52 Best Hotels in The Florida Keys, Florida

Ambrosia Key West

$$$ | 615, 618, 622 Fleming St., FL, 33040, USA

If you desire personal attention, a casual atmosphere, and a dollop of style, stay at these twin inns spread out on nearly 2 acres. Ambrosia is more intimate, with themed rooms such as the Treetop, Sailfish Suite, and Havana Cabana. Ambrosia Too is a delightful art-filled hideaway. Rooms and suites have original work by local artists, wicker or wood furniture, and spacious bathrooms. Each has a private entrance and deck, patio, or porch. A poolside full breakfast is included, and children are welcome.

Pros

  • Spacious rooms
  • Breakfast served poolside
  • Great location

Cons

  • On-street parking can be tough to come by
  • A little too spread out
  • High windows in some rooms let in the early morning light
615, 618, 622 Fleming St., FL, 33040, USA
305-296–9838
hotel Details
20 rooms
Rate Includes: Free Breakfast

Quick Facts

Angelina Guesthouse

$ | 302 Angela St., FL, 33040, USA

In the heart of Old Town, this adults-only home away from home offers simple, clean, attractively priced accommodations. The high rollers and ladies of the night were chased away long ago, but this charming guesthouse revels in its past as a gambling hall and bordello. Units range from small rooms sharing a bath to spacious rooms with king beds and sleeper sofas. Built in 1899, the yellow-and-white clapboard building has second-floor porches, gabled roofs, and a white picket fence. The current owners prettied the rooms with flower-print curtains and linens and added homemade cinnamon rolls, which receive rave reviews in the guest book, to the breakfast bar. A lagoon-style pool, fountain, and old-brick walkways accent a lovely garden.

Pros

  • Good value
  • Nice garden
  • Friendly staff

Cons

  • Thin walls
  • Basic rooms with no TVs
  • Shared balcony and four of the rooms share a bathroom
302 Angela St., FL, 33040, USA
305-294–4480
hotel Details
13 rooms
Rate Includes: Free Breakfast

Quick Facts

  • $

Azul del Mar

$$ | 104300 Overseas Hwy., FL, 33037, USA

The dock points the way to beautiful sunsets at this adults-only boutique hotel, which has been transformed from a run-down mom-and-pop place into a waterfront gem. As the innkeepers have backgrounds in the image business, the property offers great visuals, from marble floors and granite countertops to yellow-leather sofas and ice-blue bathroom tiles. Kayaks, paddleboards, barbecue grills, and a movie library are available for guest use, and two chickee huts on the beach are equipped with comfortable seating.

Pros

  • High-quality linens
  • Good location
  • Sophisticated design

Cons

  • Small beach
  • Could use a refresh
  • Minimum stays during holidays
104300 Overseas Hwy., FL, 33037, USA
305-451–0337
hotel Details
6 units
Rate Includes: No Meals

Quick Facts

  • $$

Recommended Fodor's Video

Azul Key West

$$ | 907 Truman Ave., FL, 33040, USA

The ultramodern, nearly minimalistic redo of this classic, circa-1903 Queen Anne mansion—an adults-only property—offers a break from the sensory overload of Key West's other abundant Victorian guesthouses. The boutique hotel, 3½ blocks from Duval Street, combines original trim, high ceilings, and shiny wood floors with sleek furnishings, including a curved frosted-glass-and-chrome check-in desk and leather loungers. Some of the spacious, serene rooms have private verandas, flat-screen TVs, and remote-controlled fans and lights.

Pros

  • Lovely building
  • Marble-floored baths
  • Luxurious linens

Cons

  • On a busy street
  • Modern isn't for everyone
  • Staff not on site
907 Truman Ave., FL, 33040, USA
305-296–5152
hotel Details
11 rooms
Rate Includes: Free Breakfast

Quick Facts

  • $$

Bahia Honda State Park Cabins

$ | 36850 Overseas Hwy., FL, 33043, USA

Elsewhere you'd pay big bucks for the wonderful views available at these three cabins, each of which has two two-bedroom units with full kitchens and baths, as well as air-conditioning (but no television, radio, or phone). All but one unit accommodate up to six (the other sleeps up to four and is accessible). The park also has popular campsites ($36 per night) suitable for either tents or motor homes. Some are directly on the beach—talk about a tent with a view! Cabins and campsites book up early, so reserve up to 11 months before your planned visit.

Pros

  • Great Florida Bay views
  • Beachfront camping
  • Affordable rates

Cons

  • Books up fast
  • Area can be buggy
  • Need to bring toiletries
36850 Overseas Hwy., FL, 33043, USA
305-872–2353
hotel Details
6 cabins
Rate Includes: No Meals

Quick Facts

  • $

Baker's Cay Resort Key Largo, Curio Collection by Hilton

$$$ | 97000 Overseas Hwy., FL, 33037, USA Fodor's Choice

Nestled within a “hardwood hammock” (localese for uplands habitat where hardwood trees such as live oak grow) near the southern border of Everglades National Park, this sprawling, 13-acre resort is not to be missed. There are plenty of reasons to stay on property including three dining outlets; a family activities center with on-site programs; state-of-the-art water sports; charter services and perks like outdoor movie nights, free use of fishing poles and complimentary bikes. Guest rooms, with a color palette that reflects the natural serenity of the grounds, are spacious, modern, and all have a balcony. The deluxe Baker's Cay suite with a kitchen and two bedrooms will make you want to quit your job and move to the Keys. Follow the trails to the white-sand beach for a nightly sunset celebration.

Pros

  • You never have to leave the resort
  • Pretty pools with waterfalls
  • 21-slip marina for all your boating needs

Cons

  • Some rooms overlook the parking lot
  • Pools are near the highway
  • High per-night resort fee
97000 Overseas Hwy., FL, 33037, USA
305-852–5553
hotel Details
200 rooms
Rate Includes: No Meals

Quick Facts

Big Pine Key Resort

$ | 33000 Overseas Hwy., FL, 33043, USA
Shutterstock

There's a congenial atmosphere at this lively, family-owned lodge-campground-marina—a happy mix of tent campers (who have the fabulous waterfront real estate), RVers (who look pretty permanent), and motel dwellers who like to mingle at the rooftop pool and play poker. Rooms have tile floors, wicker furniture, and doors that allow sea breezes to waft through. A skywalk joins the upper-story rooms with the pool and deck. Campsites range from rustic to full hookups. Everything is spotless—even the campground's bathhouse—and the service is good-natured and efficient. Satellite wireless means you can pick up a signal most places on the property, depending on the weather. The staff will book you a room, sell you bait, or hook you up with a fishing charter. There are plenty of family-oriented activities, so the youngsters will never complain about being bored. Discounts are available for week-long or longer stays.

Pros

  • Local fishing crowd
  • Nice pool
  • Great price

Cons

  • RV park is too close to motel
  • Deer will eat your food if you're camping
  • Some rooms could use updating
33000 Overseas Hwy., FL, 33043, USA
305-872–2351
hotel Details
16 rooms
Rate Includes: No Meals, To protect Key deer, no dogs allowed

Quick Facts

  • $

Bungalows Key Largo

$$$$ | 99010 Overseas Hwy., FL, 33037, USA Fodor's Choice

This 12-acre, adults-only hideaway has charming freestanding bungalows (some of which are waterfront) that are outfitted with a front porch with Adirondack chairs, a sitting area with a couch, and a private patio with an outdoor soaking tub, shower, and seating area. Each bungalow comes with two bikes, and there are yoga classes, paddleboards, an outdoor exercise hut equipped with a Peloton bike, and boats and floating tiki cruises available for hire from the resort's waterfront. This being an all-inclusive resort means all meals and drinks are included, with the option to dine at three sit-down restaurants: Fish Tales, Bogie & Bacall’s, and Sea Señor. There's also a cozy "living room" and swanky cocktail bar Hemingway's inspired by the author's home in Key West.

Pros

  • Only all-inclusive resort in the Keys
  • Relaxing atmosphere
  • A lavish spa

Cons

  • Gratuities are charged separately
  • Two-night minimum stay
  • Extra fees for early arrival and late checkout
99010 Overseas Hwy., FL, 33037, USA
305-363–2830
hotel Details
135 suites
Rate Includes: All-Inclusive

Quick Facts

Casa Marina, Curio Collection by Hilton

$$$ | 1500 Reynolds St., FL, 33040, USA
Casa Marina, A Waldorf Astoria Resort

This luxurious property is on the largest private beach in Key West, and it has the same richly appointed lobby with beamed ceilings, polished pine floor, and original art as it did when it opened in 1920 on New Year's Eve. Guest rooms are stylishly decorated in neutral colors that evoke a certain comfortable crispness. Fluffy bathrobes, Nespresso machines, and luxurious designer toiletries make it feel like a boutique hotel. Two-bedroom loft suites with balconies face the ocean. Many of the main building's rooms open onto large outdoor living rooms, and the two pools (one adult, one family) have a view of the Atlantic. For the utmost in pampering, pay a visit to Spa al Mare. You can even enjoy a treatment right on the resort's beach (the only resort in Key West to offer this indulgence). Guests also have privileges at its nearby sister property, The Reach.

Pros

  • Huge beach
  • On-site dining, bars, and water sports
  • Away from the crowds

Cons

  • Long walk to central Old Town
  • Expensive resort fee
  • Spa is across the street in a separate building
1500 Reynolds St., FL, 33040, USA
305-296–3535
hotel Details
311 rooms
Rate Includes: No Meals

Quick Facts

Casa Morada

$$$ | 136 Madeira Rd., FL, 33036, USA

This relic from the 1950s has been restyled into a suave, design-forward, all-suites property with outdoor showers and whirlpool tubs in some of the suites. Each unit claims its own design personality, with custom furnishings. Lush landscaping, a pool surrounded by a sandy area on its own island accessible by a bridge, and lounge chairs at the water's edge lend a spa-like vibe; complimentary adult yoga classes, a Zen garden, and gardens designed by Raymond Jungles complete the scene. Cool tile-and-terrazzo floors invite you to kick off your shoes and step out onto your private patio overlooking the gardens and the bay. Breakfast is served on the waterside terrace.

Pros

  • Private island connected by footbridge
  • Adults only
  • Complimentary use of bikes, kayaks, paddleboards, and snorkel gear

Cons

  • Dinner off property
  • Beach is small and inconsequential
  • Minimum two-night stay on weekends
136 Madeira Rd., FL, 33036, USA
305-664–0044
hotel Details
16 suites
Rate Includes: Free Breakfast

Quick Facts

Chesapeake Beach Resort

$$ | 83409 Overseas Hwy., FL, 33036, USA

Modern conveniences and a retro look are among the hallmarks of this boutique hotel on the beach. Rooms have a turquoise and sandstone color scheme and dark wood accents; each also has a porch or a balcony along with a mini-refrigerator and coffee maker. Most units are lined up along the long stretch of sand that all but encircles a lagoon; others overlook the tennis court. Thirteen oceanfront villas (including two stand-alones), a new tiki bar, and a boat ramp and dock round out the list of accommodations and amenities.

Pros

  • Oceanfront location
  • Reasonable prices
  • Private porches or balconies

Cons

  • No dining on site
  • $25 resort fee per night
  • No spa
83409 Overseas Hwy., FL, 33036, USA
305-664–4662
hotel Details
52 rooms
Rate Includes: No Meals

Quick Facts

  • $$

Coconut Palm Inn

$$ | 198 Harborview Dr., FL, 33070, USA
https://www.facebook.com/CoconutPalmInn/

This waterfront haven is tucked into a residential neighborhood beneath towering palms and native gumbo-limbos. No wonder it's a favorite of travel magazines. Each unit overlooks part of the 400-foot beach, where draping hammocks beckon you to nap. Prefer to paddleboard or kayak? Just slide one off the sand and go. Or take a dip in the pool. Less adventurous types can head for the Adirondack chairs along the shoreline or to those placed at the far end of the docks that jet into the bay. Units are comfortable and spacious and could be the backdrop for a Tommy Bahama ad with their upscale tropical decor and hand-carved furniture. Small patios give you your own slice of paradise. Breakfast is served beneath the bayfront chickee.

Pros

  • Secluded and quiet
  • 100% smoke-free resort
  • Sophisticated feel

Cons

  • Front desk closes early each evening
  • No access to ice machine when staff leave
  • No dining on site
198 Harborview Dr., FL, 33070, USA
305-852–3017
hotel Details
20 rooms
Rate Includes: Free Breakfast

Quick Facts

  • $$

Drop Anchor

$$ | 84959 Overseas Hwy., FL, 33036, USA

Immaculately maintained, this place has the feel of an old friend's beach house, and it's easy to find the one- or two-bedroom units, as they are painted in an array of Crayola colors. Interiors feature clean, simple furnishings and a nautical or tropical theme. Welcoming as the rooms may be, you didn't come to the Keys to sit indoors: there's a luscious expanse of white sand awaiting, and you can catch ocean breezes from your balcony, a comfy Adirondack chair, a picnic table in the sand, or a chaise lounge by the pool. A boat ramp accommodates anglers.

Pros

  • Bright and colorful
  • Very clean
  • Laid-back charm

Cons

  • Noise from the highway
  • Beach is for fishing, not swimming
  • Simplicity isn't for everyone
84959 Overseas Hwy., FL, 33036, USA
305-664–4863
hotel Details
18 suites
Rate Includes: No Meals

Quick Facts

  • $$

Eden House

$$ | 1015 Fleming St., FL, 33040, USA

From the vintage metal rockers on the street-side porch to the old neon hotel sign in the lobby, this 1920s rambling Key West mainstay hotel is high on character, low on gloss. You'll get a taste of authentic Old Key West, without sacrificing convenience or comfort. Rooms come in all shapes and sizes, from shared-bath basic to large apartments with full kitchens and private decks or porches. The spacious outdoor area is shaded by towering palms. Grab a book and plop in a hammock in the outdoor library, tucked into a sun-dappled corner with a gurgling waterfall and potted bonsai.

Pros

  • Free parking
  • Hot tub is actually hot
  • Daily happy hour around the pool

Cons

  • Pricey for older rooms
  • Brown towels take getting used to
  • Parking is first-come, first-served
1015 Fleming St., FL, 33040, USA
305-296–6868
hotel Details
44 rooms
Rate Includes: No Meals

Quick Facts

  • $$

Grassy Flats

$$ | 58182 Overseas Hwy., Grassy Key, FL, 33050, USA Fodor's Choice

Owned by retired professional kiteboarder Matt Sexton, this relaxed, eco-friendly resort and beach club is popular with water-sports enthusiasts, who make regular visits to its sibling property, The Lagoon, for wakeboarding sessions. Ideal for families, the Conch House has two- and three-bedroom suites with private verandas and full kitchens. An adults-only section of the property has its own pool area and the Humidor House, where oceanfront accommodations include rooms and king suites with four-poster mahogany beds and private balconies. Suites in the Wrecker’s House have claw-foot tubs and private wraparound balconies. The resort's sustainability initiatives include using plant-based detergents, not using pesticides and herbicides in on-site gardens, and both in-house recycling and seaweed-composting programs.

Pros

  • Complimentary paddleboards and kayaks
  • No resort fee
  • Peaceful atmosphere

Cons

  • Not close to sights in Marathon
  • Conch House rooms close to highway
  • Limited food options
58182 Overseas Hwy., Grassy Key, FL, 33050, USA
305-998–4590
hotel Details
33 units
Rate Includes: No Meals

Quick Facts

  • $$

Hampton Inn Key West

$ | 3755 S. Roosevelt Blvd., FL, 33040, USA

You know what to expect from this chain hotel: well-maintained rooms, predictable service, and competitive prices. This one also happens to be on a 7-acre piece of property with ocean views next to the airport. Rooms are bright and modern with palm-frond patterns, crisp white linens, and mosaic-tiled bathrooms. Most have balconies. The palm-shaded pool and tiki bar looks over the Atlantic, and a covered picnic area with a large barbecue grill encourages socializing.

Pros

  • Big pool area
  • Popular tiki bar serves liquor and food
  • Free breakfast

Cons

  • Roar of airplanes from nearby airport
  • Limited restaurant hours
  • Far from Duval Street
3755 S. Roosevelt Blvd., FL, 33040, USA
305-296–3500
hotel Details
100 rooms
Rate Includes: Free Breakfast

Quick Facts

Harborside Motel & Marina

$ | 903 Eisenhower Dr., FL, 33040, USA

This little motel neatly packages three appealing characteristics—affordability, safety, and a pleasant location between Old Town and New Town at Garrison Bight. Units are boxy and basic, with little patios and lots of peace and quiet. For on-the-water living, book one of the four stationary houseboats with shiny new interiors; each sleeps four. Sportfishing charters are just a block away, and there's a fish-cleaning table on the dock. The pool is small but refreshing after a day exploring.

Pros

  • Grills for cookouts
  • Friendly fishing atmosphere
  • Boat slips for guests

Cons

  • More than a mile from Duval Street
  • No parking for boat trailers
  • Minimum stays for special events and holidays
903 Eisenhower Dr., FL, 33040, USA
305-294–2780
hotel Details
16 rooms
Rate Includes: No Meals

Quick Facts

  • $

Hawks Cay Resort

$$$ | 61 Hawks Cay Blvd., Duck Key, FL, 33050, USA Fodor's Choice

The 60-acre, Caribbean-style retreat with a full-service spa and six restaurants has plenty to keep the kids occupied (and adults happy). Activities at the sprawling resort  include fishing charters, snorkeling, kayaking, stand-up paddleboarding, tennis, pickleball and mini-golf.  A pirate ship with water cannons delights at the family activity center, where there are two family pools and sports fields. Kids can also swim at one of the pools at the main lodge (the other is adults only) or in the protected saltwater lagoon. An in-the-water program lets guests get up close and personal with dolphins. When the older generation wants to head to the spa or out to dinner at fine-dining restaurant Sixty-One Prime, there are supervised programs for kids up to age 12. The spacious rooms and villas have a coastal look. The room rate does not include a hefty daily resort fee, which covers the resort-wide tram and other costs. 

Pros

  • Great activities for families
  • Restful spa
  • Full-service marina and dive shop

Cons

  • No real beach
  • Far from Marathon's attractions
  • Resort-wide tram gets busy, so plan to wait or walk far
61 Hawks Cay Blvd., Duck Key, FL, 33050, USA
305-743–7000
hotel Details
431 units
Rate Includes: No Meals

Quick Facts

Isla Bella Beach Resort

$$ | 1 Knights Key Blvd., FL, 33050, USA Fodor's Choice

Combining Caribbean luxury with Keys charm, this glamorous 24-acre resort is a destination unto itself with five pools, rooms along a sandy waterfront, toes-in-the-sand dining, and amenities like kids activities, resort bikes, and morning yoga. The one- and two-bed rooms and a handful of suites with kitchenettes have white and dark-blue color schemes and bathrooms outfitted with walk-in rainfall showers. The bottom-floor rooms feature large patios that lead directly out to the sand, while the upper floors boast spacious balconies with breathtaking views. A full-service spa, fitness center, and marina with charter fishing boats round out the ample offerings.

Pros

  • Secluded setting
  • Spacious rooms
  • Full-service spa and marina

Cons

  • No real beach
  • A hefty resort fee
  • Some balconies lack privacy
1 Knights Key Blvd., FL, 33050, USA
305-481–9451
hotel Details
199 rooms
Rate Includes: No Meals

Quick Facts

  • $$

Island City House Hotel

$$$ | 411 William St., FL, 33040, USA

A private garden with brick walkways, tropical plants, and a canopy of palms sets this convivial guesthouse apart from the pack. The vintage-1880s property has wraparound verandas, pine floors, and charm to spare. Arch House, a former carriage house, has a dramatic entry that opens into a lush courtyard. Although all suites front busy Eaton Street, only Suites 5 and 6 face it. A reconstructed cigar factory has become the poolside Cigar House, with spacious rooms, porches, decks, and plantation-style teak and wicker furnishings. The private tropical garden wraps around a spacious pool area. Children are welcome—a rarity in Old Town guesthouses.

Pros

  • Lush gardens
  • Knowledgeable staff
  • Bike rentals on site

Cons

  • Spotty Wi-Fi service
  • Front desk is staffed only 8 am–8 pm
  • No parking
411 William St., FL, 33040, USA
305-294–5702
hotel Details
24 suites
Rate Includes: No Meals

Quick Facts

Island House

$$$$ | 1129 Fleming St., FL, 33040, USA

Geared specifically toward gay men, this hotel features a health club, a video lounge, a café and bar, and rooms in historic digs. Clothing is optional everywhere but in the gym.

Pros

  • Lots of privacy
  • Just the place to get that all-over tan
  • Free happy hour for guests

Cons

  • No women allowed
  • Three rooms share a bath
  • Day passes bring visitors of every age, which is a pro or con depending on your mood
1129 Fleming St., FL, 33040, USA
305-294–6284
hotel Details
34 rooms
Rate Includes: No Meals

Quick Facts

Key West Bed and Breakfast/The Popular House

$ | 415 William St., FL, 33040, USA

There are accommodations for every budget here, but the owners reason that budget travelers deserve as pleasant an experience (and as lavish a tropical continental breakfast) as their well-heeled counterparts. Local art—large, splashy canvases and a Gauguinesque mural—decorates the walls, while handmade textiles (owner Jody Carlson is a talented weaver) drape chairs, couches, and beds at this historic home. Less expensive rooms burst with bright colors (hand-painted dressers add a whimsical flourish) and balconies on the second-floor rooms overlook the gardens. Spacious, and more expensive, third-floor rooms are decorated with a paler palette and original furniture.

Pros

  • Lots of art
  • Tiled outdoor shower
  • Hot tub and sauna area is a welcome hangout

Cons

  • Some rooms are small
  • Four rooms have shared baths
  • Historic homes have thinner walls
415 William St., FL, 33040, USA
305-296–7274
hotel Details
10 rooms
Rate Includes: Free Breakfast

Quick Facts

  • $

Key West Marriott Beachside Hotel

$$$$ | 3841 N. Roosevelt Blvd., FL, 33040, USA
https://www.facebook.com/keywestmarriottbeachsidehotel/

This hotel attracts convention business by offering the biggest ballroom in Key West, but it also appeals to families with its spacious, impeccably and tastefully decorated rooms and one-, two-, or three-bedroom condo units. Designer furnishings reflect the resort's waterfront location. Real china in the kitchens and marble hot tubs add touches of luxury in the suites. Some rooms have spiral staircases down to the gardens and up to the rooftop sun decks. Families enjoy the beach and pool area. Adults enjoy the pool bar and fine on-site dining. Complimentary shuttles take guests to Old Town and the airport.

Pros

  • Private tanning beach
  • Poolside cabanas
  • Complimentary shuttle to Old Town and airport

Cons

  • No swimming at its beach
  • Lots of conventions and conferences
  • Cookie-cutter facade
3841 N. Roosevelt Blvd., FL, 33040, USA
305-296–8100
hotel Details
258 units
Rate Includes: No Meals

Quick Facts

La Pensione

$$ | 809 Truman Ave., FL, 33040, USA

Hospitality and period furnishings make this 1891 home, once owned by a cigar executive, a wonderful glimpse into Key West life in the late 19th century. Each of the rooms has a private bath and king-size or double beds. All but one has a sitting area—the exception being a wheelchair-accessible room. None have TVs, but not to worry: there's plenty of entertainment on nearby Duval Street. Rates include daily continental breakfast in the dining room or on the veranda.

Pros

  • Pine-paneled walls
  • First-come, first-served parking included
  • Some rooms have wraparound porches

Cons

  • Street-facing rooms are noisy
  • Rooms do not have TVs
  • Rooms accommodate only two people
809 Truman Ave., FL, 33040, USA
305-292–9923
hotel Details
9 rooms
Rate Includes: Free Breakfast

Quick Facts

  • $$

La Siesta Resort & Marina

$$$ | 80241 Overseas Hwy., FL, 33036, USA

With 6 acres of oceanfront property, accommodations that range from studio units to a glamorous three-bedroom waterfront home, and staffers who go the extra mile, this resort has everything a visitor to the Keys could want. Units are clean and bright with kiwi-color accents and a sunny vibe. With garden views, ocean views, a freshwater zero-entry pool, a long stretch of sand (dotted with lounge chairs) right on the Atlantic, and beach games, all you need is a drink—and they have that, too. The poolside café, Wild & Lime, serves light meals and beer and wine. You can resort-hop to its sister properties and enjoy even more amenities.

Pros

  • Free use of kayaks, paddleboards, bicycles, and fishing rods
  • Free Wi-Fi
  • Access to sister properties

Cons

  • $40 nightly resort fee
  • Bar-café only open util 7
  • Not a swimming beach
80241 Overseas Hwy., FL, 33036, USA
305-664–2132
hotel Details
53 rooms
Rate Includes: Free Breakfast

Quick Facts

Largo Resort

$$$$ | 101740 Overseas Hwy., FL, 33037, USA

Behind 10-foot, dark-wood Kong gates is a Bali-inspired world, where tranquility washes over you like a rain shower. The entire property is spa-like with lush palms, buttonwoods, and orchids everywhere. The bungalows have a king bed in one room and a queen in the other, along with European fixtures, separate baths, and a small kitchenette stocked with water bottles. Relax in the large infinity pool, at the beach, or on the deck. Snorkel in the private lagoon, or just catch a magical Key Largo sunset. If you want even more space and privacy, rent the 5,000-square-foot Grand Lodge that sleeps eight.

Pros

  • Unrivaled privacy
  • Free kayaks and paddleboards
  • Weekday special rates

Cons

  • No food or drinks on site for purchase
  • Removed from sights
  • Quietude isn't for everyone
101740 Overseas Hwy., FL, 33037, USA
305-451--0424
hotel Details
6 bungalows
Rate Includes: No Meals

Quick Facts

Little Basin Villas

$$$$ | 84 Johnson Rd., FL, 33036, USA

These two-story, state-of-the-art, 1,600-square-foot villas could easily be the set for a Coastal Living magazine shoot. Interiors are white with lots of natural light, and each of the three bedrooms has its own spacious bathroom. You'll feel right at home with a gourmet kitchen, smart TV, audio system, keyless entry, and washer and dryer. There is even dock space for a small boat. Take advantage of the location and explore the numerous shops, restaurants, museums, and historic sites—all within walking distance.

Pros

  • Great location
  • Nice pool and tiki huts
  • Floating dock for launching kayaks

Cons

  • No office on site
  • Mangroves block full water views
  • No daily housekeeping
84 Johnson Rd., FL, 33036, USA
305-363–8999
hotel Details
9 villas
Rate Includes: No Meals

Quick Facts

Margaritaville Beach House

$$ | 2001 S. Roosevelt Blvd., FL, 33040, USA Fodor's Choice

This property, which definitely has a modern-beach-house feel, features a lagoon-style pool with a waterfall; lush landscaping with pathways, hammocks, and lawn games; and Jimmy Buffet–inspired flair with poolside entertainment and colorful artwork. Rooms—handsomely outfitted with whitewashed accents and reclaimed wood—have kitchenettes with microwaves and mini-refrigerators. Although the hotel is a bit removed from Duval Street, there's a complimentary shuttle bus to all the action, and Smathers Beach is a two-minute walk away. Breakfast, lunch, and dinner are served on an elevated, covered patio overlooking the pool at the Tin Cup Chalice restaurant, where dishes are often classics with a twist (perhaps pineapple beet salad or curry shrimp). Daily lobby refreshments include LaVazza coffee in the morning and fresh-baked cookies in the afternoon.

Marquesa Hotel

$$$ | 600 Fleming St., FL, 33040, USA Fodor's Choice

In a town that prides itself on its laid-back luxury, this complex of four restored 1884 houses stands out. Guests—typically shoeless—relax among two richly landscaped pools, rock waterfalls, and peaceful gardens. Elegant rooms surround a courtyard and have antique and reproduction furnishings, earthy tones with black-and-white accents, marble baths, and outdoor sitting areas. The lobby has several outstanding works by local artists. The clientele varies from mature and affluent to baby boomers who've discovered its romance.

Pros

  • Room service
  • Romantic atmosphere
  • Turndown service

Cons

  • Street-facing rooms can be noisy
  • Expensive rates
  • No elevator
600 Fleming St., FL, 33040, USA
305-292–1919
hotel Details
27 rooms
Rate Includes: No Meals, No children under age 14 allowed.

Quick Facts

NYAH: Not Your Average Hotel

$$$ | 420 Margaret St., FL, 33040, USA
https://www.facebook.com/NYAHotels/

From its charming white picket fence, it may look similar to other Victorian-style Key West B&Bs, but that’s where the similarities end, as this adults-only property's minimalistic rooms (all with upscale, private baths) have customizable sleeping arrangements: up to six can stay in one room, and all get their own bed. Each person also gets a twin USB charging station and RFID-locking closet. It’s high-tech meets laid-back Key West—and a marriage made in budget-savvy heaven. NYAH is a unique concept and it might not be for everyone, but if you've ever been on a cruise ship, you'll get it. Socializing outdoors is encouraged by the lack of furniture and space indoors---you can enjoy three pools, two Jacuzzis, and numerous sun decks in a glorious, tropical setting. The Historic Seaport is only two blocks away and Duval is four.

Pros

  • Central location
  • Perfect for traveling with a group of friends
  • Free daily happy hour

Cons

  • Small rooms, even smaller closets
  • Street parking only
  • No toiletries provided
420 Margaret St., FL, 33040, USA
305-296–2131
hotel Details
36 rooms
Rate Includes: Free Breakfast, Age 18 and over only

Quick Facts