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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.

Sunny Oasis | Outdoor Pool. Island Experience - Key West, FL
9.2 25 reviews

Sunny Oasis | Outdoor Pool. Island Experience

B&B, Key West
This studio is located in Historic Old Town on Key West's Atlantic Coast, a 5-minute walk to the Southernmost Point Buoy and Mallory Square.
This accommodation offers a Petite Queen bed, a modern bathroom, a sitting area, and access to resort amenities including three heated pools, two private beaches, and a 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.

Bootlegger Bay ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches! - Key West, FL
10 3 reviews

Bootlegger Bay ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!

B&B, Key West
This adults-only guesthouse, the Bootlegger Bay B&B, is located directly on Duval Street in Old Town Key West, a few blocks from the beach and the Southernmost Point.
This 190-square-foot B&B offers 1 bedroom and 1 bathroom, accommodating up to 2 guests with amenities including a fridge, microwave, air conditioning, and Wi-Fi, plus access to a celebrated Rum Bar and unique Prohibition-era themed decor.

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.

Knowles Main House With Pool - Key West, FL
9.8 6 reviews

Knowles Main House With Pool

apartment, Key West
This 5-bedroom, 5-bathroom house is located in downtown Key West, steps from Duval Street and within walking distance of the Southernmost Point and Ernest Hemingway Home and Museum.
This family-friendly residence accommodates up to 10 guests and features a private main house with en-suite bathrooms, a shared pool, rooftop deck, BBQ area, and on-site parking for one vehicle.
Apartment ∙ 2 Bedrooms ∙ 6 Guests - Key West, FL
No reviews

Apartment ∙ 2 Bedrooms ∙ 6 Guests

apartment, Key West
The Mesa House, Dos, a two-bedroom Key West suite in Old Town, offers easy walking access to numerous attractions.
This vacation rental sleeps six, features a full kitchen, in-unit laundry, two cable TVs, free WiFi, central AC, a terrace, and parking is available nearby.
Suite Dreams Inn By The Beach - Key West, FL
8.8 133 reviews

Suite Dreams Inn By The Beach

B&B, Key West
The Suite Dreams Inn is located in the Casa Marina Area of Key West, just three blocks from the beach and a 20-minute walk from Duval Street. The inn has earned very good ratings for cleanliness and overall experience, as well as an excellent rating for its location.
The inn offers a variety of suites with modern amenities and a tropical garden with a lagoon-style pool. Guests can enjoy complimentary breakfast bars, chocolates, snacks, coffee, tea, and fruit, as well as on-site massage therapy, in-stay packages, and a restaurant with room service.
Tropical Heron Hideaway With Hot Tub, Pool - Key West, FL
9.6 13 reviews

Tropical Heron Hideaway With Hot Tub, Pool

apartment, Key West
This Key West apartment rental is a 17-minute walk from Higgs Beach and close to the Ernest Hemingway Home and Museum, Duval Street, and the Southernmost Point, offering easy access to Key West's major attractions.
This 600-square-foot unit features one bedroom, one bathroom, sleeps seven guests, and includes a private pool, hot tub, fully equipped kitchen, fitness center, spa access, and a terrace with garden views.

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.

The Elizabeth Suite | 1 Bedroom Condo, Shared Pool - Key West, FL
9.4 50 reviews

The Elizabeth Suite | 1 Bedroom Condo, Shared Pool

apartment, Key West
The Fleming Suite at The Bayview House in Key West, Florida offers convenient access to local attractions and landmarks, although specific distances aren't provided.
This one-bedroom, one-bathroom suite features a queen-size bed, fully equipped kitchenette, and accommodates up to four guests, boasting a swimming pool and parking on-site.

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
Caribbean House - Key West, FL
9.0 806 reviews

Caribbean House

B&B, Key West
The Artist House - Key West, FL
9.4 296 reviews

The Artist House

B&B, Key West
Two-bedroom, Two-bath Condo Close To The Ocean. Full Kitchen, Living R & Balcony - Key West, FL
9.2 47 reviews

Two-bedroom, Two-bath Condo Close To The Ocean. Full Kitchen, Living R & Balcony

apartment, Key West

Best Key West, FL lodging with a kitchen

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

One Bedroom Suite | Beachside Resort

apartment, Key West
Sunrise Suites Condo With Balcony - Shared Pool - Key West, FL
9.1 249 reviews

Sunrise Suites Condo With Balcony - Shared Pool

apartment, Key West
The Bolivar, A Key West Monthly Vacation Rental - Key West, FL
10 2 reviews

The Bolivar, A Key West Monthly Vacation Rental

apartment, Key West
Atlantic Breeze ~ 2b/2ba Renovated Retreat W/ Pool, Fitness Area & Beach! - Key West, FL
9.8 230 reviews

Atlantic Breeze ~ 2b/2ba Renovated Retreat W/ Pool, Fitness Area & Beach!

apartment, Key West

Best Key West, FL lodging with laundry available

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
Oceanfront Oasis Smathers Beach Condo Sunrise Views Island Charm Book Today - Key West, FL
9.8 18 reviews

Oceanfront Oasis Smathers Beach Condo Sunrise Views Island Charm Book Today

apartment, Key West
Oceanfront Condo In Key West - Key West, FL
9.9 40 reviews

Oceanfront Condo In Key West

apartment, Key West
Oceanfront 4-bed 3-bath Home With Pool - Key West, FL
9.6 96 reviews

Oceanfront 4-bed 3-bath Home With Pool

apartment, Key West
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