Vacation Rentals in Key West, FL

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Key West, FL holiday rentals
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3183 Holiday rentals and Airbnb in Key West, FL

Best family friendly Key West, FL holiday rentals

Among the 3183 accommodations in Key West, FL, here are the 4 best family friendly rentals

2 Bedroom 1 Bath Condo At Bayfront Suites & Marina - Cleaning Fee Included - Key West, FL
9.6 803 reviews
Key West, FL
20/06 – 27/06
A$1208/nighttotal: A$8456 (7 )

2 Bedroom 1 Bath Condo At Bayfront Suites & Marina - Cleaning Fee Included

3 1
apartment , Key West
This apartment is located in the Meadows district of Key West, just a short walk from Duval Street, the Hemingway Home, and the beaches. It has consistently received excellent ratings for its location, cleanliness, and overall user experience. The apartment itself offers a comfortable and well-equipped space for your stay. Guests can enjoy a range of amenities including a swimming pool, tennis court, fitness centre, and a restaurant, as well as a private balcony and a fully equipped kitchen.
Casa Marina Key West, Curio Collection By Hilton - Key West, FL
8.2 1056 reviews
Key West, FL
02/09 – 05/09
A$508/nighttotal: A$1524 (3 )

Casa Marina Key West, Curio Collection By Hilton

1 2
resort , Key West
Casa Marina Key West, Curio Collection By Hilton is a historic 1920s resort situated directly on a private beach, approximately 1.1 kilometres by car from Duval Street.
This hotel offers two oceanfront swimming pools, oceanside massages, and is conveniently located for activities such as deep-sea fishing, windsurfing, and exploring Fort Zachary Taylor Historic State Park, which is 1.8 kilometres away.
Apartment ∙ 2 Bedrooms ∙ 6 Guests - Key West, FL
Key West, FL
20/06 – 27/06
A$674/nighttotal: A$4718 (7 )

Apartment ∙ 2 Bedrooms ∙ 6 Guests

2 2
apartment , Key West
This Key West apartment is situated a short distance (under 1.6km) from Key West International Airport, providing easy access to the downtown area and the Historic Seaport within a 10-minute drive.
Sleeping up to eight guests, this two-bedroom, two-bathroom dwelling boasts a spacious open-plan layout, a private balcony overlooking Key West's natural landscape, in-unit laundry facilities, and access to shared amenities including a pool, hot tub, and tennis courts; pets under 30lbs are welcome for a nightly fee.
Breezy Retreat - 2bd/2bath - Windward Park - Pool - 5min Walk To Duval! - Key West, FL
10 24 reviews
Key West, FL
17/10 – 24/10
A$1927/nighttotal: A$13489 (7 )

Breezy Retreat - 2bd/2bath - Windward Park - Pool - 5min Walk To Duval!

2 2
apartment , Key West
This Key West Historic District property is a short walk from the Tennessee Williams Key West Exhibit and Duval Street, and within 1 km of the Ernest Hemingway Home and Museum and Florida Keys beaches.
This 145-square-metre house, sleeping four guests in two bedrooms and two bathrooms, boasts a private fenced yard, swimming pool, tennis court, and concierge service, offering a luxurious Key West getaway.

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

Royal Palm Studio At Travelers Palm Inn Key West - Key West, FL
Key West, FL
13/09 – 27/09
A$405/nighttotal: A$5670 (14 )

Royal Palm Studio At Travelers Palm Inn Key West

1 2
studio , Key West
ROYAL PALM STUDIO is centrally located in Key West, Florida, 0.6km from the city centre and an 8-minute walk from South Beach, placing it within easy reach of Mallory Dock and the Key West Aquarium (1.9km).
This self-catering apartment sleeps two guests in one bedroom, boasts a kitchenette with fridge and microwave, a private terrace, and access to an on-site swimming pool and tennis court; free Wi-Fi and parking are also provided.
The Mallory Suite At Inn On Fleming Key West! - Key West, FL
9.5 2 reviews
Key West, FL
21/12 – 18/01
A$775/nighttotal: A$21700 (28 )

The Mallory Suite At Inn On Fleming Key West!

1 1
house , Key West
The Mallory Suite is a centrally located Key West apartment, 1.6km from Mallory Square, 0.9km from the city centre, and a 16-minute walk from Simonton Street Beach.
This 20 square metre self-catering flat offers one bedroom, one bathroom, sleeps two guests, and includes a swimming pool, tennis court, parking, and Wi-Fi.
New Grenada Suite - Parking Pool & Pets 209 - Key West, FL
9.0 144 reviews
Key West, FL
14/10 – 16/10
A$591/nighttotal: A$1182 (2 )

New Grenada Suite - Parking Pool & Pets 209

2 2
house , Key West
The NEW Grenada Suite is located in Key West, just a short drive from Duval Street and Mallory Square, offering a peaceful retreat while still being close to the action. The property has consistently received excellent ratings for its location, cleanliness, and overall experience, making it a popular choice for travellers.
This two-bedroom property can accommodate up to six guests, making it ideal for families or groups of friends. The house offers a range of amenities including a private pool, a jacuzzi, a fully equipped kitchen, and a fitness centre, ensuring a comfortable and enjoyable stay.
Atlantic Breeze ~ 2b/2ba Renovated Retreat W/ Pool, Fitness Area & Beach! - Key West, FL
9.8 227 reviews
Key West, FL
13/09 – 27/09
A$467/nighttotal: A$6538 (14 )

Atlantic Breeze ~ 2b/2ba Renovated Retreat W/ Pool, Fitness Area & Beach!

2 2
apartment , Key West
This apartment is located in a quiet, gated waterfront community in Key West, just a short distance from the airport, beaches, restaurants, and Duval Street. It has received excellent user ratings, making it a popular choice for travellers.
The property is a two-bedroom, two-bathroom apartment that can accommodate up to six guests. You can enjoy a range of amenities, including a swimming pool, jacuzzi, terrace, garden, sauna, and concierge service, as well as a fully equipped kitchen.

Frequently asked questions about holiday rentals in Key West, FL

  • What should a first-time visitor not miss in Key West, FL?

    You definitely want to visit the Southernmost Point of the Continental US, the Hemingway House, and take a sunset cruise. And don't forget to try a Key Lime Pie, a local favourite!
  • 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 and proximity to Duval Street. If you prefer a quieter vibe, try the New Town area, which is known for its beautiful beaches and relaxed atmosphere.
  • 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 Butterfly and Nature Conservatory is always a hit with kids, and the Key West Aquarium is a great place to learn about local marine life. The Fort Zachary Taylor Historic State Park is a good option for a family picnic and exploring the fort.
  • 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, but prices tend to be highest during the peak season from December to April. If you're looking for a better deal, consider visiting during the shoulder seasons, from April 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 Fantasy Fest in October is a huge celebration with parades and costumes, while the Key West Songwriters Festival in May is a great event for music lovers. The Key West Food & Wine Festival in January is another popular choice.
  • What are the best rentals or Airbnbs with a jacuzzi in Key West, FL?

    The best holiday rentals or Airbnb with a jacuzzi in Key West, FL are Leaward Isle Island Retreat, Key West Villas and Southernmost Sanctuary.

  • 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?

    Strolling along Duval Street, visiting the Key West Cemetery, and enjoying the free sunset at Mallory Square are all great ways to experience Key West without breaking the bank. You can also take a walk or bike ride around the island, enjoying the views and the fresh air.
  • What are the best restaurants with local dishes in Key West, FL?

    For authentic Key West cuisine, try the Blue Heaven, a historic restaurant with a charming atmosphere, or the Lazy Lobster, known for its fresh seafood. The Hogfish Bar & Grill is another favourite for its casual atmosphere and delicious dishes.
  • What are the best walking or cycling routes in Key West, FL?

    The scenic route along the waterfront, from the Southernmost Point to Mallory Square, is a popular choice for walking and cycling. The Key West Historic District is also a great place to explore on foot, with its charming streets and historic buildings.
  • Are there pet-friendly attractions in Key West, FL?

    Many restaurants and bars in Key West are pet-friendly, and you can often find dog-friendly beaches. The Key West Butterfly and Nature Conservatory is also pet-friendly, allowing well-behaved dogs on a leash.
  • What are the benefits of choosing a vacation rental in Key West, FL?

    Vacation rentals often offer more space and privacy than hotels, and they can be a more affordable option, especially for families or groups. You can also find rentals in different locations, giving you the opportunity to experience different parts of the island.
  • What are the top sports attractions and facilities in Key West, FL?

    Key West is a great place for watersports, with opportunities for sailing, fishing, kayaking, and windsurfing. The Key West Yacht Club offers facilities for sailing and other water activities. There are also several golf courses on the island, including the Key West Golf Club.

Destinations nearby

Best Key West, FL holiday rentals with a balcony

In Good Spirits ~ Waterfront Condo, Wrap-around Balcony & Community Pool! - Key West, FL
9.4 192 reviews
Key West, FL
13/09 – 27/09
A$488/nighttotal: A$6832 (14 )

In Good Spirits ~ Waterfront Condo, Wrap-around Balcony & Community Pool!

2 2
apartment , Key West
This beachfront Key West apartment, situated in the Beachside neighbourhood, offers direct access to Smathers Beach and is a short distance from Duval Street and Key West International Airport.
This 170 square metre condo boasts two king-sized bedrooms, two bathrooms, and sleeps six, featuring a well-equipped kitchen, private terrace with ocean views, and access to a swimming pool, Jacuzzi, and concierge services.
Charming 2nd-story Apartment With Balcony & Lighthouse View - Walk Everywhere - Key West, FL
8.8 16 reviews
Key West, FL
14/10 – 16/10
A$564/nighttotal: A$1128 (2 )

Charming 2nd-story Apartment With Balcony & Lighthouse View - Walk Everywhere

1 2
apartment , Key West
This one-bedroom flat is located in Old Town Key West, a short walk from Duval Street and the Key West Lighthouse, with the Ernest Hemingway Home and Museum and Southernmost Point nearby.
This 46 square metre apartment offers accommodation for two guests and features a private balcony, a modern kitchen, air conditioning, free WiFi, and concierge services, with jet skiing and cycling opportunities in the vicinity.
Sunrise Suites Condo With Balcony - Shared Pool, Hot Tub, Tennis, Free Parking - Key West, FL
9.0 144 reviews
Key West, FL
14/10 – 16/10
A$620/nighttotal: A$1240 (2 )

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

2 2
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.
Honeymoon Banyan Suite Near Higgs Beach - Key West, FL
9.8 8 reviews
Key West, FL
23/06 – 24/06
A$761/nightfor 1 night

Honeymoon Banyan Suite Near Higgs Beach

1 2
apartment , Key West
This Midtown Key West apartment, a short walk from Higgs Beach and White Street Pier and a 1.6km drive from Key West's downtown area, offers convenient access to local attractions.
The 33 square metre flat features a king-size bed, flat-screen TV, kitchenette with microwave and fridge, and accommodates two guests, with access to a shared garden, bikes, and the option to rent the adjoining Palm Suite.

Best Key West, FL holiday rentals with parking

Parrot Key Hotel & Villas - Key West, FL
8.5 4732 reviews
Key West, FL
20/06 – 27/06
A$432/nighttotal: A$3024 (7 )

Parrot Key Hotel & Villas

1 2
resort , Key West
Parrot Key Hotel & Villas is located in Florida Bay, a short drive from the historic Old Town of Key West, offering a peaceful escape from the bustling city centre. This resort consistently receives very good ratings for its location, cleanliness, and overall experience.
The hotel features a range of accommodation options, including villas and rooms, all with private terraces offering stunning ocean views. Guests can enjoy a variety of amenities, activities and features, from multiple swimming pools and a fitness centre to kayaking excursions and on-site dining.
Waterfront Dock Pool Penthouse Near Duval St - Key West, FL
9.8 498 reviews
Key West, FL
02/07 – 03/07
A$2000/nightfor 1 night

Waterfront Dock Pool Penthouse Near Duval St

4 5
apartment , Key West
This Key West penthouse condo, located in the historic downtown area less than 1.6km from Duval Street and close to attractions such as the Historic Seaport and Hemingway House, offers breathtaking waterfront views.
The 172 square metre property boasts four bedrooms, four bathrooms, sleeping up to sixteen guests, and includes a private boat slip (up to 35ft), a heated pool, and a full kitchen; on-site amenities also include a tiki bar & grill and bike rentals.
Ocean Vista 403e La Brisa - Key West, FL
10 1 review
Key West, FL
13/09 – 27/09
A$529/nighttotal: A$7406 (14 )

Ocean Vista 403e La Brisa

2 2
apartment , Key West
Ocean Vista 403E La Brisa is a beachfront apartment in Key West, Florida, situated 0.7km from Smathers Beach and 3km from the Southernmost Point.
This 108 square metre, two-bedroom, two-bathroom flat sleeps seven guests and boasts a fully equipped kitchen, air conditioning, a terrace, swimming pool, spa, tennis court, parking, and free Wi-Fi.
House Of The Royal Palms In Old Town - Key West, FL
Key West, FL
20/06 – 27/06
A$3423/nighttotal: A$23961 (7 )

House Of The Royal Palms In Old Town

4 7
apartment , Key West
This Key West villa is situated just a few blocks from Duval Street, offering convenient walking access to numerous restaurants, entertainment venues, and attractions.
This property comprises a main house and a guest house, accommodating up to eight guests across four bedroom suites, and features a private swimming pool, a BBQ grill, and off-street parking for one vehicle.
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