Rolling Hills Vacation Rentals

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Check prices for these dates

Tonight
Dec 15 - Dec 16
Tomorrow
Dec 16 - Dec 17
This weekend
Dec 19 - Dec 21
Next weekend
Dec 26 - Dec 28

Our top choices for Rolling Hills vacation rentals

Fridge, microwave, coffee/tea maker, toaster
Segovia Studio Units

Segovia Studio Units

Segovia Studio Units
3.0 star property
Sabana Abajo
8.6 out of 10, Excellent, (731)
"Good, clean room easy check in and out "
United States
Cali
Segovia Studio Units
Family Villa (Marcela) | Beach/ocean view
Picuas Village

Picuas Village

Picuas Village
3.0 star property
Zarzal
7.4 out of 10, Good, (59)
"Tranquil"
United States
Edia
The price is ￥26,738
￥40,296 total
includes taxes & fees
Dec 17 - Dec 18
Picuas Village
Exclusive Tent, River View | 1 bedroom, Egyptian cotton sheets, premium bedding
Casa Parcha

Casa Parcha

Casa Parcha
3.5 star property
Naguabo
10.0 out of 10, Exceptional, (32)
"Loved the scenery and the bed was ver comfortable. Quick response was awesome as well. Will definitely come back. "
United States
Aurora
The price is ￥26,352
￥30,521 total
includes taxes & fees
Dec 29 - Dec 30
Casa Parcha
Interior
Casa Dulce

Casa Dulce

Casa Dulce
2.0 star property
Ciénaga Baja
8.6 out of 10, Excellent, (4)
"We were pleased with our stay. Great value for the space. Easy access to El Yunque. Host provided coffee, but no other food or spices. Beds were comfortable. We would stay here again. "
United States
Bruce H.
The price is ￥12,317
￥26,298 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Casa Dulce
Superior Studio Suite | In-room safe, iron/ironing board, free WiFi, bed sheets
Mare 1562

Mare 1562

Mare 1562
4.0 star property
Isla Verde
9.2 out of 10, Wonderful, (83)
"Room was very clean and comfortable "
United States
Stanzetta
Mare 1562
Interior
apartment 5 minutes from airport

apartment 5 minutes from airport

apartment 5 minutes from airport
Sabana Abajo
7.2 out of 10, Good, (46)
"great stay i would stay again "
United States
Jaquan
The price is ￥14,369
￥20,963 total
includes taxes & fees
Dec 29 - Dec 30
apartment 5 minutes from airport
Private kitchen
Cozy house near SJ w/ light 24/7

Cozy house near SJ w/ light 24/7

Cozy house near SJ w/ light 24/7
Puerto Nuevo
9.4 out of 10, Exceptional, (16)
"The apartment was amazing. Location was great and quiet. Close to everything. Loved it. 10/10"
United States
Cedric J.
The price is ￥10,851
￥17,199 total
includes taxes & fees
Dec 29 - Dec 30
Cozy house near SJ w/ light 24/7
Interior
2019 Cacique by Stay with Bear

2019 Cacique by Stay with Bear

2019 Cacique by Stay with Bear
3.0 star property
Santurce
8.8 out of 10, Excellent, (33)
"clean place and super friendly and communicative hosts! would love to stay here again ! very safe community too"
United States
citlaly
The price is ￥16,204
￥17,663 total
includes taxes & fees
Dec 17 - Dec 18
2019 Cacique by Stay with Bear
Private kitchen
Cozy Apartment in San Juan with light 24/7

Cozy Apartment in San Juan with light 24/7

Cozy Apartment in San Juan with light 24/7
Puerto Nuevo
9.2 out of 10, Wonderful, (17)
"The place was cute & quaint. Good place to go in and out. We ate at El Rancho Crioĺlo small place, however the food was delicious."
United States
Nancy S.
The price is ￥9,301
￥15,540 total
includes taxes & fees
Dec 29 - Dec 30
Cozy Apartment in San Juan with light 24/7
Hallway
Romeo Gay Hotel

Romeo Gay Hotel

Romeo Gay Hotel
4.0 star property
San Juan Antiguo
9.0 out of 10, Wonderful, (140)
"Great place"
United States
pietro
Romeo Gay Hotel
Property grounds
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 Villa Santa Juana 2 Fully Equipped 2BR Home with SOLAR PANELS /A/C / WIFI
Caguas
9.8 out of 10, Exceptional, (18)
"Best place ever stay."
United States
Jesus M.
The price is ￥14,444
￥29,720 total
includes taxes & fees
Dec 17 - Dec 18
Caguas Villa Santa Juana 2 Fully Equipped 2BR Home with SOLAR PANELS /A/C / WIFI
Beach nearby, beach towels
Beautiful Beachside Studio in Luquillo with WIFI

Beautiful Beachside Studio in Luquillo with WIFI

Beautiful Beachside Studio in Luquillo with WIFI
Mata de Plátano
8.4 out of 10, Very Good, (70)
"Space was super clean when we got there, directions easy to follow. Linda was very accommodating with our stay. Luqillo is a great town a lot to do and easy drive to San Juan. "
United States
Alexis
The price is ￥12,309
￥29,102 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Beautiful Beachside Studio in Luquillo with WIFI
Smart TV
Mami's Corner in Carolina with WiFi, AC, Near Airport, Beaches, Malls and more

Mami's Corner in Carolina with WiFi, AC, Near Airport, Beaches, Malls and more

Mami's Corner in Carolina with WiFi, AC, Near Airport, Beaches, Malls and more
2.0 star property
Sabana Abajo
9.4 out of 10, Exceptional, (9)
"Great spot for our family to stay for two nights while exploring Baya los Pinones, San Juan, and El Yunque."
United States
Edwin G.
The price is ￥20,255
￥33,592 total
includes taxes & fees
Dec 18 - Dec 19
Mami's Corner in Carolina with WiFi, AC, Near Airport, Beaches, Malls and more
Beach nearby
Emi&Mar Retreat

Emi&Mar Retreat

Emi&Mar Retreat
2.0 star property
Playa Fortuna
10.0 out of 10, Exceptional, (2)
"Very responsive, fairly quick to answer my questions and concerns. We loved staying here and would 100% stay again on a next visit. Lugares como este me hacen amar y extrañar más a Mi Isla del Encanto. Te Amo Puerto Rico"
United States
Angel J.
The price is ￥14,881
￥19,023 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Emi&Mar Retreat
Beach nearby, sun loungers, beach towels
Beach Villa

Beach Villa

Beach Villa
Mata de Plátano
9.8 out of 10, Exceptional, (50)
"We loved the location where this property is located"
United States
Fnu p.
The price is ￥12,138
￥32,253 total
includes taxes & fees
Dec 17 - Dec 18
Beach Villa
Smart TV
Las Mariposas Suite Apt. 1

Las Mariposas Suite Apt. 1

Las Mariposas Suite Apt. 1
Hoyo Mulas
8.8 out of 10, Excellent, (13)
"Good place to stay..very quiet place "
United States
Dean
The price is ￥7,906
￥25,658 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Las Mariposas Suite Apt. 1
Exterior detail
M/H HOUSE(#3)⭐️ cozy apt near the airport and the beach

M/H HOUSE(#3)⭐️ cozy apt near the airport and the beach

M/H HOUSE(#3)⭐️ cozy apt near the airport and the beach
Sabana Abajo
9.2 out of 10, Wonderful, (53)
"It was in a great location close to everything. Very comfortable for a couple, would love to stay again in the future. "
United States
Jose C.
M/H HOUSE(#3)⭐️ cozy apt near the airport and the beach
Courtyard
MANSION MIRAFLORES

MANSION MIRAFLORES

MANSION MIRAFLORES
3.0 star property
Santurce
9.4 out of 10, Exceptional, (138)
"Clean room , amenities and great location"
United States
Elisabeth
The price is ￥23,558
￥31,622 total
includes taxes & fees
Dec 17 - Dec 18
MANSION MIRAFLORES
Family House, Terrace (Is in 4 San Justo San Juan PR 00901) | Terrace/patio
Old San Juan Rentals

Old San Juan Rentals

Old San Juan Rentals
3.5 star property
Old San Juan
8.6 out of 10, Excellent, (680)
"Amazing stay and staff was always available for us"
United States
Dominique
The price is ￥21,388
￥32,234 total
includes taxes & fees
Dec 17 - Dec 18
Old San Juan Rentals
Family Studio, Beach View | Beach/ocean view
ESJ by PMI Puerto Rico

ESJ by PMI Puerto Rico

ESJ by PMI Puerto Rico
3.5 star property
Isla Verde
7.2 out of 10, Good, (31)
"Very comfortable, great view and clean "
United States
Daniela
The price is ￥17,318
￥32,121 total
includes taxes & fees
Dec 17 - Dec 18
ESJ by PMI Puerto Rico
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

San Juan Marriott Resort and Stellaris Casino

San Juan Marriott Resort and Stellaris Casino

10/10 Excellent
"So clean, great hospitality and perfect location. "
selanda 3-night trip
Posted 8 hours ago
San Juan Marriott Resort and Stellaris Casino

Find out more about Rolling Hills

Search for holiday rentals in Rolling Hills on Expedia! You can easily find your home rentals, villas, holiday apartments in Rolling Hills using one of the methods below:

  • View our selection of featured holiday rentals in Rolling Hills
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  • Enter your travel dates to view the best deals on holiday rentals in Rolling Hills while they last

Look no further and take a look at our great range of rental properties in Rolling Hills!

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?

150 Sol by Stay with Bear: This vacation home rental outside of Rolling Hills is in the historical district and equipped with air-conditioning and Netflix 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 Pan American Pier.

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.