Our research is editorially independent but we may earn a commission for purchases made through our links.

Top 10 Vrbo Rentals in Key West

The southernmost city in the contiguous United States, Key West is the perfect vacation spot for those who want to relax and have fun in the sun. Known as the Conch Republic, Key West has always been a place where artists, musicians and those who might not have been accepted in other communities have called home. Located 165 miles south of Miami and only 100 miles north of Cuba, heading to Key West sometimes feels like being in another world. Home to historical homes, a naval air base, state and national parks, unique restaurants and breathtaking sunsets, Key West has a little something for everyone. Here are some of top Vrbo rentals in Key West that are great for couples and large groups alike.

Casa Loca - One of a Kind Estate Half Block From Duval Casa Loca
Credit: Casa Loca by www.vrbo.com

Casa Loca - One of a Kind Estate Half Block From Duval

An open floor plan, living room, dining room, galley kitchen and breakfast nook make this 3 bedroom, 2.5 bathroom home a welcoming place to make your home base when staying in Key West. Located less than a half a mile from Duval Street, you’ll be close to all of the action. And when you’re ready for some downtime, spend time in the heated, private swimming pool or sit on the front porch to enjoy a drink and relax. 

The Palms - A Beautiful Space in the Perfect Place The Palm living area
Credit: The Palm living area by www.vrbo.com

The Palms - A Beautiful Space in the Perfect Place

Located on the second floor in the historic Truman Annex Shipyard complex, this two bedroom, one bathroom condo has a balcony to sit on and enjoy a glass of wine. Located around the corner from Fort Zachary Taylor State Park and Beach and the Truman Waterfront Park, the condo also is within close proximity to Duval Street and Bahama Village so you won’t miss out on any of the action. There’s also a small kitchen with refrigerator, oven and sink to make quick meals or a cup of coffee. 

Island Pearl - Cozy Nightly Rental in the Heart of Key West Island Pearl
Credit: Island Pearl by www.vrbo.com

Island Pearl - Cozy Nightly Rental in the Heart of Key West

Within walking distance to restaurants, bars and shops but secluded behind the main house, this first floor unit is cozy with a living area and loft for its main sleeping area. Sleeping three, this one bedroom, one bath has an outdoor deck and shared pool to relax in after exploring the island.

Atlantis House's Garden Suite - Voted Top 25 in USA Atlantis House's Garden Suite
Credit: Atlantis House's Garden Suite by www.vrbo.com

Atlantis House's Garden Suite - Voted Top 25 in USA

This one bedroom, one bathroom bungalow is perfect for a romantic getaway for two. The French doors open to the outside world while the loveseat and living area let you cuddle up and get cozy. The sleeping area has a queen sized bed and the bathroom has a two-person Jacuzzi tub, open shower design and nine-foot vaulted ceilings. There’s also a small wet bar area with a mini fridge, microwave and coffee maker. Within walking steps of the beach, the bungalow is also close to attractions and less than one mile from Duval Street.

Darling of Duval at Old Town Estate Cottage + Spa Darling of Duval
Credit: Darling of Duval by www.vrbo.com

Darling of Duval at Old Town Estate Cottage + Spa

Less than a mile from Fort Zachary Taylor Historic State Park’s beautiful beaches and in the middle of the top sightseeing spots and restaurants of Key West, this two story, two bedroom, two bathroom cottage sleeps four in the middle of Old Town. A private hot tub, BBQ and patio give you outdoor living space while each bedroom is on it’s own level and has its own kitchenette so couples can stay together but still have their own privacy. There’s also on-premises washer and dryer and, a rarity in Key West, an off street parking spot for visitors.

Bonaire Suite - A Beautiful Island Retreat with Shared Pool in Gated Compound Bonaire Suite
Credit: Bonaire Suite by www.vrbo.com

Bonaire Suite - A Beautiful Island Retreat with Shared Pool in Gated Compound

Enter the courtyard of this gated compound and you’ll forget you’re only a half block from the parties and entertainment of Duval Street. With two beds and a sofa bed, it can sleep six people and you can also enjoy the shared pool and lots of tropical plants and flowers when not in the one bedroom 1.5 bathroom cottage. No car is needed since all of the island’s activities are within walking or biking distance.

El Corazon Renovated Home with Direct Access to Duval St. with Pool & Parking El Corazon Living Area
Credit: El Corazon Living Area by www.vrbo.com

El Corazon Renovated Home with Direct Access to Duval St. with Pool & Parking

Finding a larger home in the heart of Key West isn’t easy. At 2,300 square feet, this five bedroom, 3.5 bathroom gated home is a wonderful surprise for those who want to bring their entire family to enjoy the island. The open concept living area downstairs allows everyone to sit and dine together while the sitting area upstairs offers an additional area if the kids want to watch television or play games. The porches allow you to open the doors to the living and sleeping areas while the dip pool lets you rest your weary feet after walking around all day. Less than a half mile from Duval Street, the Ernest Hemingway House, the Key West Lighthouse and other activities, you and your friends and family will be right in the action, but still have plenty of room to relax after your day is over.

Steps From Duval St. Historical Charm Meets Modern Design in Old Town Key West Steps From Duval St Home
Credit: Steps From Duval St Home by www.vrbo.com

Steps From Duval St. Historical Charm Meets Modern Design in Old Town Key West

Everyone goes to Key West for the fun and nightlife but you might not feel like leaving this home once you get in. A large pool with water feature and ambiance lighting set the tone for the almost 2,000 square foot home. A six-foot privacy fence ensures you won’t have to see the neighbors and plenty of tropical plants fill the backyard. But it’s not only about the outdoor space. This three bedroom, three bathroom home has a living area, dining area, den with pullout couch and full chef’s kitchen. When you’re finally ready to leave the house, you’ll find you’re close to everything fun and exciting Key West has to offer.

Real World MTV House - Not Just a House Your Own Private Resort Real World MTV House
Credit: Real World MTV House by www.vrbo.com

Real World MTV House - Not Just a House Your Own Private Resort

Ready for a place to bring friends and family and have your own secluded resort living? With over 6,000 square feet of living space and 500 feet of oceanfront access, this 10 bedroom, 5.5 bathroom house is the property where MTV’s Real World Key West was filmed. So you’ll be sleeping in the steps of television history! You’ll never need to leave the property with its pool, tennis court, paddle boards, bikes, kayaks, basketball court, boat dock and plasma TVs throughout. Perfect for a family reunion, bachelorette party or business retreat.

Solaris Garden Enjoy Old Town Living in a Perfect Location Solaris Garden
Credit: Solaris Garden by www.vrbo.com

Solaris Garden Enjoy Old Town Living in a Perfect Location

Are you ready to explore Key West on a romantic couple’s getaway? Lay your heads in this cozy one bedroom, one bathroom home right in Old Town. A true artist’s cabin, it features a kitchen with full sized refrigerator and stove, walk-in shower and shared deck area with a grill and washer and dryer. There are plenty of activities and restaurants within walking distance and Mallory Square, where you can see spectacular sunsets every night, is only a five-minute bike ride away.

Travel Deals

5-Nt Dominican Daze Cruise | 70% Off 2nd Guest

$168+ pp/pn

7-Day Mediterranean Cruise w/ All-Inclusive Upgrade

$2499+

7-Nt Alaska Celebrity Cruise | Up to 75% Off 2nd Guest

$306+

Air & 7-Day Italy Guided Tour: 5 Cities & 9 Meals

$2399+

Air & 9-Day Essential Spain Guided Value Group Tour

$1999+

7-Day Costa Rica & Panama Canal Cruise w/ All-Inclusive Upgrade

$2899+

7-Day Irish Pub Tour in Luxe Vehicle w/ Private Driver

$2199+

8-Day Ireland Home of Thrones Tour w/ Rental Car

$1683+

Air & 14-Day Small Group Tour of Rajasthan, India

$1699+

7-Day Tahiti Cruise w/ All-Inclusive Upgrade

$2999+

The Yucatan | Adults-Only All-Incl. Playa del Carmen

$95+ pp/pn

Air & 12-Day New Zealand Vacation w/ 9 Tours

$4599+

Escape to Greece | 7 to 12-Day Tours w/ Airfare

$1799+

$100 Off | Air & 11-Day Scandinavia Guided Tour

$3699+

7-Day Independent Tour of Edinburgh & London

$1599+