This adults-only guesthouse is ideally located in Key West's Old Town, just 0.5 kilometres from Duval Street. The renovated Victorian property offers a private cabana room with a king-size bed, ensuite bathroom, sitting area, and access to a saltwater pool; it sleeps two guests.
10 1 review
Key West, FL
01/08 – 08/08
A$2072/nighttotal: A$14504 (7 )
3 Traditional Two Queen, Pier House, Spa Access
3 11
B&B , Key West
This Key West guesthouse enjoys a prime Duval Street location, within easy walking distance of Ernest Hemingway's Home and the Southernmost Point buoy. Offering three rooms, each with two queen-size beds and ocean views, this pet-friendly (maximum 9kg per pet, extra charge applies) establishment sleeps up to twelve guests and boasts a swimming pool, fitness centre, and on-site parking.
8.9 1251 reviews
Key West, FL
14/10 – 16/10
A$337/nighttotal: A$674 (2 )
The Casablanca Hotel
1 2
B&B , Key West
This charming guesthouse sits in Old Town Key West, just a stone's throw from the Ernest Hemingway Home and Museum, placing you right in the heart of the island's historic district. Guests consistently rate it highly for its cleanliness, location and overall experience. Each room in this beautiful property has its own private balcony, providing a peaceful retreat from the bustling streets. Amenities include a swimming pool, a garden, a bar, free Wi-Fi and parking, ensuring you have everything you need for a relaxing and enjoyable stay.
Key West, FL
29/12 – 27/01
A$3707/nighttotal: A$107503 (29 )
Captains Cove Canalfront With Pool And Boat Lift
4 2
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.
10 1 review
Key West, FL
24/07 – 25/07
A$3464/nightfor 1 night
2-bedroom Hotel Suite - 2 Beds
2 4
B&B , Key West
This guest house is located in Key West's Old Town, just a short walk from Mallory Square, offering views of the historic district. The accommodation sleeps up to four guests in two bedrooms, featuring a King bed, a Queen bed, a Queen sleeper sofa, air conditioning, Wi-Fi, a swimming pool, a Jacuzzi, a garden, and valet parking.
This Old Town Key West flat is ideally located just steps from Duval Street and the San Carlos Institute, within a 2.4km radius of the Ernest Hemingway Home and Museum and beaches. The self-catering apartment, sleeping two guests, boasts a private balcony, free Wi-Fi, and amenities including a refrigerator, coffee maker, TV, and hairdryer; a swimming pool, tennis court and concierge services are also available.
10 2 reviews
Key West, FL
27/06 – 28/06
A$1610/nightfor 1 night
Perfect For Groups! 2 Pet-friendly Units!
2 7
B&B , Key West
This Key West guesthouse is situated in the downtown area, a short walk from the Ernest Hemingway Home and Museum and Duval Street. Offering two 34-square-metre rooms each sleeping four, this pet-friendly lodging boasts a heated pool, complimentary breakfast, bicycles, and Wi-Fi, with a nightly pet fee of £40.
9.8 28 reviews
Key West, FL
20/07 – 27/07
A$313/nighttotal: A$2191 (7 )
Hemingway Suite @ Inn On Fleming~adults Only 2nd Lvl King 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 main attractions. The Hemingway Suite, a 24-square-metre apartment, features a king-size bed, en-suite bathroom, private deck, and amenities including free Wi-Fi and bike rentals for two guests, with concierge services available for booking local activities.
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.
9.4 225 reviews
Key West, FL
26/10 – 28/10
A$805/nighttotal: A$1610 (2 )
The Artist House
2 4
B&B , Key West
The Artist House B&B is situated in Old Town Key West, a short walk from Duval Street and a mile from the Southernmost Point, making it ideal for exploring the island's vibrant atmosphere. The B&B has consistently received excellent ratings for its location, cleanliness, and overall experience. This charming guest house offers a peaceful retreat, despite its proximity to the action. Guests can enjoy a daily continental breakfast, relax in the spa hot tub, and benefit from amenities such as free Wi-Fi, parking, and a garden.
8.9 1253 reviews
Key West, FL
31/07 – 02/08
A$457/nighttotal: A$914 (2 )
Caribbean House
1 2
B&B , Key West
Caribbean House is situated in Key West, just 0.4 km from Duval Street and 1.4 km from Fort Zachary Taylor Beach, offering a peaceful escape close to the lively heart of the city. The property boasts consistently high ratings for both location and user experience, indicating a comfortable and enjoyable stay. This guesthouse features 16 square metre rooms, each with a private bathroom and a small refrigerator, accommodating up to two guests. Guests can enjoy a range of amenities, including a terrace or balcony in select rooms, free Wi-Fi, air conditioning, and bike hire for exploring the island's many attractions.
10 1 review
Key West, FL
23/06 – 24/06
A$413/nightfor 1 night
Bootlegger Bay ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!
1 2
B&B , Key West
This guesthouse in Old Town Key West is located directly on Duval Street, offering immediate access to galleries, restaurants, and bars, and is just 0.3 kilometres from the beach and the Southernmost Point. The 18 square metre 'Bootlegger Bay' room accommodates two guests, features a stocked kitchenette with a fridge and microwave, air conditioning, internet, and private outdoor seating, with the property also boasting a celebrated Rum Bar and an adults-only policy.
Best Key West, FL bed and breakfasts with breakfast included
9.1 2654 reviews
Key West, FL
06/01 – 08/01
A$1376/nighttotal: A$2752 (2 )
Ambrosia Key West
2 5
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.
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.
9.5 1253 reviews
Key West, FL
24/07 – 25/07
A$683/nightfor 1 night
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.
9.0 2870 reviews
Key West, FL
30/10 – 04/11
A$774/nighttotal: A$3870 (5 )
The Grand Guesthouse
1 2
B&B , Key West
This adults-only guesthouse is located in Key West, just a 1.6 kilometre walk from Duval Street and the Atlantic Ocean, offering a peaceful retreat close to the island's bustling centre. The accommodation has received excellent ratings for its cleanliness, location and overall experience. Each room features local Caribbean artwork and private entrances, providing a unique and intimate stay. The guesthouse offers amenities like bike rentals, free Wi-Fi, flat-screen cable TVs, iPod docking stations, a continental breakfast, a swimming pool, a garden, and a restaurant and bar.
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
9.1 16 reviews
Key West, FL
02/07 – 05/07
A$572/nighttotal: A$1716 (3 )
Near Smathers Beach + Pool. Breakfast. Shuttle.
1 4
B&B , Key West
Blue Flamingo Resort Key West, a guesthouse situated at the gateway to Old Town, offers easy access to Duval Street and other Key West attractions, being just minutes from the Southernmost Point and Mallory Square. This pet-friendly (35lb weight limit, £40 per night surcharge) property features one bedroom, one bathroom, and sleeps four guests in either two double or two queen beds, boasting a fitness centre, multiple pools with cabanas and poolside dining, and a complimentary shuttle to Old Town.
9.9 27 reviews
Key West, FL
29/12 – 31/12
A$1258/nighttotal: A$2516 (2 )
Secluded Island Escape | Sailing. Pool
1 2
B&B , Key West
This studio apartment is located on Key West harbour in Old Town, offering proximity to Mallory Square and Duval Street, approximately 500 meters from the latter. This 37-square-meter studio, suitable for up to four guests, features air conditioning, internet, access to three swimming pools, a garden, and an on-site bar and restaurant, with pets allowed under certain restrictions.
9.7 7 reviews
Key West, FL
29/12 – 31/12
A$1064/nighttotal: A$2128 (2 )
Beachfront Key West + Free Breakfast, Bar & Pool
1 2
B&B , Key West
This studio apartment is situated in Historic Old Town, Key West, on the Atlantic Coast, offering easy access to the Southernmost Point Buoy, Key West Lighthouse Museum, and Mallory Square, all within a short walk. This guesthouse accommodates two guests and features a king-size bed, a sitting area, a coffee maker, and access to resort amenities including three heated swimming pools, two private beaches, and a fitness centre.
9.8 75 reviews
Key West, FL
14/10 – 16/10
A$355/nighttotal: A$710 (2 )
Marrero's Guest Mansion Adult Only (21+) Room 11
1 2
B&B , Key West
Marrero's Guest Mansion, an adults-only guesthouse in Key West's Old Town, is located just 0.08 kilometres from Duval Street, the island's main tourist area. This renovated Victorian property offers one bedroom with a queen-size bed, a private bathroom, and a private courtyard with a saltwater pool; it also provides a complimentary continental breakfast and daily happy hour.
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
Key West, FL
31/07 – 02/08
A$602/nighttotal: A$1204 (2 )
Steps To Duval St + Free Breakfast, Pool & Bar
1 2
B&B , Key West
This guesthouse, located at the western end of Duval Street, offers direct access to a private beach and is a 3-minute walk from the Southernmost Point Buoy and South Beach. This adult-focused sanctuary provides a sophisticated Key West experience with access to three heated pools, lush tropical gardens, and a world-class spa, featuring beach-chic decor in its single King bedroom accommodating two guests.
9.4 24 reviews
Key West, FL
08/07 – 09/07
A$509/nightfor 1 night
Coastal Luxe | Outdoor Pool. Island Experience
1 2
B&B , Key West
This Key West studio apartment is situated in Historic Old Town, a short walk from the Southernmost Point buoy and within easy reach of Mallory Square. The self-catering unit, sleeping two, boasts a king-size bed, modern bathroom, private balcony with architectural views, and access to resort amenities including multiple pools, beaches, and a spa; plus, it offers a coffee maker, flat-screen TV and air conditioning.
9.4 2547 reviews
Key West, FL
29/12 – 27/01
A$753/nighttotal: A$21837 (29 )
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.
9.5 215 reviews
Key West, FL
02/07 – 05/07
A$549/nighttotal: A$1647 (3 )
Near Old Town Key West + Pool. Dining. Shuttle.
1 4
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 air conditioning
9.2 35 reviews
Key West, FL
26/10 – 28/10
A$647/nighttotal: A$1294 (2 )
Geiger Suite @ Inn On Fleming~adults Only 2 Br 3rd Floor & Shared Heated Pool
2 4
B&B , Key West
This Old Town Key West flat, a former Board of Education chair's residence dating from 1894, is situated two blocks from the Historic Seaport and a short walk from Duval Street. The 32-square-metre Geiger Suite, sleeping up to four guests in a king and full-size bed, boasts a pool and garden view, plus a mini-fridge, coffee maker, and flat-screen TV; concierge services arrange local activities such as snorkelling and kayaking.
9.6 24 reviews
Key West, FL
21/12 – 18/01
A$601/nighttotal: A$16828 (28 )
Gato Room @ Inn On Fleming~adults Only 2nd Floor Queen W/ Shared Heated Pool!
1 1
B&B , Key West
This Key West apartment, situated in Old Town, is two blocks from the Historic Seaport and a short walk from Duval Street, offering easy access to Key West's attractions. The 15-square-metre (0.015-hectare) studio flat sleeps two, features a private bathroom, and includes amenities such as a swimming pool, garden, and concierge service; bicycle rental is also available for exploring the island.
9.1 16 reviews
Key West, FL
22/08 – 29/08
A$463/nighttotal: A$3241 (7 )
Sunny Oasis | Outdoor Pool. Island Experience
1 2
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.
10 5 reviews
Key West, FL
29/12 – 31/12
A$925/nighttotal: A$1850 (2 )
The Jungle Room
1 2
B&B , Key West
Ambrosia Key West, a guesthouse in Key West's Old Town Historic District, offers a tropical resort experience within walking distance of local attractions. This accommodation provides a complimentary buffet breakfast, access to three swimming pools, lush gardens, and rooms or suites with private entrances and decks, accommodating up to two guests with amenities like microwaves and refrigerators in select units.