Old San Juan holiday rentals

We found 432 holiday rentals — enter your dates for availability

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September 2025

October 2025

Discover a selection of 19 homes, 129 apartments and other holiday rentals in Old San Juan that are perfect for your trip. Holiday homes offer the best amenities for you and your friends, family or even pets, such as Wi-Fi and a washer and dryer. At the end of the day, you'll be sure to find a property to rent for everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts - Old San Juan

Showing deals for:19 Dec - 26 Dec

Exceptional

(6 reviews)

EL SOL OCEAN VIEW / EXCLUSIVE

San Juan

8% off

for 7 nights, 1 apartment

AU$325 per night

includes taxes & fees

Exceptional

(26 reviews)

New beautiful bath and floors. Kitchen. Dine in a balcony with ocean view.

San Juan

8% off

for 7 nights, 1 apartment

AU$506 per night

includes taxes & fees

Exceptional

(53 reviews)

Private balconies / walking distance to historic sites & restaurants

San Juan

21% off

for 7 nights, 1 apartment

AU$320 per night

includes taxes & fees

Newly painted building. Parking allowed on both sides of the street.

Exceptional

(11 reviews)

5 min walk to a beautiful beach and a big shady park! 25min walk to Old San Juan

San Juan

8% off

for 7 nights, 1 apartment

AU$486 per night

includes taxes & fees

Very good

(25 reviews)

Walking distance to Old SJ, Cruise Ports & Beaches - WIFI - Queen size bed -

San Juan

8% off

for 7 nights, 1 apartment

AU$229 per night

includes taxes & fees

Exceptional

(78 reviews)

Beautiful Loft, walking distance to the beach, Old San Juan & Condado

San Juan

8% off

for 7 nights, 1 apartment

AU$331 per night

includes taxes & fees

Exceptional

(41 reviews)

Newly renovated! And What a view! Bed view is an ocean view superb location

San Juan

8% off

for 7 nights, 1 apartment

AU$506 per night

includes taxes & fees

Very good

(27 reviews)

Amazing 2 BR Apartment near Old San Juan, Cruise Ports and Airport-WIFI-Parking

San Juan

8% off

for 7 nights, 1 apartment

AU$273 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find properties near top attractions in Old San Juan

Castillo San Felipe del Morro

Find the best place to stay - Old San Juan

Hugo's Rental

Sleeps 2 · 1 bedroom

Premier Host

Villa Azulejo | Old San Juan | Heart of the Historic 500 Year Old City

Sleeps 6 · 2 bedrooms · 1 bathroom

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 home accommodation in Old San Juan?

Apartments are the most popular type of holiday home in Old San Juan, according to our data. Even if you've got a different idea about what you want, Stayz has holiday homes in a variety of sizes and shapes. Look over our options to find your perfect fit.

How much does it cost to rent a holiday home in Old San Juan?

Different factors can influence how much you'll pay for a holiday home in Old San Juan, like the time of year, length of stay and property type. But, all of our holiday homes have something in common — incredible value. Simply enter your travel dates to find your ideal match.

How much does it cost to rent a beach house in Old San Juan?

The average price for a holiday home by the beach in Old San Juan will depend on when you'll be there and the size and type of property you're searching for. You can quickly and easily find prices on Stayz by entering your destination and preferred travel dates. Then use our handy filter tool to select the number of bedrooms and amenities that you need, like air conditioning, a pool and WiFi.

Are there pet-friendly holiday homes in Old San Juan?

There are, yes. You can pick from 138 stays that welcome pets in Old San Juan on Stayz. Our furry best friends need to get away from it all too, so simply use our search function for pet-friendly holiday homes to find a perfect pad where Spot can share in the good times.

Can I rent a house with a pool in Old San Juan?

Check the "pool" box in our handy filter tool and you can choose from 54 houses with private pools in Old San Juan on Stayz. Morning soak, afternoon splash or midnight swim? Leisure activities are up to you when your Stayz holiday home boasts a swimming pool.

What are popular home amenities in Old San Juan?

Some of the most popular home amenities people prefer in Old San Juan are a fireplace, nearby museums and a barbecue grill. Whether you're on the road with pals, family or even pets, Stayz holiday homes feature the best amenities for beginning new traditions with the people who matter most.

Are there large group holiday homes in Old San Juan?

With three properties that can sleep 10 people or more in Old San Juan, there's no need to cross anyone off the invite list. From fun family holidays to special events like Christmas or New Year's Eve parties, Stayz will help you find a large group home to suit the occasion.

Are there holiday homes in Old San Juan that welcome kids?

Old San Juan has 134 family-friendly holiday homes. And booking a stay that welcomes little ones is easy with our "Properties good for families" filter. As well as having the entire place to yourselves, you'll also get access to perks and amenities such as multiple bedrooms, pools and kitchens.

What are the top attractions for families in Old San Juan?

There's a ton of fun things to see and do with the family in Old San Juan, including:

Condado Beach
Escambron Beach
Playa del Caribe Hilton

Are there one-bedroom holiday homes in Old San Juan?

Yes, you can choose from 95 one-bedroom homes in Old San Juan. Whether you'd like a comfy cottage or an upmarket condo, Stayz's one-bedroom homes are ideal if you don't need tons of space. One of the best parts about having your own digs? You'll never need to share your trip with strangers.

Can I find two-bedroom holiday homes in Old San Juan?

Gather your family and enjoy total privacy and comfort in one of the 33 two-bedroom holiday properties Old San Juan has to offer.

Are there holiday homes with WiFi in Old San Juan?

Whether you want to keep up with the news, look over emails or surf your social networks, there are 96 holiday homes with WiFi in Old San Juan. Check the "WiFi" box when searching on Stayz and stay connected on your holiday.

How can I find holiday homes with air conditioning in Old San Juan?

Decide on your travel dates and then use our filters to search for holiday homes with air conditioning in Old San Juan on Stayz. With 136 air-conditioned properties to choose from here, you can look forward to a cool and comfy stay.

How old do you have to be to rent a holiday home in Old San Juan?

We recommend checking with the Old San Juan holiday home you're looking at on Stayz as age restrictions differ. However, generally it's 16, 18 or 21.

How long can I rent a holiday home in Old San Juan for?

It all depends on the Old San Juan property. To see all available options offering extended stays, just type your dates and guest number into Stayz. You can enjoy having the property to yourself, along with home comforts like a fully-equipped kitchen, air conditioning and an outdoor space where the little ones can play. Keep your eyes open for long-term stays that offer discounted weekly or monthly prices.