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

Lagoon-style Pool And Tropical Paradise - Charming Key West Retreat - Key West, FL
10 1 review

Lagoon-style Pool And Tropical Paradise - Charming Key West Retreat

house, Key West
This private Key West house offers a secluded escape, located a short distance from Duval Street and Mallory Square, providing convenient access to historical sites such as the Hemingway Home and the Shipwreck Museum.
This family-friendly holiday home accommodates four guests across two bedrooms, featuring a lagoon-style pool with a waterfall, a spacious gazebo with a television for outdoor entertainment, and off-street parking for up to three cars, including space for a boat and trailer.
Duval Delight | Recently Remodeled Condo On Duval! - Key West, FL
9.8 10 reviews

Duval Delight | Recently Remodeled Condo On Duval!

apartment, Key West
This newly remodelled loft-style condo is situated on the quieter end of Duval Street, just 150 metres from the Ernest Hemingway Home and Museum and the Key West Butterfly and Nature Conservatory.
This family-friendly apartment offers accommodation for up to eight guests, featuring a fully equipped kitchen, private laundry facilities, air conditioning, Wi-Fi, a fitness centre, and a private parking space, with dogs up to 18 kilograms welcome for a nightly fee.
Charming Deck And Inviting Living Space - Serene Coastal Retreat - Key West, FL
10 50 reviews

Charming Deck And Inviting Living Space - Serene Coastal Retreat

cottage, Key West
Colony Poolside is a secluded cottage located within The Colony compound, just a short walk from Duval Street, placing you within easy reach of Key West's beaches, shops, and restaurants.
This one-bedroom, one-bathroom holiday let accommodates up to four guests and features a private deck, a shared swimming pool, and air conditioning, with a fully equipped kitchen and complimentary internet access.
The Tortuga At Sunrise Suites - Balcony & Pool - Key West, FL
9.2 122 reviews

The Tortuga At Sunrise Suites - Balcony & Pool

apartment, Key West
This two-bedroom condominium is located on Key West's southeast side, 1.6 kilometres from the beach and a 10-minute drive from Duval Street, offering proximity to Mallory Square's Sunset Celebration.
This pet-friendly apartment accommodates up to six guests and features a fully equipped kitchen, a private balcony overlooking salt marshes, and access to resort amenities including a shared hot tub, heated pool, walking paths, biking trails, and a tennis court.

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

~Vista Fresco~ Oceanside Condominiums With Resort-style Amenities - Key West, FL
9.6 151 reviews

~Vista Fresco~ Oceanside Condominiums With Resort-style Amenities

apartment, Key West
This two-bedroom apartment is located on 1800 Atlantic in Key West, just east of Smathers Beach, the island's largest beach. The property has excellent user, location, and cleanliness ratings.
The apartment is 122 square metres and can accommodate up to six guests. It offers a range of amenities including a swimming pool, a jacuzzi, a sauna, a spa, a fitness centre, and a garden.
Andy's Attic | Budget-friendly! - Key West, FL
8.0 42 reviews

Andy's Attic | Budget-friendly!

apartment, Key West
This Old Town Key West apartment is situated less than 0.8 km from Duval Street and within 0.8 km of Florida Keys Beaches, offering easy access to the Ernest Hemingway Home and Museum, Southernmost Point, and South Beach (all within 1.6 km).
The one-bedroom, one-bathroom flat sleeps two guests and includes a private patio, swimming pool access, tennis courts, and amenities such as a refrigerator, microwave, and Wi-Fi.
Oceanview Home With Private Pool & Lush Landscaping! - Key West, FL
9.8 144 reviews

Oceanview Home With Private Pool & Lush Landscaping!

apartment, Key West
This Northside Resort property is conveniently located within 5km of Duval Street, Mallory Square, and the Unitarian Universalist Fellowship of Key West.
This 368 square metre Key West house boasts four bedrooms, three bathrooms, sleeps eight, and includes a private pool, Jacuzzi, and fully equipped kitchen; barbecue grills and housekeeping are available.
Two Duval Street Condos W Parking And Pool - Key West, FL
9.9 1121 reviews

Two Duval Street Condos W Parking And Pool

house, Key West
This Key West condo is ideally situated on Duval Street, a short walk (less than 1.5km) from Mallory Square, South Beach, and the Ernest Hemingway Home and Museum.
The two-bedroom property offers free Wi-Fi, cable TV, a fully equipped kitchen with dishwasher, in-unit laundry, air conditioning, a private parking space, swimming pool and jacuzzi, making it perfect for small families or groups.

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

Seas The Breeze, Poolside Condo Near The Beach - Key West, FL
10 1 review

Seas The Breeze, Poolside Condo Near The Beach

apartment, Key West
This Key West residence is located 6.4 kilometres from the Southernmost Point and 6.9 kilometres from the Ernest Hemingway Home and Museum, offering a peaceful pool view near the beach and convenient access to attractions such as Duval Street (6.9 kilometres) and Mallory Dock (7.6 kilometres), with Key West International Airport a mere 0.9 kilometres away.
This two-bedroom, two-bathroom flat, spanning 74 square metres and accommodating up to 11 guests, features air conditioning, free Wi-Fi, a fully equipped kitchen, and a private balcony with a pool view, ensuring a comfortable stay for families and groups.
Apartment ∙ 2 Bedrooms ∙ 6 Guests - Key West, FL
10 2 reviews

Apartment ∙ 2 Bedrooms ∙ 6 Guests

apartment, Key West
This Key West apartment, situated near Key West International Airport, offers convenient access to the island's attractions.
Sleeping up to six guests, this two-bedroom, two-bathroom second-floor suite features a king and queen bedroom, a queen sofa bed, private balcony, in-unit laundry, and designated parking; amenities include a swimming pool, garden, and free Wi-Fi.
Sandpiper On The Ocean - Key West, FL
No reviews

Sandpiper On The Ocean

house, Key West
Holiday rental listing. Your accommodation will be located in Key West.
Facilities and services: a fitness center, a terrace and a washing machine. This house in Key West also has air conditioning!
Beachside Resort & Residences - Key West, FL
8.2 4555 reviews

Beachside Resort & Residences

resort, Key West
The Key West Marriott Beachside Hotel is located on the beach in Key West, just under 1.2 miles from Key West Airport and a short shuttle ride from the city centre. The hotel has consistently received very good ratings for its location, cleanliness, and overall guest experience.
The hotel offers a range of accommodation options, from comfortable rooms to suites with upgraded amenities. Guests can enjoy a private sandy beach, a swimming pool, a hot tub, a fitness centre, a spa, and a choice of dining options, including a steakhouse and a bar.

Best Key West, FL holiday rentals with parking

Reynolds Paradise | Walk To Higgs Beach - Key West, FL
10 1 review

Reynolds Paradise | Walk To Higgs Beach

apartment, Key West
This newly renovated flat is located in Key West's Casa Marina district, a 500-meter walk from Higgs Beach and within easy reach of the area's dining and shopping.
This two-bedroom flat accommodates up to eight guests and features a private garden with a jacuzzi, an outdoor dining area, and a chef's kitchen.
Seaport Suite - Key West, FL
9.2 247 reviews

Seaport Suite

apartment, Key West
Commodore Compound, a centrally located Key West apartment, is less than 0.8 km from Simonton Street Beach, Mallory Dock, and the Key West Aquarium, and under 5 km from Key West International Airport.
This eight-bedroom property, perfect for large groups, boasts a fully equipped kitchen, in-unit laundry, private entrance, Jacuzzi, terrace, garden, parking, and free Wi-Fi; nearby attractions include the Key West Butterfly and Nature Conservatory.
Sugar Palm Studio At Travelers Palm Inn Key West - Key West, FL
No reviews

Sugar Palm Studio At Travelers Palm Inn Key West

studio, Key West
Sugar Palm Studio, a centrally located Key West apartment, is less than 1.6km from the Key West Aquarium and Mallory Square, and an 8-minute walk from South Beach.
This self-contained unit sleeps two, features a kitchenette with fridge and microwave, a private terrace, and access to a swimming pool and tennis court; free Wi-Fi and parking are also provided.
Ann Street Cottage - Key West, FL
9.3 3 reviews

Ann Street Cottage

house, Key West
Ann Street Cottage, a holiday home in Key West, is located on Ann Street, just a 4-minute walk from the Key West Aquarium and 400 metres from Mallory Dock, placing it within 800 metres of the city centre and a 5-minute walk to Simonton Street Beach.
This detached property, covering 62 square metres, accommodates up to three guests with one bedroom and two bathrooms, offering air conditioning, a fully equipped kitchen including a fridge, microwave oven, and dishwasher, a swimming pool, garden, spa, tennis court, and parking, with free Wi-Fi and a television provided.
©2026 cozycozy.com