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Uptown - Upper Duval, Key West, Florida, United States of America

Uptown - Upper Duval holiday homes

We found 329 holiday rentals — enter your dates for availability

Discover a selection of 329 holiday homes in Uptown - Upper Duval that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Bookabach holiday homes have the best amenities for hanging out with the people that matter most, including pool and private pool. Prices start at NZ$ 427 per night, and holiday houses and cottages are popular options for a stay in Uptown - Upper Duval. Either way, you'll find accommodation for everyone's needs.
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Find spaces that suit your style

Houses

View 179 Houses

Cottages

View 40 Cottages

Bungalows

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Condos/Apartments

View 88 Condos/Apartments

Cabins

View 40 Cabins

Studios

View 33 Studios

Townhouses

View 18 Townhouses

Hotels

View 59 Hotels

Find the best place to stay — Uptown - Upper Duval

Casa De Cuba a Beach House - Cuban Flair Steps from Duval

Sleeps 6 · 3 Bedrooms · 2 Bathrooms
NZ$ 1,346 avg/night
(62)

Tropical family-friendly home w/private pool, 1/2 block from Duval St. - dogs ok

Sleeps 8 · 3 Bedrooms · 3 Bathrooms
NZ$ 1,152 avg/night
(147)

~ PETITE MAISON ~ Luxury Home Steps to Duval St w/ Private Parking. Dogs OK

Sleeps 4 · 2 Bedrooms · 2 Bathrooms
NZ$ 961 avg/night
(61)

Tucked away near the Southernmost Point, Louisa's Hideaway is it!

Sleeps 6 · 3 Bedrooms · 3 Bathrooms
NZ$ 1,576 avg/night
(108)

Sunshine Daydream: Private Home 1/2 Block Off Duval in Gallery District -

Sleeps 4 · 2 Bedrooms · 2 Bathrooms
NZ$ 853 avg/night
(110)

Catherine House: A charming Old Town Key West cottage

Sleeps 4 · 2 Bedrooms · 2 Bathrooms
NZ$ 908 avg/night
(122)

Search 329 holiday rentals

Top rated rentals — Uptown - Upper Duval
Stayed Apr 2021

Family and friends getaway

The house was perfect for the 8 of us. Was very well equipped with everything we needed, we brought pillows and sure didn't need them. Had plenty in every room. Location was perfect to catch the bus or just walk. It was so refreshing to have the pool...

Sandra B.
Sandra B.
Stayed Apr 2021

Never staying in a hotel in Key West again!

We have been doing annual trips with two other couples for years....this was our first time renting a home and this house was perfect! Super spacious and clean plenty of space for 6 adults to spread out! The backyard with the pool was like an oasis. ...

Babette B.
Babette B.
Stayed Apr 2021

Fantastic Location

We have stayed in Key West many times. The location to all activities was a short walk away. Being located only a block away from our favorite breakfast location (La Grignote) was only a bonus. Great amenities, pool was better than most, and the sepe...

Richard T.
Richard T.
Stayed Apr 2021

Perfect location!!

Pete’s West was the perfect place for a girls weekend away. The place was spotless and better than we expected. We appreciated the quieter end of Duval Street at night after spending time at the restaurants and bars. Everything was within waking dist...

Melissa L.
Melissa L.
Stayed Apr 2021

First trip to Key West

Great location! Enjoyed renting bikes for the week-gated area beside unit provided safe storage for bikes. Unit was exactly as pictured- comfortable and well stocked/furnished. Surprisingly quiet end of Duval Street-had no trouble sleeping :) Beach t...

Lynne M.
Lynne M.

Raleigh, NC

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

518 Catherine St Key West

Wonderful house! Perfect for two couples in our case. The house had terrific setup for traveling renters. Everything was labeled, access was perfect, supplies and amenities were as expected and the home was beautiful. Location is perfect as we chose ...

Chris M.
Chris M.
Stayed Mar 2021

Perfect Location

This property is perfectly located one-half block off of Duval! The house was extremely clean and has very nice decorating touches! Although it was just me on this trip, the house could easily accommodate additional guests. The pool, although small, ...

Lori M.
Lori M.
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How many holiday homes are available around Uptown - Upper Duval?

Our 2021 holiday accommodation listings offer a large selection of 329 holiday rentals around Uptown - Upper Duval. From 179 holiday houses to 40 cottages, find unique holiday house for you to enjoy a memorable stay with your family and friends for a long holiday or a weekend break.

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