Long known for its free-spirited vibe and its identity as the iconoclastic “Conch Republic,” Key West welcomes you to come as you are, whether that means strolling past street-roaming roosters in your finest cowboy hat and Daisy Dukes, joining the revelers on Duval Street à la Mardi Gras , enjoying family time on the beach, or just staying put around your hotel pool “wasting away again in Margaritaville.” (Jimmy Buffett actually wrote the final verses of the song circa 1977 while stuck in traffic on the Seven Mile Bridge heading back to the Florida Keys , then debuted it on Duval Street shortly thereafter.) It’s definitely a place that caters to hedonistic tendencies at land’s end, especially during Fantasy Fest and other wild celebrations throughout the year, but it’s equally suited to soaking up the sun and embracing an IDGAF attitude. Beneath the more recent commercialization of Key West lies a deeper charm, reflected in its eclectic mix of resorts. The most sought-after stays are in Old Town, which occupies the island’s western edge, touching both the Gulf of Mexico and the Atlantic Ocean. Old Town is remarkably walkable, with fabulous restaurants, historic sites, and kitschy dive bars never more than a short stroll away. True, there are plenty of places to stay in New Town, often at lower rates. But why rely on an hourly shuttle to Old Town or stare at a chain mall parking lot from your room when so much of the fun of Key West is crawling back to your hotel through picturesque neighborhoods and lush gardens after a night of debauchery? There’s also something to be said for actually sleeping in one of the historic cottages and buildings that speak to Key West's earlier days, recalling the words of Hemingway and lyrics of Buffett. Whether you’re after a romantic retreat, a fun weekend with your besties, a gay nudist escape , or a laid-back family vacation, you’ll find it among our picks for the best hotels in Key West. Explore our complete Key West travel guide , which includes: The Best Things to Do in Key West The Best Restaurants in Key West The Best Beaches in the Florida Keys How we choose the best hotels in Key West Every hotel review on this list has been written by a Condé Nast Traveler journalist who knows the destination and has visited that property. When choosing hotels, our editors consider properties across price points that offer an authentic and insider experience of a destination, keeping design, location, service, and sustainability credentials top of mind. This gallery has been updated with new information since its original publish date. Courtesy Ella's Cottages Save to wishlist Courtesy Ella's Cottages Save to wishlist Courtesy Ella's Cottages Save to wishlist Courtesy Ella's Cottages Save to wishlist Ella's Cottages For travelers drawn to the historic side of Key West, Old Town's Ella’s Cottages is an intimate collection of 22 rooms and suites tucked behind a white picket fence on Simonton Street. The original version of the property was housing for local cigarmakers in the 1800s. It became a hotel in the 1930s, and today is part of Key West Historic Inns. The shady tropical gardens, porches, and vintage architectural details recall the Key West of another era, while interiors have been refreshed with breezy, beach-inspired furnishings and modern comforts. Many accommodations here have private patios, adding to the feeling of staying in a gracious island home rather than a conventional hotel. The property is also dog-friendly, welcoming pets (without breed or weight restrictions) for $50 per night, a rarity that makes it especially appealing for travelers bringing four-legged family members. Ella’s is also a member of Small Luxury Hotels of the World and participates in the Hilton Honors program. Best of all, its central Old Town location puts Duval Street and many of Key West’s restaurants, bars, and attractions within easy walking distance. Read Full Review Check Availability at Booking.com Check Availability at Expedia Courtesy Ella's Cottages Save to wishlist Courtesy Ella's Cottages Save to wishlist Courtesy Ella's Cottages Save to wishlist Courtesy Ella's Cottages Save to wishlist Ella's Cottages For travelers drawn to the historic side of Key West, Old Town's Ella’s Cottages is an intimate collection of 22 rooms and suites tucked behind a white picket fence on Simonton Street. The original version of the property was housing for local cigarmakers in the 1800s. It became a hotel in the 1930s, and today is part of Key West Historic Inns. The shady tropical gardens, porches, and vintage architectural details recall the Key West of another era, while interiors have been refreshed with breezy, beach-inspired furnishings and modern comforts. Many accommodations here have private patios, adding to the feeling of staying in a gracious island home rather than a conventional hotel. The property is also dog-friendly, welcoming pets (without breed or weight restrictions) for $50 per night, a rarity that makes it especially appealing for travelers bringing four-legged family members. Ella’s is also a member of Small Luxury Hotels of the World and participates in the Hilton Honors program. Best of all, its central Old Town location puts Duval Street and many of Key West’s restaurants, bars, and attractions within easy walking distance. Check Availability at Booking.com Check Availability at Expedia Save to wishlist Save to wishlist Save to wishlist Save to wishlist La Concha Key West, Autograph Collection Following a $35 million facelift in the run-up to the property’s 2026 centennial, La Concha brings both style and substance at 100, combining rich history with modern energy in a prime Duval Street location. Its new identity under Marriott’s Autograph Collection is also reason to celebrate for Bonvoy point collectors and redeemers. The fun starts with a double-height lobby splashed in pink and green and flowing into El Dom Cuban Café, Tropicado Mojito Bar, and Perla restaurant. Upstairs, 160 rooms and suites mix island chic with a sense of place through leafy wallpaper, handsome headboards, and artwork by local artists depicting roosters and vintage island scenes; “Conched Out” Do Not Disturb signs add a cheeky touch. But the seventh-floor Grand Dame Villas at the Rooftop remain the splurge: just seven rooms in a sophisticated red palette with black-and-white flamingo wallpaper, floor-to-ceiling windows, telescopes, and push-button blackout curtains. Between the lively new public spaces, rooftop accommodations, and location steps from Key West’s bars, restaurants, and shops, La Concha finally feels worthy of its landmark address. Read Full Review Check Availability at Expedia Check Availability at Booking.com Save to wishlist Save to wishlist Save to wishlist Save to wishlist La Concha Key West, Autograph Collection Following a $35 million facelift in the run-up to the property’s 2026 centennial, La Concha brings both style and substance at 100, combining rich history with modern energy in a prime Duval Street location. Its new identity under Marriott’s Autograph Collection is also reason to celebrate for Bonvoy point collectors and redeemers. The fun starts with a double-height lobby splashed in pink and green and flowing into El Dom Cuban Café, Tropicado Mojito Bar, and Perla restaurant. Upstairs, 160 rooms and suites mix island chic with a sense of place through leafy wallpaper, handsome headboards, and artwork by local artists depicting roosters and vintage island scenes; “Conched Out” Do Not Disturb signs add a cheeky touch. But the seventh-floor Grand Dame Villas at the Rooftop remain the splurge: just seven rooms in a sophisticated red palette with black-and-white flamingo wallpaper, floor-to-ceiling windows, telescopes, and push-button blackout curtains. Between the lively new public spaces, rooftop accommodations, and location steps from Key West’s bars, restaurants, and shops, La Concha finally feels worthy of its landmark address. Check Availability at Expedia Check Availability at Booking.com Ocean Key Save to wishlist Ocean Key Resort & Spa Save to wishlist Ocean Key Resort & Spa Save to wishlist Ocean Key Resort & Spa Readers' Choice Awards 2017, 2018, 2019, 2020, 2021, 2023, 2024 A Key West favorite, Ocean Key completed a prolonged renovation in 2026 to much fanfare, unveiling a redesigned lobby, bar, and lounge to complement its 100 guestrooms and suites, which were redone in 2025 with pastel-hued walls, cheery floral and striped fabrics, and colorful rugs. Post-renovation, suffice to say, it’s tropical island vacation décor to a tee, but done with an elegant touch. Balconies overlook the Gulf of Mexico or Duval Street, adding to the sense of place. Eating and drinking are important elements of an Ocean Key stay, too. At Sunset Pier, rainbow-hued tables and chairs, each with its own colorful umbrella, stretch along a wooden pier surrounded by 360-degree water views and anchored by a lively round bar. There’s also the new Sweet Bird lobby bar and Marina View Lounge, the latter with panoramic harbor views and an indoor-outdoor setup. But our favorite remains Hot Tin Roof, where knockout Key West cuisine, from plantain-crusted swordfish to Cuban bread pudding, comes with front-row seats to one of the island’s best sunset shows. Read Full Review Check Availability at Expedia Check Availability at Booking.com Ocean Key Save to wishlist Ocean Key Resort & Spa Save to wishlist Ocean Key Resort & Spa Save to wishlist Ocean Key Resort & Spa A Key West favorite, Ocean Key completed a prolonged renovation in 2026 to much fanfare, unveiling a redesigned lobby, bar, and lounge to complement its 100 guestrooms and suites, which were redone in 2025 with pastel-hued walls, cheery floral and striped fabrics, and colorful rugs. Post-renovation, suffice to say, it’s tropical island vacation décor to a tee, but done with an elegant touch. Balconies overlook the Gulf of Mexico or Duval Street, adding to the sense of place. Eating and drinking are important elements of an Ocean Key stay, too. At Sunset Pier, rainbow-hued tables and chairs, each with its own colorful umbrella, stretch along a wooden pier surrounded by 360-degree water views and anchored by a lively round bar. There’s also the new Sweet Bird lobby bar and Marina View Lounge, the latter with panoramic harbor views and an indoor-outdoor setup. But our favorite remains Hot Tin Roof, where knockout Key West cuisine, from plantain-crusted swordfish to Cuban bread pudding, comes with front-row seats to one of the island’s best sunset shows. Check Availability at Expedia Check Availability at Booking.com Courtesy of Casa Marina Key West, Curio Collection by Hilton Save to wishlist Courtesy of Casa Marina Key West, Curio Collection Save to wishlist Courtesy of Casa Marina Key West, Curio Collection Save to wishlist Courtesy of Casa Marina Key West, Curio Collection Save to wishlist Casa Marina Key West Readers' Choice Awards 2017, 2018, 2019, 2020, 2025 Opened on New Year’s Day in 1920 by Henry Flagler, Casa Marina has lived many lives over the past century, including a stint housing the U.S. Navy and later serving as the U.S. Army’s Sixth Missile Battalion headquarters during the Cuban Missile Crisis. Following an $80 million renovation, Key West’s grande dame returned to peak form in 2025 with a soothing, tropical-inspired take on the historic property. The high-ceilinged lobby retains restored wooden pillars and arched windows, while all 311 rooms and suites have been completely redone in a handsome mix of rattan, woven fabrics, wooden furnishings, and open cabinetry. But the real calling card remains outside: Casa Marina’s 1,100 feet of private beach, lined with loungers and framed by two piers, is the largest in Key West, where rocky shores are otherwise the norm. Add two oceanfront pools, watersports, and beachfront dining at Dorada, and no other property on the island captures the true resort feel quite like this. Read Full Review Check Availability at Hilton Check Availability at Booking.com Courtesy of Casa Marina Key West, Curio Collection by Hilton Save to wishlist Courtesy of Casa Marina Key West, Curio Collection Save to wishlist Courtesy of Casa Marina Key West, Curio Collection Save to wishlist Courtesy of Casa Marina Key West, Curio Collection Save to wishlist Casa Marina Key West Opened on New Year’s Day in 1920 by Henry Flagler, Casa Marina has lived many lives over the past century, including a stint housing the U.S. Navy and later serving as the U.S. Army’s Sixth Missile Battalion headquarters during the Cuban Missile Crisis. Following an $80 million renovation, Key West’s grande dame returned to peak form in 2025 with a soothing, tropical-inspired take on the historic property. The high-ceilinged lobby retains restored wooden pillars and arched windows, while all 311 rooms and suites have been completely redone in a handsome mix of rattan, woven fabrics, wooden furnishings, and open cabinetry. But the real calling card remains outside: Casa Marina’s 1,100 feet of private beach, lined with loungers and framed by two piers, is the largest in Key West, where rocky shores are otherwise the norm. Add two oceanfront pools, watersports, and beachfront dining at Dorada, and no other property on the island captures the true resort feel quite like this. Check Availability at Hilton Check Availability at Booking.com Courtesy Hyatt Key West Resort and Spa Save to wishlist Hyatt Centric Key West Resort & Spa Save to wishlist Hyatt Centric Key West Resort & Spa Readers' Choice Awards 2018, 2021, 2022, 2024, 2025 A trusted, unfussy brand with a prime waterfront location, Hyatt Centric Key West Resort & Spa spreads across four low-rise buildings on the Gulf of Mexico at the start of Harbor Walk, a half-mile pathway along the Historic Seaport. Duval Street and Mallory Square are also a short walk away, though there’s plenty of reason to stay put. Every room has a balcony, most with at least partial ocean views, plus breezy white linens, light wood accents, and teal penny tile in the bathrooms. Dining is a highlight, especially Four Flamingos, the second outpost of Top Chef Richard Blais’ popular Orlando restaurant, where signatures include a bone-in swordfish chop crusted in preserved black Key lime. Between meals, toggle among the main pool, two slivers of man-made beach, and the swing at the end of the dock. World of Hyatt members can earn and redeem points here, too. Read Full Review Check Availability at Expedia Check Availability at Booking.com Courtesy Hyatt Key West Resort and Spa Save to wishlist Hyatt Centric Key West Resort & Spa Save to wishlist Hyatt Centric Key West Resort & Spa A trusted, unfussy brand with a prime waterfront location, Hyatt Centric Key West Resort & Spa spreads across four low-rise buildings on the Gulf of Mexico at the start of Harbor Walk, a half-mile pathway along the Historic Seaport. Duval Street and Mallory Square are also a short walk away, though there’s plenty of reason to stay put. Every room has a balcony, most with at least partial ocean views, plus breezy white linens, light wood accents, and teal penny tile in the bathrooms. Dining is a highlight, especially Four Flamingos, the second outpost of Top Chef Richard Blais’ popular Orlando restaurant, where signatures include a bone-in swordfish chop crusted in preserved black Key lime. Between meals, toggle among the main pool, two slivers of man-made beach, and the swing at the end of the dock. World of Hyatt members can earn and redeem points here, too. Check Availability at Expedia Check Availability at Booking.com Key West Historic Inns Save to wishlist Key West Historic Inns Save to wishlist Key West Historic Inns Save to wishlist Key West Historic Inns Save to wishlist Winslow's Bungalows Readers' Choice Awards 2021 A campus of whitewashed cottages and former homes cast predominantly in classic Key West architectural style, Winslow’s Bungalows is a history-steeped retreat two blocks from Duval Street. With 85 units, it’s the largest of the five Key West Historic Inns and also a member of Small Luxury Hotels of the World, allowing Hilton Honors members to earn and redeem points here. Despite its size, Winslow’s feels intimate, more like a collection of private homes than a conventional hotel. Several pools, including a large heated one, and plenty of tucked-away places to relax, hammocks included, dot the landscaped grounds, while continental breakfast comes standard with every stay. Considering the campus includes one of Key West’s oldest homes and oldest lodgings, dating to 1856, it’s worth asking the front desk for a quick primer on Winslow’s history. Read Full Review Check Availability at Expedia Check Availability at Booking.com Key West Historic Inns Save to wishlist

Key West Historic Inns Save to wishlist Key West Historic Inns Save to wishlist Key West Historic Inns Save to wishlist Winslow's Bungalows A campus of whitewashed cottages and former homes cast predominantly in classic Key West architectural style, Winslow’s Bungalows is a history-steeped retreat two blocks from Duval Street. With 85 units, it’s the largest of the five Key West Historic Inns and also a member of Small Luxury Hotels of the World, allowing Hilton Honors members to earn and redeem points here. Despite its size, Winslow’s feels intimate, more like a collection of private homes than a conventional hotel. Several pools, including a large heated one, and plenty of tucked-away places to relax, hammocks included, dot the landscaped grounds, while continental breakfast comes standard with every stay. Considering the campus includes one of Key West’s oldest homes and oldest lodgings, dating to 1856, it’s worth asking the front desk for a quick primer on Winslow’s history. Check Availability at Expedia Check Availability at Booking.com Save to wishlist Save to wishlist Save to wishlist Save to wishlist Island House Key West Resort Key West has long been a refuge for those rebelling against imposed social norms, and the adults-only, clothing-optional Island House remains a testament to the island’s progressive, free-spirited ethos. Cloaked in dense foliage at the edge of Old Town, the resort caters specifically to gay men, with a large pool and surrounding bar at its center, plus a sundeck, multiple hot tubs, steam room, sauna, and fitness center. Most rooms were renovated in 2024, trading an old Florida look for something more contemporary, though accommodations still vary widely in size and style, from small queens with shared baths to apartments with full kitchens, private porches, and dedicated parking. In early 2026, the resort debuted its most ambitious accommodations to date: Island Mates Manor, a pair of three-story villas offered as month-long luxury vacation rentals rather than nightly stays. Each has a chef’s kitchen, extensive custom woodwork, two king suites, 2.5 baths, private balconies, built-in desks, and a washer and dryer; the villas share a pool with in-water ledge loungers and a six-person hot tub. Villa guests also have access to all Island House amenities, including its 24-hour outdoor café and bar and four complimentary alcoholic drinks during daily happy hour. Duval Street’s bars and restaurants are about a 15- to 20-minute walk away, including LGBTQ+ favorites 801 Bourbon Bar, One Saloon, and Bourbon Street Pub. Read Full Review Check Availability at Island House Key West Resort Save to wishlist Save to wishlist Save to wishlist Save to wishlist Island House Key West Resort Key West has long been a refuge for those rebelling against imposed social norms, and the adults-only, clothing-optional Island House remains a testament to the island’s progressive, free-spirited ethos. Cloaked in dense foliage at the edge of Old Town, the resort caters specifically to gay men, with a large pool and surrounding bar at its center, plus a sundeck, multiple hot tubs, steam room, sauna, and fitness center. Most rooms were renovated in 2024, trading an old Florida look for something more contemporary, though accommodations still vary widely in size and style, from small queens with shared baths to apartments with full kitchens, private porches, and dedicated parking. In early 2026, the resort debuted its most ambitious accommodations to date: Island Mates Manor, a pair of three-story villas offered as month-long luxury vacation rentals rather than nightly stays. Each has a chef’s kitchen, extensive custom woodwork, two king suites, 2.5 baths, private balconies, built-in desks, and a washer and dryer; the villas share a pool with in-water ledge loungers and a six-person hot tub. Villa guests also have access to all Island House amenities, including its 24-hour outdoor café and bar and four complimentary alcoholic drinks during daily happy hour. Duval Street’s bars and restaurants are about a 15- to 20-minute walk away, including LGBTQ+ favorites 801 Bourbon Bar, One Saloon, and Bourbon Street Pub. Check Availability at Island House Key West Resort Billy Joe Hoyle/Eden House Save to wishlist Eden House The oldest operating hotel in Key West, Eden House opened in 1924 as the Gibson Hotel and expanded over the decades to incorporate several neighboring conch houses. Today, wooden pathways connect the historic main building to a cluster of converted cottages, with a heated pool and tiki bar at the heart of it all. The 35 accommodations are refreshingly individual, ranging from compact rooms with shared baths to deluxe kings with porches overlooking Fleming Street and loft suites sleeping up to four. There’s history everywhere: vintage photos line the walls, original banisters remain in the main house, and the 1990 Goldie Hawn film Criss Cross was shot here, inspired by a novel written on property back in 1976. Yet Eden House is hardly stuck in the past, thanks to continuous upgrades. On-site Azur turns out excellent New American cooking with Italian influences, while the residential Fleming Street location puts Duval Street and the Historic Seaport within easy walking distance. Read Full Review Check Availability at Expedia Check Availability at Booking.com The oldest operating hotel in Key West, Eden House opened in 1924 as the Gibson Hotel and expanded over the decades to incorporate several neighboring conch houses. Today, wooden pathways connect the historic main building to a cluster of converted cottages, with a heated pool and tiki bar at the heart of it all. The 35 accommodations are refreshingly individual, ranging from compact rooms with shared baths to deluxe kings with porches overlooking Fleming Street and loft suites sleeping up to four. There’s history everywhere: vintage photos line the walls, original banisters remain in the main house, and the 1990 Goldie Hawn film Criss Cross was shot here, inspired by a novel written on property back in 1976. Yet Eden House is hardly stuck in the past, thanks to continuous upgrades. On-site Azur turns out excellent New American cooking with Italian influences, while the residential Fleming Street location puts Duval Street and the Historic Seaport within easy walking distance. Check Availability at Expedia Check Availability at Booking.com Southernmost Beach Resort Save to wishlist Southernmost Beach Resort Save to wishlist Southernmost Beach Resort Save to wishlist Southernmost Beach Resort Save to wishlist Southernmost Beach Resort Readers' Choice Awards 2017, 2018, 2019 This vast tropical temptation is a stone’s throw from the southernmost point in the continental U.S., in a relatively quieter part of Key West. Spread over 6.5 acres and multiple blocks, Southernmost Beach Resort encompasses eight pastel-blue low-rises housing 244 units and four guest houses—Avalon, La Mer, Duval Gardens, and Dewey Houses—with another 52 rooms. Palm trees, swimming pools, and, in some cases, ocean blues fill the spaces in between. Building rooms were renovated between 2021 and 2022, while the guest house accommodations were reimagined in late 2023 with new-fashioned takes on Victorian-style interiors and thoughtful touches like hand-stenciled walls. Relaxation beckons at the resort’s oceanfront west lawn, strewn with hammocks and wooden lounge chairs. Meanwhile, fun in the sun awaits at Southernmost’s three lounger-lined swimming pools (don’t miss the daily live music at Pineapple Pool) and two beach areas, where guests are guaranteed two chairs and an umbrella as part of the daily resort fee. Read Full Review Check Availability at Expedia Southernmost Beach Resort Save to wishlist Southernmost Beach Resort Save to wishlist Southernmost Beach Resort Save to wishlist Southernmost Beach Resort Save to wishlist Southernmost Beach Resort This vast tropical temptation is a stone’s throw from the southernmost point in the continental U.S., in a relatively quieter part of Key West. Spread over 6.5 acres and multiple blocks, Southernmost Beach Resort encompasses eight pastel-blue low-rises housing 244 units and four guest houses—Avalon, La Mer, Duval Gardens, and Dewey Houses—with another 52 rooms. Palm trees, swimming pools, and, in some cases, ocean blues fill the spaces in between. Building rooms were renovated between 2021 and 2022, while the guest house accommodations were reimagined in late 2023 with new-fashioned takes on Victorian-style interiors and thoughtful touches like hand-stenciled walls. Relaxation beckons at the resort’s oceanfront west lawn, strewn with hammocks and wooden lounge chairs. Meanwhile, fun in the sun awaits at Southernmost’s three lounger-lined swimming pools (don’t miss the daily live music at Pineapple Pool) and two beach areas, where guests are guaranteed two chairs and an umbrella as part of the daily resort fee. Check Availability at Expedia Courtesy Pier House Resort & Spa Save to wishlist Courtesy Pier House Resort & Spa Save to wishlist Pier House Resort & Spa Readers' Choice Awards 2017, 2018, 2019, 2021, 2025 Another Key West icon, Pier House made its name in the 1970s as a haven for the creative set. Today, it remains a favorite among repeat visitors who favor the coveted dockside suites with excellent waterfront views and the property’s range of activities, sprawling spa, state-of-the-art fitness center, and multiple drinking and dining options. Among them is the legendary Chart Room Bar, famed for its strong cocktails, live music, and its place in Jimmy Buffett lore as the site of one of his earliest Key West gigs. The resort’s four low-rise buildings, two waterfront and two inland, are surrounded by lush greenery, helping soften the somewhat dated brown exteriors. Rooms reflect an Old Florida aesthetic with a mix of wooden and rattan furnishings, while suite patios and balconies provide prime perches for a Key West sunset. Pier House also has a small private beach and nearby pool, giving guests two waterfront options for spending the day in the sun. Read Full Review Check Availability at Expedia Check Availability at Booking.com Courtesy Pier House Resort & Spa Save to wishlist Courtesy Pier House Resort & Spa Save to wishlist Pier House Resort & Spa Another Key West icon, Pier House made its name in the 1970s as a haven for the creative set. Today, it remains a favorite among repeat visitors who favor the coveted dockside suites with excellent waterfront views and the property’s range of activities, sprawling spa, state-of-the-art fitness center, and multiple drinking and dining options. Among them is the legendary Chart Room Bar, famed for its strong cocktails, live music, and its place in Jimmy Buffett lore as the site of one of his earliest Key West gigs. The resort’s four low-rise buildings, two waterfront and two inland, are surrounded by lush greenery, helping soften the somewhat dated brown exteriors. Rooms reflect an Old Florida aesthetic with a mix of wooden and rattan furnishings, while suite patios and balconies provide prime perches for a Key West sunset. Pier House also has a small private beach and nearby pool, giving guests two waterfront options for spending the day in the sun. Check Availability at Expedia Check Availability at Booking.com Courtesy Sunset Key Cottages Save to wishlist Save to wishlist Courtesy Sunset Key Save to wishlist Save to wishlist Sunset Key Cottages Readers' Choice Awards 2017, 2018, 2019, 2020, 2021, 2024 Sunset Key is a private-island splurge that feels worlds away from Key West proper. The tropical island comprises private homes and a boutique resort of 40 pastel cottages, surrounded by lush gardens loaded with frangipani, sand, and turquoise waters. Spacious cottages are perfectly beachy, though some are more modern than others. At a minimum, each has a living room, pull-out sofa, and kitchenette pre-stocked with complimentary select drinks, snacks, and wine, with additional items available for a fee. There’s a zero-entry pool at the heart of the island, but the best water action is around the beach, where lounge chairs, palapas, and a volleyball net await. Latitudes restaurant offers a front-row seat to the water and can be visited even if you’re not staying at Sunset Key Cottages. Getting here requires a quick seven-minute ride from the resort’s private boat launch on the mainland, located in front of sister property Opal Key Resort & Marina, with boats running twice per hour. Read Full Review Check Availability at Expedia Check Availability at Skylark Courtesy Sunset Key Cottages Save to wishlist Save to wishlist Courtesy Sunset Key Save to wishlist Save to wishlist Sunset Key Cottages Sunset Key is a private-island splurge that feels worlds away from Key West proper. The tropical island comprises private homes and a boutique resort of 40 pastel cottages, surrounded by lush gardens loaded with frangipani, sand, and turquoise waters. Spacious cottages are perfectly beachy, though some are more modern than others. At a minimum, each has a living room, pull-out sofa, and kitchenette pre-stocked with complimentary select drinks, snacks, and wine, with additional items available for a fee. There’s a zero-entry pool at the heart of the island, but the best water action is around the beach, where lounge chairs, palapas, and a volleyball net await. Latitudes restaurant offers a front-row seat to the water and can be visited even if you’re not staying at Sunset Key Cottages. Getting here requires a quick seven-minute ride from the resort’s private boat launch on the mainland, located in front of sister property Opal Key Resort & Marina, with boats running twice per hour. Check Availability at Expedia Check Availability at Skylark The Marquesa Hotel Save to wishlist The Marquesa Hotel Save to wishlist The Marquesa Hotel Save to wishlist The Marquesa Hotel Save to wishlist The Marquesa Hotel You’re in for a special stay at this historic hotel on the National Register of Historic Places, just a block off Duval Street. The vibe is old Key West to the max, in the best way imaginable, including a tropical interior courtyard where a patio overlooks the pool and butterflies flit among the foliage. Well-appointed rooms are housed in separate Key West-style cottages, while sister property Marquesa 414 sits across the street and half a block away in a newer building. There are 44 rooms between the two, collectively known as The Marquesa Hotel, along with three pools and the illustrious Café Marquesa, often cited as Key West’s top restaurant. Standout dishes like yellowtail snapper over Key West shrimp Creole and creamy yellow grits and grilled swordfish piccata are every bit the heavenly seafood experience travelers covet in an island destination, while the doughy, sugar-dusted beignets are true dessert divinity—and superior to any we’ve sampled in New Orleans . Read Full Review Check Availability at Expedia Check Availability at Tripadvisor The Marquesa Hotel Save to wishlist The Marquesa Hotel Save to wishlist The Marquesa Hotel Save to wishlist The Marquesa Hotel Save to wishlist The Marquesa Hotel You’re in for a special stay at this historic hotel on the National Register of Historic Places, just a block off Duval Street. The vibe is old Key West to the max, in the best way imaginable, including a tropical interior courtyard where a patio overlooks the pool and butterflies flit among the foliage. Well-appointed rooms are housed in separate Key West-style cottages, while sister property Marquesa 414 sits across the street and half a block away in a newer building. There are 44 rooms between the two, collectively known as The Marquesa Hotel, along with three pools and the illustrious Café Marquesa, often cited as Key West’s top restaurant. Standout dishes like yellowtail snapper over Key West shrimp Creole and creamy yellow grits and grilled swordfish piccata are every bit the heavenly seafood experience travelers covet in an island destination, while the doughy, sugar-dusted beignets are true dessert divinity—and superior to any we’ve sampled in New Orleans . Check Availability at Expedia Check Availability at Tripadvisor This gallery has been updated with new information since its original publish date.