Best Historic Inns and Stays in Key West
Historic stays in Key West are mostly small inns in Old Town, the grid of wooden houses between Duval Street, the Ernest Hemingway Home and Museum and the Southernmost Point. Many group several restored houses around shared pools and gardens: Simonton Court has four pools, Winslow's Bungalows three, and Silver Palms Inn & Historic Homes combines rooms with balconies and an outdoor pool a short walk from the Hemingway house. Four of the best-rated inns admit adults only. One listing, Coconut Mallory Resort and Marina, is a modern apartment resort by a marina rather than a historic house, and I treat it separately below.
Key West sits at the end of the Overseas Highway, closer to Havana than to Miami. Old Town keeps its wooden houses with wide porches and shutters, its streets lined with palms and bougainvillea, and its evenings built around the sunset at Mallory Square. Duval Street carries the bars and crowds, while the side streets a block or two away stay quiet enough for a guesthouse breakfast by the pool.
Where to stay
Old Town inns, adult retreats and family houses
A historic inn in Key West puts you in Old Town, where Duval Street, the Hemingway house, the seaport and the Southernmost Point are all reachable on foot or by bicycle, and several inns rent bikes on site. Most include a continental breakfast and a pool, which matters on an island where the afternoon heat sends everyone back to the shade.
For couples, the adults-only inns lead this list. Almond Tree Inn and Orchid Key Inn both score 9.4: the Almond Tree has an outdoor pool, a hot tub, a sun deck and a complimentary happy hour, while Orchid Key sits on Duval Street with a heated pool, a hot tub, an on-site bar and some suites with a spa bath. Douglas House, also for adults only, scores 9 across more than 2,200 reviews and sits a short walk from the Hemingway house and the Southernmost Point. I would pick Almond Tree for a quiet stay and Orchid Key for evenings on Duval Street.
Pool lovers should look at the inns spread across several houses. Simonton Court Historic Inn & Cottages, also for adults only, offers four outdoor pools, bicycle hire and a garden, with Duval Street and the Hemingway house close by, and it scores 9.1. Winslow's Bungalows has three pools, landscaped gardens and sun terraces within walking distance of Duval Street and the Southernmost Point, and it accepts pets. Silver Palms Inn & Historic Homes, the most reviewed historic stay here with more than 3,300 reviews, adds private balconies and an outdoor pool a short walk from the Hemingway museum.
Families have fewer options among the historic inns, since several only admit adults. Island City House scores 9 and offers Victorian-inspired rooms with hardwood floors, a seating area and a kitchen, plus an outdoor pool and a garden, a short walk from the Key West seaport. The Palms Hotel adds a heated pool, picnic and barbecue facilities, bicycle rentals and some rooms with kitchenettes. Lighthouse Hotel stands opposite the Ernest Hemingway Home and Museum with a heated pool and a poolside bar, and it accepts pets. My advice for a family is Island City House, where the kitchens make longer stays easier.
Two practical notes complete the picture. Ridley House and Ella's Cottages are smaller boutique inns with outdoor pools and continental breakfast: Ridley House welcomes pets and sits within walking distance of Duval Street and the museums, while Ella's Cottages offers a heated pool, a tropical garden and rooms with hardwood floors in Old Town. Coconut Mallory Resort and Marina, by contrast, is a modern resort of apartments with kitchens, two pools, a hot tub and marina access, not a historic building, so book it for space and water sports rather than for Old Town character.
A traveler's perspectiveIf I were planning a couple's trip to Key West, I would book the Almond Tree Inn, an adults-only historic inn that scores 9.4, with an outdoor pool, a hot tub and a complimentary happy hour. From Old Town, the Ernest Hemingway Home and Museum and Duval Street are an easy walk or bike ride, and the sunset at Mallory Square closes the day at the western edge of the island.
Almond Tree Inn - Adults Only
Key West
298 reviews
Historic adults-only inn with a pool, hot tub, and daily breakfast
Check availabilityWhy guests love itThis is an adults-only inn, so I would not recommend it for a family trip with children, and I say so plainly. For couples and friends it makes sense: guests rate it 9.4 across 298 reviews, and it is a short walk from the Ernest Hemingway House and Museum. The outdoor pool, hot tub and sun deck are on site, a continental breakfast is included, and a happy hour offers free drinks.
Orchid Key Inn - Adults Only
Key West
285 reviews
Historic adults-only inn with a heated pool and a lively bar on Duval Street
Check availabilityWhy guests love itOrchid Key Inn is adults only, so I would not suggest it for a stay with children, whatever its labels say. For couples or friends traveling without kids, it is a strong choice on historic Duval Street: a heated pool with a hot tub, an on-site bar and a continental breakfast every morning. Rooms have a flat-screen TV and a Keurig coffee machine, and some suites add a spa bath. Guests rate it 9.4 out of 10 over 285 reviews.
Simonton Court Historic Inn & Cottages
Key West
993 reviews
Historic adult-only inn with four pools and charming cottages
Check availabilityWhy guests love itSimonton Court is an adults-only inn, so I would not suggest it to families with children; it suits couples and friends looking for calm in Key West. Four outdoor pools spread through the property and its garden, a light continental breakfast is included, and bicycles can be hired for exploring the island. Rooms have a refrigerator and a balcony or patio, and WiFi is free. Duval Street and the Ernest Hemingway Home and Museum are close by. A 9.1 from 993 reviews is an outstanding score.
Island City House
Key West
778 reviews
Historic Key West hotel with outdoor pool and Victorian-inspired rooms
Check availabilityWhy guests love itI would choose Island City House for a Key West stay that wants Victorian character with a kitchen. Rooms are Victorian-inspired with hardwood floors, a seating area and a kitchen, and guests rate the hotel 9.0 across 778 reviews, a score I trust. An outdoor pool, a garden and free WiFi are on site, and the Key West seaport is a short walk away.
Douglas House Adult Only
Key West
2,291 reviews
Adults-only inn with a pool, tropical garden, and historic charm
Check availabilityWhy guests love itDouglas House accepts adults only, so I would not send families with children here; it suits couples or friends looking for a quiet base in Key West. The shared outdoor pool sits in a tropical garden, and rooms have a microwave, a refrigerator and coffee-making facilities for simple breakfasts. The Ernest Hemingway Home and Museum and the Southernmost Point are a short walk away, and pets are accepted. A score of 9 from 2,291 reviews is excellent.
Silver Palms Inn & Historic Homes
Key West
3,354 reviews
Historic Key West inn with an outdoor pool and private balconies
Check availabilityWhy guests love itSilver Palms Inn & Historic Homes sits in historic Key West, a short walk from the Ernest Hemingway Museum, so families can explore Old Town on foot. The outdoor pool is a cool break between outings, and every room has a private balcony, a microwave and a refrigerator, practical for snacks and simple meals. A complimentary continental breakfast is served, and covered parking spares families the search for a space.
Ridley House - Key West Historic Inns
Key West
248 reviews
Historic boutique hotel with a pool, close to Duval Street
Check availabilityWhy guests love itWalking distance to Duval Street, museums and water sports is what I would highlight for families at Ridley House, part of Key West Historic Inns. The outdoor pool gives children a break between outings, a continental breakfast is served every morning, and pets are welcome. Rooms are air-conditioned with free WiFi. As a small historic boutique inn, it feels more intimate than a large resort, so it suits calm families best. Guests rate it 8.6 out of 10 over 248 reviews.
Ella's Cottages - Key West Historic Inns
Key West
238 reviews
Historic boutique inn with a heated pool and tropical garden in Old Town
Check availabilityWhy guests love itElla's Cottages is a boutique historic inn in Old Town Key West, and its tropical garden and heated outdoor pool give it a quiet center after a day on foot. Rooms and suites have hardwood floors, a flat-screen cable TV and a mini-fridge, WiFi is free and a continental breakfast is served by the pool. Pets are welcome and the property has spa and wellness facilities. Guests rate it 8.6 from 238 reviews.
Coconut Mallory Resort and Marina
Key West
135 reviews
Apartments with kitchens, two pools, and marina access in Key West
Check availabilityWhy guests love itCoconut Mallory Resort and Marina is built for families who need more room than a standard hotel room gives. The apartments come with fully equipped kitchens and private balconies, so breakfast and quiet evenings stay simple. Two outdoor pools and a hot tub keep the downtime varied, and the on-site bicycle and water sports rentals make it easy to get moving without arranging anything beforehand. Direct access to Coconut Mallory Marina is a plus for anyone drawn to the water around Key West.
The Palms Hotel
Key West
2,386 reviews
Historic Key West hotel with a heated pool and pet-friendly amenities
Check availabilityWhy guests love itThe heated pool and the daily continental breakfast are why I would put The Palms Hotel on a family list for Key West. Some rooms add a kitchenette and a seating area, which helps with younger children, and there is a picnic area with barbecue facilities for an easy dinner outdoors. Bicycles can be rented on site, a good way to explore the island together, and pets are welcome. WiFi is free. An 8.5 from 2,386 reviews is a very good score.
Winslow's Bungalows - Key West Historic Inns
Key West
1,236 reviews
Historic bungalows with three pools and lush gardens in Key West
Check availabilityWhy guests love itWinslow's Bungalows has three swimming pools, so children rarely have to share a busy one, and the landscaped gardens are full of hammocks and swings. A continental breakfast is included each morning, and every room has a small refrigerator for drinks and snacks. Duval Street and the Southernmost Point are within walking distance, which makes evenings and photo stops easy without a car. Pets are welcome, so the family dog can join the trip.
Lighthouse Hotel - Key West Historic Inns
Key West
630 reviews
Historic Key West hotel with a heated pool and poolside bar
Check availabilityWhy guests love itI would choose the Lighthouse Hotel for a Key West stay in a historic building with a pool. It sits opposite the Ernest Hemingway Home and Museum, and guests rate it 8.4 across 630 reviews, a score I trust. An outdoor heated pool and a poolside bar are on site, a complimentary continental breakfast is included, and rooms have free WiFi and private bathrooms. Bicycle rentals are available, and pets are welcome.
Local tips
- 1Check whether an inn is adults only before booking with children, since Almond Tree, Orchid Key, Douglas House and Simonton Court all are.
- 2Rent a bicycle, which several inns offer on site, to cover Old Town, the seaport and the Southernmost Point.
- 3Pick Simonton Court or Winslow's Bungalows if you want a choice of pools rather than a single shared one.
- 4Travelling with a dog? Winslow's Bungalows, Lighthouse Hotel and Ridley House accept pets.
- 5Families should look at Island City House or The Palms Hotel, where some rooms include kitchens or kitchenettes.
- 6Remember that Coconut Mallory Resort is a modern marina resort, not a historic inn in Old Town.