If you’ve ever wondered which part of the US is closest to Cuba, the answer is Key West, Florida. Located on the southern end of the state, this city is known for unspoiled beaches, energetic nightlife scenes, historic attractions, and watersport activities. As you explore its neighborhoods, you’ll notice Caribbean-inspired houses and historic buildings, such as the Ernest Hemingway House and Donkey Milk House. If you love taking inspiration from nature views, head to Mallory Square to get the finest views of the sunset. Do you want to unravel Key West’s hidden gems with your partner on a romantic getaway to this island city? For accommodations, check out the most romantic hotels in Key West, Florida.
We handpicked these listings carefully, considering (wherever possible) recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to couple-friendly amenities and activities. The image galleries get refreshed with the latest updates regularly. They were last updated on March 14, 2024.
1. Pegasus International Hotel (from USD 459)
In Key West’s lively core, this hotel is a hidden gem, offering a tranquil sanctuary ideal for romance and relaxation. Imagine basking beside a sunlit, heated pool or unwinding in a bubbling hot tub, letting go of life’s tensions. The hotel boasts diverse room options, from cozy Queen rooms to expansive Superior Queen Suites, each equipped with modern amenities such as flat-screen TVs, perfect for intimate movie evenings.
Its art deco elegance, combined with facilities such as a radiant terrace and a lavish breakfast, sets the stage for an unforgettable retreat. Attention to details, from convenient parking to complimentary Wi-Fi, is meticulously considered, ensuring a seamless, romantic journey.
Pegasus International Hotel
Address: 501 Southard Street
445 meters (0.3 ft) from The Hemingway Home and Museum
2. The Mermaid & The Alligator (from USD 495)
Nestled near South Beach, this charming boutique hotel fuses romance with opulence. Its themed rooms—like the SunRoom and Caribbean Queen—offer plush double beds, creating cozy sanctuaries. Experience tranquility at the outdoor pool, an oasis set amidst verdant gardens. Enjoy intimate breakfasts under Florida’s radiant sun, with complimentary Wi-Fi ensuring connectivity.
Discover nearby treasures, from Higgs Beach to the Hemingway Home and Museum. Merely a short drive away from Key West International Airport, this enchanting retreat perfectly balances convenience and serenity, ideal for couples desiring a magical getaway.
The Mermaid & The Alligator
Address: 729 Truman Avenue
562 meters (0.4 ft) from The Hemingway Home and Museum
3. The Garden Hotels (from USD 998)
Lounge at the private balcony while you reminisce your milestones as a couple when you stay in one of the quaint rooms in The Gardens Hotel. This romantic accommodation features two swimming pools, wellness packages, and a garden, perfect for creating lasting memories with your beau.
Guest rooms here come with a fridge and a flat-screen TV. If you’re staying on a weekend, don’t miss the live jazz music every Sunday night.
The Gardens Hotel
Address: 526 Angela Street
352 meters (0.3 ft) from The Hemingway Home and Museum
4. Havana Cabana at Key West (from USD 399)
Havana Cabana at Key West is a modern hotel that’s just five minutes away from the airport. It features facilities that are ideal for a romantic getaway, such as an outdoor pool with a waterfall, a wellness center, an on-site bar, and a cafe.
Rooms have a large flat-screen TV, perfect for movie streaming nights. If you want a more romantic stay, you can opt for premium rooms with a balcony or a patio.
Havana Cabana at Key West
Address: 3420 N Roosevelt Blvd
4.49 km (2.8 mi) from The Hemingway Home and Museum
5. Barbary Beach House Key West (from USD 518)
Barbary Beach House Key West boasts a prime location because it is close to numerous romantic dining spots, top attractions, and pristine beaches. The hotel’s heated pool is the ultimate place to loosen up after a day of exploring Key West. You can also relax at the hot tub with your significant other in the hotel’s wellness center.
When you book your accommodation here, you can expect well-appointed rooms with beach views.
Margaritaville Beach House Key West
Address: 2001 South Roosevelt Boulevard
2.85 km (1.8 mi) from The Hemingway Home and Museum
6. The Capitana Key West (from USD 395)
This is one the best hotels for couples in Key West and offers elegantly designed rooms with a TV, a desk, and a private bath. For traveling couples, you can choose between a King or Queen room with a balcony for a more intimate experience.
While here, you and your partner enjoy wine while soaking in the hotel’s hot tub. There’s also an outdoor swimming pool for relaxation. Hot continental breakfast is served daily from 8 am to 10 am.
The Capitana Key West
Address: 2401 North Roosevelt Boulevard
2.64 km (1.7 mi) from The Hemingway Home and Museum
7. Hilton Garden Inn Key West / The Keys Collection (from USD 265)
If you want to treat your partner to a romantic stay in an upscale hotel, then consider Hilton Garden Inn for your accommodation in Key West. In terms of facilities, the hotel offers stylish rooms, some featuring a bathtub and a balcony. For intimate mornings, you may request an in-room breakfast from the on-site restaurant.
Amenities include an outdoor pool, a hot tub, and a tiki bar. If you feel like unwinding outdoors, you can access the garden or head to nearby beaches.
Hilton Garden Inn Key West / The Keys Collection
Address: 3850 North Roosevelt Boulevard
5.25 km (3.3 mi) from The Hemingway Home and Museum
8. Fairfield Inn & Suites by Marriott Key West at The Keys Collection (from USD 359)
Indulge in luxury and world-class services with your beloved while having a spectacular vacation at Fairfield Inn & Suites by Marriott Key West. What makes this hotel romantic are facilities such as an outdoor pool, rooms with a private bath, a hot tub, and a sun terrace.
For an additional charge, you can also engage in outdoor activities such as cycling or diving. Buffet breakfast is available every morning.
Fairfield Inn & Suites by Marriott Key West at The Keys Collection
Address: 3852 North Roosevelt Boulevard
5.25 km (3.3 mi) from The Hemingway Home and Museum
9. Orchid Key Inn (from USD 423)
Reasonable pricing for a central location in Key West, with added value amenities like free breakfast and complimentary poolside drinks.
Modern, clean rooms with comfortable beds, small fridge, and coffee machine. Lovely pool area with sunbeds and a bar. Free suntan lotion and beach towels provided.
Conveniently located just off Duval Street, offering easy access to attractions, dining, and nightlife while maintaining a quiet atmosphere. Walking distance to the beach and various entertainment options.
Complimentary continental breakfast by the pool each morning, with a variety of options including fresh fruits and yogurt. The on-site bar offers a great selection and a nightly happy hour with complimentary drinks.
Orchid Key Inn boasts facilities that are perfect for relaxation. These include a heated pool with a hot tub, a garden, and a pool oasis. You and your partner can also enjoy a complimentary happy hour where you can spend time savoring a glass of wine.
Rooms in this hotel come with a microwave, a mini-fridge, and a flat-screen TV. You can also opt for a suite with a spa bath for a more intimate stay with your partner.
Orchid Key Inn - Adults Only
Address: 1004 Duval Street
151 meters (0.1 ft) from The Hemingway Home and Museum
10. Courtyard by Marriott Key West Waterfront (from USD 358)
Treat your significant other to a cozy stay at Courtyard by Marriott Key West Waterfront. Every room is spacious, guaranteeing a comfortable stay. Here, you and your partner can enjoy facilities such as an outdoor pool with a hot tub, a pool bar, an on-site coffee house, and a restaurant.
You can also bond over your fitness goals while you’re here, thanks to the in-house gym.
Courtyard by Marriott Key West Waterfront
Address: 3031-41 North Roosevelt Boulevard
3.61 km (2.3 mi) from The Hemingway Home and Museum
11. The Marquesa Hotel (from USD 560)
If you and your partner want to spend your vacation in style, choose this boutique hotel situated in a historic site downtown. The Marquesa Hotel features luxurious rooms with air conditioning, a modern private bathroom, and a fridge.
This hotel is a perfect choice if you want to take your partner on a date at Mallory Square, which is just four blocks away. You’ll also love the romantic amenities offered here, such as an outdoor pool, a garden, and a sun terrace.
The Marquesa Hotel
Address: 600 Fleming St
627 meters (0.4 ft) from The Hemingway Home and Museum
Bond with your partner in Key West
Deepen your bond with your partner while also falling in love with the several exciting things to do in Key West, Florida. Enjoy the unspoiled beaches or have a romantic dining experience while here. Most of all, book your stay in one of the most romantic hotels listed above.
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