Vacation Rentals in Key West, FL

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Key West, FL vacation rentals
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4265 Vacation rentals and Airbnb in Key West, FL

Best family friendly Key West, FL vacation rentals

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

The Cayo Coco | Key West Condo With Pool, Hot Tub! - Key West, FL
No reviews

The Cayo Coco | Key West Condo With Pool, Hot Tub!

apartment, Key West
This two-bedroom condo in Key West's Sunrise Suites community offers proximity to Smathers Beach, Higgs Beach, and Duval Street, with Key West International Airport just a few kilometres away.
This family-friendly apartment sleeps up to six guests and features resort-style amenities including a heated swimming pool, hot tub, on-site tennis court, and a private balcony, with a fully equipped kitchen and on-site parking.
Parrot Key Hotel & Villas - Key West, FL
8.5 4770 reviews

Parrot Key Hotel & Villas

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.
Apartment ∙ 4 Bedrooms ∙ 16 Guests - Key West, FL
No reviews

Apartment ∙ 4 Bedrooms ∙ 16 Guests

apartment, Key West
This Duval Street duplex, situated in the heart of Key West's Old Town, offers easy walking access to numerous attractions.
Sleeping up to 18 guests in four bedrooms and two bathrooms across two adjacent historic lofts, this Key West property boasts fully equipped kitchens, a terrace overlooking Duval Street, a garden, and a washer/dryer in each unit; free Wi-Fi is also provided.
Luxury 3-bedroom Waterfront Home With Pool And Dock! - Key West, FL
9.8 150 reviews

Luxury 3-bedroom Waterfront Home With Pool And Dock!

apartment, Key West
This architect-designed waterfront holiday home is located in Key West's historic Meadows district, offering direct views of Garrison Bight and the marina, and is a short distance from attractions such as the Ernest Hemingway Home and Museum and Southernmost Point.
Spanning 265 square meters, this luxury dwelling accommodates up to eight guests with three en-suite bedrooms, a fully equipped kitchen featuring Viking appliances, air conditioning, a swimming pool, and a private balcony, all within close proximity to water sports and cycling routes.

Best Key West, FL vacation rentals with a pool

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

Poolside Hide-away @ Palm Gardens Offered By Rent Key West Vacations - Key West, FL
10 2 reviews

Poolside Hide-away @ Palm Gardens Offered By Rent Key West Vacations

apartment, Key West
This Key West apartment, a first-floor condo in the Historic District, is situated six blocks (approximately 0.96 km) from Duval Street and the Historic Seaport.
The 42-square-metre (452 sq ft) one-bedroom flat sleeps four, boasting a full kitchen with granite countertops, a private hot tub, in-unit laundry, and access to Palm Gardens' pool and BBQ area.
New Casa Caribe By Brightwild- Two-story Condo Rooftop Pool - Key West, FL
8.2 19 reviews

New Casa Caribe By Brightwild- Two-story Condo Rooftop Pool

house, Key West
This two-bedroom Key West condo, a short walk from South Beach and Duval Street, is centrally located less than 1.6km from the Southernmost Point buoy.
The 116 square metre property boasts a rooftop pool, fully equipped kitchen, three bathrooms, and accommodates up to six guests, offering free Wi-Fi and air conditioning.
Dog-friendly Condo With Pool, Hot Tub, Balcony, Central Ac, W/d, & Fitness Room - Key West, FL
8.8 125 reviews

Dog-friendly Condo With Pool, Hot Tub, Balcony, Central Ac, W/d, & Fitness Room

apartment, Key West
This two-bedroom flat in Key West's Sunrise Suites Resort is situated by the sea, offering views of the Salt Ponds Preserve from its balcony, and is less than 1 kilometre from the Southernmost Point and the Ernest Hemingway Home and Museum.
This 74 square metre apartment accommodates up to six guests, featuring air conditioning, a kitchen with a fridge, microwave, and dishwasher, and access to shared amenities including a swimming pool and hot tub, with a fitness room and tennis court also available at the resort.
Key West Sunrise Condo - Pool & Parking! - Key West, FL
10 7 reviews

Key West Sunrise Condo - Pool & Parking!

apartment, Key West
This two-bedroom Key West condo, part of the Sunrise Condo complex in the Seaside district, offers convenient access to attractions such as Smathers Beach and Fort Zachary Taylor Historic State Park, though precise distances aren't provided.
The 111-square-metre (1194 square feet) property sleeps six, boasting two bathrooms, a fully equipped kitchen including a dishwasher, a private terrace, a shared swimming pool and Jacuzzi, free Wi-Fi, parking, and pet-friendly accommodation (one dog up to 11 kg, fee applies); reduced rates are available until the end of September with a minimum two-night stay.

Frequently asked questions about holiday rentals in Key West, FL

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

    You really must visit the Southernmost Point of the Continental US, it's iconic. You can't miss the Hemingway House, it's full of history and six-toed cats. And for a taste of Key West's history, visit the Fort Zachary Taylor Historic State Park.
  • What are the best Airbnb and vacation rentals in Key West, FL?

    Leaward Isle Island Retreat, Mango Hideaway @ The Eyebrow House Off Duval and At Mine | Lovely Suite Steps From Duval Street are the most popular Airbnb and vacation rentals in Key West, FL among travelers.

  • 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 the heart of Key West, with lots of shops, restaurants, and bars. If you want a quieter stay, consider the historic Bahama Village, known for its vibrant culture and colourful houses.
  • 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 favourite for kids, and the Butterfly Conservatory is a beautiful place to learn about exotic insects. For some outdoor fun, the Key West Wildlife Center is a great place to see native animals.
  • What are the best vacation 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 popular year-round, but if you want to avoid the crowds and get the best deals, book your vacation rental in the shoulder seasons, like April-May or September-October.
  • What are the best rentals for families and kids in Key West, FL?

    The best rentals for families and kids in Key West, FL are Leaward Isle Island Retreat, Mango Hideaway @ The Eyebrow House Off Duval and Key West Villas.

  • 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 wild and colourful celebration, and the Key West Songwriters Festival in May is great for music lovers. The Hemingway Days Festival in July is a fun event celebrating the famous author.
  • 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, Mango Hideaway @ The Eyebrow House Off Duval and Key West Villas.

  • 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 Duval Street and enjoy the street performers, or visit the Key West Cemetery for a unique and interesting historical experience. You can also enjoy the free sunset celebrations at Mallory Square.
  • What are the best restaurants with local dishes in Key West, FL?

    For authentic Key West cuisine, try the Blue Heaven for their famous chicken and waffles, or the Hogfish Bar for their fresh seafood. The Cuban Coffee Queen is a great spot for a traditional Cuban breakfast.
  • What are the best walking or cycling routes in Key West, FL?

    The Key West Historic Seaport is a great place to start a walk or bike ride. The route along the waterfront offers stunning views, and you can also explore the charming streets of Old Town.
  • Are there pet-friendly attractions in Key West, FL?

    The Key West Butterfly & Nature Conservatory welcomes well-behaved dogs on a leash, and many of the beaches in Key West allow dogs, but make sure to check the specific rules.
  • What are the benefits of choosing a vacation rental in Key West, FL?

    Vacation rentals offer more space and privacy than hotels, and often come with amenities like kitchens and laundry facilities. They can also be more affordable, especially for larger groups or families.
  • What are the top sports attractions and facilities in Key West, FL?

    Key West is a popular destination for watersports, with great opportunities for sailing, fishing, diving, and kayaking. You can also find tennis courts and golf courses in the area.

Popular destinations

Best Key West, FL holiday rentals with a balcony

The Mesa House-close To Duval! - Key West, FL
No reviews

The Mesa House-close To Duval!

house, Key West
House rental. Your accommodation will be based in Key West.
Facilities and services include an iron, a washing machine and a kitchen.
Paradise Found Cayo Hueso - Key West, FL
9.3 229 reviews

Paradise Found Cayo Hueso

house, Key West
Paradise Found Cayo Hueso, near Smathers Beach in Key West, Florida, offers convenient access to attractions such as the Southernmost Point (2.6 km) and Ernest Hemingway's Home (3.2 km).
This 126-square-metre, two-bedroom, two-bathroom apartment boasts a balcony with sea views, a fully equipped kitchen, private parking, complimentary Wi-Fi, and access to a swimming pool, Jacuzzi, sauna, fitness centre, and tennis court.
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.
Kwss202 Sunrise Suites - Big Kahuna Suite 202 - Key West, FL
No reviews

Kwss202 Sunrise Suites - Big Kahuna Suite 202

house, Key West
This Key West apartment is situated approximately 1 kilometre from Key West International Airport and 6.4 kilometres from the Southernmost Point and Ernest Hemingway Home and Museum, with Duval Street a further 6.4 kilometres away.
This 72 square metre residence accommodates up to seven guests and features two bedrooms, two bathrooms (one with a hot tub), air conditioning, a well-equipped kitchen, a balcony, and access to a communal swimming pool, fitness centre, and tennis court.

Best Key West, FL holiday rentals with parking

Turtle Nest Condo - Pool - 2nd Floor - Key West, FL
10 2 reviews

Turtle Nest Condo - Pool - 2nd Floor

apartment, Key West
This Key West flat is located in Key West, a 17-minute walk from Higgs Beach and 3 kilometres from Key West International Airport.
This one-bedroom flat, covering 56 square metres and accommodating up to seven guests, offers a private pool, a year-round outdoor swimming pool, a balcony with garden views, and complimentary WiFi.
Casa Havana | Old Town Condo W/ Pool & Balcony - Key West, FL
9.5 11 reviews

Casa Havana | Old Town Condo W/ Pool & Balcony

house, Key West
This Old Town Key West condo is situated on the 1000 block of Duval Street, offering a 10-minute walk to downtown attractions and immediate access to dining within Duval Square, placing you within 1 kilometre of the Hemingway Home and beaches.
This 2-bedroom, 2-bathroom property accommodates up to 4 guests and features a fully equipped kitchen, in-unit washer and dryer, central air conditioning, free WiFi, a private deck, balcony, garage parking, and access to a rooftop swimming pool.
Sundial  Luxurious 2 Bedroom Ocean View Condominium- Quality At Its Best. - Key West, FL
9.6 35 reviews

Sundial Luxurious 2 Bedroom Ocean View Condominium- Quality At Its Best.

apartment, Key West
This Key West beachside apartment is located less than 3.2km from Duval Street and under 4.8km from Mallory Square, offering easy access to Key West's attractions.
The 125 square metre property boasts three bedrooms, two bathrooms, sleeps six, and includes a swimming pool, jacuzzi, and tennis court, alongside a fully equipped kitchen and free Wi-Fi.
Heated Rooftop Pool, Gated Parking - Casa Caribe - Key West, FL
9.4 51 reviews

Heated Rooftop Pool, Gated Parking - Casa Caribe

apartment, Key West
This two-storey townhouse, situated on the quieter end of Duval Street at its junction with Truman Avenue, Key West, offers easy access (within 1.6km) to the Southernmost Point and downtown attractions.
The property boasts two en-suite bedrooms, sleeping up to six guests, and features a private hot tub, a shared rooftop pool with Duval Street views, and a fully equipped kitchen including a fridge, freezer, microwave, and a washer/dryer; off-street parking is also provided.
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