Key West, FL Short term rentals

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Key West, FL short term rentals
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Best Short term and Weekly rentals in Key West, FL

Best Key West, FL short term rentals with a balcony

Ocean Vista 403e La Brisa - Key West, FL
10 1 review

Ocean Vista 403e La Brisa

apartment, Key West
Ocean Vista 403E La Brisa is a beachfront apartment in Key West, Florida, situated 0.7km from Smathers Beach and 3km from the Southernmost Point.
This 108 square metre, two-bedroom, two-bathroom flat sleeps seven guests and boasts a fully equipped kitchen, air conditioning, a terrace, swimming pool, spa, tennis court, parking, and free Wi-Fi.
Courtyard Access And Shared Pool - Stylish Urban Retreat - Key West, FL
No reviews

Courtyard Access And Shared Pool - Stylish Urban Retreat

apartment, Key West
This three-bedroom, two-bathroom flat in Old Town, Key West, is situated above shops and restaurants in the Duval Square complex, offering direct views of Duval Street from its shared pool and sunning area.
This family-friendly accommodation for up to eight guests features air conditioning, a kitchen with a fridge, microwave, and dishwasher, a swimming pool, spa, tennis court, parking, and a balcony, providing access to a classic Key West walk-up experience.
Key West Harbor Inn - Adults Only - Key West, FL
9.2 258 reviews

Key West Harbor Inn - Adults Only

B&B, Key West
Key West Harbor Inn - Adults Only is located in the heart of Key West, just a short walk from the bustling Mallory Square, the beautiful Simonton Street Beach, and the lively Duval Street. The inn has consistently received excellent ratings for its location, cleanliness, and overall guest experience.
The inn offers a choice of rooms, each with a private bathroom and accommodating up to two guests. Guests can enjoy a range of amenities including a swimming pool, a garden, a terrace, a bar, and free Wi-Fi, as well as the opportunity to rent bicycles and explore the surrounding area.
Simonton Studio, An Old Town Get-away For 2 - Key West, FL
9.8 347 reviews

Simonton Studio, An Old Town Get-away For 2

studio, Key West
This Old Town Key West studio apartment is situated on Simonton Street, a short walk from the Hemingway House, Butterfly Conservatory, and Duval Street's shops and restaurants.
The pet-friendly self-catering unit sleeps two, boasting a king-size bed, a terrace, and a kitchen equipped with a fridge, freezer, and microwave; nearby attractions include Southernmost Beach (approximately 0.96 km) and Fort Zachary Taylor State Park beach.

Explore Family-Friendly Holiday Rentals in Key West, FL

Kid-friendly short-term lets in Key West, FL with family-friendly amenities make your holiday stress-free.

Spacious Layout And Natural Light - Elegant Historic Studio Retreat - Key West, FL
No reviews

Spacious Layout And Natural Light - Elegant Historic Studio Retreat

apartment, Key West
This studio flat is located on Caroline Street, 50 metres from Duval Street and within walking distance of the Historic Seaport, Mallory Square, the Shipwreck Museum and the Mel Fisher Maritime Museum.
This family-friendly apartment sleeps four, offering a private courtyard, a modern kitchen with a microwave and dishwasher, and air conditioning, with contactless check-in available.
Charming Outdoor Oasis With Shared Pool - Inviting Tropical Retreat - Key West, FL
No reviews

Charming Outdoor Oasis With Shared Pool - Inviting Tropical Retreat

apartment, Key West
This two-bedroom, two-bathroom apartment is situated in Old Town, Key West, offering a 10-minute walk to the beach and a 15-minute walk to Duval Street.
This pet-friendly accommodation features a shared swimming pool, a fully equipped galley kitchen, air conditioning, and parking, accommodating up to nine guests with a 10:00 AM check-out.
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, a 17-minute walk from Higgs Beach and 3km from Key West International Airport, offers easy access to the Ernest Hemingway Home and Museum and Duval Street.
The 56-square-metre flat features one bedroom, one bathroom, sleeps seven guests, and includes a private pool, hot tub, fully equipped kitchen, and access to on-site spa and fitness facilities.
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, situated on Garrison Bight Marina, offers direct marina views and is a short cycle ride (approximately 1-2 km) from Duval Street and a short walk from Bayview Park.
Sleeping up to six guests, this two-bedroom, two-bathroom apartment boasts a fully equipped kitchen, shared swimming pool, garden, parking and excellent guest ratings; enjoy tennis and basketball at the nearby park.

Frequently asked questions about short term rentals in Key West, FL

  • Which top landmarks you shouldn't miss in Key West, FL?

    You've got to see the Southernmost Point Buoy, it's the most southerly point in the continental US. Then there's the Ernest Hemingway Home and Museum, a beautiful house with lots of six-toed cats. And don't forget Mallory Square, it's a lively spot to watch the sunset.
  • What are the best short term rentals in Key West, FL?

  • What kind of weather can travelers expect in Key West, FL?

    Key West has a tropical climate, so expect warm temperatures year-round. It's usually sunny and humid, with an average temperature around 25 degrees Celsius. The rainy season runs from May to October, but even then, showers are usually short and intense.
  • What are the best short term rentals with a pool in Key West, FL?

  • What are the most popular festivals and events in Key West, FL?

    Key West is famous for its lively festivals. The Fantasy Fest in October is a big one, with parades and parties. The Hemingway Days in July celebrates Ernest Hemingway with a look-alike contest and other events. And the Key West Food and Wine Festival in January is a great way to sample local cuisine.
  • What are the best short term rentals with a jacuzzi in Key West, FL?

  • Are there any famous stadiums or sports arenas in Key West, FL?

    Key West doesn't have any major sports stadiums or arenas. It's more of a laid-back island town, focused on its beaches and unique atmosphere. But you can find plenty of places to play some casual beach volleyball or go for a swim.
  • What are the best short term rentals for families and kids in Key West, FL?

  • What notable natural landmarks are near Key West, FL?

    Just a short boat trip from Key West is the Dry Tortugas National Park, home to Fort Jefferson, a massive brick fort. It's a great place to snorkel and see the coral reefs. And if you're looking for a bit of history, you can visit the Key West Lighthouse, built in 1848.
  • What part of Key West, FL is ideal for finding lodging?

    Old Town is a popular spot, with lots of historic buildings and restaurants. The area around Duval Street is lively and full of shops and bars. If you prefer something quieter, you can try the area around Smathers Beach, which is less crowded and more relaxed.

Popular destinations

Find the Best Seaside Short-Term Rentals in Key West, FL

Anchor your next coastal holiday at comfortable shoreside short-term rentals in Key West, FL near the waterfront.

Gato Room @ Inn On Fleming~adults Only 2nd Floor Queen W/ Community Pool! - Key West, FL
9.8 26 reviews

Gato Room @ Inn On Fleming~adults Only 2nd Floor Queen W/ Community Pool!

B&B, Key West
This Key West apartment, situated in Old Town, is two blocks from the Historic Seaport and a short walk from Duval Street, offering easy access to Key West's attractions.
The 15-square-metre (0.015-hectare) studio flat sleeps two, features a private bathroom, and includes amenities such as a swimming pool, garden, and concierge service; bicycle rental is also available for exploring the island.

Best Key West, FL short term rentals with a kitchen

Colony Calypso - A Quaint 1 Bedroom Cottage Just Two Blocks To Duval - Key West, FL
9.4 142 reviews

Colony Calypso - A Quaint 1 Bedroom Cottage Just Two Blocks To Duval

cottage, Key West
Colony Calypso is a one-bedroom bungalow in Old Town Key West, just 0.3 km from Duval Street and its lively atmosphere. The cottage has received excellent ratings for location, cleanliness and user experience.
The bungalow is 49 square metres and comfortably sleeps two guests. Guests can enjoy a private deck with a gas grill, a shared swimming pool, and access to a spa.
Magical Ocean Penthouse  Top-floor Ocean View Condo In Key West - Key West, FL
9.8 236 reviews

Magical Ocean Penthouse Top-floor Ocean View Condo In Key West

apartment, Key West
This waterfront apartment is located in Key West's Beachfront district, a short walk from the Florida Keys Beaches and 1.8 kilometres from Clarence S. Higgs Memorial Beach Park, offering boat and bicycle rentals on-site.
This spacious 126 square metre condominium sleeps six guests and features a private terrace, air conditioning, free Wi-Fi, a full kitchen with a dishwasher, and access to a communal swimming pool and hot tub.
Honeymoon Palm Suite Near Higgs Beach - Key West, FL
9.6 5 reviews

Honeymoon Palm Suite Near Higgs Beach

apartment, Key West
This Midtown Key West flat is a short walk from Higgs Beach and White Street Pier, and a 10-minute (approx. 6 km) drive from Key West's downtown area, Duval Street, and the waterfront.
The 60 square metre self-catering property features a king-size bed, a spa-like bathroom with a jet tub, a breakfast bar, and a shared garden with barbecue facilities; it sleeps two guests and offers bike hire.
Blue Moonshine Upgrades Throughout Modern Finishes, Close To Smathers Beach - Key West, FL
9.6 170 reviews

Blue Moonshine Upgrades Throughout Modern Finishes, Close To Smathers Beach

apartment, Key West
This apartment is situated in Beachside, Key West, just a short walk from Florida Keys Beaches and Clarence S. Higgs Memorial Beach Park, and a short drive from the vibrant Duval Street and Mallory Square. This property has received excellent ratings for its location, cleanliness, and overall user experience.
This two-bedroom apartment, with a floor area of 130 square meters, comfortably accommodates up to six guests. Enjoy a range of amenities, including a swimming pool, jacuzzi, terrace, garden, fitness centre, sauna, and tennis court, making this an ideal choice for a relaxing and enjoyable stay in Key West.

Best Key West, FL short term rentals with laundry available

Kingfish Keep | Lively Escape On Duval! Balcony! - Key West, FL
9.8 37 reviews

Kingfish Keep | Lively Escape On Duval! Balcony!

apartment, Key West
Pool, Laundry, And Grilling Area - Key West, FL
9.8 10 reviews

Pool, Laundry, And Grilling Area

apartment, Key West
Apartment ∙ 3 Bedrooms ∙ 8 Guests - Key West, FL
9.0 2 reviews

Apartment ∙ 3 Bedrooms ∙ 8 Guests

apartment, Key West
Sunrise Suite 203 - Key West, FL
9.7 3 reviews

Sunrise Suite 203

apartment, Key West

Discover Short-Term Rentals with Parking in Key West, FL

Park up and enjoy the coast and local beaches. These short-term lets in Key West, FL come with a free car park on-site.

Ambrosia At Azul Mansion Key West - Key West, FL
8.0 1 review

Ambrosia At Azul Mansion Key West

house, Key West
Andrews Inn & Garden Cottages - Key West, FL
9.5 826 reviews

Andrews Inn & Garden Cottages

B&B, Key West
Southernmost Point Guest House & Garden Bar - Key West, FL
9.4 2876 reviews

Southernmost Point Guest House & Garden Bar

B&B, Key West
Waterfront Condo With Dock, Pool, Downtown Key West Near Duval - Key West, FL
9.7 226 reviews

Waterfront Condo With Dock, Pool, Downtown Key West Near Duval

apartment, Key West

Top Holiday Lets with a Jacuzzi in Key West, FL

These short-term lets near the water in Key West, FL come with a hot tub or jacuzzi, ideal for a private hot tub soak after a.

Kwss210 Sunrise Suites Bonaire Suite #210 - Key West, FL
8.7 245 reviews

Kwss210 Sunrise Suites Bonaire Suite #210

apartment, Key West
Botanical Island Delight  Key West Fantastic Discounts For Summer & Fall - Key West, FL
9.0 155 reviews

Botanical Island Delight Key West Fantastic Discounts For Summer & Fall

apartment, Key West
Ocean Front Suite With Direct Beach Access - Key West, FL
No reviews

Ocean Front Suite With Direct Beach Access

apartment, Key West
Kw Luxury 2/2 Beachfront Resort  Tropical Oasis - Key West, FL
9.8 200 reviews

Kw Luxury 2/2 Beachfront Resort Tropical Oasis

apartment, Key West