Rolling Hills holiday homes

We found 2,644 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in Rolling Hills that are perfect for your trip. Whether you're travelling with a group or just with your pet, holiday homes have the amenities that you need and want for your stay, which might include cable TV and a washer and dryer. You'll be sure to find a property to rent for everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – Rolling Hills

Showing deals for:13 Nov - 20 Nov

Pool
Living area
Living area
Room
Exceptional
(16 reviews)

Mansion Laura - a master room for everyone.

Guaynabo

5% off
NZ$14,263
for 7 nights, 1 home
NZ$2,038 per night
includes taxes & fees
Mansion Laura - a master room for everyone.
Dining
Isla Verde Beach to 15 min
Private pool (not shared) only for you and your partner.
Exterior
Exceptional
(25 reviews)

San Juan, Garden suite w/private POOL, outdoor kitchen/BBQ & peaceful

San Juan

9% off
NZ$1,868
for 7 nights, 1 villa
NZ$267 per night
includes taxes & fees
San Juan, Garden suite w/private POOL, outdoor kitchen/BBQ & peaceful
Outdoor dining
Exterior
Dining
Heated private pool.  It fits around 10 people and is for lounging purposes.
Wonderful
(30 reviews)

Los Cayos Beach House

San Juan

8% off
NZ$12,224
for 7 nights, 1 home
NZ$1,746 per night
includes taxes & fees
Los Cayos Beach House
This stunning living room seamlessly blends comfort and style. Plush sofas, large windows, and warm wooden accents create a cozy, inviting space, enhanced by modern decor and ample natural light—a perfect retreat for relaxation and socializing.
Relax in Villa Azure’s master suite, featuring a desk, sitting area, and breathtaking ocean and pool views. Enjoy private access to two terraces, one overlooking the pool and another offering a stunning ocean backdrop.
Experience pure bliss by the shimmering pool of Villa Azure, adorned with plush loungers and a graceful water fountain. The outdoor dining area offers shade and space for 10, alongside a refreshing shower, completing this luxurious retreat.
Villa Azure's chic dining area, where stunning views of Ultimo Trolley Beach create a picturesque backdrop. This space perfectly blends modern design with coastal beauty, offering a tranquil setting for meals & gatherings just steps from the ocean.
Exceptional
(56 reviews)

Luxury 4000 sq ft Luxury Beach Villa Azure/Pool, Ocean Views & more

San Juan

8% off
NZ$22,172
for 7 nights, 1 home
NZ$3,167 per night
includes taxes & fees
Luxury 4000 sq ft Luxury Beach Villa Azure/Pool, Ocean Views & more
Room
Room
Interior
Bathroom
Exceptional
(28 reviews)

Carolina Studio close drive anywhere, no cleaning fee

Carolina

9% off
NZ$792
for 7 nights, 1 apartment
NZ$113 per night
includes taxes & fees
Carolina Studio close drive anywhere, no cleaning fee
Private kitchen
Interior
Exterior
Room
Wonderful
(48 reviews)

Isla Verde- Beach/Bar/Restaurants Near Airport For Same Day Booking Message me

Carolina

8% off
NZ$1,447
for 7 nights, 1 home
NZ$207 per night
includes taxes & fees
Isla Verde- Beach/Bar/Restaurants Near Airport For Same Day Booking Message me
Room
Private kitchen
Exterior detail
Bathroom
Exceptional
(21 reviews)

Apartment in Carolina, close drive anywhere, no cleaning fee

Carolina

9% off
NZ$854
for 7 nights, 1 apartment
NZ$122 per night
includes taxes & fees
Apartment in Carolina, close drive anywhere, no cleaning fee
Exterior
Outdoor dining
Bathroom
Room
Excellent
(68 reviews)

Isla Verde Beach+ Bars+ Restaurants perfect for Stop-N-Go near Airport in/out

Carolina

8% off
NZ$880
for 7 nights, 1 home
NZ$126 per night
includes taxes & fees
Isla Verde Beach+ Bars+ Restaurants perfect for Stop-N-Go near Airport in/out
Room
Interior
Children’s area
Pool
Wonderful
(7 reviews)

San Juan, garden Cozy suite w/private pool, BBQ, nearby & peaceful

San Juan

9% off
NZ$1,620
for 7 nights, 1 villa
NZ$231 per night
includes taxes & fees
San Juan, garden Cozy suite w/private pool, BBQ, nearby & peaceful
Private kitchen
Interior
Exterior
Terrace/patio
Exceptional
(6 reviews)

"Tropical Villa Isabel" - your Puerto Rico paradise!

San Juan

20% off
NZ$5,758
for 7 nights, 1 home
NZ$823 per night
includes taxes & fees
"Tropical Villa Isabel" - your Puerto Rico paradise!
Exterior
Outdoor dining
Exterior detail
Room
Excellent
(57 reviews)

Isla Verde Beach -Bars-Restaurants Great for Near Airport Stop-N-Go

Carolina

8% off
NZ$880
for 7 nights, 1 home
NZ$126 per night
includes taxes & fees
Isla Verde Beach -Bars-Restaurants Great for Near Airport Stop-N-Go
Bathroom
Room
Room
Exterior
Exceptional
(5 reviews)

Apt 4 Sagitario a 5 Mins to SJU Airport | Modern Studio for 2 near Isla Verde

Carolina

8% off
NZ$1,137
for 7 nights, 1 apartment
NZ$162 per night
includes taxes & fees
Apt 4 Sagitario a 5 Mins to SJU Airport | Modern Studio for 2 near Isla Verde
Beach
Room
Private kitchen
Property grounds
Exceptional
(13 reviews)

308 Cozy Beachfront Studio

Carolina

6% off
NZ$1,376
for 7 nights, 1 apartment
NZ$197 per night
includes taxes & fees
308 Cozy Beachfront Studio
Living area
Room
Terrace/patio
Private kitchen
Exceptional
(19 reviews)

San Juan HOME, less than 20 minutes. from Everything

San Juan

8% off
NZ$2,181
for 7 nights, 1 home
NZ$312 per night
includes taxes & fees
San Juan HOME, less than 20 minutes. from Everything
Exterior detail
Room
Room
Interior
Very good
(10 reviews)

Caracoles #3 Apartment 7 Min to Airport & FREE WI-FI

Carolina

7% off
NZ$850
for 7 nights, 1 apartment
NZ$121 per night
includes taxes & fees
Caracoles #3 Apartment 7 Min to Airport & FREE WI-FI
Pool
Beach
Bar (on property)
Room
Exceptional
(31 reviews)

Tropical Isla Verde 2-Bedroom Condo w/ Beach Access

Carolina

13% off
NZ$3,583
for 7 nights, 1 apartment
NZ$512 per night
includes taxes & fees
Tropical Isla Verde 2-Bedroom Condo w/ Beach Access
Interior
Private kitchen
Dining
Room
Exceptional
(25 reviews)

The Charming Unit (5 minutes from Airport)

Carolina

7% off
NZ$1,061
for 7 nights, 1 apartment
NZ$152 per night
includes taxes & fees
The Charming Unit (5 minutes from Airport)
Stylish Studio
Picnic area
Queen Size bed
Beach Front Condo with easy and Secure direct access to the beach
Exceptional
(21 reviews)

🌴Spectacular Beach Front Studio 🌴 19th Floor View of Beach, El Yunque Mt. & City

Carolina

8% off
NZ$2,315
for 7 nights, 1 apartment
NZ$331 per night
includes taxes & fees
🌴Spectacular Beach Front Studio 🌴 19th Floor View of Beach, El Yunque Mt. & City
Interior
Room
Kitchen
Bathroom sink & Vanity.  Usually, extra towels on top shelve.
Exceptional
(60 reviews)

Apt102 Beachfront Studio Steps to The Beach

Carolina

7% off
NZ$1,511
for 7 nights, 1 apartment
NZ$216 per night
includes taxes & fees
Apt102 Beachfront Studio Steps to The Beach
The view of the shared backyard from the desk in master bedroom
Outdoor shower (shared amenity) to rinse off after a day at the beach
Street view of the building (note the reserved parking on the left)
Dining area with the view of the living room
Wonderful
(18 reviews)

Family Stay 4 min to Beach: Grill, Crib & Parking

San Juan

13% off
NZ$3,892
for 7 nights, 1 apartment
NZ$556 per night
includes taxes & fees
Family Stay 4 min to Beach: Grill, Crib & Parking
Private kitchen
Room
Dining
Living area
Excellent
(24 reviews)

Da Vinci Suites 501

San Juan

9% off
NZ$3,447
for 7 nights, 1 apartment
NZ$492 per night
includes taxes & fees
Da Vinci Suites 501
Exterior detail
Beach
Private kitchen
Room
Exceptional
(5 reviews)

Deluxe Lodge in San Juan

San Juan

8% off
NZ$957
for 7 nights, 1 apartment
NZ$137 per night
includes taxes & fees
Deluxe Lodge in San Juan
Property grounds
Pool
Exterior
Private kitchen
Exceptional
(29 reviews)

Apartment With Direct Access to the Beach

Carolina

8% off
NZ$2,614
for 7 nights, 1 apartment
NZ$373 per night
includes taxes & fees
Apartment With Direct Access to the Beach
Interior
Living area
Room
Pool
Excellent
(18 reviews)

Isla Verde Beach Front Condo-Experience the best beach in Puerto Rico!

Carolina

8% off
NZ$2,226
for 7 nights, 1 apartment
NZ$318 per night
includes taxes & fees
Isla Verde Beach Front Condo-Experience the best beach in Puerto Rico!
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Book a holiday rental for your Rolling Hills getaway

Learn about the unique charm of Rolling Hills with a stay in a holiday home rental. This city has something for everyone. Condado Beach and Port of San Juan are just a couple of the must-see attractions in the area. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in Rolling Hills

Are you searching for things to do while you're in town? Venture out of your holiday home and check out everything that Rolling Hills has to offer. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Coco Beach Golf and Country Club (12.2 mi / 19.6 km)
  • Carabali Rainforest Park (14.5 mi / 23.4 km)
  • Wyndham Rio Mar Golf Course (14.7 mi / 23.6 km)
  • The Palm (1 mi / 1.6 km)
  • Hipodromo Camarero (5 mi / 8 km)
  • Toro Verde Urban Park (8.7 mi / 14 km)

Exploring the natural features in Rolling Hills

Whether you're an outdoor enthusiast or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Rolling Hills. These are a few of the area's noteworthy sights, all within 30 miles (48.2 km) of the city centre:

  • Condado Beach (8.4 mi / 13.6 km)
  • Isla Verde Beach (4.9 mi / 7.9 km)
  • El Yunque National Forest (14 mi / 22.5 km)
  • Balneario de Carolina (4.6 mi / 7.4 km)
  • Pinones State Forest (5.1 mi / 8.1 km)
  • Playa Ocean Park (7.1 mi / 11.4 km)

Transport to and around Rolling Hills

Fly into San Juan (SJU-Luis Munoz Marin Intl.), the closest airport, located 4.2 mi (6.7 km) from the city centre.

Frequently asked questions

How much does it cost to rent a holiday home in Rolling Hills?
Property type, length of stay and time of year are among the factors that can influence the price of a holiday home. Simply click on your dates of travel to find your perfect fit. From comfy cottages to expansive villas, all Bookabach holiday homes provide unbeatable value.
How much does it cost to rent a beach house in Rolling Hills?
When you travel and the size and style of the property will determine the cost of your beachside holiday home. Type in your Rolling Hills travel dates to see all your options on Bookabach. Did someone just say "private pool"? Use our filters to pick the features and amenities you want in your home.
What are the top attractions for families in Rolling Hills?
Keep the kids occupied at these fabulous family-friendly attractions in Rolling Hills:
  • Carolina Beach
  • Isla Verde Beach
  • Balneario de Carolina
How old do you have to be to rent a holiday home in Rolling Hills?
The minimum required age is normally 16, 18 or 21. It can vary from property to property on Bookabach, so look at the rules of your preferred Rolling Hills holiday home before booking your trip.
How long can I rent a holiday home in Rolling Hills for?
The amount of time you can book a Rolling Hills holiday home for is up to the property. Simply enter your preferred travel dates to view available options offering longer term stays. They include the things you need to make your extended getaway more enjoyable and convenient, such as kitchens and yards. Some properties might also offer discounted weekly or monthly prices, so you can stay even longer for less.

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