Rolling Hills Vacation Rentals

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Our top choices for Rolling Hills vacation rentals

Casa Parcha

Casa Parcha
1.0 star property
Naguabo
10.0 out of 10, Exceptional, (49 reviews)
"Excellent place and very calming and soothing environment. The staff was amazing and accommodating. "
United States
Ahmed
The price is CA $198
CA $232 total
includes taxes & fees
Jun 3 - Jun 4
Casa Parcha

Picuas Village

Picuas Village
3.0 star property
Zarzal
7.4 out of 10, Good, (68 reviews)
"Everything was amazing the view perfect recommend 100%"
United States
Liliana
The price is CA $361
CA $489 total
includes taxes & fees
May 27 - May 28
Picuas Village

El Yunque Rainforest

El Yunque Rainforest
3.5 star property
Naguabo
10.0 out of 10, Exceptional, (54 reviews)
"What a beautiful place, clean, private, and well equipped with everything you would need to enjoy a relaxing stay."
United States
Kelly
The price is CA $336
CA $405 total
includes taxes & fees
May 22 - May 23
El Yunque Rainforest

CARIBBEAN STARS

CARIBBEAN STARS
4.0 star property
Sabana Abajo
7.8 out of 10, Good, (58 reviews)
"Very nice spot with close parking and shopping. Excellent service and very clean and neat."
United States
Lance
The price is CA $123
CA $141 total
includes taxes & fees
Jun 10 - Jun 11
CARIBBEAN STARS

SanJuanHome Beach Restaurants Excursions

SanJuanHome Beach Restaurants Excursions
2.0 star property
Hato Rey Norte
10.0 out of 10, Exceptional, (1 review)
"What a nice place! As advertised. Host was great and his cleaning cousin and her husband were super nice."
United States
RANDY
The price is CA $273
CA $459 total
includes taxes & fees
May 20 - May 21
SanJuanHome Beach Restaurants Excursions

Spectacular Studio Apt With Spectacular Ocean View, Right Across A

Spectacular Studio Apt With Spectacular Ocean View, Right Across A
Mata de Plátano
9.8 out of 10, Exceptional, (22 reviews)
"Comfortable, well stocked studio in a great location. Loved having beach chairs and a cooler to use. View from balcony was spectacular. Host was helpful and responsive. Highly recommend!"
United States
Marjorie
The price is CA $178
CA $313 total
includes taxes & fees
May 16 - May 17
Spectacular Studio Apt With Spectacular Ocean View, Right Across A

Caguas Villa Santa Juana 2 Fully Equipped 2BR Home with SOLAR PANELS /A/C / WIFI

Caguas Villa Santa Juana 2 Fully Equipped 2BR Home with SOLAR PANELS /A/C / WIFI
Caguas
9.8 out of 10, Exceptional, (20 reviews)
"Great Host , always checking making sure we had everything, Clean house , i am coming back ."
United States
Rudy R.
The price is CA $247
CA $406 total
includes taxes & fees
May 16 - May 17
Caguas Villa Santa Juana 2 Fully Equipped 2BR Home with SOLAR PANELS /A/C / WIFI

Luxury Tiny home with pool & amazing view

Luxury Tiny home with pool & amazing view
Caguas
10.0 out of 10, Exceptional, (12 reviews)
"Great stay in a beautiful spot. We had a blast looking into the mountains from the pool. "
United States
David S.
The price is CA $401
CA $567 total
includes taxes & fees
Jun 4 - Jun 5
Luxury Tiny home with pool & amazing view

Sabana River Villa Las Paylas

Sabana River Villa Las Paylas
Sabana
9.4 out of 10, Exceptional, (13 reviews)
"Wonderful stay! Met all our expectations!"
United States
Michelle E.
The price is CA $240
CA $499 total
includes taxes & fees
May 19 - May 20
Sabana River Villa Las Paylas

Las Casitas de Village

Las Casitas de Village
3.0 star property
Carolina
7.4 out of 10, Good, (32 reviews)
"Receptionist was very helpful. Nice accommodations."
United States
Julia
The price is CA $212
CA $274 total
includes taxes & fees
May 18 - May 19
Las Casitas de Village

El Yunque Waterfalls Romantic Stay

El Yunque Waterfalls Romantic Stay
Puerto Rico
10.0 out of 10, Exceptional, (25 reviews)
"This place is beyond amazing. It is the perfect little house to stay with great decor. Every attention to detail "
United States
Donald
The price is CA $377
CA $559 total
includes taxes & fees
May 18 - May 19
El Yunque Waterfalls Romantic Stay

Beautiful Beachside Studio in Luquillo with WIFI

Beautiful Beachside Studio in Luquillo with WIFI
Mata de Plátano
8.6 out of 10, Excellent, (79 reviews)
"The amenities were good and the closeness to the beach was excellent."
United States
Damariz V.
The price is CA $105
CA $251 total
includes taxes & fees
May 26 - May 27
Beautiful Beachside Studio in Luquillo with WIFI

Steps from the Beach - Quiet Condo

Steps from the Beach - Quiet Condo
Mata de Plátano
8.6 out of 10, Excellent, (16 reviews)
"In a good location close to the beach."
United States
Abby F.
The price is CA $125
CA $282 total
includes taxes & fees
Jun 2 - Jun 3
Steps from the Beach - Quiet Condo

Beachfront Family Stay · Courtyard View · AC All Rooms · Remodeled

Beachfront Family Stay · Courtyard View · AC All Rooms · Remodeled
Mata de Plátano
9.8 out of 10, Exceptional, (16 reviews)
"It was great to stay in Luquillo. We had so much fun."
United States
alexandra v.
The price is CA $158
CA $374 total
includes taxes & fees
Jun 10 - Jun 11
Beachfront Family Stay · Courtyard View · AC All Rooms · Remodeled

Casa Pelayo

Casa Pelayo
3.0 star property
San Juan Antiguo
7.8 out of 10, Good, (17 reviews)
"the location is very nice , not directly in the center but close to everything "
United States
Issac
The price is CA $129
CA $166 total
includes taxes & fees
May 17 - May 18
Casa Pelayo

Cozy house near SJ w/ light 24/7

Cozy house near SJ w/ light 24/7
Puerto Nuevo
9.4 out of 10, Exceptional, (21 reviews)
"Very nice host"
United States
Alexander B.
The price is CA $96
CA $152 total
includes taxes & fees
May 18 - May 19
Cozy house near SJ w/ light 24/7

LaChanel QnRoomPool ResortVibe NearBeach

LaChanel QnRoomPool ResortVibe NearBeach
3.0 star property
Santurce
The price is CA $239
CA $329 total
includes taxes & fees
May 18 - May 19
LaChanel QnRoomPool ResortVibe NearBeach

Tu escape al Campo cerca de la Cuidad

Tu escape al Campo cerca de la Cuidad
Trujillo Alto
9.8 out of 10, Exceptional, (6 reviews)
"We had a great stay! The house itself was nice and clean, and the hot tub was amazing. As others have noted, the driveway is incredibly steep but all in all, it was a very nice place to stay for our visit to PR"
United States
Ashley L.
The price is CA $265
CA $505 total
includes taxes & fees
May 18 - May 19
Tu escape al Campo cerca de la Cuidad

Segovia Studio Units

Segovia Studio Units
3.0 star property
Sabana Abajo
8.6 out of 10, Excellent, (845 reviews)
"It was a very comfortable place, conveniently located near the airport and Old San Juan. The facilities were beautiful and comfortable, and the lady who welcomed us was always very friendly and helpful."
United States
Alondra
The price is CA $69
CA $118 total
includes taxes & fees
May 27 - May 28
Segovia Studio Units

Ocean Front-Great Location

Ocean Front-Great Location
Playa Fortuna
9.8 out of 10, Exceptional, (52 reviews)
"This unit was very nicely laid out and updated. The kitchen and bathrooms were well stocked with lots of essentials. The view from the big balcony was amazing."
United States
Joni
The price is CA $154
CA $345 total
includes taxes & fees
May 19 - May 20
Ocean Front-Great Location
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Rolling Hills. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Rolling Hills?

Yes, we give you a choice of vacation rentals near top sights in Rolling Hills, or you can choose a more remote option if you're looking for relaxation.

What are some of the best vacation rentals in Rolling Hills?

1120 Vieques by Stay with Bear: This vacation home rental outside of Rolling Hills is near the airport and equipped with air-conditioning and free WiFi 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 like Port of San Juan and Casino del Mar at La Concha Resort.

What’s a vacation rental in Rolling Hills like?

A vacation rental is a private property you can stay in for short or long periods in Rolling Hills. Vacation rentals offer amenities such as hot tubs, fire pits, and patios so you'll have everything you need. If you're concerned about a sanitized environment, a vacation rental can provide a sense of safety away from shared hotel elevators and busy reception areas while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a popular choice for small groups.