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[3% CashBack] Best VRBO Vacation Rentals In Key West Old Town, Florida - Updated 2020

vrbo key west old town

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
169 reviews
condo 2 Guests 1 Bedroom 1 Bathroom
Top guest reviews
Amenities & Room:
nice furniture and updated bathroom/shower
full kitchen laundry cable tv
The apartment is actually larger and more spacious than it appears in the photos with great amenities: keyless entry
The bikes that were included with the condo came in very handy
The deck and pool provided hours of relaxation
The condo was very clean and tidy
the owner sent perfect directions and had a very simple set up to get into the unit even with our late arrival
and she did a wonderful job-again
Susan is wonderful and is always available for any questions or concerns that may arise
What a great location Susan was very helpful
Unit was close to swimming pool which was nice
Mallory Square is also within walking distance
The condo itself has a great location
The condo is located in a very quiet community just away from the hustle and bustle of KW yet easily within walking distance
It is within walking distance of so much Only two blocks to Duval Street
It's a dessert restaurant that is very fun and romantic
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2. Tropical-style unit in Duval Street

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!!!!
118 reviews
condo 5 Guests 2 Bedrooms 1 Bathroom
Top guest reviews
Amenities & Room:
The beds were comfy plenty of linens and the kitchen was fully stocked
the car came in handy with the A/C instead of walking home after a long day at the beach
We rented a car and the gated parking was great
The "8" on the microwave is the only button that works
I used it every night and realized I could have packed much lighter
The washer and dryer came in
The condo was beautifully decorated and very clean Loved the location
The waters were crystal clear and there were plenty of shaded areas as well
Again I can't say enough how beautiful and clean this condo was
Within walking distance to everything Owner was great responsive and accommodating
Only personal recommendation would be to add a couple of wall hooks in bedrooms
Excellent location ~ all shops/restaurants/bars all in walking distance as well as port for water tours yet off of Duvall for quiet Very clean unit
We saw barracudas and sharks Would highly recommend that excursion
That made us feel right at home
Just left KW Property is
but this was the only night from Sunday through Thursday
My favorite Bar in Old Town is the Green Parrot and it's a block and a half
Loved the location and the decor
It's located right on Duval Street
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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!
116 reviews
condo 4 Guests 2 Bedrooms 1 Bathroom
Top guest reviews
Amenities & Room:
The condo pool was warm and there was plenty of lounge chairs
The grounds are meticulously cared for; sitting on the back deck is like visiting a jungle
The condo was very clean with sufficient space for 4 people
You don't need to rent a car
The kitchen was fully equipped and we did cook a number of meals in the condo really convenient to the grocery store
The condo is large clean and very comfortable
It is so clean and comfortable
Jean and Lowell for being so great to work with
They 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 place
If you want to know about the island ask Lowell he knows and cares so much about things that created this paridise
and we absolutely love it
We absolutely love it there and were so sad to have to leave
A 20 minute walk to Fort Zachary Taylor State Park and 5 minutes to the downtown strip on Duval St
It is within walking distance of everything
This is the perfect location Close to everything but quiet retreat
Ride the bikes everywhere or walk
This gated community is beautifully landscaped quiet and relaxing
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4. Grand mansion for eight (from USD 1908)

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.

90 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
118 reviews
townhome 4 Guests 2 Bedrooms 3 Bathrooms
Top guest reviews
Amenities & Room:
The other bedroom has a full size bed and that room is fairly small
Kitchen has everything for cooking
The place was immaculate and very cozy
There are 2 bedrooms; one has a poster bed and is very comfortable
Parking is tight but we parked a full size SUV so it can be done
The place was very clean
This 2 bedroom 2 bath condo was very nicely furnished and very comfortable for 4 adults
He was equally as responsive
Some difficulty finding the unit; a map before arriving would have been helpful as well as a map to find our way in and out since there are a lot of walkways and several entrances
We even heard the lovely roosters every morning though 4am was a bit early
Upon check in we needed some new keys and she was quick to respond via phone and email and put us in touch with Alistair
property Owner persona lily reached out to introduce herself and was very thorough and timely with responses to any question I had Highly recommend
The location is good for the beach Little White House
We love staying in Truman Annex because it is close to everything but tucked away in a quiet gated community
There is really no shelf space (except tucked away in the closet) and no dresser
The proximity to downtown makes Truman Annex an ideal location
Everything was within walking distance for us restaurants bars
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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
99 reviews
townhome 6 Guests 2 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
you own private kitchen living room
Nice comfortable big double bed
My only change would be to have a bigger kitchen because I like to cook a lot on vacation
beach towels and a cooler are provided Plenty of room for 4 adults
Townhouse was stocked with extras like kitchen spices cleaners
We find it very clean and inviting
The washer and dryer are another convenience I appreciate as is the internet access
The Boli is a great; exactly like it's pictured
It is clean quiet and comfortable
The unit is clean and in good repair nicely decorated well stocked and the location was very good
He was very helpful when we had questions
John was very responsive to our questions
The owner was very nice and very accommodating
We have coffee out there every morning with the flora and fauna
The pool was so convenient and peaceful too John was great at communicating directions for arrival and departure at the house Overall good experience
The location is perfect if you want to walk downtown or drive in any direction
Condo was in a great location easy to walk to everything
We could get to many places by walking
It was great to walk less than 5 minutes to the busy area but be in a lovely quiet neighborhood to rest our weary heads
the Green Parrot Bar for friday nite sound check and do not miss sunset on Mallory Square
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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
94 reviews
condo 5 Guests 2 Bedrooms 1 Bathroom
Top guest reviews
Amenities & Room:
Even the beds and pillows were comfortable
The kitchen was well stocked and the outdoor grill was great for cooking fresh fish
beautiful 2 bedroom condo with everything you need great location
The washer & dryer are much needed for the weather conditions of Key West
You can leave your car in the gated area and walk all over town
The place is neat and clean
The owner was very helpful and provided us with all the information we needed in advance to make check in a breeze
They make sure you have all kinds of info prior to your arrival to make for a great vacation
and he was quick to assist with any questions we had
all new inside made us feel right at home
contacted us and shared a tremendous amount of information that was quite helpful when planning our trip
Great place within walking distance to just about everything
It is in a perfect location a walks away from beaches and Duval
Perfect location to stay while visiting Key West Walking distance
the minute you walk in
The location is perfect walk to wherever you need to go
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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
96 reviews
condo 4 Guests 2 Bedrooms 1 Bathroom
Top guest reviews
Amenities & Room:
the bedrooms had mirror sliding doors
The kitchen had everything we needed
We did take Lyft one night for our anniversary because it was so hot and humid
The plants and flowers in the courtyard are beautiful and makes you feel like you are secluded
Condo was immaculate Washer and Dryer in condo and easy to use Fastest Wifi
It was decorated very nicely and very comfortable
The house was very nicely decorated and included everything we needed
The common pool was heated in Dec which was great
It is very comfortable and clean
location is great rental is clean and comfortable and enjoyed the pool
We were super close to Duval street with all the good attractions
was 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 ones
The pool is was very nice and refreshing
Everyone we talked to in the community was very friendly
Highly recommend this rental Unit was very clean well stocked
It is within a few blocks of Duval Street where a lot of restaurants shopping and bars are
You can walk to shops restaurants and of course the bars
Very close walk to everything while still far enough for peace and quietness
there was a playground 3 min away and Duval street is only a few blocks away
Condo is close to everthing we walked 95 percent of the time
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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
96 reviews
townhome 8 Guests 4 Bedrooms 3 Bathrooms
Top guest reviews
Amenities & Room:
The kitchen was well stocked Comfortable furniture
The TV's in every bedroom and the living room worked perfectly
Anything and everything that you need are provided by the owner
the kitchen is well stocked with pots/pans/plates/etc
These items in kitchen would have been appreciated: tea pot
The rooms were spacious spotless and extremely comfortable
The rooms were spacious spotless and extremely comfortable
Everything was perfect and the location was fantastic
Everything was clean and neat as a pin And lounging in the back yard and pool
The owner was extremely accommodating and reachable
The owner was very responsive to any questions we had
We can not wait until next year to return for another vacation
pantry items etc needed a convenient assigned parking spot and was clean neat well decorated and maintained The pool and outdoor area was private and had a tropical feel
there's almost nothing else we could have asked of this rental From the welcome and accomodating first contact on the phone with the owner to everything working precisely as advertised and advised
Everywhere in Key West is within walking distance
However since it is in a gated community
It is in a quiet neighborhood minutes from the waterfront
every bar or restaurant one would want to visit is within a 10 minute walk
You could get downtown by walking about 5 minutes and you were on
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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.

89 reviews
townhome 4 Guests 2 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
The only place we have stayed more than once
The condo had everything you need and its location to the pool is perfect
Had everything we needed Love that they supply shampoo conditioner and body wash Less liquids to carry thru TSA
Seriously stop researching b/c
The condo is off the main drag and is a great location
Very clean and again location to Duval and Mallory Sq are all walkable Highly recommend this place for a clean and organized condo
The owners Patty & Scott were extremely nice
She made our check in process so nice by meeting us at the property and showing us where things were
They were always available to help with any of our needs
Patty the owner is so sweet
Pattie is a wonderful and responsive owner
Scott and Patty are gracious host
The location is perfect and you can walk to just about everything from there
The place is in a perfect location close to all the great bars
Comfortable and quite 2Br/2bath townhome within walking distance to everything Key West including the pool
From the Little White House
made some suggestions on local restaurants and a lovely sunset sail
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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 a storyteller from Manila. She's been to Europe and Asia but still dreams of going around her home, the Philippines. When she's not traveling, you can find her in your nearest bookstore.

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