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Key West Historic District vacation rentals

We found 1,249 vacation rentals — enter your dates for availability

Discover a selection of 1,000 vacation rentals in Key West Historic District that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $90 per night, and houses and condos are popular options for a stay in Key West Historic District. Either way, you'll find a rental for everyone's needs.
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Find spaces that suit your style

Houses

View 652 Houses

Condos/Apartments

View 464 Condos/Apartments

Cabins

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Bungalows

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Cottages

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Townhouses

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Studios

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Villas

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Resorts

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Hotels

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Find the best place to stay — Key West Historic District

Lennon's Lodge-2 BR Luxury Cottage w/Private 6 person Spa, 2 Heated Pools!

Sleeps 6 · 2 Bedrooms · 1 Bathroom
$388 avg/night
(46)

Architect's Personal Residence, Private Pool, 1 Blk. to Duval

Sleeps 6 · 2 Bedrooms · 2 Bathrooms
$498 avg/night
(142)

Southernmost Retreat: 2 Blocks from Duval in Old Town.

Sleeps 8 · 3 Bedrooms · 2 Bathrooms
$320 avg/night
(161)

ELIZABETH'S SECRET - 2/2-Old Town WEEKLY vacation rental-Private pool-Parking

Sleeps 4 · 2 Bedrooms · 2 Bathrooms
$441 avg/night
(112)

The Hollinsed House - Harvey's Haven - Great Location!!

Sleeps 2 · 1 Bedroom · 1 Bathroom
$168 avg/night
(67)

Stone Throw Famous Duval Street Location-No Contact Check-In

Sleeps 10 · 4 Bedrooms · 2 Bathrooms
$117 avg/night
(13)

Search 1,249 vacation rentals

Top rated rentals — Key West Historic District
Stayed Apr 2021

Best House in Key West!

Look no further if you are staying with a family in Key West! I have been to Key West 8 times and I can say that this house is the best accommodation I have stayed at in Key West! A true gem! We will be staying here again if it's not already booked u...

Michael P.
Michael P.
Stayed Mar 2021

Perfect location!

Five of us stayed here to celebrate my 40th birthday in Key West. Everything about this place was perfect. It was clean, easy to get to, and within walking distance to so many things. Everyone loved it. With 5 girls, and even more suitcases, we still...

Courtney V.
Courtney V.
Stayed Mar 2021

So good, I don't want to tell you...

...because if I do, it'll get booked forever! I live in the keys, and Friends were coming down for one week's day they wanted to stay in Key West for a night so that we wouldn't have to make the 35-minute ride home... Brilliant idea This place was...

Dan N.
Dan N.
Stayed Mar 2021

Never wanted to leave

Quintessential Key West property in the perfect location. The owner was very responsive, the pool and hot tub were heavenly, and home was well appointed. We rented bikes from the shop just up the street (less than a block). This property was a great ...

VIRGINIA F.
VIRGINIA F.
Stayed Feb 2021

Perfect location!

The Lennon Lodge was perfect for our short getaway. Located just off Duval, we were able to enjoy several nights out without worrying about transportation. The outdoor living area was great! We thoroughly enjoyed the sitting area, the hot tub and the...

Sherri P.
Sherri P.
Stayed Feb 2021

2 night stay

Good location. Parking is a nightmare. Unit smelled so musty. Glad I brought candle.. Furniture in middle of floor in living area. Trashcan with utensils sitting on kitchen counter. Looks like someone started to prep unit and left. Overall fine for 2...

Kelly C.
Kelly C.
Stayed Feb 2021

Lovely studio in the heart of Old Town Key West.

Perfect location for walking around Old Town Key West. Just a block off the quieter end of Duval, but a fun and safe walk to the hoppin West end to see the sunset and enjoy the nightlife. We had a car and got super lucky with parking right in front,...

Cindy M.
Cindy M.
Stayed Feb 2021

Perfect little spot

We stayed from Thursday through Sunday. Just 6-7 blocks from Duval and not a bad walk. The place was clean and comfortable. Had a nice little deck to relax on. We were arriving at 2am from Fort Lauderdale Airport and had to leave to go home at 3am an...

Buffy J.
Buffy J.
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How many vacation rentals are available around Key West Historic District?

Our 2021 property listings offer a large selection of 1,249 vacation rentals around Key West Historic District. From 652 house rentals to 464 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

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