Old Town Key West holiday homes, FL, USA: Houses & more

Select from 727 houses, 282 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:3 Oct - 10 Oct

Exceptional

(9 reviews)

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

Key West, FL

9% off

S$1,514 per night

includes taxes & fees

Galley style kitchen, full frig, ice maker, microwave, cooktop, granite counters

Exceptional

(34 reviews)

'LA DOLCE VITA' OLD TOWN! STEPS TO DUVAL! SLEEPS 2-4, 3 BLOCKS TO SOUTH BEACH!

Key West, FL

7% off

S$354 per night

includes taxes & fees

This home is one of the most photographed homes in Key West. It's a quintessential Conch house in an incredible location.

Exceptional

(9 reviews)

Just steps to Duval- Sleeps 10- Pool House

Key West, FL

8% off

S$1,584 per night

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

S$1,170 per night

includes taxes & fees

Wonderful

(199 reviews)

DUVAL SQUARE, KEY WEST Lovely 2 Bedroom 2.5 Bath Condo in a GREAT Location!

Key West, FL

8% off

S$821 per night

includes taxes & fees

Exceptional

(144 reviews)

"LA DOLCE VITA", OLD TOWN!! STEPS TO DUVAL! SLEEPS 2-4, 3 BLOCKS TO SOUTH BEACH!

Key West, FL

11% off

S$335 per night

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

Showing deals for: 1 Oct - 4 Oct

Perfectly located and a short walk from Duval

TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!

Sleeps 4 · 1 bedroom · 1 bathroom

for 3 nights, 1 apartment

S$428 per night

includes taxes & fees

Casa Cristol- Family and Pet Friendly - Classic KW Charm Superb Location!

Sleeps 6 · 3 bedrooms · 3 bathrooms

for 3 nights, 1 home

S$1,151 per night

includes taxes & fees

VanGogh Studio | Updated, Old Town, Heated Pool

Sleeps 2 · 1 bedroom · 1 bathroom

for 3 nights, 1 apartment

S$247 per night

includes taxes & fees

Duval Delight | Recently Remodeled Condo on Duval!

Sleeps 8 · 1 bedroom · 1+ bathroom

for 3 nights, 1 apartment

S$546 per night

includes taxes & fees

June Spec 129.+ 6-15 til 6-19 NEWLY Redone. Not shown in current pics

Sleeps 2 · 1 bedroom · 1 bathroom

for 3 nights, 1 home

S$252 per night

includes taxes & fees

Luxury two floor apartment in prime location of famous Duval Street

Sleeps 6 · 2 bedrooms · 1+ bathroom

for 3 nights, 1 home

S$869 per night

includes taxes & fees

Top rated rentals - Old Town Key West

Surrounded by lush tropical vegetation, SVII truly is a hidden gem.

Premier Host

AMAZING PROPERTY - BEST LOCATION

This is the third stay in this property in three years! It fits our needs PERFECTLY!! The owner and property manager take great care of the property and immediately deal with issues (issues are extremely rare)! We will continue to enjoy this property for years to come!

Tim G.

Stayed Sept 2022

Peace of mind
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 rental accommodation in Old Town Key West?

Houses are the most popular type of holiday rental in Old Town Key West, according to our data. Even if you've got something different in mind, Vrbo 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 rental 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 Vrbo holiday rentals provide incredible value.

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

The average price for a holiday rental 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 Vrbo 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 rentals in Old Town Key West?

With 1,312 holiday rentals 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 rentals and find a stay that'll set tails wagging on Vrbo.

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 Vrbo, then spend carefree days playing and splashing in a swimming pool that's for your exclusive use.

What are popular rental amenities in Old Town Key West?

When it comes to rental amenities that people look for in Old Town Key West, a barbecue grill, a chef and mountain views rank highest. With Vrbo holiday rentals, 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 rentals 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 rentals in Old Town Key West that welcome kids?

With 1,307 family-friendly holiday rentals 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 rentals in Old Town Key West?

Yes, you can pick from 359 one-bedroom rentals in Old Town Key West. Whether you're on the lookout for a cosy chalet or an upmarket condo, our one-bedroom rentals 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 rentals 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 rentals with WiFi in Old Town Key West?

Old Town Key West has 413 holiday rentals 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 Vrbo homes make it a cinch to go online.

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

You can choose from 1,266 holiday rentals 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 rental in Old Town Key West?

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

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

How long you can book a holiday rental 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.