water is mesmerizing. Enjoy the calm waters while paddling alongside nature.

Top Accommodation: Rated by traveler favorites

  • Sugarloaf Lodge (2 stars, 7.9 good ratings, 8.7 for location) – Right on the water you can wake up and go to sleep to the sound of the waves, breathtaking. There is an onsite pool and chairs and tables to enjoy outdoor dining at its finest. Spacious and neatly decorated, everything you need to enjoy your stay away from home.
  • Sunrise Point at Sugarloaf (3 stars, 3/5 ratings for amenities) – This holiday home has 3 bedrooms so it is perfect for big families and traveling parties, and is right on the water so the kids can play and swim and you can watch them from the comfort of your deck chair 5-meters away with a well-deserved chilled drink.

Key West Old Town

key west old town

The rocky beach and nature trails are just some of the best ways to enjoy this historic area, then simply stroll along the coast browsing in quirky decorated and decked out shops and sip coffee at the bars while watching the scenery and walkers. A relaxing atmosphere that settles you into a holiday mood.

Top Sightseeing: Rated by top things to do.

  • Conch Train Tour – Kids love a good old outdoor train, and this one is perfect to see the sights while keeping off your feet, and learning about the places. Fun for the whole family, and nice to see the buildings and their bespoke architecture.
  • Hemmingway House – Yes, the famous Ernest Hemmingway lived here for many years during the 1930s, and the home turned museum is a great way to look at his life and artifacts from his time.

Top Excursions: Rated for the more adult demographic

  • Duval Street – Nights and lights will make your trip complete when visiting this tourist-packed street of bars, music, and people letting go. And why not, you’re on holiday right? This strip of entertainment is a great way to unwind after a long day, let your hair down, and just enjoy yourself carefree.
  • Ghost Tour – Thrilling and exhilarating, and not for the faint-hearted. Stories and tales have been told for decades and seeing the sights where hosts have been known to lurk and the cemetery is a fun way to get the pulse going.

Top Accommodation: Rated by top picks (where is the best place to stay in Key West)

  • H2O Suites (4 stars, 9.4 superb ratings, 9.5 for location) – Spending time alone with your partner and with no one around is easily done at this hotel (the best place to stay in Key West for couples), rooms with private pools to enjoy at your leisure, and a fully fitted room with added amenities. Luxury living while on vacation, and free happy hour for guests make it one level above others.
  • Hyatt Residence Club, Beach house ( 4 stars, 9.0 superb ratings, 8.7 for location) – This property hosts an enormous outdoor pool so no feeling overcrowded here, and an onsite bar with snacks are available to guests. Hop on a bike to hire from the hotel and take a ride along the beachfront taking in the fresh air and soaking up the sun.

Staying in Key West FL.

It is absolutely somewhere gorgeous for you to put your bags down during your vacation and enjoy the island for all its beauty, and no matter your budget or traveling party, Key West will welcome you with open arms.

This friendly community, rich in history and fantastic cuisine (be sure to try the conch and key lime pie) is a bucket-list holiday for so many people around the world. Make the most of your trip to Key West, and your stay while here.

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