Key West is the place to go if you're looking for fantastic diving and snorkeling whilst maintaining all the benefits of a city break. It is ideal for any type of stay, from a weekend getaway to a longer vacation. Relish a quiet seaside break and soak up the Caribbean vibes by staying in a Key West vacation rental. Key West has it all, from tranquil seaside nooks to lively entertainment.
Choose the perfect vacation rental
Best Vacation Home Deals in Key West
5,531 amazing vacation homes from 6 providers, including FeWo-direkt and Booking.com, are available in Key West. All of the accommodations from our partner websites are instantly compared by the search engine so you can save up to 77%.
Top-Rated Rentals and Accommodations in Key West
Recommended Vacation Rentals in Key West
Find your perfect vacation rental in Key West: from $162 per night
Budget-friendly Vacation Rentals in Key West
Vacation rentals and apartments with air conditioning
Keep cool during your trip to Key West and book a vacation rental with air conditioning.
Apartments and vacation rentals with a kitchen
Cook up a feast on your next vacation and book a Key West rental with full kitchen.
Vacation rentals with Wi-Fi
Stay connected while traveling and book a Key West accommodation with high-speed internet.
Popular Rental Amenities in Key West
You will have a large selection of properties to choose from if you are looking for an accommodation offering a pool in Key West. Hotel room with pools in Key West are a fantastic choice for groups of 5 and cost, on average, $844 a night. You can also compare and find a property offering a pool near the water, which is the case for nearly all of the rentals in this destination.
Waterfront Vacation Rentals in Key West
Searching for the ideal beach vacation rental in Key West?
Try out the 'distance to water' filter during your search and find the best beach houses for your vacation. There is a variety of vacation rentals in Key West that are located within walking distance from the beach. From dog-friendly homes by the beach to waterfront rentals with jacuzzis, the perfect accommodation in Key West is waiting - discover it now via HomeToGo.
The Weather in Key West
7-Day Weather Forecast in Key West
The 10 Best Restaurants Close to Your Key West Accommodation
1. Blue Heaven
Enjoy alfresco garden dining with live music in this restaurant dishing out American, Caribbean and Mediterranean specialties. Try the Caribbean BBQ shrimp with Red Stripe beer glaze.
2. Hogfish Bar and Grill
Devour hogfish-based dishes like the "Killer" sandwich, hogfish fingers, or fried hogfish tacos in this open-air restaurant at Safe Harbor Marina. There's plenty of chilled beer and live entertainment too.
3. Bad Boy Burrito
This joint features Mexican-style organic homemade specialties like Key West pink shrimp, taco trio, ancho chili relish, and various fresh salads, smoothies, and juices.
4. B.O.'s Fish Wagon
Come to this restaurant for seafood favorites, like the grouper sandwich served on soft Cuban bread, seafood platters, and conch fritters.
Spend a special occasion in this upscale restaurant on Sunset Key. Savor the freshest fish delicacies while feasting your eyes on the beautiful sunsets outside.
6. Better Than Sex
Dig your sweet tooth into award-winning desserts like Peanut Butter Perversion, Cookie Nookie Pie and Tongue Bath Truffle. It's the ultimate in decadence.
7. Onlywood Pizzeria Trattoria
Hidden away on Duval Street, this is where you'll eat the most authentic Italian pizza around. Watch it being freshly made and baked in an oak-fired oven before digging in.
8. Matt’s Stock Island Kitchen & Bar
This restaurant is known for its classy southern and creole dishes, made using the freshest seafood. There's also great views of the water.
9. El Siboney
Sample some of the region’s best Cuban food in this old town restaurant. From spiced picadillo to the rich creamy flan, the food is full of flavor and soul here.
10. Conch Republic Seafood
Company Located in the Key West Bight district, this restaurant with attractive marine décor is famed for its seafood. Stuffed shrimp, conch fritters, and lobster tail are just a few of the many favorites.
More Information About Key West Cuisine
Cuisine in Key West is a tantalizing mix of Bahamian, Cuban, and New England influences, drawing on the best the sea has to offer. Key West is known affectionately as the "Conch Republic." This mollusk is served in salads, chowders, and as part of main courses.
Do not leave any restaurant without sampling the famous Key lime pie, a sinful concoction of condensed milk and Key limes perched on a Graham cracker crust and topped with decadent whipped cream.
Sunshine Year Round
Key West is a year-round travel destination, as it is blessed with a tropical climate similar to the Caribbean. The coolest month is January and the hottest is July. The island has two main seasons: wet (May to October) and dry (November to April).
History and More
Apart from diving, swimming, snorkeling, and water-based activities, there is plenty to see on land. Visit the attractive Old Town with its pastel-hued, conch-style houses, and don't forget to check out the Fort Zachary Taylor. The latter is a historic state park that is now used as a venue for events such as Civil War reenactments.
Stop at Mallory Square, a plaza known for its "Sunset Celebration." People gather here to view arts and crafts, eat from food carts, enjoy street performances, and watch the remarkable sunset. The New Town, which is on the east side of the island, features malls, shopping centers, schools, and residential zones.
Another famous attraction in Key West is the replica of a buoy made from concrete located at South and Whitehead Streets, which marks the "southernmost point" of the Continental USA.
Key West Culture
When it comes to culture and history, Key West has so much to offer. Explore the Audubon House and Tropical Gardens, a museum dedicated to the American painter, naturalist, and ornithologist John James Audubon.
Another must-visit for art enthusiasts is the Studios of the Key West, a community for artists which comprises work spaces, an exhibition hall, sculpture garden, and houses and cottages. An excellent program of performances, talks, and concerts is sure to cater to all tastes and interests.
In addition, be sure to check in advance if there are performances by the Key West Contemporary Dance Company, based at the Waterfront Playhouse. The Tennessee Williams Theater is another cultural hotspot, with a program packed with dance, theater, and musical performances.
8 Must-See Attractions in Key West
1. Key West Nature Preserve Park
If you're ready to leave your vacation home to enjoy some fresh air, head to this beautifuly preserved corner of town to enjoy a short hike through a lush mangrove forest.
2. Key West Marine Park
If your kids love swimming and snorkeling, look no further than this protected underwater park that stretches across 40 acres. Its two beaches are the perfect place for patient parents to relax while the kids enjoy the water.
3. Harry S. Truman Little White House
The winter White House for former president Harry S. Truman is a great place to learn about Key West's history. Local guides add color to the experience with their anecdotes.
4. Ernest Hemingway Home and Museum
Learn about the literary icon's numerous romantic relationships, friendships and writings through a guided tour of his erstwhile residence.
5. Dry Tortugas National Park
Seventy miles from Key West, this secluded park is home to Fort Jefferson, wild birds, coral reefs and marine life. It's the ideal location for a camping excursion.
6. Key West Butterfly and Nature Conservatory
Kids in particular will love this conservatory where nearly 60 species of butterflies thrive in a climate-controlled, glass-enclosed habitat.
7. Florida Keys Eco-Discovery Center
With such rich marine diversity in this part of Florida, it is only natural that Key West boasts a top-quality discovery center. Interactive displays about reefs and mangroves help visitors learn more and connect with nature.
8. Astro City
One of the most popular playgrounds in town located just across from Higgs Beach, Astro City is a great location for your kids to make new friends and precious memories.
The 3 Best Beaches Near Your Key West Vacation Home
1. Smathers Beach
Boasting close to 2 miles of shoreline, this mangrove-fringed beach is great for families. There's lots of swimming, parasailing, kayaking, and snorkeling opportunities.
2. Fort Zachary Taylor State Park
Beach Visitors often come here for sunbathing and snorkeling. Walk, run, or bike on the various nature trails. Take a guided tour of the pre-Civil War vintage fort on the grounds.
3. Rest Beach
Although only less than 1,000 feet long, the beach promises a tranquil experience. Visit here on early mornings for spectacular sunrises and beautiful views of the Atlantic. The beach also features a yoga deck where classes are held.
5 Important Events Worth Visiting for
1. Super Boat Races
Key West rentals fill up fast in the fall, when the annual Super Boat International World Championships take place. Races last for 3 days, while events go on for 7 days. Hire your own private boat to enjoy the races right on the water. Admire the powerboats on display during the Duval Street Party, and participate in fun parties and parades.
2. Half Marathon
Another good time to visit is during the Key West Half Marathon, held in balmy mid-January. Get your running shoes on for this scenic race covering the region’s historic Old Town and the beautiful waterfront.
3. Fantasy Fest
Held every last week of October, live music from different genres and fancy costumes are at the core of this event. Book your accommodation in advance if visiting during this 10-day event. This adults-only event has been held every year since 1979. Be a part of the merrymaking, filled with creative costumes, libations, and parades.
Celebrate summer with fresh lobster, great drinks, and live music during this 4-day festival. Sample delicacies like Caribbean lobster ceviche, grilled lobster, lobster rolls, and much more.
5. Fourth of July in Key West
Every year, the island hosts a Key Lime Festival which includes five days of cooking classes, culinary tastings, unique cocktails, and scavenger hunts. The festival ends on the Fourth of July with a Key Lime Pie eating contest and fireworks at the White Street Pier. Travelers will also get the chance to visit Ernest Hemingway's house and the Southernmost Point of the Continental US.
Self-catering in Your Key West Vacation Rental
One of the best ways to experience the island is to stay in a Key West vacation rental. You will have lots of room if you are traveling with family or friends, as well as complete privacy. What's more, you can enjoy that home-away-from-home feeling and unwind after a long day of exciting activities.
Most Key West vacation rentals also come with a fully fitted kitchen, allowing you the flexibility to cook at home when it suits you.
Frequently Asked Questions
How many holiday homes are available to book in Key West?
September has the highest amount of available House rental and Apartment rental in Key West, so you can expect plenty of offers, even for last-minute bookings.
What amenities are most popular for holiday homes in Key West?
Travelers look for Internet, TV, and Pool when booking a vacation rental in Key West.
Are pets allowed in vacation rentals in Key West?
If traveling with a dog in Key West, 20% of vacation homes are pet-friendly.
What's the best month to travel to Key West?
The warmest months in Key West are August and July, with temperatures around 89 °F. The coldest months in Key West are January and February, with 65 °F on average.
We list offers from thousands of providers, including:
Vacation Destinations Near Key West
Cudjoe Key Vacation Rentals
Big Pine Key Vacation Rentals
House Rentals in Marathon
Key Colony Beach Vacation Rentals
Duck Key Vacation Rentals
Long Key Vacation Rentals
Vacation Rentals in Islamorada
Tavernier Vacation Rentals
Vacation Rentals in Key Largo
Condos in Marco Island
Homestead Vacation Rentals
Condo & House Rentals in Naples
Vanderbilt Beach Vacation Rentals
Kendall Vacation Rentals
North Naples Vacation Rentals
South Miami Vacation Rentals
Condos in Coral Gables
Vacation Rentals in Bonita Springs
Doral Vacation Rentals
Key Biscayne Vacation Rentals
Top Vacation Ideas
- South Padre Island Spring Break Hotels & Vacation Rentals
- Valentines in New York City
- Miami Spring Break Hotels & Vacation Rentals
- Valentines in Japan
- Texas Spring Break Vacation
- Romantic Getaways in Ohio
- Valentines in Spain
- Valentines in Chicago
- Romantic Getaways in Florida
- Romantic Getaways in Texas
- Valentines in Mexico
Explore More Vacation Ideas
Cabins with Hot Tubs in Wisconsin
Nashville Hotels & Vacation Rentals for the 4th of July
Lake House Rentals in Indiana
Spring Break in Corpus Christi
Must-See Events in Massachusetts
North Carolina Cabin Rentals
San Francisco Hotels & Vacation Rentals for New Year's Eve
Valentines in Orlando
Florida 4th of July Vacation
Seattle Monthly Rentals
Hotels in Denver
Branson, MO Cabin Rentals
Family Vacation in Washington D.C.
Denver Hotels & Vacation Rentals for the 4th of July
Romantic Getaway in Maine
Weekend Trip Ideas in Cincinnati
Detroit Hotels & Vacation Rentals for New Year's Eve
Spring Break Destinations East Coast
Cabins with Hot Tubs in West Virginia
Romantic Getaway in Mississippi
Destin Spring Break Hotels & Vacation Rentals