The best hotels in Key West

Rustic and handsome, this award-winning resort is named after the Commodore Perry. The hotel's decor scheme is made up of a variety of dark woods, warm brown textiles, and white walls and linens, and recalls the seafaring and shipbuilding days of Old Key West.

Relaxed and roomy, The Perry Hotel Key West is an ideal place to sprawl out for an extended stay, especially if you're in town to fish, boat, or otherwise take advantage of nature. That's because the 100-room hotel is located in Stock Island Marina Village, which has 288 private slips and plenty of opportunities to book charters.

You may also swim in two attractively designed waterfront pools, decked out with white umbrellas and teepee-shaped daybeds, and dine at three dockside restaurants. Concierge services help to plan water activities including snorkeling, diving, sailing, fishing, and more.

Trip Advisor Ranking: 11 out of 52 hotels in Key West

Booking.com Rating: 8.9 out of 10

Pros: The menu at Matt's Stock Island Kitchen & Bar is reason enough to visit, but the restaurant also features live music on Friday and Saturday nights. Additionally, Key West Distilling, also located at Stock Island Marina Village, gives complimentary tours to Perry Hotel guests every Friday at 3 p.m. A welcome glass of Champagne at check-in tells you everything you need to know about the hospitality here.

Cons: The hotel is located on an island that's actually adjacent to Key West, and it's five miles to the center of town. You'll need to take the shuttle service to Old Town. Also, the website says all rooms have ocean views, but that's not true. Plenty overlook the street and parking lot.

Parrot Key & Villas, with new and refurbished lodgings, offers one of the best values on Key West. The rooms and suites feature three different views: garden, garden/water, and waterfront, and every glance brings a feast for the eyes, especially if you're facing the Gulf of Mexico. The inside is soothing as well, with breezy textiles in shades of whites and neutrals, which makes for a pleasant canvas next to all the outdoor colors. Conch-inspired artwork completes the Key West charm.

While a standard garden king or double queen begins at $159 in the off-season, I suggest booking a garden suite for $214, or a waterfront king for $230. Regardless, all rooms and suites have a porch, patio or balcony, in-room Keurig coffee makers, L'Occitane products, and come with access to four beautifully landscaped pools, which are cleansed with minerals instead of chlorine.

Trip Advisor Ranking: 29 out of 52 hotels in Key West

Booking.com Rating: 8.9 out of 10

Pros: A fitness center is on-site, and a complimentary shuttle to Smathers Beach departs daily at 10 a.m., noon, 2 p.m., and 4 p.m. The Smathers Beach trips include towels, chairs, and return service.

Cons: While water sports equipment such as kayaks, paddle boards, and Waverunners are available on property, they cost an extra rental fee. Parrot Key is also over two miles to Duval Street, but again, the shuttle will take you there.

Tropical outside, majestic inside with stone floors, polished dark furniture, and marble bathrooms, Key West Marriott Beachside is a good all-around destination resort, especially if you're traveling with a family or group. A 16-slip marina allows ocean access for water sports rentals (kayaks and Jet-Skis) and boat charters. A tiny beach allows for tanning — or sweating — opportunities only, but you can slip into the waterfront pool to cool down. The 24/7 fitness center also looks out over the Gulf, so you feel like you're running outside even when while on the treadmill. Bike rentals are also available.

In September, book a standard King room for as low as $210. But these lowest-priced rooms are sometimes the locked-off extra rooms of suites. It might be wise to indulge in a Presidential Suite with a resort view, which includes a full-service kitchen and dining room, for less than $100 more. You can also request grocery service so you don't have to take time out of your day.

Trip Advisor Ranking: 28 out of 52 hotels in Key West

Booking.com Rating: 8.4 out of 10

Pros: Positioned on seven acres, this resort is large and able to host destination weddings and other events. Live music Thursday through Saturday makes you feel like you're in the heart of Key West. The breakfast buffet, on-site dining at Tavern N Town, happy hour, and room service are all good and helpful options.

Cons: More corporate and less charming than other local entities, the resort is about 3.5 miles from the center of Old Town. Guests can bike, use cars or ride-share services, or take the complimentary shuttle, though it is frequently full. Recent reviewers have complained about rooms needing attention and staff issues.

For some of the most comfortable pillowtop beds and updated rain shower bathrooms in Key West, check into the 142-room Pier House Resort & Spa. While a traditional Double Queen starts at $249 in sultry September, for an extra $100 you can score an Island Suite with a patio or balcony.

Rooms come with plantation shutters to keep the room cool or let in as much light as you choose, coffee and water, bathrobes, and umbrellas for the unexpected tropical storm. Morning coffee at the beach bar, fruit-infused water stations, and a welcome drink all speak to the hospitality to be expected here.

The spa is also one of the finest on the island, with 10,000 square feet and 10 treatment rooms offering everything from the signature "Milk and Honey" treatment, which includes an exfoliation, body wrap, and scalp massage, to a Thai foot massage. The facility includes a full fitness center, Vichy showers, and cosmetic services.

Trip Advisor Ranking: 19 out of 52 hotels in Key West

Booking.com Rating: 8.6 out of 10

Pros: Located at One Duval Street in an ideal waterfront setting, Pier House is one of the very few hotels to boast a private beach, as well as a pool surrounded by tropical landscaping. At both, towels, chairs, umbrellas, and attendants are available, and a 24-hour front desk with express check-in and check-out is helpful for travelers coming and going at odd hours. A Tesla charging station is an unusual plus.

Cons: The busy downtown location is not for everyone and the beach and pool get crowded quickly, so plan to stake your claim on a chair early. There's also live music on the beach so if someone also wants to listen to their own music it becomes a noisy competition. Housekeeping doesn't always show up early enough in the day.

Simonton Court Historic Inn and Cottages provides one of the most authentic and charming lodging experiences on the island. Stay in your choice of reclaimed historic buildings that range from an 1880s cigar factory to a shotgun Conch house. Room categories are numerous, and include double occupancy in the Victorian mansion to quadruple occupancy in wood-framed, pastel-painted cottages.

Follow the brick pathway through the grounds, which are extraordinary and well-maintained, to explore all four pools and a lovely, complimentary breakfast is served poolside, Continental-style, every morning. Aside from free Wi-Fi, that's about it for amenities. But the inn is a block from Duval Street, and concierge services will help arrange whatever tours and charters you like; the staff overall is extremely helpful and well-meaning.

Trip Advisor Ranking: 17 out of 52 hotels in Key West

Booking.com Rating: 9.2 out of 10

Pros: For adults only, Simonton Court Historic Inn and Cottages can easily accommodate groups of many different sizes and configurations. The location especially is ideal if you're in Key West for a bachelor, bachelorette party, or reunion.

Cons: For some accommodations, a minimum stay is required. Noise from the neighborhood may interfere with the sleep for those who retire on the early side, and the vintage nature of the buildings means the occasional maintenance issue does crop up.

Jimmy Buffett practically owns Key West, in both the overarching philosophy that his feel-good music provides and in the very real sense of his local businesses. Margaritaville Key West Resort & Marina manifests Buffett directly, with quotes from songs painted on the aqua and blue walls, and bolster pillows emblazoned with slogans like "attitude" and "latitude."

Stay on-site for activities ranging from sunbathing at the pool, where complimentary popsicles and fruit kebabs are served every afternoon, to spa treatments on manicured patios. You may also purchase a $20 day pass for a short boat ride to Margaritaville's sister resort, Sunset Key Cottages, which offers a white-sand beach with tiki umbrellas and food and beverage service.

In low season, standard rooms begin at 375 square feet with a balcony and complimentary Wi-Fi for $226. Upgrade to a pool view, marina view, ocean view, oceanfront view for better vantage points, though, the best deal is a recently renovated one-bedroom suite with a family room, sleeper sofa, and dining table, starting at $303.

Trip Advisor Ranking: 38 out of 52 hotels in Key West

Booking.com Rating: 8.7 out of 10

Pros: Bistro 45 for brunch is delicious, and drinking margaritas on Sunset Deck while watching the sky change hues is positively serene. From Sunset Deck, you can also watch the arguably more crowded nightly celebration at The Pier, or just join them. There's really nothing like it.

Cons: Margaritaville Key West Resort & Marina itself can be like one big block party thanks to a 37-slip marina on one side — one of the three cruise ports — and Duval Street/Mallory Square on the other. If the masses aren't your vibe, miss this one.

If your idea of Key West is lounging on a brightly-hued Adirondack chair while gazing at the calm Florida Straits, then Southernmost Beach Resort will deliver.

The resort, located in between Duval and Simonton streets, is in a prime location and one of the largest in town, covering six acres and two city blocks. Formerly known as the Southernmost Hotel Collection, it comprises two properties with similar names: Southernmost on the Beach and Southernmost Hotel, as well as La Mer Hotel and Dewey House. The last two are adults-only. The website doesn't really clarify this, so it's best to call and ask about the differences in room styles and prices when you go to book.

Charming and relaxed, the waterfront resort features a number of opportunities to park yourself waterside, including two beaches (one private, the other public) and three pools. While there's a fitness center with the usual treadmills, ellipticals, and weights, the beach and aqua yoga sessions are much more appealing. Likewise, the Petite Spa offers plenty of treatments, but you can also get a massage in a three-sided oceanfront cabana on the beach.

Trip Advisor Ranking: 27 out of 52 hotels in Key West

Hotels.com Rating: 8.6 out of 10

Pros: The Key West Old Towne Trolley, which offers tours of the island, stops at the resort, and you can also buy tickets at a counter there. Not into group activities? Get a coffee from Starbucks, also on-site, and walk to all the action.

Cons: The room categories are not only confusing but range in size, too, so you might end up with something as small as 290 square feet. And, despite a $45 resort fee, a lounge chair on the beach — if you can get one — costs an additional $10. You should also plan to get up early to score seats at the pools.

The Marquesa Hotel is my favorite place in Key West. I even seriously considered naming my daughter after it. This boutique resort is made up of a collection of restored historic properties: the main house, or the original Marquesa, and three newly renovated buildings (including a cottage), known as 4-1-4- Marquesa. Situated across the street, they're clustered around a gorgeously landscaped pool and fountain.

All told, the resort offers three pools, which you have access to wherever you stay, and furnishings reflect the environment with antique reproductions, lots of wicker, and airy, colorful fabrics, as well as updated bathrooms.

Although a standard Queen in the main house with a city view goes for as little as $250 in summer, I suggest upgrading to the more private, fresher rooms. A Balcony Deluxe with a King bed, private covered balcony, two lounge chairs, and a table is only $50 more during the same time period. Likewise, the Poolside Standards, on the first and second floors adjacent to the main house, feature either a terrace or balcony.

Trip Advisor Ranking: 6 out of 52 hotels in Key West

Booking.com Rating: 9.4 out of 10

Pros: The on-site Café Marquesa is one of the finest restaurants on the island. Additionally, rooms equipped with bathrobes, wet bars, refrigerators, and modern bathrooms with quality, contemporary fixtures all make for enticing accommodations. Free parking and the Old Town location means that you can leave your vehicle and walk to attractions and the ocean.

Cons: The main house doesn't have elevator access, so if you want to stay in the original building, but stairs are a problem, you're out of luck. While the location is great and only one block from Duval Street and four blocks from Mallory Square, it's very close to the thick of the action during high season, which can mean crowds.

With hues of lime, aqua, and turquoise plus rattan and wicker accent furniture running throughout both guest rooms and public spaces, Ocean Key Resort & Spa, a Noble House Resort, truly honors its surroundings. Self-described as "kitschy," while still high on the luxury scale, the resort is located between Key West Harbor and Mallory Square, smack in the middle of Old Town. In fact, the address is Zero Duval Street. Think of it as the anchor of Old Town, keeping you firmly embedded in the playground of Key West.

Three restaurants and bars — Hot Tin Roof, LIQUID Pool Bar & Lounge, and Sunset Pier —all offer views and access to the open air, so there's no excuse not to toast the infamous sunset, as the locals do. For an escape, retreat to your balcony and order in a "Craft and Charcuterie" experience with beer and a cured meat board (keep the board), or "The Ultimate Cuba Libre" with 10 Cane rum, Mexican Coca-Cola, fresh limes, and miniature Cuban sandwiches (keep the Riedel Coca-Cola glasses).

Trip Advisor Ranking: 13 out of 52 hotels in Key West

Booking.com Rating: 8.9 out of 10

Pros: SpaTerre at Ocean Key features signature treatments such as the "Ocean Devotion" massage and the "Key Lime Margarita Spa Pedicure." They may sound punny, but they're as luxe as you could want. I also like that the pool is heated, so during those rare cold fronts, you can still take a dip.

Cons: Water sports and activities all need to be arranged for an extra fee with the concierge. Also, the Sunset Pier becomes extremely crowded at — you guessed it — sunset, with tourists from all over the island, not just the hotel. Finally, know that ocean views can be blocked by cruise ships when they're in port, and the rooms are a little dated.

Overlooking the Key West Harbor, The Marker debuted in 2014, making it one of the newer properties in town. Contemporary and clean-lined with large-format, refillable Key West Aloe brand toiletries in the bathroom to prevent plastic waste, the hotel offers a variety of room categories, including several stringently ADA accessible formats. The resort also focuses on sustainability, with several features dedicated to improving the environment.

Very few hotels in Key West, or anywhere in South Florida, feature wall-to-wall, wavy-patterned threads underfoot, but all 96 rooms at the two-acre Marker Waterfront Resort include carpeting. A blue-and-white color scheme is reflected throughout the property, including at the three pools and the pool bar. One of those pools is adult-only, a nice option if you don't have kids. You might want to get there early, though, to stake a claim on a lounge chair or daybed. Folks hang out all day long, enjoying the poolside service, and talented technicians at the bar keep you hooked on craft cocktails and tequila tastings. When hunger strikes, dine at Cero Bodega, the Cal-Mex restaurant on-site.

Trip Advisor Ranking: 18 out of 52 hotels in Key West

Hotels.com Rating: 8.8 out of 10

Pros: Improve your fitness on-site in the modern gym, or ask the "Conchierge" to help you book water sports activities to work out naturally. You can also rent bicycles, but it's just as easy to walk to Duval Street and Mallory Square. The Marker is at the tip of all the action and is a primo spot to Instagram the sunset.

Cons: The bar books live bands, which you can hear in some of the rooms. You should expect both late-night and early-morning crowds given the Duval Street and seaport location. The underground parking lot is valet only and costs $35 per night.