Old Town Key West holiday rentals

We found 1,597 holiday rentals — enter your dates for availability

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September 2025

October 2025

Select from 619 houses, 273 flats and other holiday rentals to find the perfect place for your stay in Old Town Key West. Whether you’re staying in a holiday home with family or friends, you'll have the amenities that you expect and more, such as parking and air conditioning. Whatever you're looking for, you're sure to find a property to rent to meet everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts - Old Town Key West

Showing deals for:5 Dec - 12 Dec

Exceptional

(113 reviews)

The Island Suite at KW Vacation

Key West, FL

8% off

for 7 nights, 1 apartment

AU$783 nightly

Includes taxes & fees

Exceptional

(9 reviews)

The Cathouse, an Old Town tropical poolside oasis with huge, heated pool

Key West, FL

10% off

for 7 nights, 1 home

AU$2,147 nightly

Includes taxes & fees

Exceptional

(87 reviews)

Tranquility by AvantStay | Close to Duval St w/ BBQ & Shared Pool

Key West, FL

6% off

for 7 nights, 1 home

AU$730 nightly

Includes taxes & fees

Did someone say "hot tub time?" Enjoy a space to dine, chill, or catch some sun on the sun porches and patios.

Exceptional

(16 reviews)

Near Duval: Hot Tub, Sleeps 6, Top Location

Key West, FL

8% off

for 7 nights, 1 home

AU$1,635 nightly

Includes taxes & fees

Exceptional

(82 reviews)

Luxury two floor apartment in prime location of famous Duval Street

Key West, FL

8% off

for 7 nights, 1 home

AU$882 nightly

Includes taxes & fees

Exceptional

(26 reviews)

Great Location- Remodeled Condo- Old Town-Truman Annex Close to all attractions

Key West, FL

5% off

for 7 nights, 1 apartment

AU$929 nightly

Includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find properties near top attractions in Old Town Key West

Southernmost Point

Find the best place to stay - Old Town Key West

DELANEY HOUSE ~ NEW 4 BR/4 Ba Listing w/Pool & Parking in Prime Old Town!

Sleeps 8 · 4 bedrooms · 4 bathrooms

GEIGER SUITE @ Inn on Fleming~ADULTS ONLY 2 BR 3rd Floor Suite w/Shared Pool!

Sleeps 4 · 2 bedrooms · 1 bathroom

WHITEHEAD ROOM @ Inn on Fleming ~ ADULTS ONLY 2nd Floor Queen & Shared Pool

Sleeps 2 · 1 bedroom · 1 bathroom

CORNISH SUITE @ Inn on Fleming ~ ADULTS ONLY 3rd Floor 2 BR w/Shared Pool!

Sleeps 4 · 2 bedrooms · 1 bathroom

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Our Book with Confidence Guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

Frequently asked questions

What is the most popular type of holiday home accommodation in Old Town Key West?

Houses are the most popular type of holiday home in Old Town Key West, according to our data. Even if you've got something different in mind, Stayz has properties in loads of sizes and shapes. Browse our many options to find your perfect Old Town Key West pad.

How much does it cost to rent a holiday home in Old Town Key West?

Season, length of stay and property type are some factors that can affect the price of a holiday home. Simply enter your dates of travel to find your ideal fit. From comfy cabins to plush villas, all Stayz holiday homes provide incredible value.

How much does it cost to rent a beach house in Old Town Key West?

The average price for a holiday home by the beach in Old Town Key West depends on when you're going and the size and style of property you're searching for. Find prices easily on Stayz by entering your destination and preferred travel dates. Then make use of the filter tool to choose the number of bedrooms and amenities that you prefer, such as WiFi, a pool and air conditioning.

Are there pet-friendly holiday homes in Old Town Key West?

With 1 ,312 holiday homes that allow pets, your little buddy can join in on your Old Town Key West holiday. Use our filter tool to search our pet-friendly holiday homes and find a stay that'll set tails wagging on Stayz.

Can I rent a house with a pool in Old Town Key West?

Add another level of fun to your trip by booking your group into one of the 1 ,057 houses with a private pool in Old Town Key West. Use our search filter to find properties with pools on Stayz, then spend carefree days playing and splashing in a swimming pool that's for your exclusive use.

What are popular home amenities in Old Town Key West?

When it comes to home amenities that people look for in Old Town Key West, a barbecue grill, a chef and mountain views rank highest. With Stayz holiday homes, you'll enjoy choices to suit your style and taste, whether you're going away with your partner, your family or even pets.

Are there large group holiday homes in Old Town Key West?

Old Town Key West has 100 holiday properties that can accommodate 10 or more guests. These properties come with the space and privacy you need to share good times with family and friends.

Are there holiday homes in Old Town Key West that welcome kids?

With 1 ,307 family-friendly holiday homes available in Old Town Key West, now is a superb time to introduce your little ones to the thrills of travel. Just check our "Properties good for families" filter to search for stays that come with conveniences ideal for travelling families, such as living rooms, swimming pools, bunk beds and hot tubs.

What are the top attractions for families in Old Town Key West?

There are tons of wonderful things to see and do with the family in Old Town Key West, such as:

Smathers Beach
South Beach
Higgs Beach

Are there one-bedroom holiday homes in Old Town Key West?

Yes, you can pick from 359 one-bedroom homes in Old Town Key West. Whether you're on the lookout for a cosy chalet or an upmarket condo, our one-bedroom homes are great if you don't require huge amounts of space. One of the best things about having your own pad? You won't ever need to share your trip with strangers.

Can I find two-bedroom holiday homes in Old Town Key West?

Choose from 500 two-bedroom homes in Old Town Key West. Settle the kids into the second room or maybe fill it with a couple of your best buddies. There's ample space for whoever's lucky enough to come along for the ride.

Are there holiday homes with WiFi in Old Town Key West?

Old Town Key West has 413 holiday homes with WiFi, so you'll be able to stay connected while on holiday. Simply check the "WiFi" box in our search filter for a list of properties with this feature. From streaming movies with the family to posting pics on social media, these Stayz homes make it a cinch to go online.

How can I find holiday homes with air conditioning in Old Town Key West?

You can choose from 1 ,266 holiday homes with air conditioning in Old Town Key West offering that gentle, cool breeze and extra level of comfort. Simply enter your preferred travel dates and then use our handy filter tool to look for properties with air conditioning.

How old do you have to be to rent a holiday home in Old Town Key West?

We recommend you check with the Old Town Key West holiday property you're looking at on Stayz as the minimum age varies. However, generally it's 16, 18 or 21.

How long can I rent a holiday home in Old Town Key West for?

How long you can book a holiday home in Old Town Key West is up to the property. Just enter your chosen travel dates to view a list of options offering extended stays. With loads of creature comforts such as full kitchens and air conditioning, as well as some offering weekly or monthly discounts, you're sure to get somewhere perfect to call your home away from home in Old Town Key West.