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

Find the Best Seaside Short-Term Rentals in Key West, FL

Plan a relaxing maritime getaway at coastal short-term rentals in Key West, FL, situated short distances from local shoreside communities.

Gato Room @ Inn On Fleming~adults Only 2nd Floor Queen W/ Community Pool! - Key West, FL
9.8 26 reviews

Gato Room @ Inn On Fleming~adults Only 2nd Floor Queen W/ Community Pool!

B&B, Key West
This Key West Old Town apartment, two blocks from the Historic Seaport and a short walk from Duval Street, offers easy access to Key West's attractions.
The 160-square-foot studio features one bedroom, one bathroom, accommodates two guests, and includes a swimming pool, free Wi-Fi, and concierge services for arranging activities like snorkeling and sunset sails.

Check Out 5-Star Lodgings in Key West, FL

Experience the best of Key West, FL with an upscale rental that prioritizes both style and convenience.

Henry's Piece Of Paradise On The Ocean In Key West - Key West, FL
9.6 144 reviews

Henry's Piece Of Paradise On The Ocean In Key West

apartment, Key West
This beachfront condo is located within 3 miles of Duval Street, Mallory Square, and Florida Keys Beaches, and a 15-minute drive from Clarence S. Higgs Memorial Beach Park and the Key West AIDS Memorial.
This 1,350-square-foot Key West apartment features two bedrooms, two bathrooms, a fully equipped kitchen, a private balcony, and access to a swimming pool, jacuzzi, fitness center, tennis court, and more, comfortably accommodating up to four guests.

Frequently Asked Questions about short term rentals in Key West, FL

  • Which top landmarks you shouldn't miss in Key West, FL?

    You can't miss the Southernmost Point Buoy, the iconic marker at the bottom of the continental US. The Hemingway House is a must-see, especially if you're a fan of the author. And of course, you have to stroll down Duval Street with its shops and restaurants.
  • What are the best short term rentals in Key West, FL?

  • What types of short-term rentals are available in Key West?

    If you are looking for accommodations in Key West you can look for short-term rentals which would allow you to get the best experiences. These short-term rentals can offer you more comfort and privacy than hotels. Hence, many families visiting Key West prefer to choose them over hotels. Short-term rentals allow you to stay longer and get all the facilities and amenities you need with your family. Also, you can find many pet-friendly short-term rentals which would allow you to bring your pet along. These apartments and condos come with various modern kitchen and bathroom facilities and amenities offering you excellent holiday experiences.
  • 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. You'll see the most rain during the summer months, but even then, it's usually just a quick shower. Don't forget to pack sunscreen and a hat!
  • What are the best short term rentals with a pool in Key West, FL?

  • What are the best kid-friendly attractions in Key West?

    1. Shipwreck Treasure Museum - When you are with the kids you can visit the Shipwreck Treasure Museum where kids can hold and explore once-lost treasures and various shipwreck artefacts.
    2. Mallory Square - If you are with the kids you can head to Mallory Square where kids can enjoy food and drinks and even get the best entertainment on the streets and in live theatres.
    3. Fort Zachary Taylor State Park - Kids would love to explore the Fort Zachary Taylor State Park where they can swim and lounge and make the most of their time on the island.
  • What are the most popular festivals and events in Key West, FL?

    Key West is known for its lively events, like Fantasy Fest in October, a colorful celebration with parades and costumes. The Key West Songwriters Festival in May is a great time to catch live music. And don't forget the annual Hemingway Days in July, celebrating the famous author.
  • 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's the best neighbourhood to stay close to the city centre?

    If you are planning to stay in Key West you can look for White Street Gallery District which is close to the city centre and Old Town. This is one of the best locations on the island which allows you to move in any direction. Hence, you can look for rental apartments and even hotels which you can find here based on your requirements and budget. This also allows you to be close to many of the locations like Fort Zachary Taylor Historic State Park. This neighbourhood sits right between the Old Town and New Town making it convenient for you to explore either side of the island.
  • 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 island vibe, focused on beaches and water activities.
  • What are the best short term rentals for families and kids in Key West, FL?

  • What are the best shopping malls in Key West?

    1. Searstown Shopping Center - If you have shopping on your mind you can head to Searstown Shopping Center where you can find plenty of local shops and boutiques where you can shop conveniently.
    2. Overseas Market - When you intend to shop for local products and groceries and much more you can head to Overseas Market where you can find various local stores and departmental shops on the island. . Duval Square Mall - While it might not be a huge mall as you would expect Duval Square Mall can offer you a good shopping experience when you are shopping in Key West.
  • What notable natural landmarks are near Key West, FL?

    Just a short boat ride from Key West, you'll find the beautiful Dry Tortugas National Park, home to Fort Jefferson, a massive 19th-century fort. The park is also a great place to snorkel or dive among colorful coral reefs.
  • What is the best place to book a short-term rental for the Key Lime Festival in Key West?

    If you are visiting Key West for the Key Lime Festival on the island you should look for short-term rentals in White Street Gallery District. Being close to the Old Town, this is one of the best neighbourhoods that offer a strategic position to explore more on the island. You can find plenty of rental apartments and condos here that allow you to stay like a local. Also, you can be close to many local attractions which allows you to save time and ensure that you can cover more restaurants, bars, breweries, museums and entertainment venues.
  • What part of Key West, FL is ideal for finding lodging?

    Old Town is a great area for lodging, with lots of historic buildings and charming guesthouses. You'll be close to Duval Street and all the action. If you prefer a quieter stay, you can find more secluded options on the quieter side of the island, like the Sunset Key area.

Popular destinations

Search Family Short-Term Rentals in Key West, FL

Waterfront family vacations in Key West, FL work best with proximity to the beach and plenty of room for everyone to spread out.

Mar Y Sol Luxurious Oceanfront  Key West Breathta - Key West, FL
9.3 250 reviews

Mar Y Sol Luxurious Oceanfront Key West Breathta

apartment, Key West
This Key West condo is a beachfront gem, just 15 minutes from Florida Keys Beaches and a short walk from Duval Street and Southernmost Point. Guests rave about its excellent location, cleanliness, and user ratings.
The condo's spacious layout (2000 sq ft) features 3 bedrooms, accommodating up to 8 guests. It offers a fully equipped kitchen, a private balcony, and access to on-site amenities such as a swimming pool, Jacuzzi, sauna, and fitness center. There's also a tennis court, parking, and free WiFi.
Charming Deck And Inviting Living Space - Serene Coastal Retreat - Key West, FL
No reviews

Charming Deck And Inviting Living Space - Serene Coastal Retreat

cottage, Key West
Colony Poolside, a cottage within The Colony, is located in a secluded compound just steps from Duval Street, offering convenient access to award-winning restaurants, shopping, and beaches.
This family-friendly cottage accommodates up to 4 guests with 1 bedroom and 1 bathroom, featuring a private deck for grilling and al fresco dining, a fully equipped kitchen, air conditioning, and access to a shared swimming pool and a porch with Adirondack chairs.
Knowles Guest House W/pool - Key West, FL
8.4 5 reviews

Knowles Guest House W/pool

apartment, Key West
This 2-bedroom, 3-bathroom apartment in Key West's Historic District offers prime walkability, placing you within 0.2 miles of the Southernmost Point and 0.3 miles of the Ernest Hemingway Home and Museum.
This pet-friendly, family-friendly vacation rental accommodates up to 6 guests and features a shared outdoor area with a pool, BBQ, and patios, plus complimentary parking for one vehicle.
Gated Oceanfront Condo At Smather's Beach - Key West, FL
9.2 152 reviews

Gated Oceanfront Condo At Smather's Beach

apartment, Key West
LaBrisa Beachfront Condo offers a prime beachfront location on Smather's Beach, voted among Florida's top 10 beaches, with direct access to the white sands and crystal-clear waters. This beachfront condo has earned excellent user ratings, ensuring a high-quality stay.
The condo features a spacious layout with 1100 square feet of living space, two bedrooms, two bathrooms, and a guest capacity of six. It offers a fully equipped kitchen, entertainment options, and a private terrace or balcony. Guests can enjoy resort-style amenities such as a heated pool, whirlpool spa, sauna, tennis court, and lounges.

Neighborhoods and points of interest in Key West, FL

Top Dog-Friendly Lodgings in Key West, FL

Each dog-friendly coastal short-term rental in Key West, FL provides a comfortable space for you and your pet.

Caribbean Conch 5 Minutes To Smathers Beach & 10 M - Key West, FL
9.2 158 reviews

Caribbean Conch 5 Minutes To Smathers Beach & 10 M

apartment, Key West
This Key West apartment is located in the Beachside neighborhood, just a short walk from beautiful beaches and a popular beach park, and within a 2-mile radius of Duval Street and the Southernmost Point. This rental has received excellent ratings for location, cleanliness, and overall experience.
The apartment has two bedrooms and two bathrooms, making it perfect for families or groups of friends. Guests can enjoy a fully equipped kitchen, free Wi-Fi, a swimming pool, a Jacuzzi, a sauna, a fitness center, a tennis court, and a garden.

Best Key West, FL lodging with a balcony

Seas The Breeze  Poolside Condo Near The Beach - Key West, FL
No reviews

Seas The Breeze Poolside Condo Near The Beach

apartment, Key West
Kw23 Atlantic Ocean View - Key West, FL
8.9 157 reviews

Kw23 Atlantic Ocean View

apartment, Key West
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
Blue Heaven At The Truman Annex In Key West - Key West, FL
9.0 51 reviews

Blue Heaven At The Truman Annex In Key West

apartment, Key West

Best Key West, FL lodging with a kitchen

Suite Dreams Inn By The Beach - Key West, FL
8.9 141 reviews

Suite Dreams Inn By The Beach

B&B, Key West
Turtle Nest Condo + Pool  2nd Floor - Key West, FL
8.8 5 reviews

Turtle Nest Condo + Pool 2nd Floor

apartment, Key West
Rooftop Penthouse - Key West, FL
9.8 246 reviews

Rooftop Penthouse

apartment, Key West
The Grenada At Sunrise Suites - Shared Pool - Key West, FL
8.8 13 reviews

The Grenada At Sunrise Suites - Shared Pool

apartment, Key West

Best Key West, FL lodging with laundry available

Casa Atlantica One Bedroom - Key West, FL
No reviews

Casa Atlantica One Bedroom

apartment, Key West
The Saint Kitts Suite | Breathtaking View, Heated Pool - Key West, FL
9.8 7 reviews

The Saint Kitts Suite | Breathtaking View, Heated Pool

apartment, Key West
Dog-friendly Retreat With Pool, Hot Tub, Tennis - Balcony With Pool Views - Key West, FL
No reviews

Dog-friendly Retreat With Pool, Hot Tub, Tennis - Balcony With Pool Views

apartment, Key West
Heart Of Old Town Key West - Key West, FL
9.4 168 reviews

Heart Of Old Town Key West

apartment, Key West
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