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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.

Pete's West Cottage Steps From Duval - Key West, FL
9.6 408 reviews

Pete's West Cottage Steps From Duval

apartment, Key West
This charming Key West cottage is located in Old Town, just a short walk from the Banana Cafe Restaurant and Coffee and Tea house, offering easy access to delicious food and drinks. The cottage boasts excellent ratings for location, cleanliness, and user experience, ensuring a comfortable and enjoyable stay.
The cottage features a spacious living area with a spiral staircase leading to a loft bedroom, as well as a semi-private deck and lounge area for relaxation. Guests can enjoy the large kidney-shaped pool with a waterfall, a fully equipped kitchen, and the convenience of keyless entry.

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.

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
This Key West condo at Sunrise Suites Resort is located by the sea, adjacent to the Salt Ponds Preserve and within a short drive of Southernmost Point and the Ernest Hemingway Home and Museum.
This 800 sq ft suite accommodates up to 6 guests with 2 bedrooms and 2 bathrooms, featuring a private balcony, a full kitchen with a dishwasher, air conditioning, and access to shared amenities including a pool and hot tub.

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.

Yellowfin Ledge | Ideal Getaway On Duval! Balcony - Key West, FL
No reviews

Yellowfin Ledge | Ideal Getaway On Duval! Balcony

apartment, Key West
This one-bedroom, one-bathroom condo is situated directly on Duval Street in Key West, placing you just 5 blocks from the Ernest Hemingway House and 4 blocks from the Southernmost Point beach.
This dog-friendly unit accommodates up to four guests and features air conditioning, a kitchenette with a fridge and microwave, complimentary WiFi, and a private balcony, with check-out at 11:00 AM.
Apartment ∙ 3 Bedrooms ∙ 8 Guests - Key West, FL
9.0 2 reviews

Apartment ∙ 3 Bedrooms ∙ 8 Guests

apartment, Key West
This three-bedroom, three-bathroom Key West condo is conveniently located near Duval Street, offering easy access to Key West attractions via a complimentary shuttle service (9 am-11 pm).
The 3-bedroom beachfront rental boasts a fully equipped kitchen, private balcony, in-unit washer/dryer, and access to on-site bike and watercraft rentals through Brightwild Adventures, accommodating up to eight guests.
Apartment ∙ 2 Bedrooms ∙ 6 Guests - Key West, FL
10 2 reviews

Apartment ∙ 2 Bedrooms ∙ 6 Guests

apartment, Key West
This Key West condo offers convenient access to Duval Street via a complimentary shuttle (9 am–11 pm), placing you near the island's renowned nightlife and attractions.
The two-bedroom, two-bathroom unit sleeps six, features king beds in both bedrooms and a queen sleeper sofa, a full kitchen with stainless steel appliances, a private balcony, and access to an on-site marina with boat rentals and watersports.
Courtney's Place Historic Cottages & Inns - Key West, FL
9.0 1056 reviews

Courtney's Place Historic Cottages & Inns

B&B, Key West
Courtney's Place Historic Cottages & Inns is located just a minute's walk from Duval Street in Key West, putting you close to the lively nightlife, shops, and restaurants of the city's heart. This B&B has earned excellent ratings for cleanliness, location, and overall experience.
Courtney's Place offers a variety of room options, including cottages with full kitchens and seating areas for longer stays. Guests can enjoy amenities like a swimming pool, BBQ facilities, free parking, and a continental breakfast.

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.

Captain's Quarters ~ A Vintage Key West Retreat That Is Full Of Charm!! - Key West, FL
9.6 216 reviews

Captain's Quarters ~ A Vintage Key West Retreat That Is Full Of Charm!!

apartment, Key West
This Key West vacation home, located in the Historic District, is less than a mile from Higgs Beach and South Beach, and within 1.7 miles of Smathers Beach and Fort Zachary Taylor Beach.
This 1650-square-foot property boasts a spacious layout with Dade County pine and high ceilings, sleeps 8-10 guests in three bedrooms and a one-bedroom cottage, and includes a lagoon-style heated pool, gas grill, and concierge service.

Best Key West, FL lodging with a balcony

**Havana Especial @ Duval** Cottage & Hot Tub + Last Key White Glove Service... - Key West, FL
No reviews

**Havana Especial @ Duval** Cottage & Hot Tub + Last Key White Glove Service...

apartment, Key West
Modern Waterfront Luxury Home With Heated Pool! - Key West, FL
9.6 109 reviews

Modern Waterfront Luxury Home With Heated Pool!

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

Apartment ∙ 2 Bedrooms ∙ 6 Guests

apartment, Key West
Sombrero Reef Light Suite - Key West, FL
No reviews

Sombrero Reef Light Suite

house, Key West

Best Key West, FL lodging with a kitchen

Commodore's Cove - One Block From Duval St - Key West, FL
No reviews

Commodore's Cove - One Block From Duval St

apartment, Key West
Orchid Suite @ The Old Town Villas, Steps From - Key West, FL
9.5 109 reviews

Orchid Suite @ The Old Town Villas, Steps From

apartment, Key West
Harbor Luxe Celebration Suites - Key West, FL
10 2 reviews

Harbor Luxe Celebration Suites

apartment, Key West
Duval's Duet - Double Balconies Duval Street - Key West, FL
No reviews

Duval's Duet - Double Balconies Duval Street

apartment, Key West

Best Key West, FL lodging with laundry available

Penthouse Waterfront Dock Pool Condo Near Duval St - Key West, FL
9.8 303 reviews

Penthouse Waterfront Dock Pool Condo Near Duval St

apartment, Key West
74 M² Condo ∙ 2 Bedrooms ∙ 6 Guests - Key West, FL
No reviews

74 M² Condo ∙ 2 Bedrooms ∙ 6 Guests

apartment, Key West
Resort Escape | Pool+hot Tub | Sleeps 6 - Key West, FL
9.8 72 reviews

Resort Escape | Pool+hot Tub | Sleeps 6

apartment, Key West
The Butterfly Nest | Newly Updated W/ Shared Pool - Key West, FL
9.8 32 reviews

The Butterfly Nest | Newly Updated W/ Shared Pool

apartment, Key West
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