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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.

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
This oceanfront condo at 1800 Atlantic in Key West offers direct beach access and proximity to Key West's attractions.
The 2-bedroom, 2-bathroom unit sleeps 6, features a 40-foot private balcony with Atlantic Ocean views, a full kitchen, in-unit laundry, and access to 1800 Atlantic's amenities including a heated pool, jacuzzi, and fitness center.

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.

Chagall's Corner | Newly Remodeled! - Key West, FL
9.0 45 reviews

Chagall's Corner | Newly Remodeled!

apartment, Key West
This Old Town Key West condo is a short walk from Duval Street and Florida Keys beaches, less than a 5-minute walk to Duval Street and within 10 minutes of the Southernmost Point and South Beach.
The one-bedroom, one-bathroom unit sleeps two guests and features a private patio, free WiFi, a swimming pool, tennis courts, and in-unit amenities including a refrigerator, microwave, and washer.

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.

The James Suite | Ground Floor King - Key West, FL
No reviews

The James Suite | Ground Floor King

apartment, Key West
This historic James House apartment on Caroline Street offers 1-bedroom, 1-bathroom accommodations for up to 4 guests, placing you steps from Duval Street's dining and nightlife and a short walk to Mallory Square and the Historic Seaport. Guests enjoy exclusive access to the Curry Mansion's swimming pool, complimentary internet, air conditioning, a kitchen with a fridge and microwave, and pet-friendly options for pets under 40lbs with an additional fee.
Sunnyside Up - Shared Pool - Key West, FL
9.6 14 reviews

Sunnyside Up - Shared Pool

apartment, Key West
This Key West apartment is located in the Historic District, just a short walk from Duval Street, the Key West Firehouse Museum, and the beaches. It has received excellent user ratings.
The 1160-square-foot apartment comfortably accommodates up to 9 guests in two bedrooms and two bathrooms. You can enjoy a private balcony, a fully equipped kitchen, a swimming pool, a garden, and parking on-site.
Kamp - Rooftop Penthouse Overlooking Duval - Key West, FL
No reviews

Kamp - Rooftop Penthouse Overlooking Duval

apartment, Key West
This historic penthouse, formerly Jimmy Buffett's Margaritaville HQ and David Wolkowsky's residence, is situated on the 400/500 block of Duval Street in Old Town Key West, placing it within a 1-mile radius of the Ernest Hemingway House, Mallory Square, and the Key West Lighthouse.
This family-friendly apartment offers 2 bedrooms, 2 bathrooms, and accommodates up to 6 guests, featuring a spacious open-concept living area, a fully equipped galley kitchen, and a private rooftop deck with panoramic island views, perfect for enjoying ping pong or listening to records.
Apartment ∙ 3 Bedrooms ∙ 8 Guests - Key West, FL
No reviews

Apartment ∙ 3 Bedrooms ∙ 8 Guests

apartment, Key West
This spacious Key West condo, part of a resort with a complimentary shuttle to Duval Street, offers convenient access to Key West attractions.
The three-bedroom, three-bathroom unit features a fully equipped kitchen with stainless steel appliances, a private balcony with resort pool views, and accommodates up to eight guests; on-site amenities include bike and watercraft rentals through Brightwild Adventures and garage parking with electric vehicle charging stations (fee applies).

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.

Resort-style Amenities And Expansive Pool - Stunning Oceanfront Retreat - Key West, FL
No reviews

Resort-style Amenities And Expansive Pool - Stunning Oceanfront Retreat

apartment, Key West
This oceanfront condo is situated on 400 feet of beach, directly next to Smathers Beach and 1.5 miles from Old Town Key West's shopping and dining.
This family-friendly apartment offers 2 bedrooms, 2 bathrooms, and can accommodate up to 4 guests, featuring amenities like a swimming pool, jacuzzi, fitness center, tennis courts, and a balcony with ocean views.

Best Key West, FL lodging with a balcony

**The Sophisticated Sandpiper** Home & Pool + Last Key White Glove Service... - Key West, FL
10 3 reviews

**The Sophisticated Sandpiper** Home & Pool + Last Key White Glove Service...

apartment, Key West
L'habitation Guesthouse- Adult Exclusive - Key West, FL
9.3 3523 reviews

L'habitation Guesthouse- Adult Exclusive

B&B, Key West
Waterfront 4-bed 3-bath Condo @ Bayfront Suites - - Key West, FL
9.6 891 reviews

Waterfront 4-bed 3-bath Condo @ Bayfront Suites -

apartment, Key West
Apartment ∙ 2 Bedrooms ∙ 8 Guests - Key West, FL
No reviews

Apartment ∙ 2 Bedrooms ∙ 8 Guests

apartment, Key West

Best Key West, FL lodging with a kitchen

Pelican Suite | Cozy Cottage, Hot Tubs, Close To D - Key West, FL
9.8 46 reviews

Pelican Suite | Cozy Cottage, Hot Tubs, Close To D

apartment, Key West
Poinciana Treetop ~ Casual Second Floor Duplex - Key West, FL
9.9 43 reviews

Poinciana Treetop ~ Casual Second Floor Duplex

apartment, Key West
Ocean Front Two Bedroom Residence - Key West, FL
10 1 review

Ocean Front Two Bedroom Residence

apartment, Key West
Pool, Laundry, And Grilling Area - Key West, FL
9.0 4 reviews

Pool, Laundry, And Grilling Area

apartment, Key West

Best Key West, FL lodging with laundry available

La Casa De Luces - Key West, FL
9.6 43 reviews

La Casa De Luces

apartment, Key West
**Summer Solstice @ Old Town** 9br Compound + Last Key White Glove Service... - Key West, FL
9.9 364 reviews

**Summer Solstice @ Old Town** 9br Compound + Last Key White Glove Service...

apartment, Key West
Sky Suites Retreat - Balcony Overlooking Duval - Key West, FL
No reviews

Sky Suites Retreat - Balcony Overlooking Duval

apartment, Key West
Sunrise Suite 203 - Key West, FL
9.2 84 reviews

Sunrise Suite 203

apartment, Key West
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