Key West Condos & Vacation Rentals

Our Favorite Vacation Rentals in Key West

  • Quiet Tropical Town Home | Great Location and Amenities!
     Townhouse
    RedAwning
    From
    $652
  • Southern Palms
     Country House
    Booking.com
    From
    $351
  • Houseboat Trawler MV Coconuts: Once in a Lifetime Vacation With Pool Access
    Good3br Boat
    HolidayLettings
    From
    $665
  • Quiet Town Home Just a Stroll from all the Action | 3 Pools On-Site
     Townhouse
    RedAwning
    From
    $652
  • Rose Lane Villas
     6br Country House
    Booking.com
    From
    $629
  • Spacious 3BR/3BA Catamaran as Private Sailing Charter up to 7 nights in Key West
    Excellent3br Boat
    HolidayLettings
    From
    $2,462
  • Dog-friendly studio w/ private deck & hot tub - 1 block to Duval St!
    Good-1br Studio
    HolidayLettings
    From
    $538
  • Rustic Sailboat in Key West! Enjoy Ocean living.
     Home/Apartment
    Airbnb
    From
    $168

Check prices for these upcoming dates

Key West Vacation Rentals with a Pool

  • 2BRPrivateBeachHouseResortOasis 3-6K /WeeklyRental
     2br Home/Apartment
    Airbnb
    From
    $791
  • Houseboat Trawler MV Coconuts: Once in a Lifetime Vacation With Pool Access
    Good3br Boat
    Airbnb
    From
    $684
  • 2BR Sunset Harbor Oasis in the Heart of Key West
     2br Home/Apartment
    Airbnb
    From
    $1,003

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

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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
83° 54°
2
85° 64°
1
85° 62°
2
87° 67°
2
94° 74°
4
93° 75°
1
93° 74°
3
94° 76°
4
92° 76°
4
89° 75°
4
88° 67°
1
85° 61°
8
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Rainy days

This climate histogram shows you the weather patterns in Key West. The warmest months in Key West are May and August, when temperatures reach 94 ˚F. The coolest month is December, when temperatures drop to 54 ˚F. The wettest month in Key West is January with 7.71 inches of rain, while the driest month is July with 0.88 inches of rain.

What Expert Travelers Think

  • — Site is easy to use; clean, laid out well, good colors and branding, fun logo and title that connects to the purpose of the brand. The blog, vacation destinations, and rental destinations is a great feature and really make the brand stand apart from other sites!

    Laurelle McVicker
    Laurelle McVickerLaurelle McVicker
  • — 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 how AllTheRooms shows a map with room price tags straight away when you search, it makes it so quick and easy to choose the right hotel, at the right price in the right location. Perfect for those with busy lifestyles! The AllTheRooms website is so user friendly. WiFi. Brilliant!

    Amanda Alston
    Amanda AlstonAmanda Alston

Vacation Rentals in Key West

At AllTheRooms.com we have accommodations from all of the leading providers - Airbnb, Priceline, Agoda and many more. Key West has 3,854 hotels, vacation rentals and other unique places to stay, with prices to suit careful travellers, luxury travelers and everything in between. The average price of a rental is $935 per night.

If you would like to stay connected during your trip, then you can choose from over 679 accommodations in Key West that have WiFi. 46 of our accommodations include a breakfast in the price. Choose from 195 places to stay that provide gym facilities, so you don't miss a single workout. Driving to Key West? Then choose one of the 616 places to stay that comes with a parking spot included. We track 574 accommodations that have a pool or jacuzzi.

AllTheRooms has 265 pet-friendly places to stay in Key West, so if you're traveling with your pet you won't have any trouble.

In Key West AllTheRooms currently aggregates hotels, vacation rentals, hostels from more than 6 providers, including 637 places to stay from Airbnb, 17 accommodations from Priceline and 17 places to stay from Agoda.

2,123 accommodations in Key West have been reviewed; 50% are rated highly. 1,497 places to stay in are instantly bookable.

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