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

Tropical Tee-time: 2br Townhome In Key West Golf Club With Two Shared Pools, Fitness Center, Dogs Ok - Key West, FL
9.0 2 reviews

Tropical Tee-time: 2br Townhome In Key West Golf Club With Two Shared Pools, Fitness Center, Dogs Ok

apartment, Key West
This Key West pet-friendly holiday home is conveniently located near the Key West Golf Club and a two-minute drive (approximately 1.6km) from the Key West Tropical Forest and Botanical Garden.
The 75 square metre property offers two bedrooms, two bathrooms, sleeps four guests, and includes a fully equipped kitchen, laundry facilities, Wi-Fi, air conditioning, a swimming pool, and a terrace – perfect for enjoying Key West's outdoor lifestyle.
Mallory Suite @ Inn On Fleming~adults Only 1st Lvl King W/ Community Pool - Key West, FL
9.2 36 reviews

Mallory Suite @ Inn On Fleming~adults Only 1st Lvl King W/ Community Pool

B&B, Key West
This Mallory Suite apartment in Old Town Key West is situated two blocks from the Historic Seaport and a short walk from Duval Street, offering easy access to restaurants and shops.
The 20-square-metre (215-square-foot) self-catering flat features a king-size bed, private patio, en-suite bathroom with shower/tub, and amenities including a mini-fridge and flat-screen TV; it sleeps two guests and includes access to a swimming pool and concierge services.
Charming Space With Breezy Balcony - Relaxing Island Escape - Key West, FL
No reviews

Charming Space With Breezy Balcony - Relaxing Island Escape

apartment, Key West
This one-bedroom flat is situated directly on Duval Street, offering immediate access to Key West's attractions, and is located 560 metres from the Southernmost Point and 480 metres from South Beach.
This family-friendly apartment accommodates up to six guests with a queen sleeper sofa and a loft bedroom featuring two queen beds, and includes a fully equipped kitchen, air conditioning, a private balcony, and access to a communal garden, spa, and tennis court.
Turtle Nest Condo - Pool - Key West, FL
No reviews

Turtle Nest Condo - Pool

apartment, Key West
This Key West flat is located in Key West, a 17-minute walk from Higgs Beach and 3 kilometres from Key West International Airport.
This one-bedroom flat, covering 56 square metres and accommodating up to seven guests, offers a private pool, a year-round outdoor swimming pool, a balcony with garden views, and complimentary WiFi.

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.

Charming Condo With Relaxing Veranda - Modern Coastal Retreat - Key West, FL
No reviews

Charming Condo With Relaxing Veranda - Modern Coastal Retreat

apartment, Key West
This one-bedroom flat offers a prime location in Key West's historic Old Town, just a short walk from Duval Street and numerous eateries.
This ground-level condo, accommodating up to four guests, features an open-plan living area, a king-sized bed, a private veranda, and in-unit laundry, with access to a communal garden, spa, and tennis court.
Apartment ∙ 1 Bedroom ∙ 4 Guests - Key West, FL
No reviews

Apartment ∙ 1 Bedroom ∙ 4 Guests

apartment, Key West
This one-bedroom Key West apartment is situated in Old Town, a short walk or cycle from Simonton Street and numerous attractions.
The self-catering suite, sleeping four, offers a full kitchen, private washer/dryer, two cable TVs, free Wi-Fi, and a relaxing porch; nearby parking is available at 204 Simonton Street and other car parks.
Apartment ∙ 1 Bedroom ∙ 4 Guests - Key West, FL
No reviews

Apartment ∙ 1 Bedroom ∙ 4 Guests

apartment, Key West
This Key West apartment is centrally located in downtown Key West, approximately 1.6km from Key West International Airport (EYW) and within walking distance of many attractions.
The one-bedroom flat sleeps four, featuring a newly renovated kitchen with modern appliances, a private washer/dryer, central air conditioning, free Wi-Fi, a terrace, and a king-size bed plus a queen-size sleeper sofa; nearby paid parking is available.
Bottoms Up Bungalow - Perfect  2 Bed/2 Bath Private Pool - Key West, FL
10 131 reviews

Bottoms Up Bungalow - Perfect 2 Bed/2 Bath Private Pool

apartment, Key West
Bottom's Up Bungalow is situated in the Key West Historic District, just under 1.6 kilometres from Duval Street, the beaches, and the marina. This charming property has received excellent user ratings, making it a popular choice for travellers.
The bungalow has 2 bedrooms and 2 bathrooms, spanning 114 square metres and accommodating up to 6 guests. It offers a range of amenities, including a private pool, a spa, a terrace, and a garden, providing a relaxing and enjoyable stay.

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.

The Samana Cay | Tropical, Airy Retreat W/ Private Balcony, Pool! - Key West, FL
10 33 reviews

The Samana Cay | Tropical, Airy Retreat W/ Private Balcony, Pool!

apartment, Key West
This Key West apartment, ideally situated just under a kilometre from Key West International Airport and a short drive from Mallory Square, Ernest Hemingway Home and Museum, and Duval Street, offers easy access to the island's key attractions.
This three-bedroom, two-bathroom dwelling boasts 74 square metres of living space, comfortably accommodating six guests and featuring a private balcony, a shared swimming pool, a fully equipped kitchen, in-unit laundry, and one designated parking space (#158) under the building.

Best Key West, FL short term rentals with a kitchen

Leo's Lodge | Newly Updated! - Key West, FL
9.0 33 reviews

Leo's Lodge | Newly Updated!

apartment, Key West
This Key West Historic District flat is less than 0.8 km from Duval Street and under 1.6 km from the Southernmost Point, offering easy access to beaches and the Ernest Hemingway Home and Museum.
The one-bedroom, one-bathroom apartment sleeps two guests and includes a private patio, shared swimming pool, in-unit laundry, and free Wi-Fi; enjoy its convenient location for exploring Key West's attractions.
Apartment In Key West - Key West, FL
10 2 reviews

Apartment In Key West

apartment, Key West
This one-bedroom duplex flat in a residential district of Key West offers a private entrance and is a short distance from the city's main attractions.
This recently renovated accommodation can host up to four guests and features a kitchenette with a full-size fridge and microwave, a coffee bar, and Roku TV, with pets welcome and parking provided.
Heated Pool And Charming Courtyard - Blissful Island Retreat - Key West, FL
No reviews

Heated Pool And Charming Courtyard - Blissful Island Retreat

apartment, Key West
Banana's Foster Guest House, a substantial historic property on the corner of Caroline and Simonton Streets, offers a prime location just 160 metres from Duval Street, providing immediate access to Key West's bars, nightlife, and restaurants, and is also conveniently situated near the Historic Seaport. This pet-friendly establishment features seven bedrooms and seven bathrooms across six separate units accommodating up to 19 guests, with amenities including air conditioning, a private heated swimming pool, and four on-site parking spaces, all within easy reach of local markets.
Cheerful 3 Bedroom With Pool, Off Street Parking - Key West, FL
10 19 reviews

Cheerful 3 Bedroom With Pool, Off Street Parking

apartment, Key West
This Key West apartment, perfect for families, is conveniently located near Key West's attractions, though precise distances require further information.
Sleeping six guests across four bedrooms and two bathrooms, this recently renovated property boasts a new kitchen, a newly resurfaced pool, and a family-friendly atmosphere.

Best Key West, FL short term rentals with laundry available

**Set Sail @ Coconut Mallory** Condo + Last Key White Glove Service... - Key West, FL
9.8 140 reviews

**Set Sail @ Coconut Mallory** Condo + Last Key White Glove Service...

apartment, Key West
Walking On Sunshine By Last Key Realty - Key West, FL
10 1 review

Walking On Sunshine By Last Key Realty

apartment, Key West
The Cat Island Suite | Charmingly Renovated! Pool! - Key West, FL
10 10 reviews

The Cat Island Suite | Charmingly Renovated! Pool!

apartment, Key West
Beach Club #104 - Unique Oceanfront Living With - Key West, FL
10 2 reviews

Beach Club #104 - Unique Oceanfront Living With

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.

Seaside Escape- 2 Bed/2 Bath Condo With Shared Pool & Parking - Key West, FL
9.6 5 reviews

Seaside Escape- 2 Bed/2 Bath Condo With Shared Pool & Parking

apartment, Key West
~ Casablanca ~ Fabulous Home W/ Private Pool/parking, In A Quiet Location. - Key West, FL
9.8 157 reviews

~ Casablanca ~ Fabulous Home W/ Private Pool/parking, In A Quiet Location.

apartment, Key West
Tropical Vineyard At The Truman Annex In Key West - Key West, FL
9.2 53 reviews

Tropical Vineyard At The Truman Annex In Key West

apartment, Key West
Our Happy Place ~ Adorable 2 Bedroom, 2 Bath Condo Steps From The Beach! - Key West, FL
9.2 7 reviews

Our Happy Place ~ Adorable 2 Bedroom, 2 Bath Condo Steps From The Beach!

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.

Two Bedroom Residence - Key West, FL
8.0 4 reviews

Two Bedroom Residence

apartment, Key West
Beach House- Ocean & Beach View-upgraded-over 146 Five Star Reviews - Key West, FL
9.6 168 reviews

Beach House- Ocean & Beach View-upgraded-over 146 Five Star Reviews

apartment, Key West
Mar Y Sol Luxurious Oceanfront  Key West Breathtaking Atlantic Sunrise Views - Key West, FL
9.3 250 reviews

Mar Y Sol Luxurious Oceanfront Key West Breathtaking Atlantic Sunrise Views

apartment, Key West
Pool View Suite | Beachside Resort - Key West, FL
9.5 304 reviews

Pool View Suite | Beachside Resort

apartment, Key West
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