Puerto Rico Island Vacations from $580
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Your Puerto Rico Island Vacation
Choose one of our vacation packages to Puerto Rico Island and discover everything this destination has to offer. From its culture to its many other highlights, this place is a wonderful combination of excitement and adventure. Begin your trip to Puerto Rico Island with a couple of days in Río Grande visiting popular sights like Luquillo Beach and El Yunque National Forest. Dorado is another city that lures crowds from far and wide. Dorado Beach and Dorado Del Mar are two of the top places to see here. If you're ready to stop daydreaming and start doing, Expedia will help turn your Puerto Rico Island vacation into a reality.
The Latest Puerto Rico Island vacation packages
Price found within the past 48 hours. Click for updated prices.
The Oliver Hotel
San Juan Antiguo
Save 100% on your flight
Price was $1,076, price is now $580 per person
$580
per person
Feb 14 - Feb 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to San Juan (SJU)
9/10 Wonderful! (50 reviews)
Centrico, comodo, perfecto para estar cerca de todo y tener tranquilidad
Reviewed on Nov 28, 2025
Ola Boutique Hotel
Condado
Price was $1,367, price is now $593 per person
$593
per person
Feb 14 - Feb 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to San Juan (SJU)
9.2/10 Wonderful! (589 reviews)
Very nice staff. And the complementary breakfast was fabulous! Would definitely come back
Reviewed on Dec 1, 2025
OLV Fifty Five - Adults Only
Condado
Save 100% on your flight
Price was $1,631, price is now $886 per person
$886
per person
Feb 14 - Feb 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to San Juan (SJU)
8.6/10 Excellent! (577 reviews)
The staff was amazing, best hotel stay I’ve had in awhile
Reviewed on Nov 30, 2025
Hotel Puerto Valdes
San Juan Antiguo
Save 100% on your flight
Price was $1,782, price is now $985 per person
$985
per person
Feb 15 - Feb 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to San Juan (SJU)
9/10 Wonderful! (500 reviews)
Very modern and clean. We stayed in the penthouse that is extremely spacious. Attentive staff and welcoming.
Reviewed on Nov 24, 2025
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See all available trips from Chicago to Puerto Rico Island
View all tripsWhere to stay in Puerto Rico Island
Find the best Puerto Rico Island areas and neighborhoods for the activities you enjoy most. Learn more about Puerto Rico Island
Isla Verde
4/5(687 area reviews)
White-sands, beautifully clear water and excellent water sports make this beach one of the most popular in Puerto Rico.
Discover the most popular places to visit in Puerto Rico Island
El Yunque National Forest
4.5/5(1,177 reviews)
This tropical rainforest offers many great hiking options, including stunning mountain views and beautiful waterfalls.
La Guancha
4/5(152 reviews)
Take a stroll down Ponce’s waterfront boardwalk and experience its lively dining scene, local music, playgrounds, boat rides and views out to Isla Caja de Muertos.
Puerto Rico Convention Center
4.5/5(545 reviews)
Learn about the events happening at Puerto Rico Convention Center during your trip to San Juan. Amble around this vibrant area's beautiful beaches or experience its acclaimed art scene.
What to do in Puerto Rico Island
Culebra Day Trip from Fajardo by Catamaran
$180
per adult
90% of travellers recommend
Catamaran Sail & Snorkeling in the Caribbean with Lunch
$184
per traveler
90% of travellers recommend
Puerto Rico: UTV and Can-Am Sightseeing Tours
$68
per adult
76% of travellers recommend
Puerto Rico Island Hotel Deals
Condado Vanderbilt Hotel
1055 Ashford Avenue San Juan
Fully refundableReserve now, pay when you stay
$435 nightly
The price is $483 total per night from Dec 10 to Dec 11
$483 total
Dec 10 - Dec 11
Total with taxes and fees
9.2/10 Wonderful! (1,654 reviews)
Great respectful staff
Reviewed on Nov 30, 2025
The Royal Sonesta San Juan
5961 Isla Verde Avenue Carolina
Fully refundableReserve now, pay when you stay
$324 nightly
The price is $353 total per night from Dec 14 to Dec 15
$353 total
Dec 14 - Dec 15
Total with taxes and fees
9/10 Wonderful! (2,164 reviews)
Fantastic hotel
Reviewed on Dec 2, 2025
La Concha Resort, Puerto Rico, Autograph Collection
1077 Ashford Ave Condado San Juan
Fully refundableReserve now, pay when you stay
$348 nightly
The price is $386 total per night from Dec 14 to Dec 15
$386 total
Dec 14 - Dec 15
Total with taxes and fees
9/10 Wonderful! (2,269 reviews)
Beautiful place, super kind staff. I personally loved the beach access from the hotel, warm and cozy jacuzzi. They have a restaurant where you can order food and they will bring it out to you in the jacuzzi I think that was a 10/10 food was great too. Casino and club in the hotel made it so you would ...
Reviewed on Nov 29, 2025
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.
Find the Best Puerto Rico Island Vacation Packages
Puerto Rico Island Essential Information
Language | Spanish |
|---|---|
Currency | U.S dollars |
Local Welcome | ¡Hola! |
Local Goodbye | Adiós |
Closest Airport | Luis Munoz Marin Intl. Airport (SJU) |
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.