Key West Condos & Vacation Rentals

Our Favorite Vacation Rentals in Key West

  • Grand Marina Suite
     Country House
    Booking.com
    From
    $386
  • Shared pool, hot tub, tennis courts, & balcony - dogs OK! Family friendly!
    Excellent2br Home/Apartment
    HolidayLettings
    From
    $357
  • ocean front paradise
     Home/Apartment
    Booking.com
    From
    $382
  • Cottage w/ shared pool, private hot tub, & street parking - Dogs OK!
    GoodHome/Apartment
    HolidayLettings
    From
    $373
  • Bayview House
     Home/Apartment
    Booking.com
    From
    $310
  • Cozy, dog-friendly suite w/ shared hot tubs, grill, and patio space to relax
    Excellent-1br Studio
    HolidayLettings
    From
    $263
  • Rose Lane Villas
     6br Country House
    Booking.com
    From
    $329
  • Cozy cottage w/ private hot tub, tranquil garden & parking - dogs OK!
    Nice2br Home/Apartment
    HolidayLettings
    From
    $420

Check prices for these upcoming dates

Key West Vacation Rentals with a Pool

  • Real World MTV House Key West
    Excellent10br Home/Apartment
    Airbnb
    From
    $2,372
  • A Castle on an Island!! Your Key West Retreat !!
     8br Home/Apartment
    Airbnb
    From
    $1,976
  • the S/V Pisces
    ExcellentHome/Apartment
    Airbnb
    From
    $247
  • LAST MINUTE DISCOUNT! 48' Yacht & Other Boats
    Excellent4br Boat
    Airbnb
    From
    $989

Key West Vacation Rentals with Wi-Fi

  • STUDIO / APARTMENT
    ExcellentStudio
    Airbnb
    From
    $331
  • Newly Renovated Houseboat
    Good2br Home/Apartment
    Airbnb
    From
    $259
  • Casa Verità - Glamping on the water
     Home/Apartment
    Airbnb
    From
    $246
  • Mega yacht sunset stay key west
    Good4br Home/Apartment
    Airbnb
    From
    $429

Key West Pet-Friendly Vacation Rentals

  • Tropical getaway w/private balcony, shared pool/hot tub - dog & family friendly!
    Excellent2br Home/Apartment
    HolidayLettings
    From
    $330
  • Family friendly condo w/ shared pool, hot tub & dogs ok!
    Excellent2br Home/Apartment
    HolidayLettings
    From
    $330
  • Family friendly condo w/tennis, shared pool, hot tub, & private balcony- dogs ok
    Nice2br Home/Apartment
    HolidayLettings
    From
    $330
  • Dog-friendly condo w/ shared pool and hot tub with free parking!
    Nice2br Home/Apartment
    HolidayLettings
    From
    $369

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
88° 61°
1
86° 59°
2
79° 53°
1
83° 64°
0
83° 59°
2
86° 67°
0
86° 69°
14
90° 73°
3
94° 75°
3
94° 75°
2
95° 77°
6
91° 72°
3
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Rainy days

This climate histogram shows you the weather patterns in Key West. The hottest month in Key West is April, when temperatures peak at 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

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Vacation Rentals in Key West

Browse vacation rentals from all the best providers including Airbnb, Bed and Breakfast, Priceline and others at AllTheRooms.com. We have 4,475 vacation rentals, hotels and other places to stay in Key West ranging from low-cost options to luxury places to stay. An average rental in Key West costs on average $927 per night.

Those looking to get some work finished during their trip to Key West can choose from 703 places to stay that provide WiFi. 53 of our accommodations include a breakfast in the price. You can maintain your workout routine by staying at one of 192 accommodations that provide gym facilities. Driving to Key West? Then choose one of the 662 places to stay that comes with a parking spot included. We have 572 places to stay that have a pool or jacuzzi.

If you're traveling with a furry friend, then make sure to choose one of the 235 pet-friendly accommodations available.

In Key West AllTheRooms currently aggregates hotels, vacation rentals, hostels from more than 6 providers, including 662 places to stay from Airbnb, 24 accommodations from Bed and Breakfast and 24 places to stay from Priceline.

2,129 of the accommodations in Key West have been reviewed and rated. 47% are rated great. 1,761 places to stay in are instantly bookable.

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