Key West Condos & Vacation Rentals

Our Favorite Vacation Rentals in Key West

  • Grand Marina Suite
     Country House
    Booking.com
    From
    $547
  • Breezy dog-friendly condo w/ private deck, shared pool/hot tub, & parking space
    Excellent2br Home/Apartment
    HolidayLettings
    From
    $378
  • Bayview House
    NiceHome/Apartment
    Booking.com
    From
    $280
  • Comfortable condo w/ shared pool, private balcony, and beach access
    Nice2br Home/Apartment
    HolidayLettings
    From
    $551
  • Island Oasis
     Country House
    Booking.com
    From
    $433
  • Comfortable, dog-friendly studio w/ shared pool, patio & nearby beach access!
     -1br Studio
    HolidayLettings
    From
    $245
  • Sunrise Suites Grand Cayman Suite #309
    ExcellentHome/Apartment
    Booking.com
    From
    $232
  • Oceanfront Oasis
     2br Home/Apartment
    HolidayLettings
    From
    $698

Check prices for these upcoming dates

Key West Vacation Rentals with a Pool

  • Villas Key West
    Good7br Country House
    Booking.com
    From
    $282
  • 2/1 Sailboat, Pool/Bar/Restaurant on Site!!
    Good2br Home/Apartment
    Airbnb
    From
    $186
  • Real World MTV House Key West
    Excellent10br Home/Apartment
    Airbnb
    From
    $3,784
  • 2BR Mallory Marina Suite
     2br Home/Apartment
    Airbnb
    From
    $593

Key West Vacation Rentals with Wi-Fi

  • Old Town Suites
    Good4br 3-star Home/Apartment
    Booking.com
    From
    $199
  • STUDIO / APARTMENT
    ExcellentStudio
    Airbnb
    From
    $325
  • FORGET THE HOUSE STAY ON A YACHT KEY WEST HARBOR
     2br Boat
    Airbnb
    From
    $410
  • Beachside 1BR Presidential Suite+Several Amenities
     Home/Apartment
    Airbnb
    From
    $537

Key West Pet-Friendly Vacation Rentals

  • Family friendly condo w/tennis, shared pool, hot tub, & private balcony- dogs ok
    Nice2br Home/Apartment
    HolidayLettings
    From
    $333
  • Welcoming Sunrise Suites condo w/ balcony views, pool/hot tub- dog-friendly
    Nice2br Home/Apartment
    HolidayLettings
    From
    $352
  • Bright and sunny condo with patio, shared pool, and hot tub at Sunrise Suites
     2br Home/Apartment
    HolidayLettings
    From
    $378
  • East-facing Sunrise Suites condo w/shared pool, hot tub, tennis, private balcony
     2br Home/Apartment
    HolidayLettings
    From
    $367

Key West Travel Guide

When you visit Key West, you'll feel like you're in a tropical paradise! This island and city in the Sunshine State is home to picturesque beaches and is located in the southernmost point of the continental USA. From sailing and kayaking to snorkelling and swimming, there are lots of activities to enjoy, as well as museums, art galleries, golf courses and theaters. In particular, Duval Street is where it all happens, with souvenir and boutique shops during the day and lively restaurants, saloons and nightlife when the sun sets. Everyone loves a watering hole in Key West, and when you're in the city, don’t forget to try some Key lime pie!

Things to Do in Key West

Top things to do in Key West include visiting Smathers Beach. The beautiful beach is home to sun, sea, and sand, and is popular with vacationers. You can also climb up the Key West Lighthouse and soak in the views at the top. The Key West Butterfly and Nature Conservatory is an exciting place to spend the afternoon, with 60 colorful creatures to admire and an aviary you can walk through. Alternatively, tour the Ernest Hemingway Home and Museum and see where the author spent most of his years writing. Fun in the evenings is in Mallory Square with its lively atmosphere and array of restaurants, shops, and sunset celebrations.

Best Places to Stay in Key West

There are lots of hotels and resorts to choose from around Duval Street that are near to all the action. There are also places near to Smathers Beach. Since Key West is pretty small, you are never too far away from anything!

Best Time to Visit Key West

The temperatures can get hot in the summer in Key West, while the spring is a much more manageable heat. Accommodation prices are a lot more reasonable during March to May also.

A Local's Guide to Key West

What better place to have a break than the beautiful island paradise of Key West? Travelers looking for rentals in Key West can enjoy the laid-back atmosphere, incredible sights, and sandy beaches.

Taking a vacation in Florida Keys gives visitors a chance to relax and take in stunning ocean views.

Sun-seekers will love rental homes in Key West Florida for their full kitchens, locations near the many beaches and home comforts. Guests can choose a monthly rental which is just minutes from the main attractions including Mallory Square, Duval Street and Smathers Beach. From a vacation home, sightseers can be in the heart of the resort by just stepping outside. No need to drive to find a beach, the island is only eight square miles so everything is just a stroll, cycle ride or short cab ride away.

A Key West vacation gives sunshine-lovers more than just the chance to soak up the rays. Visitors can really get under the skin of the Florida Keys by visiting some culturally important sites such as the Ernest Hemingway Home and Museum.

Smathers Beach is the largest public beach on the island and lets sunbathers stretch out on more than half a mile of sand. Lined with coconut trees, this tropical paradise allows travelers to truly soak up the Floridian lifestyle.

Mallory Square is another must-see destination. Head out in the late afternoon to enjoy the incredible atmosphere that earned the place its catchphrase – “See you at Sunset!” Every night, hundreds of tourists flock to the plaza to watch the sun set while enjoying a two-hour festival including arts and crafts exhibitions, performances and an amazing variety of street food.

Swimming in the Atlantic is on everyone’s bucket list. And with such a small island you’re never far away from somewhere to jump right in! But if you want to cool off in some historic surroundings, head to Fort Zachary Taylor Historic State Park to scuba dive, snorkel or go for a paddle in a kayak.

The perfect place for beachgoers is Key West. With vacation rentals in Key West just minutes from the waterfront, rent a beach hut and spread out a towel for a day of relaxing with friends or family. Head to Bahia Honda State Park, Higgs Beach or even take a trip out to the Dry Tortugas. Travelers in Key West will find plenty of sandy stretches to escape and relax.

Guests that want to swim but don’t want to bring all the gear in their suitcase can just hire some for the day. Snorkels, fins and even beach chairs are available to rent for the day – just turn up and chill out!

With temperatures never dipping far, only down to around 50 degrees F in the winter months, vacation rentals in Key are a popular choice for out-of-season vacationers.

The tropical climate means during the summer temperatures can soar to more than 95 degrees F which may be a little bit too hot for some.

Most rental homes come with AC to make sure guests get a restful night’s sleep away from the heat of the evening. To avoid the crowds, vacationers can look at vacation rentals available between March and May. At this time of year, the weather will be about 70 or 80 degrees F so still plenty warm to enjoy this tropical paradise! The rainy season is between June and September so visitors should pack an umbrella and raincoat!

Condos in Key West

Visiting Key West FL is like experiencing an island paradise. The beaches are some of the softest and whitest on the west coast, particularly Snatchers Beach, while, the town of Key West is bursting with life. Spend your days swimming in the Atlantic Ocean and the evening exploring the vibrant nightlife of Ducal Street and Mallory Square. There are also culturally important sites, such as the Ernest Hemingway home and museum.

Key West condo rentals are not hard to find but they do get booked up quickly, especially in the summer months. Vacation rentals in Key West tend to come with full kitchens, ocean views, and even tennis courts. Depending on your preferences, there are additionally vacation homes with fully equipped kitchens in gated communities. The Truman Annex rentals in Florida Key is a good place to start, with many multiple bedroom and 2 bathroom properties available to host the whole family. Alternatively, the 1800 Atlantic Suites are also great condos.

Price and Availability in Key West

Most expensive
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The cheapest day to stay at a vacation rental in Key West tends to be Monday, while the most expensive day tends to be Friday. Vacation homes in Key West tend to be busiest on Fridays, while it tends to be much quieter on Tuesdays.
The most expensive month to stay in a vacation rental in Key West is in February, while the cheapest month is in August. The most popular time to book a vacation rental in Key West is in the high season in March. Key West has its low season in September, when less people are visiting and the vacation home occupancy rate drops.

The Weather in Key West

Rainy days
95 º77
6
91 º72
3
88 º61
1
86 º59
2
79 º53
1
83 º64
0
83 º59
2
86 º67
0
86 º69
14
90 º73
3
94 º75
3
94 º75
2
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Rainy days

This climate histogram shows you the weather patterns in Key West. The warmest months in Key West are April and May, when temperatures reach 95 ˚F. The coolest month is December, when temperatures drop to 53 ˚F. The wettest month in Key West is August with 14.17 inches of rain, while the driest month is September with 0.21 inches of rain.

What Expert Travelers Think

  • — AllTheRooms.com makes travel easier, enjoyable and inexpensive through its provision of ample information, data and every possible accommodation available to choose from

    ArtMatters.Info
    ArtMatters.InfoArtMatters.Info
  • — Packed full of information, from the best time of year to visit (I love NYC in Spring) to top tips from locals, All The Rooms provides the best accommodation, whether you are looking to enjoy your first time visit to New York or want to experience a new location

    Jaz
    JazThe Life of a Social Butterfly
  • — I love All the Rooms because instead of having to check one place for home rentals, another for hotel, another for bed and breakfasts, and yet another for a room rental in a private residence, I can finally see EVERYTHING at one site; saving me considerable time

    Jeff Campbell
    Jeff CampbellMiddle Class Dad

Vacation Rentals in Key West

Choose the perfect vacation rental for your trip at AllTheRooms.com. We aggregate Airbnb, Bed and Breakfast, Priceline and many more. Key West has 4,336 hotels, vacation rentals and other special places to stay, with prices to suit careful travellers, luxury travelers and everything in between. The average price of a rental is $906 per night.

Those needing to get some work done during their trip to Key West can choose from 1,386 places to stay that include WiFi. 48 places to stay include a breakfast. You can maintain your workout regime by staying at one of 285 accommodations that provide gym facilities. If you are driving to Key West, you'll want to pick from 1,255 places to stay that provide parking. 545 accommodations come with a pool or jacuzzi

Those traveling with a cat, dog or some other animal can stay in any of 439 accommodations that are designated as pet-friendly.

AllTheRooms compares vacation rentals, hotels and other bespoke accommodation types from many providers in Key West, including 626 places to stay from Airbnb, 28 accommodations from Bed and Breakfast and 24 places to stay from Priceline

2,244 of our accommodations in Key West have been reviewed and rated. 49% are rated great. You can instantly book any of 1,716 places to stay right now.

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