Book Holiday Homes in San Juan

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Featured Holiday Homes in San Juan

150 Sol by Stay with Bear

150 Sol by Stay with Bear

3 out of 5
150 Sol St San Juan San Juan
The price is NZ$274 per night from 21 Dec to 22 Dec
NZ$274
21 Dec - 22 Dec
includes taxes & fees
Stay at this holiday home in San Juan. Enjoy free Wi-Fi, Netflix and an in-room coffee maker. Popular attractions Port of San Juan and Pan American Pier are ...
Opens in a new window150 Sol by Stay with Bear
1120 Vieques by Stay with Bear

1120 Vieques by Stay with Bear

3.5 out of 5
1120 C. Vieques San Juan San Juan
Stay at this holiday home in San Juan. Enjoy free Wi-Fi, free parking and patios. Popular attractions Condado Beach and Pan American Pier are located ...
Opens in a new window1120 Vieques by Stay with Bear
Casa Parcha

Casa Parcha

3.5 out of 5
Carr 191 km 27.9 Naguabo Naguabo
The price is NZ$340 per night from 19 Dec to 20 Dec
NZ$340
19 Dec - 20 Dec
includes taxes & fees
Stay at this holiday home in Naguabo. Enjoy free parking, on-site spa services and a garden. Popular attractions El Yunque National Forest and Charco El Hippie ...
Opens in a new windowCasa Parcha
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Charming house, stunning views in brilliant Barranquitas with AC, WiFi, Parking

Charming house, stunning views in brilliant Barranquitas with AC, WiFi, Parking

2 out of 5
Barranquitas
Stay at this holiday home in Barranquitas. Enjoy free Wi-Fi, balconies and an in-room coffee maker. Popular attraction Finca Don Felix para la Naturaleza is ...
Opens in a new windowCharming house, stunning views in brilliant Barranquitas with AC, WiFi, Parking
PLAYA AZUL1 2ND FLOOR BEACHFRONT LUX  DESIGNER CONDO.

PLAYA AZUL1 2ND FLOOR BEACHFRONT LUX DESIGNER CONDO.

Luquillo Luquillo
Stay at this beach holiday home in Luquillo. Enjoy free Wi-Fi, a beach locale and laundry facilities. Popular attractions Luquillo Beach and Wyndham Rio Mar ...
Opens in a new windowPLAYA AZUL1 2ND FLOOR BEACHFRONT LUX DESIGNER CONDO.
Perfect for small group or family close to everything apt 3

Perfect for small group or family close to everything apt 3

Santurce San Juan
Stay at this holiday home in San Juan. Enjoy laundry facilities, balconies and an in-room coffee maker. Popular attractions Condado Beach and Pan American Pier ...
Opens in a new windowPerfect for small group or family close to everything apt 3
Luxury House in Old San Juan

Luxury House in Old San Juan

San Juan San Juan
The price is NZ$1,298 per night from 23 Dec to 24 Dec
NZ$1,298
23 Dec - 24 Dec
includes taxes & fees
Stay at this holiday home in San Juan. Enjoy private pools, laundry facilities and in-room jetted baths. Popular attractions Port of San Juan and Pan American ...
Opens in a new windowLuxury House in Old San Juan
Charming 3-bedroom house in San Juan with WiFi and AC

Charming 3-bedroom house in San Juan with WiFi and AC

San Juan San Juan
Stay at this holiday home in San Juan. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Isla Verde Beach and Jose Miguel Agrelot Coliseum ...
Opens in a new windowCharming 3-bedroom house in San Juan with WiFi and AC
San Juan Beach House

San Juan Beach House

Condado San Juan
Stay at this holiday home in San Juan. Enjoy a pool table, patios and cable/satellite TV service. Popular attractions Condado Beach and Pan American Pier are ...
Opens in a new windowSan Juan Beach House
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

San Juan Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our San Juan vacation homes are the perfect way for you to wing it.

Holiday houses in San Juan let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of San Juan in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local San Juan adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in San Juan with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of San Juan vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

San Juan Holiday Homes essential information

Accommodation
1124 Holiday Homes
Lowest Price
NZ$274
Highest Price
NZ$1,298
Popular accommodation
150 Sol by Stay with Bear, 1120 Vieques by Stay with Bear, Casa Parcha, Charming house, stunning views in brilliant Barranquitas with AC, WiFi, Parking, PLAYA AZUL1 2ND FLOOR BEACHFRONT LUX DESIGNER CONDO., Perfect for small group or family close to everything apt 3, Luxury House in Old San Juan, Charming 3-bedroom house in San Juan with WiFi and AC, San Juan Beach House

Top trending hotels in San Juan

Caribe Hilton

Caribe Hilton

4.5 out of 5
1 San Geronimo Street San Juan
Fully refundableReserve now, pay when you stay
The price is NZ$661 per night from 21 Dec to 22 Dec
NZ$661
21 Dec - 22 Dec
includes taxes & fees
Stay at this beach resort in San Juan. Enjoy free Wi-Fi, 3 outdoor pools and a full-service spa. Our guests praise the pool and the helpful staff in their reviews. ...
Opens in a new windowCaribe Hilton
The Condado Plaza Hotel

The Condado Plaza Hotel

4 out of 5
999 Ashford Avenue San Juan
The price is NZ$548 per night from 4 Jan to 5 Jan
NZ$548
4 Jan - 5 Jan 2026
includes taxes & fees
Stay at this beach resort in San Juan. Enjoy 2 outdoor pools, 2 restaurants and a beach locale. Our guests praise the pool and the helpful staff in their reviews. ...
Opens in a new windowThe Condado Plaza Hotel
La Concha Resort, Puerto Rico, Autograph Collection

La Concha Resort, Puerto Rico, Autograph Collection

4 out of 5
1077 Ashford Ave Condado San Juan
The price is NZ$803 per night from 5 Jan to 6 Jan
NZ$803
5 Jan - 6 Jan 2026
includes taxes & fees
Stay at this beach resort in San Juan. Enjoy free Wi-Fi, 3 outdoor pools and a full-service spa. Our guests praise the pool and the helpful staff in their reviews. ...
Opens in a new windowLa Concha Resort, Puerto Rico, Autograph Collection
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Condado Vanderbilt Hotel

Condado Vanderbilt Hotel

5 out of 5
1055 Ashford Avenue San Juan
The price is NZ$1,126 per night from 4 Jan to 5 Jan
NZ$1,126
4 Jan - 5 Jan 2026
includes taxes & fees
Stay at this luxury hotel in San Juan. Enjoy free Wi-Fi, 4 outdoor pools and a full-service spa. Our guests praise the helpful staff and the clean rooms in their ...
Opens in a new windowCondado Vanderbilt Hotel
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.