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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.

Banyan Suite - Key West, FL
No reviews

Banyan Suite

apartment, Key West
The Banyan Suite, a Key West apartment rental, is located near Rest Beach, a short drive from Key West International Airport and popular attractions like Mallory Square, Duval Street, and the Ernest Hemingway Home and Museum.
This 360-square-foot one-bedroom, one-bathroom unit sleeps three and features a kitchenette with a microwave and fridge, free Wi-Fi, air conditioning, and stunning ocean views.

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.

Sunrise Suites Resort Key West, Fl U #111 2bdr2bth - Key West, FL
9.3 271 reviews

Sunrise Suites Resort Key West, Fl U #111 2bdr2bth

apartment, Key West
This 2-bedroom, 2-bathroom condo is located directly across the street from the ocean in Key West, just steps from the ocean and minutes from popular beaches and attractions. The property has excellent user, location, and cleanliness ratings.
The condo is spacious and well-equipped with a fully functional kitchen, washer & dryer, air conditioning, a private balcony, fast Wi-Fi, and free parking. Guests can enjoy outdoor relaxation and stunning views from the private balcony. The property is also close to Duval Street, the heart of Key West's entertainment and nightlife.

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.

Sky Loft - Steps From Duval Street & Shared Pool - Key West, FL
No reviews

Sky Loft - Steps From Duval Street & Shared Pool

apartment, Key West
This one-bedroom condo is situated in the Southard Street district of Key West, just one block from Duval Street and a short walk to the Historic Seaport.
This family-friendly unit accommodates up to four guests and features a fully equipped kitchen, air conditioning, free WiFi, and access to a shared swimming pool, with a contactless check-in process.
Thompson Island  Usa !!  Your Key West Retreat !! - Key West, FL
9.6 125 reviews

Thompson Island Usa !! Your Key West Retreat !!

apartment, Stock Island
This Stock Island vacation home is located just a short distance from Key West Tropical Forest and Botanical Garden and Smathers Beach, offering a peaceful escape from the bustling city while still being close to attractions. This property has received excellent reviews for its location, cleanliness, and overall experience.
This spacious 9-bedroom house spans 8,000 square feet and provides ample room for large families or groups. Enjoy the waterfront location, private fenced yard, outdoor pool and spa, fully equipped kitchen, barbecue grills, and a tennis court for a relaxing and enjoyable vacation.
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.
Waterfront Condo Free Slip & Pool 2b2b In Key West - Key West, FL
9.9 121 reviews

Waterfront Condo Free Slip & Pool 2b2b In Key West

apartment, Key West
This Key West condo, located on Garrison Bight Marina, offers direct access to the marina with stunning water views and is a short bike ride from Duval Street and a stroll from Bayview Park.
This two-bedroom, two-bathroom unit sleeps six, features a fully equipped kitchen with dishwasher, in-unit laundry, air conditioning, a private patio, and access to a shared pool; enjoy nearby tennis and basketball courts at Bayview Park.

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.

By The Beautiful Sea - Key West Beach Front Condo - W Pool Access - Key West, FL
9.2 78 reviews

By The Beautiful Sea - Key West Beach Front Condo - W Pool Access

apartment, Key West
This beachfront Key West condo, located in a gated community across from Smathers Beach, offers easy access to Old Town.
The 1390-square-foot unit features three bedrooms, two bathrooms, sleeps six, and includes a private balcony with direct ocean views, a heated pool, sauna, and designated parking.

Best Key West, FL lodging with a balcony

Contra House Key West - Key West, FL
8.0 1 review

Contra House Key West

house, Key West
Oceanfront 4-bed 3-bath Home With Pool - Key West, FL
9.4 99 reviews

Oceanfront 4-bed 3-bath Home With Pool

apartment, Key West
Charming Key West Town Home Beach/pool - Key West, FL
8.0 7 reviews

Charming Key West Town Home Beach/pool

apartment, Key West
Sunrise Suites Condo With Views, Pool, Hot Tub - Dogs Welcome - Key West, FL
No reviews

Sunrise Suites Condo With Views, Pool, Hot Tub - Dogs Welcome

apartment, Key West

Best Key West, FL lodging with a kitchen

Atlantic Hideaway- Key West - Key West, FL
9.6 86 reviews

Atlantic Hideaway- Key West

apartment, Key West
Dog-friendly Condo With Pool, Hot Tub, Balcony, Central Ac, W/d, & Fitness Room - Key West, FL
8.8 125 reviews

Dog-friendly Condo With Pool, Hot Tub, Balcony, Central Ac, W/d, & Fitness Room

apartment, Key West
The Margaret Suite - Key West, FL
9.2 10 reviews

The Margaret Suite

apartment, Key West
Kwss210 Sunrise Suites Bonaire Suite #210 - Key West, FL
8.7 128 reviews

Kwss210 Sunrise Suites Bonaire Suite #210

apartment, Key West

Best Key West, FL lodging with laundry available

The Rigby House - Pool, One Block From Duval St - Key West, FL
10 28 reviews

The Rigby House - Pool, One Block From Duval St

apartment, Key West
Rent At Porchside Paradise - Steps To Duval - Key West, FL
9.0 80 reviews

Rent At Porchside Paradise - Steps To Duval

apartment, Key West
Soul Of Duval At Duval Street - Key West, FL
9.9 36 reviews

Soul Of Duval At Duval Street

apartment, Key West
The Bartlum Luxury Studio In Prime Location - Key West, FL
No reviews

The Bartlum Luxury Studio In Prime Location

apartment, Key West
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