Best VRBO Rentals in Key West

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Contributor, Benzinga
December 13, 2022

Quicklook: Best VRBOs in Key West, Florida

At the very tip of Florida, on a tiny island measuring just 2 miles by 4 miles, is Key West, the southernmost point of the United States. It’s connected to the other Florida Keys and the Florida mainland via the Overseas Highway. Key West is notorious for its beaches, historic sites, vibrant nightlife, watersports and pastel conch-style architecture — making it the perfect vacation destination. Whether you’re planning a long, relaxing stay or a last-minute getaway, these are some of the best VRBOs in Key West. 

Escape to a True Tropical Garden Oasis in Casa Marina

Casa Marina is known for its luxurious and spacious homes, and the Garden Oasis is no exception. This beautiful four-bedroom, tropical-themed home features furnishings that are both stylish and functional, a covered wrap-around front porch and a rear lanai, giving you several vignettes to lounge, read, relax or entertain. Relax in the heated pool, which is surrounded by a sunny patio ideal for catching some rays.

Best For: Relaxing Tropical Escape   

Unique Features:

  • Fenced-in backyard
  • Pet friendly
  • Sleeps eight
  • 10,000-square-foot property

Enjoy Panoramic Ocean Views in a Midtown West Beachfront Condo

1800 Atlantic is a spotless three-bedroom condo with stunning ocean views from every window. Located in the heart of Midtown, this condo is on the beach. In addition to the on-site amenities like a grill, wrap-around patio and pool, guests are within walking distance of the nightly Sunset Celebration at Mallory Square. 

Best For: Oceanfront view

Unique Features:

  • Sleeps up to eight 
  • Beachfront condo
  • Panoramic ocean views 
  • Jet tubs in every bathroom

Stay Near the Action or Relax by the Pool in a Spacious Midtown East Two-Story

Comfort, privacy and a distinct sense of tropical style are all present in Perfect Harmony. This zen, two-story home features a private office, a fenced-in backyard and a covered porch that overlooks the pool. This stunning Midtown East home is located just two blocks from the beach and less than a mile from Old Town, so there are plenty of entertainment options. 

Best For: Pet-friendly home near the action

Unique Features:

  • Pet friendly
  • Located near restaurants, clubs, beaches, shopping
  • Private office
  • Split floor plan

Experience a Luxury Getaway in Sunset Key

Enjoy a dream getaway in this gorgeous beachfront home on the exclusive Sunset Key island in the heart of Key West Harbor. The elegant villa is tastefully decorated and offers guests a private pool and hot tub as well as stunning views of the ocean. It features a chef's kitchen with a breakfast bar, two roomy bedrooms, 2.5 bathrooms, a dining area and a sizable living room. The main-floor master suite has a view of the water. It’s located next to a private beach, and 24-hour ferry access is available. 

Best For: Luxurious beachfront property

Unique Features:

  • Private beach
  • Pool, deck and built-in grill for entertaining 
  • Elegant decor 
  • Pet friendly 

Soak in the History of the Meadows Key West at this Cozy Home Away From Home

Enjoy the sunshine in this bright historic Key West home. Built in 1945, the house has been meticulously restored and offers modern visitors an array of amenities. High vaulted ceilings and central air conditioning work together flawlessly to create a sunny atmosphere that perfectly captures Key West. Each bedroom has a ceiling fan to keep it cool and airy along with an en suite bathroom for convenience. The home's main bedroom has a direct exit to the back deck, where you can relax in the private hot tub. The outdoor covered dining area and grill make it easy to enjoy a delicious meal at home. 

Best For: Cozy home for history lovers

Unique Features:

  • Historic home
  • En suite bathrooms 
  • Covered outdoor patio
  • Security cameras

Catch Some Rays on the Deck of a Truman Annex Key West Townhouse

Located in the prestigious gated community of the Truman Annex, this quiet townhouse makes the ideal vacation home for a couple or small families. Green Bamboo’s central location offers easy access to all of Key West's attractions via short walks or bicycle rides. The home features everything you need to make your stay comfortable and enjoyable in the newly renovated kitchen and bathroom. Have dinner or drinks on the rear patio or people-watch on the front porch. The upper deck off the master bedroom is also a great place to enjoy your morning coffee.

Best For: Sunny townhouse for small families

Unique Features:

  • Multiple decks
  • Central location
  • Gated community
  • Newly renovated

Embark on a Tranquil Getaway in this Charming Old Town Cottage 

Families and small groups of friends who want a cozy place to stay close to some major attractions will love Puerta Coralina. Some of the best spots for dining, shopping and entertainment can be found just a short stroll from the property on the renowned Duval Street. The property can accommodate up to six people. The outside spaces feature a front porch, fenced-in yard and plunge pool. 

Best For: Cottage in the heart of Old Town

Unique Features:

  •  Plunge pool
  •  Walking distance to popular destinations   
  •  Furnished deck
  • Spacious rooms

Experience True Coastal Bliss in a Stunning Key Haven Home

Coastal Bliss is a luxury home with a tropical touch located in the prestigious Key Haven Estates. The four-bedroom, four-bathroom home’s open concept floor plan is perfect for entertaining or spending quality time with the family. Go for a swim in the heated pool or catch some fish off the private dock. 

Best For: Luxury living for large families or groups
Unique Features:

  •  Heated pool
  •  Private dock
  •  Sleeps up to 12
  •  Pet friendly 

Embark on an Adventure in a Conch-Style Old Town Home

With glowing recommendations from previous guests, this conch house in the Old Key West style promises to be the ideal getaway spot. The home features a sparkling private pool with a lazy river and lush backyard. The inside of the home is clean, bright and colorful to embrace the true essence of Key West. With its proximity to Duval Street and the Hemingway House, it would be difficult to find a better place to stay on the island. Bicycles are even included in the stay.

Best For: Conch-style home with outdoor amenities 

Unique Features:

  •  Bicycles to use
  •  Lagoon 
  • Exceptional ratings   
  • Two-story home

When is the best time to stay in a vacation rental in Key West

Key West's peak tourist season is in March. The weather is great, with daily highs of 75°F and low humidity. The drawback is that lodging and travel costs will go up. In August and September, the island will have a more relaxed and laid-back atmosphere. You can expect to pay less in these months as well. 

6 Fun Things to Do in Key West

With tons of must-see sights and fun activities, there’s no shortage of things to do in Key West. 

Experience a Sunset Sail

If you’re looking for an unforgettable sunset, go for a sunset sail or boat cruise. A variety of options that offer dinner, drinks and live entertainment are available. Prices vary, but expect to pay about $90 per person for a two-hour sail. 

Rent Jet Skis

Thrill-seekers can experience the island via jet skis. Opt for a guided tour or rent the jet skis to explore on your own. Numerous companies in the area offer jet ski rentals. Some jet skis can accommodate three people. Expect to pay between $100 and $170 for a daily jet ski rental.

Explore the Island

The island is filled with tons of attractions to keep you occupied day and night. Check out the interactive Key West Aquarium — open daily, rain or shine. You’ll also want to visit Mallory Square, which is a well-known waterfront plaza that hosts the daily Sunset Celebration and is home to a variety of shops, restaurants and a sculpture garden. Every evening, large crowds of locals and tourists congregate to watch the sunset while being entertained by street performers. If you love American history, there are plenty of cool stops, including the Harry S. Truman Little White House or the Ernest Hemingway Home & Museum. If you’re looking for a quiet area with an old Key West feel, Stock Island is a charming location to experience true local life. 

Fishing Tours

Fish like never before as you sail through the beautiful blue waters of Key West on a charter boat. Private charters range in price from $600 to $1,600 per group.  

Food and Bar Walking Tours

Key West Food Tours was voted the No. 1 food tour in the area. Different food and walking tours are available, such as the Historic Seaport Food & Cultural Walking Tour and the Hemingway Experience. Prices range from $75 to $150 per person. 

Snorkel Through the Reef

Snorkeling is very popular in Key West because it is home to North America's only living coral barrier reef. Key West Dolphin Watch and Snorkel Cruise combines dolphin viewing with snorkeling for $75 per person, with equipment rental and soft drinks included in the price. 

Key West Butterfly and Nature Conservatory

Take a stroll through the towering glass-domed tropical butterfly habitat to see hundreds of free-flying butterflies, exotic birds and two magnificent flamingos at the Key West Butterfly & Nature Conservatory. It was named Best Attraction in Key West and Best Place to Take the Kids. Admission is around $12 for kids ages 4 and up and $14 for adults. 

Dry Tortugas National Park

It is definitely worthwhile to visit Dry Tortugas National Park because of its fascinating history and distinctive marine environment. The breathtaking Dry Tortugas National Park is at the southernmost point of the Florida Keys. It safeguards seven magnificent Dry Tortugas Islands.

Ideal Vacation Spot for Couples and Families

Key West is the perfect vacation destination for anyone who loves the beach and the outdoors. There’s plenty to see and experience on this beautiful Florida island. Regardless of which area of Key West you stay in, there are family and pet-friendly VRBOs to meet your needs.

Frequently Asked Questions


What is Key West best known for?


Key West is best known for being the southernmost point of the United States. It is famous for its beaches, historic sites, vibrant nightlife, watersports and pastel conch-style architecture.


How long should you spend in Key West?


A day trip to Key West is worthwhile, but the more time you have there, the better. Although three to four days are ideal if you want to see everything and still have time to unwind, you could easily spend a week in Key West.


What is the best month to go to Key West?


March through May are the ideal months to visit Key West. The temperatures are in the 70s and 80s, and the winter crowds will start to thin out.