Holiday Rentals in Key West, FL

4265 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • premierinn
  • sykescottages
  • plumguide
  • hotelscom
  • tripadvisor
  • homestay
  • tuivillas
  • hostelworld
Key West, FL holiday rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

4265 Holiday rentals and Airbnb in Key West, FL

Best family friendly Key West, FL holiday rentals

Among the 4265 accommodations in Key West, FL, here are the 4 best family friendly rentals

Colorful Retreat With Private Deck And Pool Access - Charming Escape - Key West, FL
No reviews

Colorful Retreat With Private Deck And Pool Access - Charming Escape

cottage, Key West
Colony Sunset is a secluded, gated cottage located in The Colony, a mere 200 metres from the attractions of Duval Street in Key West.
This one-bedroom, one-bathroom holiday home accommodates up to four guests and features air conditioning, Wi-Fi, a kitchen with a fridge and microwave, a private deck, and access to a large communal swimming pool, with a 16-kilometre weight limit for pets.
46 M² House ∙ 1 Bedroom ∙ 3 Guests - Key West, FL
9.3 57 reviews

46 M² House ∙ 1 Bedroom ∙ 3 Guests

house, Key West
This Key West cottage is located on a quiet street, less than 0.16 km from Duval Street, close to La Te Da restaurant and a few blocks from the Southernmost Point buoy.
This one-bedroom property, offering 37 square metres of floor space, sleeps three guests and features a king-sized bed, a sleeper sofa, a private hot tub, and shared access to a swimming pool and Jacuzzi; AvantStay support is available 24/7.
Spectacular Pool And Scenic Balcony - Luxury Coastal Sanctuary - Key West, FL
No reviews

Spectacular Pool And Scenic Balcony - Luxury Coastal Sanctuary

house, Key West
This two-bedroom, two-bathroom villa is situated in Key West, adjacent to a nature preserve and approximately 3.2 kilometres from Smather's Beach and the Atlantic Ocean.
This family-friendly property offers accommodation for six guests with amenities including an Olympic-sized swimming pool with ocean views, a jacuzzi, spa, tennis courts, a gym, and a secure gated complex with parking, with personalised concierge services available.
The James Suite | Ground Floor King - Key West, FL
No reviews

The James Suite | Ground Floor King

apartment, Key West
This historic one-bedroom flat on Caroline Street offers a prime Key West location, just 100 metres from Duval Street's amenities and a short walk to the Historic Seaport and Mallory Square, with access to the Curry Mansion's pool.
This pet-friendly accommodation sleeps four and features air conditioning, Wi-Fi, a kitchen with a fridge and microwave, and private balconies, with contactless check-in and all-day access to property bathrooms and showers.

Best Key West, FL holiday rentals with a pool

Among the 4265 accommodations in Key West, FL, here are the 4 best rentals with a pool

Poolside Suite With Direct Pool Access - Key West, FL
9.6 106 reviews

Poolside Suite With Direct Pool Access

apartment, Key West
This luxurious Key West apartment, at the Beachside Resort on the Gulf of Mexico, offers direct access to a resort pool and is within easy reach of the award-winning Tavern N Town restaurant.
The one-bedroom, one-bathroom flat sleeps four, boasts a king-size bed, fully equipped kitchen with stainless steel appliances, private balcony with pool views, a stackable washer/dryer, and access to resort amenities including a heated pool, hot tub, and fitness centre.
Blue Moonshine On The Atlantic - Key West, FL
9.5 2 reviews

Blue Moonshine On The Atlantic

house, Key West
Blue Moonshine on the Atlantic, a Key West property, is located 2.6 km from the Southernmost Point and 3.2 km from the Ernest Hemingway Home and Museum.
This 130-square-metre house boasts two bedrooms, two bathrooms, a hot tub, and sleeps up to 11 guests, offering a fully equipped kitchen, swimming pool, jacuzzi, sauna, fitness centre, tennis court, and ocean views from a private balcony, with free Wi-Fi and proximity to Smathers, Rest, and Higgs Beach.
The Salt Cay | Updated! Stunning Sunset View, Pool - Key West, FL
9.6 59 reviews

The Salt Cay | Updated! Stunning Sunset View, Pool

apartment, Key West
This Sunrise Suites condo is located on the east side of Key West, approximately 1.6km from the beach and a 10-minute drive from Duval Street.
The 74 square metre apartment sleeps six guests and boasts three bedrooms, two bathrooms, a fully equipped kitchen including a Keurig and dishwasher, in-unit laundry, and a private balcony with sunset views; shared amenities include a heated pool, hot tub and tennis court.
Osprey Studio @ The Colony-sleeps Up To 4 - Key West, FL
9.4 63 reviews

Osprey Studio @ The Colony-sleeps Up To 4

studio, Key West
Osprey studio, a ground-floor apartment in Key West's Old Town Colony neighbourhood on Olivia Street, is situated two blocks from Duval Street, offering easy access to restaurants and bars and proximity to the Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park.
This 45-square-metre self-catering unit sleeps four, featuring a queen bed, a couch, a kitchenette with microwave and refrigerator, a bathroom with shower, a private deck, and access to a shared swimming pool and spa; nearby activities include jet skiing and kayaking.

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?

  • When is the best time to come to Key West?

    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?

  • What's the best way to come to Key West?

    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?

    The best vacation rentals or Airbnb with a jacuzzi in Key West, FL are Leaward Isle Island Retreat, Key West Villas and Downtown Retreat - A++ Location W\/ Private Heated Pool\/hot Tub.

  • What's the must see sites in Key West?

    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

One Bedroom Suite | Beachside Resort - Key West, FL
10 7 reviews

One Bedroom Suite | Beachside Resort

apartment, Key West
This luxury resort in North Key West, situated on seven acres of waterfront, offers direct Gulf of Mexico views and is located 1.6 kilometres from Duval Street, placing it close to Florida Keys Beaches and Smathers Beach.
This one-bedroom, two-bathroom apartment accommodates up to four guests and features a fully equipped kitchen with stainless-steel appliances, a private balcony, access to a heated swimming pool and hot tub, and is conveniently located near attractions such as the Ernest Hemingway Home and Museum and the Southernmost Point.
Sunrise Suites Condo With Balcony - Shared Pool, Hot Tub, Tennis, Free Parking - Key West, FL
9.0 144 reviews

Sunrise Suites Condo With Balcony - Shared Pool, Hot Tub, Tennis, Free Parking

apartment, Key West
This Key West condo is situated on the eastern side of the island, offering proximity to Smathers Beach and within eight kilometres of popular attractions like Southernmost Point and the Ernest Hemingway Home and Museum.
This two-bedroom, two-bathroom apartment spans 72 square metres, accommodating up to six guests with amenities including a kitchen, air conditioning, WiFi, a swimming pool, jacuzzi, and private parking.
Coconut Palm - Key West, FL
9.0 585 reviews

Coconut Palm

house, Key West
This apartment is located in the heart of Key West, just 1.8 kilometres from South Beach and less than 1.6 kilometres from Fort Zachary Taylor State Park Beach. It has received excellent ratings for its location, cleanliness, and overall user experience.
The apartment is well-equipped and offers a comfortable stay. It features a fully equipped kitchen, a private terrace, and access to a swimming pool, jacuzzi, sauna, and parking.
Hemingways Atlantic Retreat - Key West, FL
9.2 129 reviews

Hemingways Atlantic Retreat

house, Key West
This apartment is located in Key West, a short walk from Smathers Beach and close to Rest Beach, offering easy access to the island's beautiful beaches and vibrant atmosphere. The apartment has consistently received excellent ratings for location, cleanliness, and overall user experience.
The apartment is spacious, with two bedrooms and two bathrooms, ideal for families or groups of up to six guests. It also boasts a range of amenities, including a swimming pool, a Jacuzzi, a fitness center, and a tennis court, ensuring a comfortable and enjoyable stay.

Best Key West, FL holiday rentals with parking

The Saint Kitts Suite | Breathtaking View, Heated Pool - Key West, FL
9.8 8 reviews

The Saint Kitts Suite | Breathtaking View, Heated Pool

apartment, Key West
This pet-friendly condominium in the Sunrise Suites community is situated on Key West's southeast side, approximately 3.2 kilometres from Smathers Beach and a short journey from Duval Street's attractions.
This newly renovated two-bedroom, two-bathroom condo offers 74 square metres of living space, accommodating up to six guests with a queen sofa bed, and features a private balcony, a fully equipped kitchen, air conditioning, and access to a communal heated pool, hot tub, and tennis court.
Sky Suites Retreat - Balcony Overlooking Duval - Key West, FL
No reviews

Sky Suites Retreat - Balcony Overlooking Duval

apartment, Key West
This elevated second-story loft, situated on the 700 block of Duval Street, offers immediate walking access to Key West's notable dining establishments such as Martin's and Moondog Cafe, as well as the historic Hemingway House, all within 500 metres.
This duplex accommodation, designed for up to 12 guests across two connected lofts with four bedrooms and four and a half bathrooms, features vaulted ceilings, modern decor, private balconies, two fully equipped kitchens, and off-street parking for one compact vehicle.
Tranquility By Avantstay - Key West, FL
9.6 102 reviews

Tranquility By Avantstay

house, Key West
This charming cottage is ideally located in the heart of Key West's Historic District, just a short walk from Duval Street and the Key West Cemetery, making it perfect for exploring the island's rich history and vibrant culture. The property has received excellent reviews from previous guests, highlighting its convenience, comfort and value for money.
The cottage offers a comfortable and spacious layout, with a fully equipped kitchen and modern amenities including air conditioning, a private pool and free Wi-Fi. Guests can enjoy relaxing on the terrace, making use of the barbecue facilities or simply soaking up the sun in the garden.
Charming Houseboat In Key West - Key West, FL
10 86 reviews

Charming Houseboat In Key West

barge, Stock Island
This Stock Island houseboat, situated in Cow Key Channel, offers a secluded escape approximately 1.6km from a marina by motorboat, providing easy access to Key West via kayak, water taxi, or boat trip.
The one-bedroom, one-bathroom vessel sleeps two guests and features a kitchen with a fridge and microwave, air conditioning, a garden, parking, and a spacious deck ideal for al fresco dining; kayaking in nearby mangroves and optional private boat tours are also available.
©2026 cozycozy.com