Rolling Hills holiday rentals

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

Private kitchen
Living area
Living area
Room
Exceptional
(16 reviews)

Mansion Laura - a master room for everyone.

Guaynabo

5% off
AU$11,370
for 7 nights, 1 home
AU$1,624 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.
Guest's access to the suite.
Exceptional
(25 reviews)

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

San Juan

9% off
AU$1,540
for 7 nights, 1 villa
AU$220 per night
includes taxes & fees
San Juan, Garden suite w/private POOL, outdoor kitchen/BBQ & peaceful
Heated private pool.  It fits around 10 people and is for lounging purposes.
Exterior
Outdoor dining
Cayo Elia
Wonderful
(30 reviews)

Los Cayos Beach House

San Juan

8% off
AU$9,716
for 7 nights, 1 home
AU$1,388 per night
includes taxes & fees
Los Cayos Beach House
Relax on Villa Azure's serene balcony, offering breathtaking ocean views and comfortable seating enveloped by lush tropical foliage. This idyllic retreat is just steps from the vibrant Ocean Park Beach, perfect for morning coffee or sunset watching.
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.
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.
Exceptional
(56 reviews)

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

San Juan

8% off
AU$18,304
for 7 nights, 1 home
AU$2,615 per night
includes taxes & fees
Luxury 4000 sq ft Luxury Beach Villa Azure/Pool, Ocean Views & more
Bathroom
Room
Room
Interior
Exceptional
(28 reviews)

Carolina Studio close drive anywhere, no cleaning fee

Carolina

9% off
AU$645
for 7 nights, 1 apartment
AU$92 per night
includes taxes & fees
Carolina Studio close drive anywhere, no cleaning fee
Private kitchen
Interior
Room
Exterior
Wonderful
(48 reviews)

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

Carolina

8% off
AU$1,194
for 7 nights, 1 home
AU$171 per night
includes taxes & fees
Isla Verde- Beach/Bar/Restaurants Near Airport For Same Day Booking Message me
Room
Private kitchen
Interior
Exterior detail
Exceptional
(21 reviews)

Apartment in Carolina, close drive anywhere, no cleaning fee

Carolina

9% off
AU$696
for 7 nights, 1 apartment
AU$99 per night
includes taxes & fees
Apartment in Carolina, close drive anywhere, no cleaning fee
Bathroom
Outdoor dining
Exterior
Room
Excellent
(68 reviews)

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

Carolina

8% off
AU$716
for 7 nights, 1 home
AU$102 per night
includes taxes & fees
Isla Verde Beach+ Bars+ Restaurants perfect for Stop-N-Go near Airport in/out
Children’s area
Interior
Room
Pool
Wonderful
(7 reviews)

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

San Juan

9% off
AU$1,337
for 7 nights, 1 villa
AU$191 per night
includes taxes & fees
San Juan, garden Cozy suite w/private pool, BBQ, nearby & peaceful
Private kitchen
Interior
Exterior
Room
Exceptional
(6 reviews)

"Tropical Villa Isabel" - your Puerto Rico paradise!

San Juan

21% off
AU$4,696
for 7 nights, 1 home
AU$671 per night
includes taxes & fees
"Tropical Villa Isabel" - your Puerto Rico paradise!
Bathroom
Outdoor dining
Exterior detail
Exterior
Excellent
(57 reviews)

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

Carolina

8% off
AU$716
for 7 nights, 1 home
AU$102 per night
includes taxes & fees
Isla Verde Beach -Bars-Restaurants Great for Near Airport Stop-N-Go
Bathroom
Room
Exterior
Room
Exceptional
(5 reviews)

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

Carolina

8% off
AU$927
for 7 nights, 1 apartment
AU$132 per night
includes taxes & fees
Apt 4 Sagitario a 5 Mins to SJU Airport | Modern Studio for 2 near Isla Verde
Interior
Room
Living area
Terrace/patio
Exceptional
(19 reviews)

San Juan HOME, less than 20 minutes. from Everything

San Juan

8% off
AU$1,840
for 7 nights, 1 home
AU$263 per night
includes taxes & fees
San Juan HOME, less than 20 minutes. from Everything
Private kitchen
Room
Property grounds
Interior
Exceptional
(13 reviews)

308 Cozy Beachfront Studio

Carolina

6% off
AU$1,122
for 7 nights, 1 apartment
AU$160 per night
includes taxes & fees
308 Cozy Beachfront Studio
Room
Room
Bathroom
Exterior detail
Very good
(10 reviews)

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

Carolina

7% off
AU$693
for 7 nights, 1 apartment
AU$99 per night
includes taxes & fees
Caracoles #3 Apartment 7 Min to Airport & FREE WI-FI
Pool
Beach
Interior
Bar (on property)
Exceptional
(31 reviews)

Tropical Isla Verde 2-Bedroom Condo w/ Beach Access

Carolina

13% off
AU$2,959
for 7 nights, 1 apartment
AU$423 per night
includes taxes & fees
Tropical Isla Verde 2-Bedroom Condo w/ Beach Access
Bathroom
Private kitchen
Dining
Interior
Exceptional
(25 reviews)

The Charming Unit (5 minutes from Airport)

Carolina

8% off
AU$866
for 7 nights, 1 apartment
AU$124 per night
includes taxes & fees
The Charming Unit (5 minutes from Airport)
Queen Size bed
Picnic area
Beach Front Condo with easy and Secure direct access to the beach
Interior
Exceptional
(21 reviews)

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

Carolina

8% off
AU$1,952
for 7 nights, 1 apartment
AU$279 per night
includes taxes & fees
🌴Spectacular Beach Front Studio 🌴 19th Floor View of Beach, El Yunque Mt. & City
Interior
Room
Bathroom sink & Vanity.  Usually, extra towels on top shelve.
Exterior
Exceptional
(60 reviews)

Apt102 Beachfront Studio Steps to The Beach

Carolina

7% off
AU$1,247
for 7 nights, 1 apartment
AU$178 per night
includes taxes & fees
Apt102 Beachfront Studio Steps to The Beach
Bright living area with two AC units and an access to the private terrace
Outdoor shower (shared amenity) to rinse off after a day at the beach
The view of the shared backyard from the desk in master bedroom
Street view of the building (note the reserved parking on the left)
Wonderful
(18 reviews)

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

San Juan

13% off
AU$3,214
for 7 nights, 1 apartment
AU$459 per night
includes taxes & fees
Family Stay 4 min to Beach: Grill, Crib & Parking
Interior
Room
Dining
Private kitchen
Excellent
(24 reviews)

Da Vinci Suites 501

San Juan

9% off
AU$2,869
for 7 nights, 1 apartment
AU$410 per night
includes taxes & fees
Da Vinci Suites 501
Exterior detail
Beach
Room
Private kitchen
Exceptional
(5 reviews)

Deluxe Lodge in San Juan

San Juan

8% off
AU$780
for 7 nights, 1 apartment
AU$111 per night
includes taxes & fees
Deluxe Lodge in San Juan
Property grounds
Pool
Private kitchen
Living area
Exceptional
(29 reviews)

Apartment With Direct Access to the Beach

Carolina

8% off
AU$2,205
for 7 nights, 1 apartment
AU$315 per night
includes taxes & fees
Apartment With Direct Access to the Beach
Room
Living area
Living area
Pool
Excellent
(18 reviews)

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

Carolina

8% off
AU$1,878
for 7 nights, 1 apartment
AU$268 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 Stayz 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 Stayz. 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 Stayz, 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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