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Best Short term and Weekly rentals in Key West, FL

Authors Key West Guesthouse - Key West, FL
8.9 3193 reviews
Key West, FL
4 2
$977/nighttotal: $2931 (3 )

Authors Key West Guesthouse

B&B - Key West
Authors Key West Guesthouse is located in Old Town Key West, a short walk from Duval Street, Ernest Hemingway Home and Museum, and the Southernmost Point, offering a peaceful retreat from the bustling downtown area. The guesthouse has received very good ratings for its location, cleanliness, and overall experience.
The guesthouse has one bedroom and one bathroom, and features a swimming pool, a sun terrace, and a picnic area. Guests can enjoy a continental breakfast each morning, free Wi-Fi, and concierge services.
Kwss212 Sunrise Suites Saint Croix Suite #212 - Key West, FL
8.2 134 reviews
Key West, FL
2 2
$328/nighttotal: $2296 (7 )

Kwss212 Sunrise Suites Saint Croix Suite #212

apartment - Key West
This dog-friendly resort condo is located in Key West, within 2 miles of the historic Fort East Martello Museum and Gallery. The resort has very good user, location, and cleanliness ratings.
The condo is 780 square feet and has 2 bedrooms, a fully equipped kitchen, and a sofa bed that can accommodate up to 4 additional guests. It also has a private balcony, a fitness center, a swimming pool, a hot tub, and a tennis court.
Rose Key Cottage - Private Pool & Near Duval - Key West, FL
9.2 21 reviews
Key West, FL
5 2
$1226/nighttotal: $2452 (2 )

Rose Key Cottage - Private Pool & Near Duval

apartment - Key West
This Key West vacation rental is located in a quiet neighborhood, just steps from Duval Street and the heart of Key West's downtown area.
The two-bedroom, two-bathroom house sleeps six guests and features two fully equipped kitchens, a private pool, outdoor shower, in-unit laundry, and allows up to two pets under 30 lbs for an additional nightly fee.
3-bedroom 3-bath Condo At Bayfront Suites & Marina - Key West, FL
9.6 824 reviews
Key West, FL
5 3
$1559/nighttotal: $6236 (4 )

3-bedroom 3-bath Condo At Bayfront Suites & Marina

apartment - Key West
This Key West apartment is located in the Meadows district, just a short walk from Duval Street, Hemingway House, and the beaches. It has received excellent ratings for location, cleanliness, and overall user experience.
The apartment has two bedrooms, providing ample space for families or groups of friends. Enjoy the convenience of amenities like a swimming pool, tennis court, fitness center, and concierge services.
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, FL
2 2
$559/nighttotal: $3913 (7 )

Key West Condo Close To The Ocean. 1 Mile To Smathers & 3 Miles To Duval St.

apartment - Key West
This Key West golf condo is located in the heart of the city, within walking distance of major tourist attractions and landmarks. It has excellent user ratings and offers a private balcony with scenic views, a fully equipped kitchen, and access to an outdoor pool, fitness center, and spa tub.
The apartment has a floor area of 800 square feet, 2 bedrooms, 2 bathrooms, and a guest capacity of 6. It also features free WiFi, barbecue grills, and a smoke-free environment.
Sunrise 103-2br/2ba Condo Near Beaches With Pool, Parking, Balcony - Key West, FL
9.2 57 reviews
Key West, FL
5 2
$306/nighttotal: $2142 (7 )

Sunrise 103-2br/2ba Condo Near Beaches With Pool, Parking, Balcony

apartment - Key West
This two-bedroom condo is located near Smather's Beach, just a short drive from Key West International Airport, offering a peaceful retreat away from the hustle and bustle of downtown. The apartment boasts excellent ratings for user experience, location, and cleanliness.
The apartment comfortably sleeps up to six guests and features a fully equipped kitchen, a private balcony with pool views, and a shared lagoon-style pool. Enjoy the convenience of having a washer and dryer in the unit, plus access to a shared garden, parking, and a Jacuzzi.
Tranquility - Tucked Away In The Meadows - Private Pool - 3bd/3bath - Key West, FL
9.8 6 reviews
Key West, FL
2 3
$811/nighttotal: $24330 (30 )

Tranquility - Tucked Away In The Meadows - Private Pool - 3bd/3bath

cottage - Key West
Tranquility Cottage, a three-bedroom, three-bathroom Key West home, is located in the Historic District, seven blocks from Duval Street and near the Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park.
This 1320-square-foot vacation rental boasts a private pool and deck, a fully equipped kitchen, free Wi-Fi, on-street parking, and accommodates up to six guests, making it perfect for families or groups.
Tropical Escape At Sunrise - Key West, FL
9.8 194 reviews
Key West, FL
2 2
$461/nighttotal: $3227 (7 )

Tropical Escape At Sunrise

apartment - Key West
This luxurious Key West condo, perfect for families or groups of up to five (25+ age restriction), boasts two bedrooms with en-suite bathrooms, a fully equipped kitchen, and a private patio overlooking the pool.
The unit includes amenities such as WiFi, a fitness center, tennis courts, and secure parking; its precise location within Key West is unspecified, but its condo complex setting suggests proximity to area attractions.
Family Suites In A Welcoming Paradise, W/ Pools! - Key West, FL
Key West, FL
8 4
$2251/nighttotal: $11255 (5 )

Family Suites In A Welcoming Paradise, W/ Pools!

B&B - Key West
This Key West guesthouse is located in Old Town, offering easy access to Duval Street and Smathers Beach, with a complimentary shuttle service to the beach.
This four-bedroom, four-bathroom inn accommodates up to eight guests and features four swimming pools, on-site kayaking, and water sports opportunities.
Thompson Island  Usa !!  Your Key West Retreat !! - Key West, FL
9.6 124 reviews
Key West, FL
8 9
$6515/nighttotal: $32575 (5 )

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.
Andys Attic | Budget-friendly! - Key West, FL
9.6 32 reviews
Key West, FL
2 1
$196/nighttotal: $1372 (7 )

Andys Attic | Budget-friendly!

apartment - Key West
This budget-friendly studio is located in Bahama Village, steps from Duval Street and attractions including the Ernest Hemingway Home and Southernmost Point.
This pet-friendly accommodation accommodates two guests and features a kitchenette with a fridge and microwave, air conditioning, and access to a shared swimming pool, sundeck, and BBQ grill.
King Bed | Key West - Best Downtown Locations - Key West, FL
9.9 14 reviews
Key West, FL
2 1
$177/nighttotal: $354 (2 )

King Bed | Key West - Best Downtown Locations

apartment - Key West
This Old Town Key West condo is a block from the ocean and a 2-minute walk to Mallory Square, placing you steps from Sloppy Joe's and the Duval Loop.
This spacious apartment accommodates up to 4 guests with a king bed and pull-out sofa, featuring a kitchen with a fridge and microwave, air conditioning, a balcony, and garden access.

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.

Charming 2 Bedroom Cottage In Old Town Key West - Key West, FL
10 1 review
Key West, FL
2 2
$256/nighttotal: $7680 (30 )

Charming 2 Bedroom Cottage In Old Town Key West

apartment - Key West
This dog-friendly Key West cottage is located in Old Town, offering a 1,320-foot walk to Duval Street, the Ernest Hemingway Home and Museum, and Southernmost Point.
This vacation rental accommodates up to six guests with two queen bedrooms, a full kitchen, air conditioning, WiFi, a washer/dryer, a swimming pool, and off-street parking.

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
Key West, FL
2 1
$781/nighttotal: $1562 (2 )

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.

Breathtaking Ocean Views And Enormous Patio - Stunning Coastal Retreat - Key West, FL
Key West, FL
2 1
$460/nighttotal: $1840 (4 )

Breathtaking Ocean Views And Enormous Patio - Stunning Coastal Retreat

apartment - Key West
This oceanfront studio condominium on the western edge of Key West offers direct, unobstructed views of the Atlantic from a top-floor private patio, located just steps from White Street Pier and Higgs Beach, and a short bike ride to Duval Street and the Historic District.
This family-friendly unit accommodates two guests with air conditioning, internet, a full kitchen, and a spa, while the property provides a garden and tennis court, with a tiki hut by the water for beach access.
Apartment ∙ 6 Bedrooms ∙ 14 Guests - Key West, FL
Key West, FL
4 6
$6525/nighttotal: $19575 (3 )

Apartment ∙ 6 Bedrooms ∙ 14 Guests

apartment - Key West
This luxurious Key West vacation home is located in the Modern Keys gated community, offering easy access to the boat ramps in Key Haven and Stock Island.
The 6-bedroom, 6-bathroom house sleeps 14 guests and features a spacious open-concept floor plan, a fully equipped kitchen, a large fenced yard, private boat excursions and chauffeur services, and driveway parking for up to four vehicles and a boat trailer.
Ambrosia Key West - Key West, FL
9.2 1761 reviews
Key West, FL
2 1
$151/nighttotal: $302 (2 )

Ambrosia Key West

B&B - Key West
This Key West bed and breakfast is located on Duval Street, a short walk from the Ernest Hemingway Home and Museum, the Southernmost Point, and Mallory Square. It has received very good user ratings, excellent location ratings, and excellent cleanliness ratings.
The property features two pools, a hot tub, and tropical courtyards. Guests can enjoy complimentary snacks and refreshments poolside, a full hot breakfast, and pet-friendly rooms.
158 M² Huoneisto ∙ 3 Makuuhuonetta ∙ 6 Vierasta - Key West, FL
Key West, FL
4 3
$257/nighttotal: $16191 (63 )

158 M² Huoneisto ∙ 3 Makuuhuonetta ∙ 6 Vierasta

apartment - Key West
This 3-bedroom, 2-bathroom Old Town Key West home offers a prime, quiet location just a short walk to Duval Street, Truman Avenue, the Marina, and the White Street Arts Walk.
This 1,700 square foot residence features a two-story layout, high ceilings, a fully equipped kitchen, in-unit laundry, a wrap-around porch, a third-floor balcony with views, and access to a large heated saltwater pool, accommodating up to 6 guests and pets.

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.

Old Town Suites - 2 Bedroom Suite #2 - Key West, FL
9.5 295 reviews
Key West, FL
2 2
$211/nighttotal: $422 (2 )

Old Town Suites - 2 Bedroom Suite #2

apartment - Key West
This Key West apartment rental is conveniently located half a block from Duval Street, offering easy walking access to the Ernest Hemingway Home, Key West Lighthouse, Southernmost Point, and South Beach.
This two-bedroom, one-bathroom unit sleeps six, features a full kitchen with a refrigerator and microwave, air conditioning, and on-site parking (fee: $25/night), and is perfect for families.

Best Key West, FL lodging with a balcony

Best Time At The Truman Annex In Key West - Key West, FL
9.6 38 reviews
Key West, FL
4 2
$195/nighttotal: $12285 (63 )

Best Time At The Truman Annex In Key West

apartment - Key West
139 M² Condo ∙ 2 Bedrooms ∙ 4 Guests - Key West, FL
10 1 review
Key West, FL
4 2
$451/nighttotal: $1353 (3 )

139 M² Condo ∙ 2 Bedrooms ∙ 4 Guests

apartment - Key West
Flamingo Retreat-waterfront 2br 2ba Condo W/ Pool & Boat Slip - Key West, FL
9.2 109 reviews
Key West, FL
2 2
$855/nighttotal: $5985 (7 )

Flamingo Retreat-waterfront 2br 2ba Condo W/ Pool & Boat Slip

apartment - Key West
Hemingway Suite @ Inn On Fleming~adults Only 2nd Lvl King W/ Community Pool - Key West, FL
9.8 29 reviews
Key West, FL
2 1
$222/nighttotal: $444 (2 )

Hemingway Suite @ Inn On Fleming~adults Only 2nd Lvl King W/ Community Pool

B&B - Key West

Best Key West, FL lodging with a kitchen

La Casa Cubana @ Cuban Club Suites - Key West, FL
9.5 178 reviews
Key West, FL
2 1
$746/nighttotal: $2984 (4 )

La Casa Cubana @ Cuban Club Suites

apartment - Key West
Cloud Suite On Duval - Key West, FL
9.7 362 reviews
Key West, FL
3 2
$1182/nightfor 1 night

Cloud Suite On Duval

apartment - Key West
Windward Isle - Key West, FL
8.9 485 reviews
Key West, FL
4 2
$1007/nighttotal: $3021 (3 )

Windward Isle

house - Key West
Caribbean House - Key West, FL
8.2 28 reviews
Key West, FL
2 1
$259/nightfor 1 night

Caribbean House

B&B - Key West

Best Key West, FL lodging with laundry available

Sailor's Story At The Truman Annex In Key West - Key West, FL
9.2 51 reviews
Key West, FL
4 2
$349/nighttotal: $21987 (63 )

Sailor's Story At The Truman Annex In Key West

apartment - Key West
Old Town Studio Apartment  Walk Everywhere! - Key West, FL
9.9 37 reviews
Key West, FL
2 1
$160/nighttotal: $4800 (30 )

Old Town Studio Apartment Walk Everywhere!

apartment - Key West
Solaris Cottage ~ Live Like A Local~close To Duval - Key West, FL
9.7 403 reviews
Key West, FL
2 1
$761/nighttotal: $3044 (4 )

Solaris Cottage ~ Live Like A Local~close To Duval

apartment - Key West
Breathtaking Ocean Views And Private Patio - Stunning Coastal Retreat - Key West, FL
Key West, FL
2 1
$786/nighttotal: $11004 (14 )

Breathtaking Ocean Views And Private Patio - Stunning Coastal Retreat

apartment - Key West
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