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You can easily book both your car rental and flight through Expedia, and while you're at it, be sure to sign up for their OneKey Rewards program. You’ll enjoy discounts, exclusive deals, and earn points and a 10% discount on your next stay right off the bat. It's too great of an offer not to share, especially if you're planning to book your flight, stay, and car rental all through Expedia (And Vrbo's count!)

And with that, let's dive in!

Key West Oasis Cottage

2 Bedroom | 2 Bath | Sleeps 4

Right out the gate with a stellar Key West Oasis is a charming 2-bedroom, 2-bath retreat located in the heart of Old Town, Key West. Guests rave about the property’s private heated pool, secluded patio, and relaxing atmosphere. With its clean, well-maintained space, it’s perfect for two couples or families with older children. The newly renovated 1906 cigar maker’s cottage features original Dade County pine and a separate private cottage with a beautiful open-air shower.

Chick-a-Pea Cottage

4 Bedroom | 2.5 Bath | Sleeps 8

This charming Key West cottage is the ideal spot for a relaxing getaway, just steps away from Duval Street and other local attractions. Another perfect 10/10 Vrbo, guests rave about the immaculate property, featuring a private pool with a tranquil waterfall, a cozy cabana, and a spacious, open living area. The cottage is surrounded by lush bougainvillea and palm trees, offering a peaceful retreat. With a modern kitchen, a cozy outdoor space, and prime location near shops and restaurants, this home is a true slice of paradise in Old Town

The Southernmost Belle

5 Bedrooms | 4 Baths | Sleeps 10

The pictures alone will make you fall in love this property ❤️Southernmost Belle is a stunning 3-story private retreat in Old Town Key West, praised for its quiet oasis feel, elegant décor, and immaculate cleanliness. This home offers a private heated pool, expansive porches, and lush tropical landscaping, offering the ultimate space for relaxation. Just steps away from shops, restaurants, and attractions downtown. Concierge services include bike, scooter, and golf cart rentals, along with a wide range of excursions like snorkeling, sunset cruises, jet skiing, parasailing, kayaking, fishing, paddle boarding, and more. They can even stock your fridge with essentials before your arrival.

Casa Victoria

5 Bedroom | 5.5 Bathroom | Sleeps 12

Casa Victoria is a charming, 3-story historic home in Old Town, just two blocks from Duval Street. Guests rave about its perfect location, with easy access to restaurants, theaters, and nightlife. The private pool and hot tub are highlights, offering a relaxing retreat after a day of exploring. The spacious indoor and outdoor living areas make it ideal for groups, with plenty of room for everyone to gather.

~ MAISONS de LUXE ~ 2 Stunning Homes

6 Bedroom | 6.5 Bathroom | Sleeps 12

Maisons de Luxe offers an exceptional retreat in Key West, perfect for larger groups or families. This stunning property features a spacious two-story main house and a stylish cottage, each thoughtfully designed with a well-laid-out floor plan and beautifully appointed interiors. Guests rave about the peaceful ambiance despite being on bustling Duval Street, with highlights including a private saltwater pool, gazebo, and lounge area. Bedrooms with en-suite bathrooms ensure comfort and privacy for all, while the open living spaces are ideal for entertaining. With its prime location and attention to detail, this home provides the ultimate Key West experience.

*Bonus Vrbo's*

Honorable Mentions

Although these Vrbo's don't have private pools, they are still highly rated, aesthetically designed, and are conveniently located in the heart of Key West.

Darling Duval

2 Bedroom | 2 Bathroom | Sleeps 4

Experience the charm of Key West from the Darling of Duval, nestled in the heart of Old Town. Guests rave about the ideal location, just steps from Duval Street, yet tucked away in a quiet estate with beautiful grounds. This unique two-story guest cottage features kitchenette suites (Not fully equipped kitchens) , a private patio with a jacuzzi, and all the comforts of home. Whether you're unwinding in your jacuzzi or exploring nearby attractions, this peaceful oasis offers the perfect blend of privacy and convenience.

Sparkling Old Town Lagoon Vrbo

3 Bedroom | 2 Bathroom | Sleeps 6

**It is also important to note that this Vrbo can only be booked for a 28 day minimum and is priced accordingly. This rental is best suited for snowbirds, digital nomads, business trips, and other visits of a longer term nature.**

Sparkling Old Town is a peaceful, beautifully maintained home in the heart of Key West, just 2 blocks from Duval Street. Enjoy the serene setting with lush palm trees, a stunning serpentine saltwater lazy river, and a large pool area. Located near Hemingway House, Blue Heaven, and top dining spots, it's ideal for a quiet retreat with easy access to attractions. Guests rave about the serene atmosphere, spacious living areas, and vibrant decor. Book your stay and discover your "happy place!"

Conclusion

Key West offers a diverse range of Vrbo homes with private pools, each providing a unique blend of style, comfort, and prime location. Whether you're seeking a peaceful retreat surrounded by tropical beauty or a luxurious base close to Key West's top attractions, these homes deliver an unforgettable experience. From cozy cottages to sprawling estates, these properties provide the perfect balance of relaxation and adventure to immerse yourself in the charm of Key West.

If you're looking for fun activities in Key West, be sure to check out my Ultimate Key West Couples Guide Blog. You can also explore my Key West Getaways Board on Pinterest for more Key West-focused pins that will help you plan a seamless and memorable trip. Finally, if you're still debating on whether or not you should book a hotel or Vrbo, read my Best Resorts in Key West Blog for more variety!

Other Helpful Articles For Your Trip From Fellow Travel Bloggers

The Ultimate Key West Food Guide

- by Jenessa

5 Best Spots to See a Key West Sunset

-by Tam

How to Day Trip to Dry Tortugas

-by Amanda

16 Best Stops From Miami to Florida

-by Victoria & Terrence

All of these blogs can also be easily accessed on

my Key West Getaways Board on Pinterest

God Bless

-Alinea