Rolling Hills Holiday Rentals

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Our top choices for Rolling Hills holiday rentals

ESJ Beach Hotel

ESJ Beach Hotel
3.5 star property
Isla Verde
6.8 out of 10, (4268)
"Great for families."
United States
Tiffany
The price is AU$322
includes taxes & fees
14 Dec - 15 Dec
ESJ Beach Hotel

MANSION MIRAFLORES

MANSION MIRAFLORES
3.0 star property
Santurce
9.4 out of 10, Exceptional, (134)
"Clean room , amenities and great location"
United States
Elisabeth
The price is AU$305
includes taxes & fees
14 Dec - 15 Dec
MANSION MIRAFLORES

San Agustin Apartments

San Agustin Apartments
3.0 star property
San Juan Antiguo
9.2 out of 10, Wonderful, (438)
"Outstanding support from the staff!"
United States
Axel
San Agustin Apartments

ESJ by PMI Puerto Rico

ESJ by PMI Puerto Rico
3.5 star property
Isla Verde
7.2 out of 10, Good, (31)
"Very comfortable, great view and clean "
United States
Daniela
The price is AU$309
includes taxes & fees
14 Dec - 15 Dec
ESJ by PMI Puerto Rico

Romeo Gay Hotel

Romeo Gay Hotel
4.0 star property
San Juan Antiguo
9.0 out of 10, Wonderful, (138)
"Great place"
United States
pietro
Romeo Gay Hotel

THE BUOY

THE BUOY
3.5 star property
Santurce
10.0 out of 10, Exceptional, (30)
"Very clean adorable had everything I needed!!!"
United States
Rebecca Sue
The price is AU$446
includes taxes & fees
14 Dec - 15 Dec
THE BUOY

Hugo's Rental

Hugo's Rental
2.0 star property
Old San Juan
9.4 out of 10, Exceptional, (251)
"Nice location right on the square in Old San Juan"
United States
Heather
The price is AU$329
includes taxes & fees
16 Dec - 17 Dec
Hugo's Rental

Casa Costera, Isla Verde Beach, Apartments by Marriott Bonvoy

Casa Costera, Isla Verde Beach, Apartments by Marriott Bonvoy
2.5 star property
Isla Verde
9.0 out of 10, Wonderful, (149)
"Spacious, modern and functional apartments. Very helpful staff. Convenient to two excellent beaches. Exceeded my expectations! "
United States
ALAN
The price is AU$364
includes taxes & fees
18 Dec - 19 Dec
Casa Costera, Isla Verde Beach, Apartments by Marriott Bonvoy

2019 Cacique by Stay with Bear

2019 Cacique by Stay with Bear
3.0 star property
Santurce
8.8 out of 10, Excellent, (33)
"clean place and super friendly and communicative hosts! would love to stay here again ! very safe community too"
United States
citlaly
The price is AU$178
includes taxes & fees
16 Dec - 17 Dec
2019 Cacique by Stay with Bear

@3050 Place

@3050 Place
4.0 star property
Isla Verde
8.0 out of 10, Very good, (83)
"Location is perfect! And very clean! "
United States
Edwin
@3050 Place

Segovia Studio Units

Segovia Studio Units
3.0 star property
Sabana Abajo
8.6 out of 10, Excellent, (730)
"Loved this place. Will come again every time I visit!"
United States
Amarys
Segovia Studio Units

Patio Elba Boutique Hotel

Patio Elba Boutique Hotel
4.0 star property
Santurce
9.0 out of 10, Wonderful, (246)
"Yes! Excellent service and facilities "
United States
Alberto Antonio Cabrera
The price is AU$317
includes taxes & fees
21 Dec - 22 Dec
Patio Elba Boutique Hotel

Villas Auxilio Mutuo 103

Villas Auxilio Mutuo 103
2.0 star property
Universidad
8.0 out of 10, Very good, (1)
The price is AU$283
includes taxes & fees
15 Dec - 16 Dec
Villas Auxilio Mutuo 103

Old San Juan Rentals

Old San Juan Rentals
3.5 star property
Old San Juan
8.6 out of 10, Excellent, (677)
"Amazing stay and staff was always available for us"
United States
Dominique
The price is AU$306
includes taxes & fees
17 Dec - 18 Dec
Old San Juan Rentals

City Beach Apartments

City Beach Apartments
2.0 star property
Santurce
9.6 out of 10, Exceptional, (5)
"this property is great for a couple, it’s nice, cozy and private, is is also really close to ocean park beach which is a really nice beach and close to a lot of shops and restaurants. definitely worth staying here and will definitely be back. "
United States
Jorge
City Beach Apartments

CARIBBEAN STARS

CARIBBEAN STARS
4.0 star property
Sabana Abajo
3.0 out of 10, (2)
"Room was clean. There was NO hot water!! I was not able to take a shower or shave. "
United States
Andy
The price is AU$169
includes taxes & fees
1 Jan - 2 Jan 2026
CARIBBEAN STARS

150 Sol by Stay with Bear

150 Sol by Stay with Bear
3.0 star property
Old San Juan
8.0 out of 10, Very good, (7)
"Great experience, on point customer service, will definitely recommend!!"
United States
Efrain
The price is AU$199
includes taxes & fees
16 Dec - 17 Dec
150 Sol by Stay with Bear

1120 Vieques by Stay with Bear

1120 Vieques by Stay with Bear
3.5 star property
Santurce
9.6 out of 10, Exceptional, (77)
"Room was clean. Good Air condition. Easy instructions for check in . Would come back :) "
United States
Sylvie
1120 Vieques by Stay with Bear

Star of the Olympus

Star of the Olympus
3.5 star property
Santurce
8.0 out of 10, Very good, (79)
"I loved my stay here. I got a small room for my stay on a business trip, nothing fancy but I don't need much- just a place to sleep and shower between business hours. The staff is very friendly and accommodating and the location of the property is walking distance to everything I needed, so I saved money on car rentals and got to enjoy the scenery while I walked to and from my destinations. I will definitely be staying here again in the future!"
United States
Gina
The price is AU$287
includes taxes & fees
11 Jan - 12 Jan 2026
Star of the Olympus

DUNA by DW

DUNA by DW
4.5 star property
Santurce
9.6 out of 10, Exceptional, (61)
"Great stay. "
United States
Albany
DUNA by DW
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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Top Rolling Hills Hotel Reviews

Find out more about Rolling Hills

Everything you need to know about Rolling Hills holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Rolling Hills holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Rolling Hills holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Rolling Hills holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Rolling Hills. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Rolling Hills holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Rolling Hills holiday rentals we have selected for you start as low as AU$178 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Rolling Hills rentals

At Expedia, we put the best Rolling Hills holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Rolling Hills rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Rolling Hills holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Rolling Hills. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Rolling Hills?

Yes, there are holiday rentals close to the most popular sights in Rolling Hills, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Rolling Hills has to offer?

150 Sol by Stay with Bear: This holiday home rental outside of Rolling Hills is in the historical district, and equipped with air conditioning and Netflix to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a stovetop and a microwave.

What’s there to see and do in Rolling Hills?

Explore the area and family-friendly sights such as Carabali Rainforest Park, or get out into nature at a spot like Condado Beach. While in the area, you can also visit popular places such as Port of San Juan and Pan American Pier.

What’s a holiday rental in Rolling Hills like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Rolling Hills. Holiday rentals feature amenities such as laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, holiday rentals can provide a sense of security away from shared hotel lifts and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for a small group gathering.