This Key West apartment is ideally located in Old Town, a short walk from Truman Avenue and Whitehead Street, placing you within easy reach of the Southernmost Point buoy and the Ernest Hemingway Home. The ground-floor flat offers one bedroom, one bathroom, sleeps two guests, and includes partial air conditioning, cable TV, free Wi-Fi, and a mini-fridge; pets are welcome for an additional fee.
10 1 review
The Margaret Suite
apartment, Key West
The Margaret Suite, a studio flat in Key West, is located 2.57 kilometres from Mallory Dock, Mallory Square, and the Key West Aquarium, and 1.93 kilometres from the Southernmost Point, offering easy access to the Ernest Hemingway Home and Museum, Duval Street, and Rest Beach, with Key West International Airport a mere 1.93 kilometres away. This 37-square-metre studio apartment accommodates up to five guests and features air conditioning, a kitchen with a fridge and microwave, complimentary on-site parking and WiFi, an outdoor swimming pool, a garden, and a private entrance for a comfortable stay.
9.5 288 reviews
Pool View Suite | Beachside Resort
apartment, Key West
This one-bedroom apartment is situated in a resort complex on a 2.8-hectare site overlooking the Gulf of Mexico in Key West, just a short distance from Duval Street and the Southernmost Point. The apartment offers a king-size bed, a queen sleeper sofa, a fully equipped kitchen, a private washer/dryer, and a private balcony, as well as access to a 24-hour heated pool, hot tub, on-site marina, restaurant, and waterview fitness centre.
9.4 70 reviews
Half Block To Duval - Stay At The Bonaire Suite
apartment, Key West
This Key West Historic District apartment is located half a block from Duval Street and within a few hundred metres of South Beach. The bi-level suite, sleeping four guests in two queen beds and a queen-size sofa bed, boasts a private courtyard, shared pool access, two bathrooms (one en-suite with a tumbled marble shower), and free Wi-Fi; nearby attractions include Duval Street's nightlife and the open-air restaurants and bars of South Beach.
8.6 8 reviews
~Royal Poinciana Cottage~ Come And Indulge Yourself In Some Kw Sunshine!
cottage, Key West
This pet-friendly Key West cottage is located in Old Town, a short walk from St Mary Star of the Sea Church and the Key West Firehouse Museum, offering easy access to the ocean. The self-catering property sleeps two guests and features a fully equipped kitchen, air conditioning, a private porch, shared pool, in-unit laundry, and Wi-Fi; nearby attractions include the Southernmost Point and the Ernest Hemingway Home and Museum.
8.7 4 reviews
Claude Monet Suite
apartment, Key West
The Claude Monet Suite is a centrally located Key West flat, a short walk (less than 0.5km) from Fort Zachary Taylor State Park Beach, the Ernest Hemingway Home and Museum, and South Beach, and close to Mallory Dock and Duval Street. This 24 square metre self-catering apartment offers a separate bedroom and living room, sleeping up to 7 guests and including a kitchenette, air conditioning, Wi-Fi, a swimming pool, and pet-friendly accommodation.
10 1 review
Gorgeous 8 Room Guest House For Private Functions
apartment, Key West
This Old Town Key West guesthouse, within walking distance of Key West's restaurants and attractions, offers eight bedrooms and nine bathrooms in a freshly remodelled 1880s building. This 16-guest property boasts two suites with separate living rooms, a private courtyard ideal for events, and expansive porches; all bathrooms feature gorgeous tiled showers.
8.6 94 reviews
Resort Condo With Pool & Hot Tub - Walk Or Bike To Beach
apartment, Key West
This Key West condominium offers a prime seaside location, within 1 kilometre of Smathers Beach and a short distance to the Southernmost Point and Ernest Hemingway Home and Museum. This 72 square metre apartment accommodates up to six guests and features two bedrooms and two bathrooms, with access to a shared swimming pool, hot tub, and fitness room, alongside opportunities for water sports and nearby botanical gardens.
No reviews
Kwss108 Sunrise Suites - Martinique Suite 108
house, Key West
KWSS108 Sunrise Suites - Martinique Suite 108 offers a convenient location in Key West, situated 1 kilometre from Key West International Airport and approximately 6.4 kilometres from Southernmost Point and Duval Street. This 72 square metre holiday apartment accommodates up to 11 guests in 2 bedrooms and features 2 bathrooms, a well-equipped kitchen with a dishwasher, microwave oven, and fridge, air conditioning, a swimming pool, jacuzzi, and a private balcony.
No reviews
Turtle Nest Condo + Pool
apartment, Key West
This 1932 Key West residence, situated in the tranquil Meadows district, offers proximity to Duval Street and the Historic Seaport, just a 10-minute walk away. This one-bedroom, one-bathroom flat accommodates up to four guests, featuring air conditioning, a fully equipped kitchen, a private porch, and access to a shared heated swimming pool and BBQ grill.
No reviews
Claro At Azul Mansion Key West
house, Key West
CLARO at Azul Mansion, a Key West apartment, is centrally located less than 0.6km from the city centre, a 12-minute walk from South Beach, and near the Ernest Hemingway Home and Museum, Duval Street, and the Southernmost Point. This one-bedroom, one-bathroom property sleeps two guests and offers a swimming pool, terrace, free Wi-Fi, on-site parking, and air conditioning; nearby attractions include Key West International Airport (3km away).
No reviews
Resort View 3br Residence
resort, Key West
The Resort View 3br Residence is located in Key West, 5km from the city centre, near the Key West Tropical Forest and Botanical Garden and the Lower Keys Medical Center. This pet-friendly three-bedroom property sleeps two guests and offers air conditioning, internet access, and is likely self-catering; enjoy easy access to Key West's attractions.
Best family friendly Key West, FL holiday rentals
Among the 3183 accommodations in Key West, FL, here are the 4 best family friendly rentals
9.3 247 reviews
Mar Y Sol Luxurious Oceanfront Key West Breathtaking Atlantic Sunrise Views
apartment, Key West
This beachfront apartment is located just 1.5 kilometres from Florida Keys Beaches and Clarence S. Higgs Memorial Beach Park, offering a peaceful retreat from the bustling Duval Street and Mallory Square, which are both within 5 kilometres. This property has received excellent ratings for user experience, location, and cleanliness. The apartment has three bedrooms, spanning 186 square metres, and can accommodate up to eight guests. Enjoy a range of amenities, including a swimming pool, Jacuzzi, sauna, fitness centre, tennis court, and a private balcony with stunning ocean views.
9.2 2442 reviews
The Perry Hotel & Marina Key West
resort, Stock Island
The Perry Hotel & Marina Key West is located on Stock Island, just 8km from Key West's Old Town and 5km from Key West International Airport. It has excellent user ratings, with particularly high marks for cleanliness and location. The hotel has a waterfront setting with two pools and direct marina access. Guests can enjoy a range of amenities, including restaurants, a spa, a fitness centre, tennis courts, and complimentary shuttle service to Old Town.
9.5 26 reviews
121 M² House ∙ 2 Bedrooms ∙ 6 Guests
house, Key West
This Old Town Key West property is a short walk from Duval Street and 0.64km from the Atlantic Ocean. This two-bedroom, two-bathroom house offers 130 square metres of living space, including a private pool, fully equipped kitchen, and accommodates up to six guests; AvantStay services are available.
9.0 2 reviews
Apartment ∙ 3 Bedrooms ∙ 8 Guests
apartment, Key West
This three-bedroom apartment is situated in Beachside Key West, just a short distance from Duval Street and its attractions. The apartment offers private parking with electric charging stations, a fully equipped kitchen, a spacious living area with a queen sleeper sofa, and a private balcony, comfortably accommodating up to eight guests.
Best Key West, FL holiday rentals with a pool
Among the 3183 accommodations in Key West, FL, here are the 4 best rentals with a pool
9.8 164 reviews
Top Floor Amazing View Toms Chicken Coop Awaits Your Next Stay. Best Value
apartment, Key West
This Key West Midtown condo is situated within 1.6km of Florida Keys Beaches, Duval Street, and South Beach, with Mallory Square, famed for its sunset celebrations, a 3.4km drive away. This 139 square metre apartment sleeps six guests, boasting three bedrooms, two bathrooms, a fully equipped kitchen, and a private terrace plus access to a swimming pool, Jacuzzi, sauna, fitness centre and tennis court.
10 5 reviews
Sea Esta Suite | Located On Iconic Duval W/ Pool
house, Key West
Sea Esta Suite, a two-storey townhouse on Duval Street in Key West, is situated on the 1000 block, a short walk (less than 0.8km) from the Southernmost Point buoy. This Key West holiday home offers two king bedrooms each with an en-suite bathroom, plus a queen-size sofa bed, accommodating up to six guests; amenities include a private garage, a shared rooftop pool, a newly renovated kitchen with modern appliances, and a private washer/dryer.
9.7 311 reviews
Anchor Drop Modern Elegance Upgrades Throughout Views Of Atlantic Ocean
apartment, Key West
This two-bedroom apartment in Beachside, Key West is just a 15-minute walk from the Florida Keys Beaches and Clarence S. Higgs Memorial Beach Park, and within a short drive of Duval Street and Mallory Square. The property has received excellent ratings for location, cleanliness and user experience. The 126 square metre apartment comfortably sleeps six guests and features a fully equipped kitchen, a terrace, a garden, a swimming pool, a Jacuzzi, a sauna, a fitness centre and a tennis court. Guests will also enjoy access to parking, air conditioning and internet.
10 50 reviews
Casa Serendipity At Old Town
house, Key West
This charming Key West cottage is situated in Old Town, just a short walk from Duval Street, the Historic Seaport, and a selection of restaurants and bars. The cottage has received excellent ratings for location, cleanliness, and overall user experience. The three-bedroom cottage comfortably sleeps six guests and features a fully-equipped kitchen, a private pool, and a spacious outdoor living area with a propane grill. Guests can enjoy the Key West sunshine by relaxing on the porch or by the pool, or explore the surrounding area on foot.
Frequently asked questions about holiday rentals in Key West, FL
What should a first-time visitor not miss in Key West, FL?
You absolutely have to visit the Southernmost Point of the Continental US, marking the very tip of Key West. A stroll down Duval Street is a must, with its vibrant atmosphere and shops. And no trip is complete without a sunset at Mallory Square, watching the street performers and enjoying the lively atmosphere.
What are the best Airbnb and holiday rentals in Key West, FL?
Are there any unusual vacation rentals I can find in Key West?
Key West has some great places to stay, but if you want something unusual, you'll get plenty to choose from. You can stay in a tiny house, a sailboat, a yacht, a houseboat, or even a camper van!
Which neighborhood in Key West, FL should you consider for a vacation rental?
Old Town is a popular choice, with its historic architecture, proximity to Duval Street, and easy access to the waterfront. For a quieter vibe, consider the New Town area, known for its charming cottages and proximity to the beach. If you want to be closer to the action, the Historic Seaport area is a good option with its lively atmosphere and proximity to the harbour.
What are the most popular Airbnbs in Key West, FL?
The months between March and May are the best time to visit Key West. Booking accommodation this time of year is going to be less pricy than in the peak winter season, but you won't miss out on the good weather.
What are the top family-friendly attractions in Key West, FL?
The Key West Aquarium is a hit with kids of all ages, with its diverse marine life and interactive exhibits. The Butterfly Conservatory is a beautiful and peaceful place to spend a few hours, and the Key West Wildlife Center offers up-close encounters with rescued animals. For a fun day out, head to the Key West Shipwreck Treasure Museum, where you can learn about the history of shipwrecks and see real treasure.
What are the best holiday rentals with a pool in Key West, FL?
What local special dishes should I try in Key West?
Key Lime Pie is perhaps Key West's most famous dessert, but if you want something savory, there's plenty still to chew through. Key West Pinks is a special local shrimp with a sweet taste that you can find eaten alone or accompanied with some bacon. Conch fritters are also something tasty and different to try and definitely a special in Key West.
When is the best time to book a vacation rental in Key West, FL?
Key West is a popular destination year-round, so it's best to book your vacation rental well in advance, especially during peak season, which runs from December to April. If you're looking for a more affordable trip, consider visiting during the shoulder seasons, from May to June or September to November.
What are the best rentals for families and kids in Key West, FL?
You have different options to get to Key West. You can fly, drive, or even take a boat. If you're traveling long distances, then you can fly into Key West with most major US carriers like Delta, American, USAir, United, Southwest, and Cape Air. However, if you want a scenic route, then driving to Key West over the Overseas Highway is a unique experience and worth the long drive (the route runs 113 miles long, or 170 miles long if you start from Miami). There are also buses and shuttle services available too.
What events or festivals should visitors check out in and around Key West, FL?
The annual Fantasy Fest in October is a wild and colourful celebration with parades, parties, and costumes. The Key West Hemingway Days Festival in July celebrates the famous author with a look-alike contest and other events. There's also the Key West Songwriters Festival in May, featuring live music and performances.
What are the best rentals or Airbnbs with a jacuzzi in Key West, FL?
Visit the southernmost point of the United States before heading back to the northern side of Key West to take in the sights and performances around Mallory Square. Of course, no trip to Key West is complete without a trip to the Ernest Hemingway House!
What are the best budget-friendly activities in Key West, FL?
Take a stroll along the waterfront and enjoy the views of the ocean and the historic buildings. Visit the Key West Cemetery, a unique and quirky attraction with interesting headstones. Explore the historic streets of Old Town and admire the architecture. Take a dip in the ocean at Smathers Beach, a popular spot for swimming and sunbathing.
What are the best restaurants with local dishes in Key West, FL?
For a taste of Key West's unique cuisine, try the famous Key Lime Pie at the Kermit's Key West Key Lime Shop. For a casual and delicious meal, head to the Blue Heaven, a popular spot for its fresh seafood and laid-back atmosphere. For a more upscale dining experience, try the Latitudes Restaurant, known for its stunning views and innovative dishes.
What are the best walking or cycling routes in Key West, FL?
The scenic route along the waterfront is a must-do, offering stunning views of the ocean and the historic buildings. For a more adventurous ride, try the Key West Bike Path, which winds its way through the city and out to the coast. For a leisurely stroll, explore the historic streets of Old Town, with its charming shops and restaurants.
Are there pet-friendly attractions in Key West, FL?
Many restaurants and shops in Key West are pet-friendly, and you'll often see dogs enjoying the sunshine on patios and sidewalks. The Key West Aquarium welcomes well-behaved dogs on leashes, and the Key West Butterfly Conservatory also allows dogs in designated areas. Smathers Beach is a popular spot for dog walking and playing.
What are the benefits of choosing a vacation rental in Key West, FL?
Vacation rentals offer more space and privacy than a hotel room, and often come with amenities like kitchens and laundry facilities. Many rentals are located in desirable neighbourhoods, offering easy access to attractions and activities. You can often find vacation rentals at more affordable rates than hotels, especially for larger groups or longer stays.
What are the top sports attractions and facilities in Key West, FL?
Key West is a popular destination for watersports, with opportunities for swimming, sunbathing, kayaking, paddleboarding, and fishing. The Key West Tennis Club offers courts and lessons for all levels. For a more active experience, try the Key West Marathon, held every year in November.
Popular destinations
Best Key West, FL holiday rentals with a balcony
9.4 17 reviews
The Flight Deck - 3 Bedroom / 3 Bathroom With Shared Pool & Fitness Center!
apartment, Key West
This three-bedroom townhouse is situated in the Coral Hammock Community on Stock Island, just 6.4 kilometres from the centre of Key West. The property offers a private escape with a garden, a swimming pool, and a terrace, perfect for families or groups of up to six guests.
No reviews
The Blue Flamingo Resort Key West
resort, Key West
The Blue Flamingo Resort Key West is located 5 kilometres from Key West's city centre, offering easy access to attractions such as the Key West Tropical Forest and Botanical Garden and the Lower Keys Medical Centre. This resort provides a variety of amenities, including indoor and outdoor swimming pools, a fitness centre, a bar, a restaurant, and family-friendly facilities, with the Blue Flamingo Resort Key West offer including live entertainment and happy hour access.
9.4 178 reviews
Direct Ocean View From Your Condo-no Contact Check-in
apartment, Key West
This Key West condo is ideally situated just steps from Smathers Beach and within 4.8 kilometres of Duval Street and Mallory Square. The 109-square-metre apartment features two bedrooms, two bathrooms, sleeps six guests, and boasts a private balcony, swimming pool, Jacuzzi, tennis court, and parking; barbecue grills are available for guest use.
10 15 reviews
The Rigby House - Pool, One Block From Duval St
apartment, Key West
This Key West Historic District property is situated a short walk from Papa's Pilar Rum Distillery and Duval Street, and within 0.9 km of Mallory Square and the Ernest Hemingway Home and Museum. This six-bedroom, seven-bathroom house offers 232 square metres of living space, accommodating up to 12 guests and boasting a private pool, fully equipped kitchen, and balcony; nearby attractions include beaches and the Florida Keys.
Best Key West, FL holiday rentals with parking
9.0 1 review
Breezy Retreat
house, Key West
Breezy Retreat, a Key West house, is centrally located, less than 0.8km from South Beach, Higgs Beach, and the Ernest Hemingway Home and Museum. This 145 square metre property sleeps seven guests across two bedrooms and two bathrooms, boasting a private pool, terrace, free Wi-Fi, and parking – a rare find in Key West – plus access to a fitness centre and tennis court.
This luxurious Key West penthouse, situated in the 1800 Atlantic Complex near Duval Street, offers breathtaking direct ocean views and is conveniently located for exploring the island's attractions. The two-bedroom, two-bathroom apartment sleeps six, boasting a king and twin beds, a queen sofa bed, a gourmet kitchen, 80-inch smart TV with Sonos sound, a zero-gravity massage chair and access to extensive complex amenities including an Olympic-size swimming pool, Jacuzzi, and tennis courts.
9.4 6 reviews
Key West's Best
house, Key West
This Key West holiday home is ideally located near Smathers, Rest, and Higgs Beaches, approximately 2.6 km from the Southernmost Point and 3.2 km from the Ernest Hemingway Home and Museum, with Key West International Airport just 1.9 km away. The two-bedroom, two-bathroom property sleeps up to 11 guests and boasts a private balcony with ocean views, a swimming pool, Jacuzzi, sauna, fitness centre, tennis court, and well-equipped kitchen; nearby activities include exploring the beaches and visiting local attractions.
This Key West Historic District property is a short 0.8km walk from Key West Cemetery and Duval Street, with the Ernest Hemingway Home and Museum and Florida Keys beaches within a 2.4km radius. The self-catering house boasts a fully equipped kitchen, private garden with barbecue, jacuzzi, and balcony; free Wi-Fi and parking are also included.