Key West, FL Short term rentals

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Key West, FL short term rentals
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Best Short term and Weekly rentals in Key West, FL

Best Key West, FL short term rentals with a kitchen

Andy's Attic | Budget-friendly! - Key West, FL
8.0 41 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.
Best Time At The Truman Annex In Key West - Key West, FL
9.6 38 reviews

Best Time At The Truman Annex In Key West

apartment, Key West
This Key West condo, a newly renovated second-floor apartment in a gated community, is situated a short distance (less than 0.2 km) from Duval Street, placing it within easy reach of Hemingway's Home and Museum and Fort Zachary Taylor Historic State Park.
The 63 square metre property boasts two bedrooms, one bathroom, and sleeps four, offering amenities including a swimming pool, garden, parking, and two private decks; pet-friendly for stays exceeding 28 days.
Seas The Breeze  Poolside Condo Near The Beach - Key West, FL
No reviews

Seas The Breeze Poolside Condo Near The Beach

apartment, Key West
This condo is located in the Sunrise Suites Resort Community, on the quieter side of Key West, 10 kilometres from Old Town's Duval Street and Mallory Square, and a short drive to Smathers Beach.
This 74 square metre apartment offers two bedrooms and three bathrooms, accommodating up to six guests, with a fully equipped kitchen, a private balcony overlooking the pool, and access to resort amenities including a heated swimming pool and hot tub.
Commodore Compound - Key West, FL
9.2 244 reviews

Commodore Compound

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.

Best Key West, FL short term rentals with laundry available

~Margarita Cottage~ Bask In Sunshine And Lounge By Your Pool In Paradise. - Key West, FL
9.6 15 reviews

~Margarita Cottage~ Bask In Sunshine And Lounge By Your Pool In Paradise.

cottage, Key West
Margarita Cottage, a Key West holiday home in Historic Old Town, is within walking distance of Duval Street, Mallory Square, and El Siboney Cuban Restaurant.
This pet-friendly (one dog up to 11 kg) self-catering property sleeps two, boasting a queen bed, updated kitchen (fridge, microwave), a smart TV, and a shared, seasonally heated pool (November-April, extra charge applies) with laundry facilities and outdoor grill.
La Casa Cubana The Cuban Club - Key West, FL
9.0 4 reviews

La Casa Cubana The Cuban Club

apartment, Key West
La Casa Cubana, a centrally located Key West apartment, is 0.4km from South Beach and close to Ernest Hemingway's Home, the Southernmost Point buoy, and Duval Street.
This 82-square-metre flat boasts one bedroom, one bathroom, sleeps eleven guests, and includes a fully equipped kitchen, a balcony, free Wi-Fi, and access to an on-site spa, swimming pool, and tennis court; bike rentals are available nearby.
Poolside Paradise Tropical Village - Key West, FL
No reviews

Poolside Paradise Tropical Village

apartment, Key West
Poolside Paradise Tropical Village offers a Key West apartment, conveniently located 2.2km from the Ernest Hemingway Home and Museum and under 1.5km from Duval Street, close to South Beach and other attractions.
This 31-square-metre flat features one bedroom, one bathroom, sleeps three, and includes a private balcony, swimming pool access, tennis court, parking, Wi-Fi, and a fully equipped kitchen with a microwave and fridge.
Contra House - Private Pool & Steps To Duval St. - Key West, FL
9.6 71 reviews

Contra House - Private Pool & Steps To Duval St.

apartment, Key West
This Key West property, a luxurious two-house complex, is ideally situated just 0.16 kilometres from Duval Street, providing easy access to the island's shops and restaurants.
The 4-bedroom, 4-bathroom dwelling boasts a private heated pool, two gourmet kitchens each with a wine cooler, and a contactless check-in process, comfortably accommodating up to 12 guests.

Frequently asked questions about short term rentals in Key West, FL

  • What kind of weather can travelers expect in Key West, FL?

    Key West has a tropical climate, so expect sunshine and warm temperatures year-round. The average temperature is around 25 degrees Celsius, and it rarely dips below 15 degrees Celsius even in the winter. You'll get plenty of sunshine, and the humidity is high.
  • What are the best short term rentals in Key West, FL?

  • What are the most popular festivals and events in Key West, FL?

    The Fantasy Fest in October is a huge party with parades and costumes, and it's a real highlight. The Key West Songwriters Festival in May is a great event for music lovers, and the Hemingway Days celebration in July is a fun way to celebrate the famous author's life.
  • What are the best short term rentals with a pool in Key West, FL?

  • Are there any famous stadiums or sports arenas in Key West, FL?

    Key West doesn't have any major stadiums or sports arenas. It's more of a laid-back, relaxed island, not a big sports hub. But you can find plenty of opportunities to enjoy water sports like fishing, kayaking, and sailing.
  • What are the best short term rentals with a jacuzzi in Key West, FL?

    The best short term rentals with a jacuzzi in Key West, FL are Secret Courtyard Cottage, Southernmost Sanctuary and Sunrise Suites Panama Suite #310.

  • What notable natural landmarks are near Key West, FL?

    The Dry Tortugas National Park is a beautiful group of islands about 110 kilometres west of Key West. You can go snorkeling or diving there, and it's home to a historic fort. The Florida Keys National Marine Sanctuary is another great place to explore the underwater world.
  • What are the best short term rentals for families and kids in Key West, FL?

  • What part of Key West, FL is ideal for finding lodging?

    Old Town is the heart of Key West and has plenty of hotels and guesthouses, but it can be a bit pricey. The area around Duval Street is bustling, and you'll find lots of restaurants, bars, and shops there. If you want something quieter, try the more residential areas like New Town or the Truman Annex.

Popular destinations

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Be Still- 4 Bedroom, 3 Bath With Pool & Guest Cottage - Key West, FL
10 8 reviews

Be Still- 4 Bedroom, 3 Bath With Pool & Guest Cottage

apartment, Key West
This Key West midtown holiday home is situated on a large corner plot, a short distance (approximately 0.8 km) from White Street Pier and Higgs Beach, offering easy access to both Old Town and New Town.
The four-bedroom, three-bathroom property sleeps eight guests and boasts a private pool with a waterfall feature (heatable November 16th-May 1st, at an extra cost), a separate guest cottage with kitchen and laundry facilities, and a lush garden with sunroom.
Apartment ∙ 6 Bedrooms ∙ 14 Guests - Key West, FL
No reviews

Apartment ∙ 6 Bedrooms ∙ 14 Guests

apartment, Key West
This luxurious six-bedroom Key West property, situated in the Modern Keys gated community, offers easy access to Key Haven and Stock Island boat ramps.
Sleeping up to 14 guests, the spacious house boasts a fully equipped kitchen, six bathrooms (five en-suite), a private terrace, garden, parking for four vehicles plus a boat trailer, and high-speed internet; private boat excursions and chauffeur services are available.
Scott's Cottage - Truman @ Duval | Perfect Spot In Old Town Key West! - Key West, FL
No reviews

Scott's Cottage - Truman @ Duval | Perfect Spot In Old Town Key West!

apartment, Key West
This first-floor studio apartment in Key West offers direct access to the city centre, placing you within 500 meters of the Key West Lighthouse and Hemingway Home and Museum, with further amenities, shops and nightlife a short walk away.
This pet-friendly studio accommodates two guests and features a fully equipped kitchen with stainless steel appliances, air conditioning, complimentary WiFi, and a private patio with outdoor dining, ideal for exploring Key West.
Apartment ∙ 5 Bedrooms ∙ 16 Guests - Key West, FL
No reviews

Apartment ∙ 5 Bedrooms ∙ 16 Guests

apartment, Key West
This spacious Key West property is centrally located in downtown, within easy walking distance of many attractions.
The three-unit compound, sleeping up to 16 guests in five bedrooms and four bathrooms, boasts fully equipped kitchens, private outdoor spaces including a hot tub and BBQ, and two on-site washer/dryers.

Popular Lodgings with a Terrace in Key West, FL, United States

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Kate's Krawl Off Duval ~ 1 Br/1 Ba Private Home/outdoor Deck/steps To Duval! - Key West, FL
9.6 93 reviews

Kate's Krawl Off Duval ~ 1 Br/1 Ba Private Home/outdoor Deck/steps To Duval!

apartment, Key West
This Key West Historic District apartment, a short walk from Duval Street and minutes from Key West's beaches, offers easy access to the Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park.
This 59-square-metre (635-square-foot) single-family home features one bedroom, one bathroom, sleeps four, and includes a fully equipped kitchen, private balcony, and on-site washer/dryer, plus concierge services for booking local activities.
Breezy Retreat - 2bd/2bath - Windward Park - Pool - 5min Walk To Duval! - Key West, FL
10 26 reviews

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

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.
Apartment ∙ 2 Bedrooms ∙ 6 Guests - Key West, FL
No reviews

Apartment ∙ 2 Bedrooms ∙ 6 Guests

apartment, Key West
The KAMP penthouse, a two-bedroom apartment situated on Duval Street in central Key West, offers unparalleled access to the island's attractions, being steps from restaurants and bars.
This luxurious Key West dwelling boasts a combined dining and games room with ping pong, a record player, and rooftop views; sleeping up to six guests, it features a fully equipped galley kitchen and modern contemporary design.
Orchid Bay Condo - Pool - Old Town - Walk To Duval - Key West, FL
9.7 178 reviews

Orchid Bay Condo - Pool - Old Town - Walk To Duval

apartment, Key West
This Key West apartment enjoys a central location, offering easy access to Simonton Street Beach, South Beach, and Fort Zachary Taylor State Park Beach.
The 46 square metre (495 square feet) self-catering flat features a bedroom, bathroom, fully equipped kitchen, private balcony, and free Wi-Fi; an outdoor swimming pool and on-site bike/car rentals are also available.

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Lighthouse Suites Collection - Key West, FL
No reviews

Lighthouse Suites Collection

aparthotel, Key West

Popular Short-Term Rentals in the CBD of Key West, FL, United States

Stay right where the island nightlife meets the beach at central island lodgings in Key West, FL, United States.

Casa Coastal East  Morning Sunrises, Evening Vibes, Island Home In Key West - Key West, FL
9.6 9 reviews

Casa Coastal East Morning Sunrises, Evening Vibes, Island Home In Key West

apartment, Key West
~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
Oceanview At 1800 Atlantic, Short Walk To Smathers - Key West, FL
9.8 16 reviews

Oceanview At 1800 Atlantic, Short Walk To Smathers

apartment, Key West
Mar Y Sol Luxurious Oceanfront  Key West Breathtaking Atlantic Sunrise Views - Key West, FL
9.3 250 reviews

Mar Y Sol Luxurious Oceanfront Key West Breathtaking Atlantic Sunrise Views

apartment, Key West

Popular Lodgings by the Sea in Key West, FL, United States

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Key West Condo Close To The Ocean. 1 Mile To Smathers & 3 Miles To Duval St. - Key West, FL
9.2 115 reviews

Key West Condo Close To The Ocean. 1 Mile To Smathers & 3 Miles To Duval St.

apartment, Key West
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