Rolling Hills Vacations from $572

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Your Rolling Hills Vacation

Say farewell to the worries of planning and hello to a Rolling Hills vacation package. With everything organized before you go, you can focus on discovering the best of this city, starting with Jaguas, which is great for nature, watersports and hiking. Fill your schedule with tours of Jose Miguel Agrelot Coliseum, Carolina Beach and Isla Verde Beach, some of the top attractions you just have to see during your trip to Rolling Hills. Don't put off your visit to this city any longer. Your dream Rolling Hills vacation is a couple of clicks away with Expedia.

The Latest Rolling Hills vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Puerto Valdes

Hotel Puerto Valdes

4 out of 5
San Juan Antiguo
Save 100% on your flight
Price was $921, price is now $572 per person
$572
per person
Jun 4 - Jun 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
8.8/10 Excellent! (594 reviews)
Hotel is very clean and Hector very friendly and helpful.thank you

Reviewed on Mar 28, 2026

Ola Boutique Hotel

Ola Boutique Hotel

4.5 out of 5
Condado
Save 100% on your flight
Price was $1,597, price is now $900 per person
$900
per person
Jun 12 - Jun 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
9/10 Wonderful! (741 reviews)
Breakfast was good and fresh

Reviewed on Mar 27, 2026

Aire de O:live

Aire de O:live

4 out of 5
Isla Verde
Save 100% on your flight
Price was $2,233, price is now $1,299 per person
$1,299
per person
Jun 3 - Jun 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to San Juan (SJU)
9.2/10 Wonderful! (469 reviews)
Great beach place. Walk right out to beach. Waited service on beach. Staff opens the door for you. Foods good. What else do you need?…

Reviewed on Mar 22, 2026

Coral by the Sea Hotel

Coral by the Sea Hotel

3 out of 5
Isla Verde
Save 100% on your flight
Price was $1,063, price is now $636 per person
$636
per person
Jun 3 - Jun 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to San Juan (SJU)
6.2/10 (2,232 reviews)
Es la tercera vez que me quedo. Es una excelente alternativa para cuando se viaja.

Reviewed on Mar 28, 2026

Hotel Milano

Hotel Milano

2 out of 5
Old San Juan
Save 100% on your flight
Price was $1,165, price is now $720 per person
$720
per person
Jun 12 - Jun 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
9/10 Wonderful! (292 reviews)
Everything look good it was a very short stay. The location is very convenient

Reviewed on Mar 28, 2026

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Discover the most popular places to visit in Rolling Hills

San Juan Cruise Port, Puerto Rico

Port of San Juan

Explore the waterfront in San Juan with a trip to Port of San Juan. Discover the area's top-notch restaurants and its acclaimed art scene.

Port of San Juan
Condado Beach

Condado Beach

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

Condado Beach
Luquillo Beach

Luquillo Beach

Sample local street food or doze under a palm tree on this picturesque stretch of coast.

Luquillo Beach

What to do in Rolling Hills

El Yunque Rainforest Guided Hiking with Waterfall Tour

El Yunque Rainforest Guided Hiking Tour

$88
per traveler
96% of travellers recommend
El Yunque Rainforest Guided Hiking Tour
UTV and Can-Am Sightseeing Tours in Puerto Rico

UTV and Can-Am Sightseeing Tours in Puerto Rico

$55
per adult
UTV and Can-Am Sightseeing Tours in Puerto Rico
FlyDining: Sunset & City Lights Dinner Over Old San Juan

FlyDining: 4 Course Sunset & City Light Dinner Over Old San Juan

$159
per adult
92% of travellers recommend
FlyDining: 4 Course Sunset & City Light Dinner Over Old San Juan
See all activities in Rolling Hills

Rolling Hills Hotel Deals

La Concha Resort, Puerto Rico, Autograph Collection

La Concha Resort, Puerto Rico, Autograph Collection

4 out of 5
1077 Ashford Ave Condado San Juan
$421 nightly
The price is $467 total per night from Apr 12 to Apr 13
$467 total
Apr 12 - Apr 13
Total with taxes and fees
9.2/10 Wonderful! (2,512 reviews)
Great beach and general area. Staff were wonderful and the food was delicious. Feeling a bit worn at the edges, but a very nice stay.

Reviewed on Mar 29, 2026

La Concha Resort, Puerto Rico, Autograph Collection
Caribe Hilton

Caribe Hilton

4.5 out of 5
1 San Geronimo Street San Juan
$335 nightly
The price is $366 total per night from Apr 26 to Apr 27
$366 total
Apr 26 - Apr 27
Total with taxes and fees
8.6/10 Excellent! (2,623 reviews)
We were there for business and didn't have time to enjoy the amenities. But the food was great. We will return for vacations.

Reviewed on Mar 30, 2026

Caribe Hilton
Costa Bahia Hotel Paseo Caribe

Costa Bahia Hotel Paseo Caribe

3.5 out of 5
1 Calle San Gerónimo San Juan San Juan
Fully refundableReserve now, pay when you stay
$166 nightly
The price is $181 total per night from Apr 9 to Apr 10
$181 total
Apr 9 - Apr 10
Total with taxes and fees
7.4/10 Good! (4,111 reviews)
The lobby is very small and not very

Reviewed on Mar 30, 2026

Costa Bahia Hotel Paseo Caribe
See all 4,301 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.

Find the Best Rolling Hills Vacation Packages

Rolling Hills Essential Information

Language
Spanish
Currency
U.S dollars
Local Welcome
¡Hola!
Local Goodbye
Adiós
Closest Airport
Luis Munoz Marin Intl. Airport (SJU)
Top Sights
Carolina Beach, Isla Verde Beach and Balneario de Carolina

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Frequently asked questions

How much does a Rolling Hills vacation package cost?
You'll find cheap prices from $572 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 vacation to Rolling Hills costs.
What are the cheapest months to go to Rolling Hills?
You're likely to find lower rates and better availability in September, October and December. Explore our cheap Rolling Hills vacation packages and you could score some great off-season deals.
How many days is enough for Rolling Hills?
With a well-organized travel plan, you can easily hit the top Rolling Hills sights in a handful of days. But if you'd like to discover hidden gems or go on day trips, think about booking your Rolling Hills vacation 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 vacation package well in advance.
Is it cheaper to book a Rolling Hills vacation as a package?
Expedia vacation 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 vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Rolling Hills?
If you have your Rolling Hills vacation 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.
Does Expedia offer Book Now, Pay Later Rolling Hills vacation packages?
Jet off on your ideal getaway to Rolling Hills with Expedia's Book Now, Pay Later vacations. No need to save up or wait until your next paycheck — we've partnered with online lender Affirm to offer you financial flexibility. Our vacation packages with payment plans mean you can split the cost across 3, 6 or 12 months. With no late payment fees or extra charges, it's a breeze to budget for your trip and snap up bargains while they last.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.