Rolling Hills holiday rentals

We found 2,681 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:1 Jan - 8 Jan

Private kitchen
Exterior
Property grounds
Pool
Wonderful
(11 reviews)

Green Nest at the Hills

Guaynabo

8% off
AU$9,420
for 7 nights, 1 home
AU$1,346 per night
includes taxes & fees
Green Nest at the Hills
Room
Interior
Pool
Exterior
Exceptional
(8 reviews)

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

San Juan

9% off
AU$1,480
for 7 nights, 1 villa
AU$211 per night
includes taxes & fees
San Juan, garden Cozy suite w/private pool, BBQ, nearby & peaceful
Exterior detail
Outdoor dining
Interior
Room
Wonderful
(52 reviews)

Isla Verde Walk To Beach -Bars-Restaurants Near Airport Good for a Stop-N-Go

Carolina

8% off
AU$865
for 7 nights, 1 home
AU$124 per night
includes taxes & fees
Isla Verde Walk To Beach -Bars-Restaurants Near Airport Good for a Stop-N-Go
Bathroom
Private kitchen
Exterior detail
Room
Exceptional
(21 reviews)

Apartment in Carolina, close drive anywhere, no cleaning fee

Carolina

9% off
AU$707
for 7 nights, 1 apartment
AU$101 per night
includes taxes & fees
Apartment in Carolina, close drive anywhere, no cleaning fee
Interior
Room
Room
Bathroom
Exceptional
(28 reviews)

Carolina Studio close drive anywhere, no cleaning fee

Carolina

9% off
AU$656
for 7 nights, 1 apartment
AU$94 per night
includes taxes & fees
Carolina Studio close drive anywhere, no cleaning fee
Terrace/patio
Exterior
Living area
Private kitchen
Exceptional
(45 reviews)

Colonial Apartment with Generator, Free Parking,

San Juan

8% off
AU$1,555
for 7 nights, 1 apartment
AU$222 per night
includes taxes & fees
Colonial Apartment with Generator, Free Parking,
Interior
Interior
Room
Interior
Very good
(5 reviews)

Startfish #2 Apartment 9 Min to Airport FREE WI-FI

Carolina

7% off
AU$810
for 7 nights, 1 apartment
AU$116 per night
includes taxes & fees
Startfish #2 Apartment 9 Min to Airport FREE WI-FI
Room
Room
Bathroom
Interior
Very good
(10 reviews)

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

Carolina

7% off
AU$704
for 7 nights, 1 apartment
AU$101 per night
includes taxes & fees
Caracoles #3 Apartment 7 Min to Airport & FREE WI-FI
Interior
Beach
Bar (on property)
Interior
Exceptional
(12 reviews)

Oceanside Penthouse Studio Apartment in Isla Verde w/ Beach Access

Carolina

12% off
AU$2,448
for 7 nights, 1 apartment
AU$350 per night
includes taxes & fees
Oceanside Penthouse Studio Apartment in Isla Verde w/ Beach Access
Property grounds
Room
Exterior
Interior
Wonderful
(26 reviews)

Centrally Located Apt w/AC, Free Parking & WiFi

Carolina

8% off
AU$1,084
for 7 nights, 1 apartment
AU$155 per night
includes taxes & fees
Centrally Located Apt w/AC, Free Parking & WiFi
Interior
Interior
Exterior
Room
Wonderful
(48 reviews)

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

Carolina

8% off
AU$1,675
for 7 nights, 1 home
AU$239 per night
includes taxes & fees
Isla Verde- Beach/Bar/Restaurants Near Airport For Same Day Booking Message me
Exterior
Room
Room
Bathroom
Exceptional
(5 reviews)

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

Carolina

8% off
AU$941
for 7 nights, 1 apartment
AU$134 per night
includes taxes & fees
Apt 4 Sagitario a 5 Mins to SJU Airport | Modern Studio for 2 near Isla Verde
Interior
Room
Private kitchen
Terrace/patio
Exceptional
(19 reviews)

Authentic San Juan HOME, less than 20 minutes. from Everything

San Juan

8% off
AU$1,869
for 7 nights, 1 home
AU$267 per night
includes taxes & fees
Authentic San Juan HOME, less than 20 minutes. from Everything
Room
Outdoor dining
Private kitchen
Interior
Exceptional
(28 reviews)

Casa de Lizzie

San Juan

8% off
AU$723
for 7 nights, 1 apartment
AU$103 per night
includes taxes & fees
Casa de Lizzie
Dining
Living area
Exterior
Interior
Wonderful
(7 reviews)

Caracoles #2 Apartment 7 Min to Airport & FREE WI-FI

Carolina

7% off
AU$810
for 7 nights, 1 apartment
AU$116 per night
includes taxes & fees
Caracoles #2 Apartment 7 Min to Airport & FREE WI-FI
Private kitchen
Terrace/patio
Bathroom
Room
Exceptional
(52 reviews)

It's always Summer here, 2 minutes walking to the beach!

San Juan

5% off
AU$1,397
for 7 nights, 1 apartment
AU$200 per night
includes taxes & fees
It's always Summer here, 2 minutes walking to the beach!
Queen Size bed
Picnic area
Stylish Studio
Beach Front Condo with easy and Secure direct access to the beach
Exceptional
(23 reviews)

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

Carolina

8% off
AU$2,089
for 7 nights, 1 apartment
AU$298 per night
includes taxes & fees
🌴Spectacular Beach Front Studio 🌴 19th Floor View of Beach, El Yunque Mt. & City
Room
Dining
Interior
Living area
Excellent
(6 reviews)

Historic Ocean Park Near Beach Water Reserve Fiber Internet Fast WiFi

San Juan

7% off
AU$2,275
for 7 nights, 1 apartment
AU$325 per night
includes taxes & fees
Historic Ocean Park Near Beach Water Reserve Fiber Internet Fast WiFi
West view from the balcony of the apartment. You are looking at Barlovento Park.
Dining room
Kitchen counter and stools
Luggage rack.
Exceptional
(80 reviews)

Spectacular Views in Condado

San Juan

8% off
AU$2,802
for 7 nights, 1 apartment
AU$400 per night
includes taxes & fees
Spectacular Views in Condado
Ocean view from the balcony
Ventana al Mar, walking distance from our building
Ventana al Mar and Vanderbildt hotel
Ocean view from balcony
Exceptional
(32 reviews)

Romantic Condado Studio | Steps to Beach + Views

San Juan

8% off
AU$2,432
for 7 nights, 1 apartment
AU$347 per night
includes taxes & fees
Romantic Condado Studio | Steps to Beach + Views
Interior
Balcony
Room
Full Kitchen
Exceptional
(57 reviews)

Paradis - Luxurious Apartment with Ocean View and Balcony.

San Juan

8% off
AU$3,050
for 7 nights, 1 apartment
AU$436 per night
includes taxes & fees
Paradis - Luxurious Apartment with Ocean View and Balcony.
Exterior detail
Outdoor dining
Property grounds
Room
Exceptional
(24 reviews)

Boho chic & cozy apartment near Hato Rey Banking area with solar panels.

San Juan

12% off
AU$853
for 7 nights, 1 apartment
AU$122 per night
includes taxes & fees
Boho chic & cozy apartment near Hato Rey Banking area with solar panels.
Bathroom
Outdoor dining
Exterior
Room
Excellent
(71 reviews)

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

Carolina

8% off
AU$759
for 7 nights, 1 home
AU$108 per night
includes taxes & fees
Isla Verde Beach+ Bars+ Restaurants perfect for Stop-N-Go near Airport in/out
Private kitchen
Room
Bathroom
Exterior
Wonderful
(50 reviews)

Isla Verde Beach+ Bars+ Restaurants

Carolina

8% off
AU$865
for 7 nights, 1 home
AU$124 per night
includes taxes & fees
Isla Verde Beach+ Bars+ Restaurants

  • 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. Port of San Juan and Casino del Mar at La Concha Resort 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)
  • Hipodromo Camarero (5 mi / 8 km)
  • Grand Reserve Golf Club (12.3 mi / 19.8 km)
  • Mandara Spa at the Westin Rio Mar Beach Resort (15 mi / 24.1 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)
  • El Yunque National Forest (14 mi / 22.5 km)
  • Balneario de Carolina (4.6 mi / 7.4 km)
  • Isla Verde Beach (4.9 mi / 7.9 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

What is the best area to stay in Rolling Hills when booking a holiday rental?
When considering a holiday rental in Rolling Hills, Puerto Rico, a popular area to stay is near the vibrant coastal neighbourhoods, which offer a delightful blend of relaxation and adventure. This region features a variety of properties, from charming villas to more modern apartments, allowing visitors to find accommodation that suits their preferences.One of the top attractions in this area is the stunning coastline, where you can enjoy beautiful beaches and partake in various water sports, such as snorkelling and paddleboarding. Additionally, the nearby nature reserves provide fantastic opportunities for hiking and observing the local wildlife, making it a great spot for nature enthusiasts.Cultural experiences are also abundant, with local markets and eateries serving authentic Puerto Rican cuisine. Staying in this lively part of Rolling Hills not only gives you access to picturesque views and outdoor activities but also immerses you in the rich culture and warmth of the local community.
What are the top attractions in Rolling Hills?
In Rolling Hills, Puerto Rico, visitors can enjoy a range of attractions that highlight the natural beauty and cultural richness of the area. The neighbourhood is known for its picturesque landscapes and proximity to stunning beaches, making it a great base for exploring the coastline.Nearby, the vibrant Luquillo Beach is famous for its golden sands and clear waters, great for sunbathing and water sports. Just a short drive away, the El Yunque National Forest offers lush hiking trails, waterfalls, and diverse flora and fauna, ideal for nature enthusiasts.Additionally, the local food scene is a highlight, with numerous kiosks and restaurants in the area serving authentic Puerto Rican cuisine, allowing visitors to experience the island's culinary delights.
Are all fees included in the Rolling Hills holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Rolling Hills holiday homes with parking?
Stayz offers a wide selection of holiday homes in Rolling Hills with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Rolling Hills holiday homes?
You can find great discounts on holiday homes in Rolling Hills on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Rolling Hills holiday home booking on Stayz?
To find Rolling Hills holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Rolling Hills?
A long-stay holiday home in Rolling Hills is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Rolling Hills holiday home?
Book your Rolling Hills holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Rolling Hills?
Prices for holiday homes in Rolling Hills vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Rolling Hills to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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