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Best VRBO Vacation Rentals In Key West Old Town, Florida

Best VRBO Vacation Rentals In Key West Old Town, Florida
Melissa
Melissa
Published

Welcome to the historic district of Florida–Key West Old Town. Those who love history can now travel back in time when they go to this town full of stories and experiences waiting to happen. Whether you’re looking for a historical adventure, unique and nostalgic nightlife, or some novel shopping finds, Key West Old Town has it all that it’s easy to see why it is becoming more popular with the tourists every year. But before the place gets too popular with the tourists, don’t miss out on your chance to explore this lovely town and book your flight to Florida now. Keep on reading for our list of the best VRBO accommodations in Key West Old Town, Florida.

1. Classic condo in Key West's Truman Annex (from USD 328)

If you’re all about the interiors, this classic condominium unit in Key West’s Truman Annex is sure to make it on your list. This unit is quiet yet its colors are loud and will make you feel like you just traveled back in time. With one bedroom and one bathroom, it can accommodate two people. Although there is a minimum stay of seven nights, you won’t even notice as there’s plenty of action from the block on Duval Street. You can also use their bicycles to get around the area for those who are tired of walking.

Condo in Old Town Key West's Truman Annex - Pool, Bicycle, Free Parking and WiFi
106-9 Southard Street
139 reviews
condo 2 guests 1 bedroom 1 bathroom

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2. Tropical-style unit in Duval Street (from USD 100)

If you love the bright tropics, then you’ll definitely love this tropical-themed condominium unit located in Duval Street. Complementing its neighborhood, this apartment is exciting as it looks. It is complete with a fully equipped kitchen, central air conditioning, washer and dryer, balcony, and has two queen-sized beds in its two bedrooms. The bedrooms have closets and fancy tables, lamps, and ceiling fans. The best part? All the fun places to shop and dine are just around the corner.

Beautiful Duval St. Condo, Location, Location!!!!
615 Duval St
117 reviews
condo 5 guests 2 bedrooms 1 bathroom

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3. Condo close to the beach (from USD 100)

Beach lovers are going to love this condominium unit exactly near the beach. The Conch Retreat Condominium is a luxurious building located in the heart and center of Old Town that everything is conveniently near. Guests won’t ever get tired of exploring and walking along the historic district with plenty to see and do. But if they do get tired, they can always use the bikes provided by the property. This accommodation can fit up to four people in two bedrooms and one private bathroom.

Truman Annex Condo, Close to Beach & Duval with 2 Bikes, Upper level, Free WIFI!
620 Thomas St
105 reviews
condo 4 guests 2 bedrooms 1 bathroom

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4. Grand mansion for eight (from USD 1510)

Traveling with your friends and family? Book this beautiful and lush grand mansion that can sleep up to eight people in six bedrooms and five-and-a-half bathrooms. Although there is a minimum stay of six nights, you’re sure to love this private mansion that you won’t even notice time passing by. Located in an exclusive private residential community, Truman Annex, you will never have to worry about crowds in this neighborhood. The entrance is secured and gated and only guests can pass through. It is also fully furnished with all your needs–comfortable beds, private pool, and a beautiful backyard for socializing.

<< NOONA'S MANSION @ THE ANNEX >> Grand Private Home & Pool + LAST KEY SERVICES...
504 Noah Lane
89 reviews
house 8 guests 6 bedrooms 6 bathrooms

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5. Rustic townhouse for four (from USD 165)

If you’re looking for a more peaceful and private vacation, you have to stay in this rustic townhouse just located in Truman Annex. Other than it being located in a quiet neighborhood, guests are sure to love the design of this townhouse. They have a private bedroom balcony and living area perfect for sipping coffee in the morning or just chatting with some friends. The townhouse can fit up to four people in two bedrooms and two-and-a-half bathrooms. While you’re at it, be sure to have yourself a breath of fresh air at your own lush private garden and deck.

Conch Get Enough! - Old Town's Truman Annex
546 Porter Ln
87 reviews
townhome 4 guests 2 bedrooms 3 bathrooms

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6. Luxurious abode for six (from USD 75)

Big groups are welcome to stay in this luxurious Boli townhouse in Truman Annex. Those opting for a more private and peaceful vacation in the city will appreciate this gated community. Perfect for a group of six, the townhouse is complete with king-sized beds in two bedrooms, two bathrooms, and a fully equipped kitchen and dining area. They also have a flat-screen television and DVD players (complete with movies) in case you want to stay in. And for those who love the outdoors, there is also a deck with a dining table, hammock, grill, and lounge chair. The pool is just outside the property.

Boli Townhouse - Luxury Rental in Key West - Truman Annex
104 Southard Street
83 reviews
townhome 6 guests 2 bedrooms 2 bathrooms

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7. Majestic paradise in the heart of Old Town (from USD 184)

Imagine waking up in this lush and private house located in the heart of Old Town Key West. This paradise isn’t called “majestic” for nothing. If you love the outdoors–greenery, fresh air, and all, you’re definitely going to want to stay here. This house can sleep up to five people in two bedrooms and one bathroom. It has a large courtyard with a wooden sun deck, outdoor grill, and heated swimming pool. Everything else is just walking distance from the property. While you are it, be sure to catch the sunset by the beach!

MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West
208 Southard St unit 9
86 reviews
condo 5 guests 2 bedrooms 1 bathroom

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8. Beach unit with waterfront park view (from USD 175)

If you’re going to visit the New Truman Waterfront Park, complete the experience and catch the water view and sunset right from your balcony. With only a few homes in the area that offer such, you have to act on this accommodation fast. Stay in this fully furnished beach-themed home and have a relaxing and fun time. This unit condominium unit can sleep up to four people in two bedrooms and one bathroom. The best part? It is just steps away from Duval Street where all the action is. This way, you’ll never be bored.

Beach Chic w a Waterfront Park View
104 Southard St #6
78 reviews
condo 4 guests 2 bedrooms 1 bathroom

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9. Charming and modern townhome (from USD 200)

Those keen on interiors will definitely find this spacious and modern townhome a lovely place to stay in. Since it’s been newly renovated, you can expect the sleek and sparkling clean interiors of the accommodation. It has four bedrooms and three full bathhouses with a private pool, walk-out balcony, and garden that can accommodate up to eight people. Don’t feel intimidated by how sophisticated it looks as it is very comfortable and feels just like home. Since it is located in the heart of the city, guests can easily just walk to Duval Street, Mallory Square,and the beaches, too.

Newly Renovated 4 bedroom/3 full bath home w/private pool in Old Town Truman Ann
500 Porter Lane
78 reviews
townhome 8 guests 4 bedrooms 3 bathrooms

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10. Bright and sunny house near the beach (from USD 110)

If you love bright and open spaces, this sunny townhouse is for you. Perfect for just about four guests, it is complete with two bedrooms, two bathrooms, and a private deck with a lush garden and grill. There is a fully-equipped kitchen and working appliances so that guests can cook up their own meals. There is also a shared pool with lounge chairs perfect for relaxing and socializing with other guests. The best part? the beach is just minutes away. You can go snorkeling and explore the island.

STARFISH - SUNNY TOWNHOME in QUIET TRUMAN ANNEX TWO BLOCKS FROM DUVAL ST.
568 Porter Ln
72 reviews
townhome 4 guests 2 bedrooms 2 bathrooms

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Fall in love with the historic district of Florida

It is no doubt that there’s plenty to do and see in Key West Old Town. You can either visit the popular tourist sites, explore the island and downtown novel shops, or experience the hustle and bustle of the city at night. There’s even a beach nearby where you can just relax. Whatever you’re looking for, this city will not disappoint. The best part? There’s always some history to it and that should be interesting. Get ready to fall in love with the city and be sure to book your stay in one of the best VRBO accommodations in Key West Old Town, Florida.

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Melissa is your storyteller from Manila. She loves learning from other cultures and listening to their stories. Having traveled to Europe and around the Philippines, she says always finds herself...Read more

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