Rolling Hills Holidays

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to S$134 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Rolling Hills Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Fairmont El San Juan Hotel

Fairmont El San Juan Hotel

5 out of 5
Isla Verde
Save 100% on your flight
Price was S$1,798, price is now S$1,081 per person
S$1,081
per person
27 Sept - 2 Oct
found 1 day ago
Return direct flight included
Toronto (YTO) to San Juan (SJU)
8.4/10 Very Good! (1,920 reviews)
The hotel is amazing. Staff super friendly. The cafe next to the lobby is really good . We had an amazing time . Hopefully coming back next year.

Reviewed on 22 Aug, 2025

OLV Fifty Five - Adults Only

OLV Fifty Five - Adults Only

4 out of 5
Condado
Save 100% on your flight
Price was S$1,964, price is now S$1,140 per person
S$1,140
per person
27 Sept - 2 Oct
found 1 day ago
Return direct flight included
Toronto (YTO) to San Juan (SJU)
8.6/10 Excellent! (528 reviews)
I like how the hotel is set up its is very romantic and couples friendly. The front desk staff was very helpful and friendly. My one complaint is that the bell boys did not do their job at all, I can count on my hand the number of times the door was opened for me and my wife with 4 guys standing outside on their phones. I was a vip customer but did not recieve that treatment at all times.

Reviewed on 7 Aug, 2025

Aire de O:live

Aire de O:live

4 out of 5
Isla Verde
Save 100% on your flight
Price was S$1,972, price is now S$1,189 per person
S$1,189
per person
27 Sept - 2 Oct
found 1 day ago
Return direct flight included
Toronto (YTO) to San Juan (SJU)
9.2/10 Wonderful! (230 reviews)
Hospitality and how personal/staff treat guests are amazing.

Reviewed on 18 Aug, 2025

Fairmont El San Juan Villa Experience

Fairmont El San Juan Villa Experience

5 out of 5
Isla Verde
Save 100% on your flight
Price was S$2,125, price is now S$1,347 per person
S$1,347
per person
27 Sept - 2 Oct
found 1 day ago
Return direct flight included
Toronto (YTO) to San Juan (SJU)
7.6/10 Good! (124 reviews)
Love this resort. I’ve been here before and we will be back!

Reviewed on 9 Jul, 2025

Condado Vanderbilt Hotel

Condado Vanderbilt Hotel

5 out of 5
Condado
Save 100% on your flight
Price was S$1,594, price is now S$1,103 per person
S$1,103
per person
27 Sept - 2 Oct
found 1 day ago
Return direct flight included
Toronto (YTO) to San Juan (SJU)
9.2/10 Wonderful! (1,534 reviews)
Loved it!! Very Luxurious and staff was very nice and helpful, always provided a smile :)

Reviewed on 21 Aug, 2025

Top hotels in Rolling Hills

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 S$357 per night from 15 Sept to 16 Sept
S$357
15 Sept - 16 Sept
includes taxes & fees
8.4/10 Very Good! (2,192 reviews)
"We really enjoyed our experience. However, on check-in day we were disappointed because the beds weren't freshly made but the hotel accomodated us by discounting a couple of fees. The indoor restaurant's breakfast was just ok."

Reviewed on 21 Aug, 2025

Caribe Hilton
Hyatt Regency Grand Reserve Puerto Rico

Hyatt Regency Grand Reserve Puerto Rico

4 out of 5
200 Coco Beach Blvd. Highway 955-I, Río Grande
Fully refundableReserve now, pay when you stay
The price is S$343 per night from 25 Aug to 26 Aug
S$343
25 Aug - 26 Aug
includes taxes & fees
8.8/10 Excellent! (2,509 reviews)
"I had a truly wonderful stay at this resort! From the moment I arrived, I felt safe, comfortable, and completely relaxed. The grounds were absolutely beautiful with palm trees and birds everywhere, creating such a peaceful and tropical atmosphere. The pools were huge, clean, and inviting. One of ..."

Reviewed on 19 Aug, 2025

Hyatt Regency Grand Reserve Puerto Rico
Fairmont El San Juan Hotel

Fairmont El San Juan Hotel

5 out of 5
6063 Isla Verde Avenue, Carolina
Fully refundableReserve now, pay when you stay
The price is S$518 per night from 25 Aug to 26 Aug
S$518
25 Aug - 26 Aug
includes taxes & fees
8.4/10 Very Good! (1,912 reviews)
"Nice plce"

Reviewed on 18 Aug, 2025

Fairmont El San Juan Hotel
See all 4,072 properties in Rolling Hills
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.

Popular places to visit

Condado Beach featuring kayaking or canoeing, tropical scenes and a beach

Condado Beach

This beach within the bustling city of San Juan is the perfect place to relax for a few hours.

Condado Beach
Escambron Beach

Escambron Beach

Swim in calm waters among colorful fish at a picturesque beach that is regularly voted one of the best in Puerto Rico.

Escambron Beach
El Morro which includes general coastal views and heritage elements

Castillo San Felipe del Morro

This walled fortress was once used to protect Puerto Rico from invading colonies, and today offers visitors a dramatic reminder of that history.

Castillo San Felipe del Morro

What to do in Rolling Hills

El Yunque Rainforest Natural Waterslide on a sunny Puerto Rico Day

El Yunque Waterslide and Waterfall Tour with Food and Photos

S$76
per adult
94% of travellers recommend
El Yunque Waterslide and Waterfall Tour with Food and Photos
Puerto Rico: UTV and Can-Am Sightseeing Tours

Puerto Rico: UTV and Can-Am Sightseeing Tours

S$87
per adult
74% of travellers recommend
Puerto Rico: UTV and Can-Am Sightseeing Tours
City Lights / GLOW

LED Kayak Night Glow Tour in Condado Lagoon

S$96
per adult
92% of travellers recommend
LED Kayak Night Glow Tour in Condado Lagoon
See all activities in Rolling Hills

Frequently asked questions

How much does a Rolling Hills holiday package cost?
You'll find cheap prices from S$1,081 on Expedia for your Rolling Hills break. However, a range of factors like the length of stay, hotel choice and season will influence how much your holiday to Rolling Hills costs.
What are the cheapest months to go to Rolling Hills?
September, October and November are great times to look for cheap Rolling Hills holiday packages. Choosing to travel in less busy periods means you can typically find reduced prices on hotels and flights.
How many days is enough for Rolling Hills?
With a well-organised itinerary, you can easily hit the top Rolling Hills attractions in a few days. But if you prefer to discover lesser-known spots or go on day tours, consider booking your Rolling Hills holiday for longer.
How to find the best Rolling Hills package deals?
Use Expedia's handy filters to help you find some unbeatable Rolling Hills package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your break for midweek, or look for Rolling Hills package deals in the off-peak season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to lock in your holiday package well in advance.
Is it cheaper to book a Rolling Hills holiday as a package?
Expedia holiday packages are designed to give you more bang for your buck. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll typically score a better deal than booking each component separately. And you'll still enjoy the freedom to create a tailored Rolling Hills holiday by choosing your preferred airline, accommodation type and car class.
When to book a holiday package to Rolling Hills?
If you have your Rolling Hills holiday dates confirmed, book as soon as you can to grab some outstanding deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous trips? Our last-minute deals are ideal for quick escapes.
How to plan a trip to Rolling Hills?

  1. Choose when to travel: Check your schedule and get packing. Your favourite time of year and the type of activities on offer will also help you decide when to holiday in Rolling Hills.
  2. Set your budget: Factor in costs like flights, transportation and food when working out how much to set aside for your trip to Rolling Hills. Then, pick a property that suits your budget, whether that's a low-cost option or a deluxe retreat.
  3. Work out your trip length: Think about how long you'd like to spend discovering Rolling Hills. Plan your days so you can get to all the attractions and experiences you're interested in without rushing.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a customised Rolling Hills holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.