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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.

Geiger Suite @ Inn On Fleming~adults Only 2 Br 3rd Floor & Community Pool - Key West, FL
9.2 40 reviews

Geiger Suite @ Inn On Fleming~adults Only 2 Br 3rd Floor & Community Pool

B&B, Key West
This Old Town Key West rental is located two blocks from the Historic Seaport and a short walk from Duval Street, offering easy access to Key West's attractions.
This 340-square-foot apartment features two bedrooms, one bathroom, sleeps four guests, and includes amenities such as a swimming pool, Wi-Fi, and concierge services for booking local activities like snorkeling and kayaking.

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.

Lighthouse Suites Collection - Key West, FL
No reviews

Lighthouse Suites Collection

aparthotel, Key West
This 4-star aparthotel in Old Town Key West is located steps from the Key West Lighthouse, Duval Street, and the Ernest Hemingway Home, with Florida Keys Beaches and the Southernmost Point a 10-minute walk away.
This lodging offers two outdoor swimming pools, on-site laundry, and private kitchens equipped with a refrigerator, stovetop, and microwave, with in-unit washer/dryers and complimentary WiFi available in spacious apartments featuring a sofa bed and dining area.

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.

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

Apartment ∙ 2 Bedrooms ∙ 6 Guests

apartment, Key West
This Key West apartment rental near Key West International Airport offers easy access to the island's attractions while enjoying tranquil salt marsh views.
The two-bedroom, two-bathroom unit sleeps six guests comfortably, featuring a fully equipped kitchen, in-unit laundry, a private balcony, and free parking; nearby activities include biking, golf cart rentals, and ride-sharing services for exploring the island.
Apartment ∙ 2 Bedrooms ∙ 6 Guests - Key West, FL
No reviews

Apartment ∙ 2 Bedrooms ∙ 6 Guests

apartment, Key West
The KAMP penthouse is a luxurious two-bedroom, two-bathroom unit located on Duval Street in Key West's historic downtown, steps from shops and restaurants, and within walking distance of Mallory Square.
This Key West vacation rental boasts a private rooftop terrace with panoramic views, an open-concept living area, a combined dining and game room with ping pong, and sleeps up to six guests.
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, located in a historic downtown neighborhood near Key West's beaches and parks, offers easy access to local attractions.
The fully renovated two-bedroom, two-bathroom vacation rental sleeps up to six guests, features a private porch with a grill, a fully equipped kitchen with stainless steel appliances, three Smart TVs, high-speed internet, and access to a nearby pool.
Apartment ∙ 1 Bedroom ∙ 4 Guests - Key West, FL
No reviews

Apartment ∙ 1 Bedroom ∙ 4 Guests

apartment, Key West
This Old Town Key West studio apartment offers private access via a courtyard attached to a historic conch home, providing easy walking distance to many Old Town attractions.
The unit features a queen-size pull-out sofa sleeping up to four guests, a chef's kitchen with stainless steel appliances, free WiFi, a terrace, and nearby parking options at 204 Simonton Street.

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.

205e La Brisa-2br 2ba Beachfront Condo W/parking, Shared Pool, Grills - Key West, FL
9.0 43 reviews

205e La Brisa-2br 2ba Beachfront Condo W/parking, Shared Pool, Grills

apartment, Key West
This beachfront Key West condo offers direct access to Smathers Beach and is 1.7 miles from Duval Street.
The 1160-square-foot unit features two bedrooms, two bathrooms, sleeps four, and includes a fully equipped kitchen, in-unit laundry, private balcony, and access to a swimming pool, tennis court, and barbecue grills.

Best Key West, FL lodging with a balcony

One Bedroom Suite | Beachside Resort - Key West, FL
10 4 reviews

One Bedroom Suite | Beachside Resort

apartment, Key West
Atlantic Hideaway- Key West - Key West, FL
9.6 82 reviews

Atlantic Hideaway- Key West

apartment, Key West
Beach Club Seabreeze #103 - Key West, FL
10 1 review

Beach Club Seabreeze #103

apartment, Key West
The Curry Poolside | Ground Floor Two Queens - Key West, FL
9.4 6 reviews

The Curry Poolside | Ground Floor Two Queens

apartment, Key West

Best Key West, FL lodging with a kitchen

Harvey's Haven Studio At The Hollinsed House - Key West, FL
9.6 66 reviews

Harvey's Haven Studio At The Hollinsed House

apartment, Key West
Kate's Krawl Off Duval ~ 1 Br/1 Ba Private Home/outdoor Deck/steps To Duval! - Key West, FL
9.6 91 reviews

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

apartment, Key West
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
Cayo Hueso - Key West, FL
9.8 144 reviews

Cayo Hueso

house, Key West

Best Key West, FL lodging with laundry available

Sandbar Suite | 2 Bed Near Duval & Waterfront - Key West, FL
9.7 32 reviews

Sandbar Suite | 2 Bed Near Duval & Waterfront

apartment, Key West
Sunrise Suites Resort, Key West Fl U #408 2bdr2bth - Key West, FL
9.5 239 reviews

Sunrise Suites Resort, Key West Fl U #408 2bdr2bth

apartment, Key West
Conch Style Home In Oldtown With Private Pool And Dock! - Key West, FL
9.8 134 reviews

Conch Style Home In Oldtown With Private Pool And Dock!

apartment, Key West
Near Smathers Beach + Pool. Breakfast. Shuttle. - Key West, FL
9.1 16 reviews

Near Smathers Beach + Pool. Breakfast. Shuttle.

B&B, Key West
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