Vacation Rentals in Key West, FL

3183 available vacation rental offers

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Key West, FL vacation rentals
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3183 Vacation rentals and Airbnb in Key West, FL

Best family friendly Key West, FL vacation rentals

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

Casa Marina Key West, Curio Collection By Hilton - Key West, FL
8.2 1056 reviews
Key West, FL
02/09 – 05/09
₹34099/nighttotal: ₹102297 (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 ∙ 8 Guests - Key West, FL
Key West, FL
20/06 – 21/06
₹122377/nightfor 1 night

Apartment ∙ 2 Bedrooms ∙ 8 Guests

2 2
apartment , Key West
This two-bedroom Key West condo, sleeping up to ten guests, is ideally located on Duval Street, offering easy walking access to numerous attractions in the heart of the city.
The property features a king-size bed, two further king-size beds in a loft, two sofa beds, a fully equipped kitchen including a fridge, microwave, and stove, a private balcony overlooking Duval Street, and a private washer/dryer; parking is available nearby.
Apartment ∙ 2 Bedrooms ∙ 6 Guests - Key West, FL
Key West, FL
20/06 – 21/06
₹107677/nightfor 1 night

Apartment ∙ 2 Bedrooms ∙ 6 Guests

2 2
apartment , Key West
The Mesa House, Dos, a two-bedroom Key West apartment, is located in Old Town, close to Simonton Street and within easy walking distance of many attractions.
This self-catering suite sleeps six, offering a king bed, two twin beds, a queen-size sofa bed, full kitchen with oven and stove, washer/dryer, two cable TVs, free Wi-Fi, air conditioning, and a terrace/balcony plus garden and parking.
Apartment ∙ 1 Bedroom ∙ 3 Guests - Key West, FL
10 1 review
Key West, FL
25/07 – 27/07
₹45390/nighttotal: ₹90780 (2 )

Apartment ∙ 1 Bedroom ∙ 3 Guests

1 3
apartment , Key West
This Key West studio apartment offers a central downtown location, within easy walking distance of many attractions.
The self-catering unit, sleeping up to four guests in a queen bed and sofa bed, boasts a full kitchen (stove/oven, fridge, microwave), private entrance, access to a shared pool and laundry facilities, and is pet-friendly (fees may apply).

Best Key West, FL vacation rentals with a pool

Among the 3183 accommodations in Key West, FL, here are the 4 best rentals with a pool

Gorgeous Romantic Private Villa, Steps From Duval! - Key West, FL
10 98 reviews
Key West, FL
02/07 – 07/07
₹54373/nighttotal: ₹271865 (5 )

Gorgeous Romantic Private Villa, Steps From Duval!

1 2
apartment , Key West
This Old Town Key West villa is situated just 18 metres from Duval Street, offering easy walking access to the Key West Lighthouse, Ernest Hemingway Home and Museum, and the Southernmost Point buoy.
The luxurious, recently remodelled two-storey property boasts a king-size bed, queen-size sleeper sofa, two 65-inch smart TVs, a fully equipped kitchen with stainless steel appliances, a private garden courtyard with shared plunge pool, and accommodates up to four guests.
Penthouse Waterfront Dock Pool Condo Near Duval St - Key West, FL
9.8 287 reviews
Key West, FL
23/06 – 24/06
₹126018/nightfor 1 night

Penthouse Waterfront Dock Pool Condo Near Duval St

4 2
apartment , Key West
This Key West penthouse condo, situated in the historic downtown area less than 1.6km from Duval Street, the Historic Seaport, and the Hemingway House, offers breathtaking waterfront views.
This 171 square metre luxury apartment sleeps up to 16 guests in four bedrooms plus a loft, boasting four en-suite bathrooms, a fully equipped kitchen, two living areas, a private boat slip (up to 40ft), and access to a heated pool, tiki bar, and bike rentals.
Lost Shaker Of Salt ~ 3 Bed, 2 Bath Pet Friendly With 40' Private Heated Pool - Key West, FL
9.8 230 reviews
Key West, FL
24/07 – 28/07
₹128341/nighttotal: ₹513364 (4 )

Lost Shaker Of Salt ~ 3 Bed, 2 Bath Pet Friendly With 40' Private Heated Pool

3 7
apartment , Key West
This Old Town Key West property on Southard Street offers a prime location, just a short walk from Duval Street's restaurants and bars, and 1.8km from Fort Zachary Taylor Beach.
This four-bedroom, two-bathroom apartment boasts 111 square metres of space, a private heated pool, fully fenced yard, and sleeps eight guests, benefiting from concierge services and a fully equipped kitchen.
Atlantic Parrot | Oceanfront Condo W/ Pool - Key West, FL
10 8 reviews
Key West, FL
02/07 – 03/07
₹81330/nightfor 1 night

Atlantic Parrot | Oceanfront Condo W/ Pool

2 5
apartment , Key West
This fourth-floor oceanfront condominium in Key West offers direct Atlantic views from its private balcony and is situated 200 metres from Smathers Beach and a short walk to Higgs Beach and its pier, with convenient access to the Florida Keys Overseas Heritage Trail for cycling and walking.
This two-bedroom, two-bathroom apartment accommodates up to five guests and features resort-style amenities including a swimming pool, hot tub, and fitness centre, along with on-site tennis courts and secure, contactless entry.

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.

Destinations nearby

Best Key West, FL holiday rentals with a balcony

53' Vintage 3-bedroom Houseboat With Ac & Pontoon` - Key West, FL
Key West, FL
21/12 – 18/01
₹36082/nighttotal: ₹1010296 (28 )

53' Vintage 3-bedroom Houseboat With Ac & Pontoon`

3 1
houseboat , Key West
This unique offshore anchored houseboat offers a secluded Key West experience, with its precise location approximately 1.6 kilometres offshore, providing unparalleled open water views and independent exploration via a self-drive dinghy to reach downtown Key West's attractions such as the Ernest Hemingway Home and Museum.
This three-bedroom, two-bathroom floating accommodation comfortably sleeps eight guests and boasts a fully equipped kitchen, extensive on-deck amenities for entertaining and fishing, and includes complimentary snorkelling gear and lobstering kits for an authentic boating lifestyle with vintage yacht ambiance.
Frost Free In Cayo Hueso - Key West, FL
9.3 232 reviews
Key West, FL
05/10 – 19/10
₹41583/nighttotal: ₹582162 (14 )

Frost Free In Cayo Hueso

2 1
house , Key West
This apartment is located just a short walk from Smathers Beach, Key West's most popular beach, and a few blocks from Rest Beach, making it ideal for enjoying the beautiful beaches and vibrant atmosphere of Key West. The apartment has received excellent ratings for its location, cleanliness, and overall experience.
This two-bedroom, two-bathroom apartment can comfortably accommodate up to six guests. It features a fully equipped kitchen, a private balcony with sea views, a swimming pool, a Jacuzzi, a fitness centre, and a tennis court.
Sunny Condo With Wifi, Hot Tub, Pool & Tennis - Key West, FL
9.4 122 reviews
Key West, FL
26/10 – 28/10
₹55295/nighttotal: ₹110590 (2 )

Sunny Condo With Wifi, Hot Tub, Pool & Tennis

2 4
apartment , Key West
This Key West condo is located on the eastern side of the island, approximately 6.4 kilometres from downtown attractions such as the Hemingway House and Southernmost Point, and is also conveniently situated near Key West International Airport and Smathers Beach.
This 72 square metre apartment offers two bedrooms, two bathrooms, and accommodation for up to four guests, featuring a private balcony, air conditioning, a kitchen equipped with a fridge, microwave, and dishwasher, and access to a shared swimming pool, hot tub, and fitness room.
Henry's Piece Of Paradise On The Ocean In Key West - Weekly / Nightly - Key West, FL
9.6 141 reviews
Key West, FL
20/06 – 27/06
₹49812/nighttotal: ₹348684 (7 )

Henry's Piece Of Paradise On The Ocean In Key West - Weekly / Nightly

2 2
apartment , Key West
This beachfront Key West condo is situated less than 5km from Duval Street and Mallory Square, offering easy access to Key West's nightlife, sunset celebrations, and Florida Keys Beaches, and a 15-minute drive from Clarence S. Higgs Memorial Beach Park and the Key West AIDS Memorial.
The 125 square metre property boasts two bedrooms, two bathrooms, a fully equipped kitchen, private balcony, in-unit laundry, and access to a swimming pool, jacuzzi, sauna, fitness centre, and tennis court; perfect for couples or small families seeking a luxurious Key West getaway.

Best Key West, FL holiday rentals with parking

Bright Condo With Homey Feel, Entertainment & Private Parking - Beach Nearby - Key West, FL
9.2 173 reviews
Key West, FL
14/10 – 16/10
₹34634/nighttotal: ₹69268 (2 )

Bright Condo With Homey Feel, Entertainment & Private Parking - Beach Nearby

1 2
apartment , Key West
This Key West condo offers a prime downtown Simonton Street position, just 100 metres from Duval Street and a short walk to the Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park.
This 47 square metre flat, accommodating up to four guests, features air conditioning, a kitchen with a fridge and microwave, and a private off-street parking space, with a covered porch providing a relaxing outdoor area.
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
₹31344/nighttotal: ₹438816 (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.
Poolside Breeze Retreat - Key West, FL
9.6 198 reviews
Key West, FL
02/09 – 05/09
₹43852/nighttotal: ₹131556 (3 )

Poolside Breeze Retreat

2 2
house , Key West
This apartment is located in Key West, just a short walk from Smathers Beach and Rest Beach, with Higgs Beach also within easy reach. The property has excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
This two-bedroom, two-bathroom flat spans 126 square metres and comfortably accommodates six guests. The apartment offers a range of amenities, including a fully equipped kitchen, a private balcony with sea views, a swimming pool, a Jacuzzi, a fitness centre, a tennis court, and free parking.
One Bedroom Suite | Beachside Resort - Key West, FL
9.6 90 reviews
Key West, FL
20/06 – 21/06
₹45056/nightfor 1 night

One Bedroom Suite | Beachside Resort

1 2
apartment , Key West
This Key West Beachside Resort condo, situated directly on the Gulf of Mexico, offers stunning Gulf views from its private balcony.
The one-bedroom apartment, sleeping up to four guests with a king bed and queen sleeper sofa, boasts a fully equipped kitchen, private washer/dryer, and access to a heated pool, hot tub, fitness centre, and on-site marina; bookable sandbar or sunset cruises enhance your stay.
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