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

The Best Family-Focused Holiday Rentals in Key West, FL, United States

Browse family holiday rentals in Key West, FL, United States with space for everyone to relax.

Sky Loft In Key West - Key West, FL
9.5 234 reviews

Sky Loft In Key West

house, Key West
Sky Loft in Key West by Brightwild is centrally located in Key West, a short walk from Simonton Street Beach and South Beach, offering easy access to the island's attractions and nightlife. This property has consistently received excellent ratings for location, cleanliness, and overall user experience.
The one-bedroom apartment is perfect for a family of four, with a spacious 63 square metres of living space. Enjoy a comfortable stay with amenities such as a fully equipped kitchen, air conditioning, a swimming pool, a terrace, a garden, and free Wi-Fi.
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.
Apartment ∙ 2 Bedrooms ∙ 8 Guests - Key West, FL
10 1 review

Apartment ∙ 2 Bedrooms ∙ 8 Guests

apartment, Key West
This Key West apartment, situated in the downtown area with a balcony overlooking Duval Street, offers easy walking access to numerous attractions.
The two-bedroom, one-bathroom dwelling sleeps eight guests, featuring a fully equipped kitchen with a stove, refrigerator, dishwasher, and Keurig coffee machine, plus a washer/dryer, and free Wi-Fi.
3-story Spacious Conch Style Home W/ Private Pool & Dock! - Key West, FL
9.8 153 reviews

3-story Spacious Conch Style Home W/ Private Pool & Dock!

apartment, Key West
This Key West house is situated in the Meadows district, just under 2 kilometres from Duval Street, Ernest Hemingway Home and Museum, and Mallory Square. The house has received excellent ratings for cleanliness, location, and user experience.
The house has four bedrooms, making it suitable for families or groups of friends. It comes with a private pool, spa tub, barbecue grill, and a fully equipped kitchen with a fridge, microwave, and dishwasher.

Holiday Rentals with a Pool in Key West, FL, United States

Walk right out of your kitchen and jump into a crystal-clear swimming pool at island holiday rentals in Key West, FL, United States.

Oceanfront Oasis Smathers Beach Condo Sunrise Views Island Charm Book Today - Key West, FL
9.8 18 reviews

Oceanfront Oasis Smathers Beach Condo Sunrise Views Island Charm Book Today

apartment, Key West
This oceanfront Key West apartment, situated in the La Brisa complex on Smather's Beach, offers direct access to the beach and is within easy reach of attractions such as the Southernmost Point and the Ernest Hemingway Home and Museum.
The 111 square metre (1194 square feet) property boasts three bedrooms, two bathrooms, sleeping six guests comfortably, and features a fully equipped kitchen, a private terrace, a shared heated swimming pool, hot tub, sauna and a stackable washer/dryer.
Henry's Penthouse On The Ocean In Key West  - Weekly / Nightly Rentals - Key West, FL
9.6 100 reviews

Henry's Penthouse On The Ocean In Key West - Weekly / Nightly Rentals

apartment, Key West
This beachfront Key West condo is located less than 5 kilometres from Duval Street, Mallory Square, and Florida Keys Beaches, and within a 15-minute drive of Clarence S. Higgs Memorial Beach Park and the Key West AIDS Memorial.
This 125 square metre apartment offers two bedrooms, two bathrooms, sleeps five guests, and boasts a private balcony, swimming pool, Jacuzzi, and free Wi-Fi, plus access to a fitness centre, tennis court, and sauna.
Bahama Village Studio @ The Galleria! - Key West, FL
9.2 18 reviews

Bahama Village Studio @ The Galleria!

studio, Key West
This Key West studio apartment is situated in the historic Bahama Village, a short walk (approximately 0.8 km) from Duval Street, the Key West Lighthouse, and the Ernest Hemingway Home and Museum.
The 13-square-metre self-catering unit features a queen-size bed, kitchenette with fridge and microwave, a bathroom, and access to a shared swimming pool and spa within the Galleria complex; it sleeps two guests and offers free Wi-Fi.
Beachside Resort & Residences - Key West, FL
8.3 4236 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.

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.

Popular destinations

Holiday Rentals with a Balcony in Key West, FL, United States

Wake up to the soothing sight of the blue ocean right from your private rental balcony in Key West, FL, United States.

The James Classic | Ground Floor King - Key West, FL
9.4 13 reviews

The James Classic | Ground Floor King

apartment, Key West
This Key West apartment is situated in the Historic District, a short distance from Duval Street and adjacent to the Curry Mansion, offering easy access to Mallory Square, the Mel Fisher Maritime Museum, and the Ernest Hemingway Home and Museum.
This self-catering unit, sleeping two guests in one bedroom and one bathroom, includes a private balcony, complimentary parking (subject to availability), a shared laundry, and direct access to the Curry Mansion's pool and amenities.
**Saltwater Harmony @ The Annex** Charming Condo & Pool + Last Key Services... - Key West, FL
10 63 reviews

**Saltwater Harmony @ The Annex** Charming Condo & Pool + Last Key Services...

apartment, Key West
This apartment is situated in Old Town Key West, just a kilometre from Duval Street and the Ernest Hemingway Home and Museum, and 1.5 kilometres from Fort Zachary Taylor Historic State Park and Mallory Square. It has received excellent reviews from previous guests.
The apartment has two bedrooms and one bathroom and covers 63 square metres, comfortably accommodating up to four guests. It offers a range of amenities, including a swimming pool, a spa, a garden, and a terrace, as well as a fully equipped kitchen and free Wi-Fi.
Key West Paradise Found - Amazing Ocean Views From Every Window - Key West, FL
9.8 339 reviews

Key West Paradise Found - Amazing Ocean Views From Every Window

apartment, Key West
This oceanfront condominium in Key West's Beachside district offers direct Atlantic views from a private balcony and is situated just 20 metres from Smathers Beach, placing it within two kilometres of Duval Street's attractions.
This three-bedroom, two-bathroom flat, covering 126 square metres and accommodating up to six guests, boasts a private terrace, a communal swimming pool, a jacuzzi, a garden, a sauna, and tennis courts, with parking also available.
Osprey Colony - Key West, FL
No reviews

Osprey Colony

house, Key West
This Key West property, situated in Osprey Colony, offers convenient access to Duval Street, South Beach, and the city centre, lying within a short walk of these key areas and less than 3km from Key West International Airport.
The 45 square metre house features one bedroom, one bathroom, sleeps seven guests and includes a private balcony, swimming pool, tennis court, free Wi-Fi, and a fully equipped kitchen; cycling opportunities abound in the surrounding area.

Best Key West, FL holiday rentals with parking

Anchor Drop Modern Elegance Upgrades Throughout Views Of Atlantic Ocean - Key West, FL
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.
Sea Glass Cottage In Historic Key West - Key West, FL
10 4 reviews

Sea Glass Cottage In Historic Key West

apartment, Key West
This Key West Conch home, situated in a historic downtown neighbourhood, offers convenient access to beaches and parks, though precise distances are not specified.
The two-bedroom, two-bathroom cottage sleeps six, features a fully equipped kitchen, three Smart TVs, air conditioning, a private porch with grill, and access to a shared pool at a sister property; a sister cottage is available for larger groups.
Sunrise Suites Condo With Balcony - Shared Pool, Hot Tub, Tennis, Free Parking - Key West, FL
9.1 248 reviews

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

apartment, Key West
This two-bedroom apartment is located on the eastern side of Key West, less than five miles from the island's most popular attractions, offering a peaceful escape while still being close to the action. The property has consistently received excellent ratings for its location, cleanliness, and overall user experience.
The apartment spans 72 square metres and comfortably accommodates up to six guests. It features a fully equipped kitchen, a private balcony, and access to a range of resort amenities, including a swimming pool, hot tub, tennis courts, and a fitness centre.
Sandpiper On The Ocean - Key West, FL
8.8 189 reviews

Sandpiper On The Ocean

house, Key West
Sandpiper on the Ocean, a Key West apartment, offers superb beachfront proximity, being a 4-minute walk from Smathers Beach and within 2.6km of the Southernmost Point and Ernest Hemingway Home.
This two-bedroom, two-bathroom flat sleeps families or groups, boasting a fully equipped kitchen, private balcony with ocean views, on-site parking, a swimming pool, Jacuzzi, and complimentary Wi-Fi; tour organisation services are also available.

Discover Luxury Holiday Rentals in Key West, FL, United States

Bask in absolute tropical privacy with upscale coastal design at luxury holiday rentals in Key West, FL, United States.

Turtle Nest Condo + Pool - Key West, FL
No reviews

Turtle Nest Condo + Pool

apartment, Key West

Downtown Holiday Rentals in Key West, FL, United States

Find holiday rentals in the heart of Key West, FL, United States close to shops and beaches.

Excitement On The Ocean Key West Oceanfront Condo Stunning Atlantic Views - Key West, FL
9.8 259 reviews

Excitement On The Ocean Key West Oceanfront Condo Stunning Atlantic Views

apartment, Key West
The Margaret Suite - Key West, FL
10 1 review

The Margaret Suite

apartment, Key West
Honeymoon Banyan Suite Near Higgs Beach - Key West, FL
9.8 8 reviews

Honeymoon Banyan Suite Near Higgs Beach

apartment, Key West
Papaya Place By Avantstay - Key West, FL
9.0 109 reviews

Papaya Place By Avantstay

house, Key West

Seashore Holiday Rentals in Key West, FL, United States

Open your glass doors and step directly from your living room onto the warm sand at seashore holiday rentals in Key West, FL, United States.

Beachy Keen Too - Key West, FL
No reviews

Beachy Keen Too

house, Key West
One Bedroom Suite | Beachside Resort - Key West, FL
9.6 103 reviews

One Bedroom Suite | Beachside Resort

apartment, Key West
Pool View Suite | Beachside Resort - Key West, FL
9.5 288 reviews

Pool View Suite | Beachside Resort

apartment, Key West
Suncoast House -Pool & Boat Dock - Key West, FL
9.7 55 reviews

Suncoast House -Pool & Boat Dock

house, Key West

Holiday Rentals with a Hot Tub in Key West, FL, United States

Soak under a canopy of stars just steps from the ocean waves at holiday rentals with a hot tub in Key West, FL, United States.

Cozy Dog-friendly Condo W/ Shared Pool, Hot Tub, Private Deck & Parking - Key West, FL
8.8 124 reviews

Cozy Dog-friendly Condo W/ Shared Pool, Hot Tub, Private Deck & Parking

apartment, Key West
Ocean Front Suite With Direct Beach Access - Key West, FL
9.6 163 reviews

Ocean Front Suite With Direct Beach Access

apartment, Key West
Botanical Island Delight  Key West Fantastic Discounts For Summer & Fall - Key West, FL
9.0 150 reviews

Botanical Island Delight Key West Fantastic Discounts For Summer & Fall

apartment, Key West
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
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