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.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on March 13, 2023.
1. Classic condo in Key West's Truman Annex (from USD 269)
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.
Top guest reviews
Amenities & Room:
nice furniture and updated bathroom/showerfull kitchen laundry cable tvThe apartment is actually larger and more spacious than it appears in the photos with great amenities: keyless entryThe bikes that were included with the condo came in very handyThe deck and pool provided hours of relaxationCleanliness:
The condo was very clean and tidyHost:
the owner sent perfect directions and had a very simple set up to get into the unit even with our late arrivaland she did a wonderful job-againSusan is wonderful and is always available for any questions or concerns that may ariseWhat a great location Susan was very helpfulUnit was close to swimming pool which was niceRead more reviewsLocation:
Mallory Square is also within walking distanceThe condo itself has a great locationThe condo is located in a very quiet community just away from the hustle and bustle of KW yet easily within walking distanceIt is within walking distance of so much Only two blocks to Duval StreetIt's a dessert restaurant that is very fun and romantic
2. Condo close to the beach (from USD 300)
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.
Top guest reviews
Amenities & Room:
The condo pool was warm and there was plenty of lounge chairsThe grounds are meticulously cared for; sitting on the back deck is like visiting a jungleThe condo was very clean with sufficient space for 4 peopleYou don't need to rent a carThe kitchen was fully equipped and we did cook a number of meals in the condo really convenient to the grocery storeHost:
Jean and Lowell for being so great to work withThey keep up on what is going on in the community and participate in local meetings to make sure that they let their guest be aware of events taking placeIf you want to know about the island ask Lowell he knows and cares so much about things that created this paridiseand we absolutely love itWe absolutely love it there and were so sad to have to leaveRead more reviewsLocation:
A 20 minute walk to Fort Zachary Taylor State Park and 5 minutes to the downtown strip on Duval StIt is within walking distance of everythingThis is the perfect location Close to everything but quiet retreatRide the bikes everywhere or walkThis gated community is beautifully landscaped quiet and relaxing
3. Grand mansion for eight (from USD 2577)
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.
4. Luxurious abode for six (from USD 300)
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.
Top guest reviews
Amenities & Room:
you own private kitchen living roomNice comfortable big double bedMy only change would be to have a bigger kitchen because I like to cook a lot on vacationbeach towels and a cooler are provided Plenty of room for 4 adultsTownhouse was stocked with extras like kitchen spices cleanersCleanliness:
We find it very clean and invitingThe washer and dryer are another convenience I appreciate as is the internet accessThe Boli is a great; exactly like it's picturedIt is clean quiet and comfortableThe unit is clean and in good repair nicely decorated well stocked and the location was very goodHost:
He was very helpful when we had questionsJohn was very responsive to our questionsThe owner was very nice and very accommodatingWe have coffee out there every morning with the flora and faunaThe pool was so convenient and peaceful too John was great at communicating directions for arrival and departure at the house Overall good experienceRead more reviewsLocation:
The location is perfect if you want to walk downtown or drive in any directionCondo was in a great location easy to walk to everythingWe could get to many places by walkingIt was great to walk less than 5 minutes to the busy area but be in a lovely quiet neighborhood to rest our weary headsthe Green Parrot Bar for friday nite sound check and do not miss sunset on Mallory Square
5. Beach unit with waterfront park view (from USD 440)
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.
Top guest reviews
Amenities & Room:
the bedrooms had mirror sliding doorsThe kitchen had everything we neededWe did take Lyft one night for our anniversary because it was so hot and humidThe plants and flowers in the courtyard are beautiful and makes you feel like you are secludedCondo was immaculate Washer and Dryer in condo and easy to use Fastest WifiCleanliness:
It was decorated very nicely and very comfortableThe house was very nicely decorated and included everything we neededThe common pool was heated in Dec which was greatIt is very comfortable and cleanlocation is great rental is clean and comfortable and enjoyed the poolHost:
We were super close to Duval street with all the good attractionswas very easy to help and answered any questions we had One suggestion--move the bathroom mirror down some It works for tall people but not for us petite onesThe pool is was very nice and refreshingEveryone we talked to in the community was very friendlyHighly recommend this rental Unit was very clean well stockedRead more reviewsLocation:
It is within a few blocks of Duval Street where a lot of restaurants shopping and bars areYou can walk to shops restaurants and of course the barsVery close walk to everything while still far enough for peace and quietnessthere was a playground 3 min away and Duval street is only a few blocks awayCondo is close to everthing we walked 95 percent of the time
6. Charming and modern townhome (from USD 786)
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.
Top guest reviews
Amenities & Room:
plenty of space at the dining table and the towel supply was great toovery comfortable for 3 couplesCleanliness:
close to everything very clean bright and airyHost:
owners were easy to reach by messaging through the vrbo appallison was very responsive to questionshome owner found this property available for us the staff at compass realty was accommodating helpful and friendlyshe was always very responsive and timely in getting back to us with any questions we might haveRead more reviewsLocation:
pool onsite was great perfect location close to duval and many attractionsgreat location nicely suited for families with childreneasy walk to state park for great sunset viewingthis townhome is located very close to duval street and many local attractions in key westsuch a great location- private pool - close to duval- comfortable bed- everything you need and more
7. Bright and sunny house near the beach (from USD 375)
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.
Top guest reviews
Amenities & Room:
The only place we have stayed more than onceThe condo had everything you need and its location to the pool is perfectHad everything we needed Love that they supply shampoo conditioner and body wash Less liquids to carry thru TSASeriously stop researching b/cThe condo is off the main drag and is a great locationCleanliness:
Very clean and again location to Duval and Mallory Sq are all walkable Highly recommend this place for a clean and organized condoThe owners Patty & Scott were extremely niceHost:
She made our check in process so nice by meeting us at the property and showing us where things wereThey were always available to help with any of our needsPatty the owner is so sweetPattie is a wonderful and responsive ownerScott and Patty are gracious hostRead more reviewsLocation:
The location is perfect and you can walk to just about everything from thereThe place is in a perfect location close to all the great barsComfortable and quite 2Br/2bath townhome within walking distance to everything Key West including the poolFrom the Little White Housemade some suggestions on local restaurants and a lovely sunset sail
8. Majestic paradise in the heart of Old Town (from USD 300)
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!
Top guest reviews
Amenities & Room:
Even the beds and pillows were comfortableThe kitchen was well stocked and the outdoor grill was great for cooking fresh fishbeautiful 2 bedroom condo with everything you need great locationThe washer & dryer are much needed for the weather conditions of Key WestYou can leave your car in the gated area and walk all over townCleanliness:
The place is neat and cleanHost:
The owner was very helpful and provided us with all the information we needed in advance to make check in a breezeThey make sure you have all kinds of info prior to your arrival to make for a great vacationand he was quick to assist with any questions we hadall new inside made us feel right at homecontacted us and shared a tremendous amount of information that was quite helpful when planning our tripRead more reviewsLocation:
Great place within walking distance to just about everythingIt is in a perfect location a walks away from beaches and DuvalPerfect location to stay while visiting Key West Walking distancethe minute you walk inThe location is perfect walk to wherever you need to go
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.
History
Get Trip101 in your inbox
Unsubscribe in one click. See our Privacy Policy for more information on how we use your data
Create an account to