Nightcap ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches!
1 2
B&B , Key West
This guesthouse, located in Old Town Key West, is situated in the historic district just 500 meters from the beach and the Southernmost Point, with Duval Street's attractions a few steps away. The 20 square meter Nightcap room accommodates two guests and features a queen bed, a stocked kitchenette with a fridge and microwave, air conditioning, outdoor seating overlooking Duval Street, and access to an on-site rum bar.
9.5 1236 reviews
Key West, FL
26/10 – 28/10
A$916/nighttotal: A$1832 (2 )
Key West Bed And Breakfast
2 4
B&B , Key West
The Key West Bed and Breakfast is located in a quiet neighbourhood just 1.1 km from Simonton Street Beach and a short walk from the bustling Duval Street. The property consistently receives excellent ratings for location, cleanliness and user experience. This charming guesthouse offers a private patio for relaxing and a fully equipped bathroom with a shower and hairdryer. Guests can enjoy free Wi-Fi, a garden, a swimming pool, a terrace, and parking.
Key West, FL
02/09 – 05/09
A$315/nighttotal: A$945 (3 )
Quiet Pour ~ On Duval St, Adult Only, Adjoining Rum Bar And Near Beach!
1 2
B&B , Key West
This guesthouse, a Speakeasy Inn, is located directly on Duval Street in Old Town Key West, placing it only 200 metres from the beach and the Southernmost Point. The accommodation offers one bedroom and one bathroom for two guests, with air conditioning, internet, a fridge, microwave, and outdoor seating, alongside a celebrated Rum Bar and a restored wraparound porch.
9.4 53 reviews
Key West, FL
20/06 – 21/06
A$425/nightfor 1 night
Deluxe Suite @ Old Town B&b
1 2
B&B , Key West
This Key West guesthouse enjoys a central location, offering easy access to Duval Street's nightlife and Mallory Square, with Smathers Beach and Higgs Beach a short drive or cycle away. Sleeping up to three guests, this one-bedroom, one-bathroom property features upscale interiors and may include amenities such as a swimming pool, breakfast, and concierge services.
8.2 164 reviews
Key West, FL
20/06 – 27/06
A$513/nighttotal: A$3591 (7 )
New Orleans House - Gay Male Adult Guesthouse
1 2
B&B , Key West
This gay-friendly guesthouse is situated on Duval Street in Key West's historic Old Town, just a short walk from the lively nightlife and the southernmost point of the continental United States. The accommodation has received very good ratings for cleanliness and location, and excellent ratings overall. The guesthouse features a swimming pool, a jacuzzi, and a terrace, as well as a restaurant, a bar, and a fitness centre. Guests can also enjoy room service, parking, and a clothing-optional sundeck.
10 4 reviews
Key West, FL
14/10 – 16/10
A$324/nighttotal: A$648 (2 )
Smuggler's Cove ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches!
1 2
B&B , Key West
This B&B is located in Old Town Key West, directly on Duval Street, placing it just 200 metres from the beach and the Southernmost Point. This adults-only guesthouse offers 24 square metres of space per room, accommodating up to four guests with one bedroom and one bathroom, and features an on-site Rum Bar with global rum tastings.
10 19 reviews
Key West, FL
14/10 – 16/10
A$345/nighttotal: A$690 (2 )
The Artist House Key West - Small Queen
1 2
B&B , Key West
This Key West guesthouse is situated near Duval Street and the Key West seaport, offering easy access to the island's main attractions. The recently renovated (2021) one-bedroom guesthouse, sleeping two, boasts a private sun room, queen-sized bed, ensuite bathroom with glass shower, a guest kitchen, and complimentary breakfast plus daily happy hour, all within a tropical garden setting including a small dipping pool.
10 2 reviews
Key West, FL
13/09 – 27/09
A$221/nighttotal: A$3094 (14 )
Hideaway ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!
1 2
B&B , Key West
This guesthouse is located directly on Duval Street in Old Town Key West, just 320 meters from the beach and the Southernmost Point, offering immediate access to galleries, restaurants, and bars, and is steeped in Prohibition-era lore. The 23 square meter 'Hideaway' room accommodates two guests with air conditioning, Wi-Fi, a fridge, and microwave, and features outdoor seating and access to a restored wraparound porch, with the property being adults-only and a short distance from the Ernest Hemingway Home and Museum.
9.4 2541 reviews
Key West, FL
20/06 – 27/06
A$408/nighttotal: A$2856 (7 )
The Garden House
1 2
B&B , Key West
Garden House is located in Old Town Key West, a short walk from the seaport, Dante's Pool Bar, and Duval Street, and less than a half-mile from Mallory Square. The establishment has consistently received excellent ratings for its location, cleanliness, and overall experience. This charming guesthouse can accommodate up to two guests in its single bedroom and bathroom. Enjoy complimentary WiFi, a continental breakfast, a swimming pool, a terrace, and bike rentals, making it a comfortable and convenient base for exploring Key West.
Key West, FL
23/06 – 24/06
A$468/nightfor 1 night
Duval Street Stay + Free Breakfast, Pool & Bar
1 2
B&B , Key West
This guesthouse offers an adult-focused sanctuary on the quieter western end of Duval Street, just 240 metres from the Southernmost Point and steps from South Beach in Key West. Guests can enjoy full access to Southernmost Beach Resort amenities, including three swimming pools and a private beach, alongside lush gardens, daily European-style breakfast, and on-site bicycle rentals for exploring the island.
9.6 1708 reviews
Key West, FL
17/10 – 24/10
A$736/nighttotal: A$5152 (7 )
Aria~adult Only, Treetop King Suite W/ Balcony & Shared Pool At Azul Mansion!
1 2
B&B , Key West
This Key West apartment is situated in the Historic District, less than 1.6km from Duval Street and the Key West Firehouse Museum, and within 2.4km of the Ernest Hemingway Home and Museum. The one-bedroom, one-bathroom flat sleeps two guests and offers a private balcony, swimming pool access, free Wi-Fi, and a concierge service; nearby attractions include the beaches of the Florida Keys and tennis courts.
9.5 215 reviews
Key West, FL
20/06 – 27/06
A$363/nighttotal: A$2541 (7 )
Near Old Town Key West + Pool. Dining. Shuttle.
1 2
B&B , Key West
Blue Flamingo Resort Key West, a self-catering guesthouse, is situated at the gateway to Old Town, minutes from Duval Street and other Key West attractions. This pet-friendly (up to 16kg) one-bedroom, one-bathroom unit at the resort sleeps four, offering a fitness centre, pool access, daily housekeeping, and a complimentary shuttle to Old Town.
Best Key West, FL bed and breakfasts with breakfast included
9.1 2654 reviews
Key West, FL
27/06 – 28/06
A$985/nightfor 1 night
Ambrosia Key West
2 7
B&B , Key West
This Key West guesthouse is conveniently located on Duval Street, just a short walk from the historic district's art galleries, cafes, and attractions, and less than a mile from the Ernest Hemingway Home and Museum, the Southernmost Point, and Mallory Square. The property consistently receives excellent ratings for location, cleanliness, and overall experience. The establishment features two outdoor pools and tropical courtyards, offering a tranquil escape from the bustling city. Enjoy a full hot breakfast each morning, relax in the hot tub or poolside, and take advantage of amenities like a fitness centre, tennis court, and in-room coffee and tea facilities.
9.4 2909 reviews
Key West, FL
02/09 – 05/09
A$375/nighttotal: A$1125 (3 )
Southernmost Point Guest House & Garden Bar
1 2
B&B , Key West
This charming bed and breakfast is ideally located on Duval Street in Key West, just a short walk from the Southernmost Point and the beach, placing you right in the heart of the lively action. The property has consistently received excellent ratings for its location, cleanliness, and overall experience. Spread across four buildings, the accommodation offers a variety of room configurations and views. Enjoy a complimentary breakfast each morning, relax in the hot tub, and take advantage of the on-site bar, barbecue facilities, and tour desk.
Alexander's Gay Lesbian Guest House is a charming guesthouse in Key West, a short walk from Mallory Dock and Mallory Square, both popular attractions in the heart of the city. The guesthouse has consistently received excellent ratings for its location, cleanliness and overall experience. The guesthouse offers a single bedroom with one bathroom, perfect for a couple or solo traveller seeking a comfortable and intimate stay. Guests can enjoy a range of amenities, including a swimming pool, hot tub, and a continental breakfast served by the pool, as well as evening cocktail hour, a lending library and concierge services.
8.9 1049 reviews
Key West, FL
24/07 – 25/07
A$703/nightfor 1 night
Old Town Manor
1 4
B&B , Key West
This Key West guesthouse is located in Old Town, just a short walk from Duval Street and the Southernmost Point. It has consistently received excellent ratings for its cleanliness, location, and overall experience. The property features a courtyard and garden, perfect for relaxing after a day exploring Key West. Guests can enjoy a daily breakfast, a swimming pool, and a sun terrace, along with modern amenities such as free Wi-Fi and flat-screen TVs.
Best Key West, FL bed and breakfasts with a pool
Among the 248 accommodations in Key West, FL, here are the 4 best B&B with a pool
9.0 1173 reviews
Key West, FL
24/07 – 25/07
A$510/nightfor 1 night
Courtney's Place Historic Cottages & Inns
1 4
B&B , Key West
Courtney's Place Historic Cottages & Inns is located in Old Town Key West, just a minute's walk from Duval Street and a 15-minute walk from Mallory Square, putting you right in the heart of the action. The property has excellent ratings for location, cleanliness and user experience. The charming cottages offer a choice of layouts, some with full kitchens, perfect for those who prefer to self-cater. Enjoy the outdoor pool, relax on the terrace or balcony, and make the most of the free continental breakfast, barbecue facilities and free on-site parking.
9.8 299 reviews
Key West, FL
22/08 – 29/08
A$503/nighttotal: A$3521 (7 )
Historic Cigar Barons Mansion
1 2
B&B , Key West
This Key West guesthouse is situated in a historic neighbourhood, a short walk from Duval Street and the attractions of Historic Downtown Key West. Offering a master suite with a private entrance, a Florida room, a heated Jacuzzi, and access to a shared pool and garden, this family-friendly property includes a fridge, freezer, microwave, dishwasher, and outdoor grill; parking is also available.
9.4 115 reviews
Key West, FL
14/10 – 16/10
A$308/nighttotal: A$616 (2 )
Minutes To Duval + Free Breakfast. Newly Renovated
1 2
B&B , Key West
Fairfield Inn & Suites Key West, situated 1.8 km from Key West International Airport, offers convenient access to Duval Street (5.1 km) and Mallory Square (6.1 km). This guesthouse features a one-bedroom suite sleeping four, complete with a pool, fitness centre, free breakfast, electric car charging, and on-site parking (charges apply), plus room amenities including a microwave and mini-refrigerator.
9.7 493 reviews
Key West, FL
20/06 – 21/06
A$655/nightfor 1 night
Andrews Inn & Garden Cottages
1 2
B&B , Key West
Andrews Inn & Garden Cottages is situated on Duval Street, within easy walking distance of Key West's lively bars, restaurants and shops, and just a short stroll from Mallory Square and the Southernmost Point. The property enjoys excellent ratings for location, cleanliness and overall guest experience. The inn offers a choice of rooms and cottages, all with modern amenities including air conditioning, free Wi-Fi and a private bathroom. Guests can enjoy a complimentary breakfast, relax by the pool, and take advantage of the on-site concierge service to plan their activities.
Frequently asked questions about bed and breakfast in Key West, FL
What are the must-see sights for first-time visitors on a day trip to Key West, FL?
For a day trip, you can't miss the iconic Southernmost Point buoy, marking the southernmost point of the continental US. Stroll down Duval Street, with its colourful shops and lively atmosphere. And don't forget to visit the Ernest Hemingway Home and Museum, where you can see the famous six-toed cats.
What are the best bed and breakfasts in Key West, FL?
In which districts of Key West, FL should you consider booking a bed and breakfast?
Old Town is a popular choice for bed and breakfasts, with its historic charm and proximity to Duval Street. The quieter, more residential areas of the New Town district offer a peaceful escape, while still being within easy reach of the main attractions.
What are the best bed and breakfasts with a pool in Key West, FL?
What is the typical weather in Key West, FL, and how does it affect outdoor plans?
Key West enjoys a tropical climate with warm temperatures year-round. Expect average highs around 27°C in the summer and 23°C in the winter. The humidity can be high, so pack light clothing and stay hydrated. The occasional tropical storm can occur, so check the weather forecast before planning any outdoor activities.
What are the best bed and breakfasts with a jacuzzi in Key West, FL?
What are the best cultural activities and events in and around Key West, FL?
Key West is a vibrant hub for culture and entertainment. You can catch a performance at the Waterfront Playhouse, a historic theatre showcasing local talent. The annual Fantasy Fest, held in October, is a colourful celebration of art, music, and costumes.
What are the best bed and breakfasts for families and kids in Key West, FL?
Which hiking trails are recommended for exploring in and around Key West, FL?
Key West is primarily a flat island, so you won't find traditional hiking trails. However, you can enjoy scenic walks along the waterfront, like the Key West Greenway, a paved trail offering views of the ocean and mangroves.
What are the best pet friendly bed and breakfasts in Key West, FL?
What amenities are commonly offered in bed and breakfasts in Key West, FL?
Bed and breakfasts in Key West typically offer a range of amenities, including complimentary breakfast, free Wi-Fi, and a swimming pool. Some may also have a shared lounge area, a garden, or a hot tub. Check the individual listings for specific amenities.
What are the best bed and breakfasts with parking in Key West, FL?
Best Key West, FL bed and breakfasts with a garden
9.7 314 reviews
Key West, FL
26/10 – 28/10
A$985/nighttotal: A$1970 (2 )
Duval St. Duplex W/balcony W/ Parking (Adult Only)
2 4
B&B , Key West
This two-storey duplex, located on Duval Street in Old Town Key West, offers direct access to restaurants, live music venues, and historic sites within 500 meters. This fully furnished accommodation features individual air conditioning units in each room, a private entrance, and access to a shared swimming pool and grounds, with a guest capacity of eight.
9.0 2616 reviews
Key West, FL
24/07 – 28/07
A$891/nighttotal: A$3564 (4 )
Westwinds Inn
2 7
B&B , Key West
The Westwinds Inn is situated in Old Town Key West, a short 0.8 kilometre walk from Duval Street and within easy reach of the beach. It has consistently received excellent ratings for location, cleanliness and overall experience. This charming guesthouse offers a range of amenities to enhance your stay, including two outdoor pools, tropical gardens, a library, free parking and laundry facilities. Guests can enjoy a continental breakfast and relax on the terrace or balcony.
9.1 16 reviews
Key West, FL
20/06 – 27/06
A$460/nighttotal: A$3220 (7 )
Sunny Oasis | Outdoor Pool. Island Experience
1 1
B&B , Key West
This studio apartment is located in Historic Old Town, Key West, on the Atlantic Coast, a short walk from the Southernmost Point Buoy and Mallory Square. This accommodation offers a Petite Queen bed, a modern bathroom, access to three heated resort pools, two private beaches, a fitness centre, and on-site bars and restaurants, with capacity for two guests.
9.0 1794 reviews
Key West, FL
14/10 – 16/10
A$595/nighttotal: A$1190 (2 )
Coco Plum Inn
1 2
B&B , Key West
Coco Plum Inn is situated in the heart of downtown Key West, a short stroll from Hemingway House and the Key West Aquarium, making it an ideal base for exploring the island's attractions. The inn has consistently received excellent ratings for its cleanliness, location, and overall experience, ensuring a comfortable and enjoyable stay. The inn offers a choice of rooms, each with a private bathroom and accommodating up to two guests. Guests can enjoy a range of amenities, including a heated outdoor pool, a garden, and complimentary WiFi. Coco Plum Inn also provides a made-to-order breakfast, concierge service, and the option of packed to-go breakfast and bicycle rentals for exploring the island.
Best Key West, FL bed and breakfasts with air conditioning
9.8 36 reviews
Key West, FL
21/12 – 18/01
A$680/nighttotal: A$19040 (28 )
Simonton Room @ Inn On Fleming~adults Only 1st Lvl King W/shared Heated Pool
1 1
B&B , Key West
This Old Town Key West flat is situated two blocks from the Historic Seaport and a short walk from Duval Street, offering easy access to Key West's attractions. The 20-square-metre self-catering apartment features one bedroom, one bathroom, sleeps two guests, and includes amenities such as a Serta PerfectSleeper mattress, flat-screen TV, mini-fridge, coffee maker, and access to a swimming pool and tropical garden.
Key West, FL
21/12 – 18/01
A$3237/nighttotal: A$90636 (28 )
Captains Cove Canalfront With Pool And Boat Lift
4 1
B&B , Key West
Captains Cove Canalfront with Pool and Boat Lift offers a canalfront stay in Key West, situated approximately 3.9 kilometres from the Southernmost Point and 4.2 kilometres from the Ernest Hemingway Home and Museum. This 222 square metre B&B features four bedrooms and four bathrooms, accommodating up to 15 guests with amenities including a private swimming pool, hot tub, fully equipped kitchen, and an outdoor dining area.
9.4 32 reviews
Key West, FL
21/12 – 18/01
A$1065/nighttotal: A$29820 (28 )
Cornish Suite @ Inn On Fleming Adults Only 3rd Floor 2 Br /Shared Heated Pool
2 1
B&B , Key West
This Old Town Key West flat, situated two blocks from the Historic Seaport and a short stroll from Duval Street, offers easy access to Key West's attractions. The Cornish Suite comprises 31 square metres, features two bedrooms, one bathroom, sleeps four guests, and includes a private deck, swimming pool, and concierge service.
Key West, FL
22/08 – 29/08
A$303/nighttotal: A$2121 (7 )
Bootlegger Bay @ Speakeasy Inn Key West!
1 2
B&B , Key West
This Key West cottage is located in the Southernmost Point district, 500 metres from the city centre, a 5-minute walk to the Southernmost Point, 500 metres from the Ernest Hemingway Home and Museum, a 7-minute walk to Duval Street, a 9-minute walk to the San Carlos Institute Casa Cuba, a 17-minute walk to the Harry S Truman Little White House, and a 4-minute walk to South Beach. This air-conditioned holiday home sleeps up to three guests and features a kitchenette with a fridge and microwave, along with complimentary WiFi.