Puerto Rico Island Vacation Packages 2025/2026 from $439

Name: Condado Vanderbilt Hotel
Price range: $244 total

Puerto Rico Island flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Lazy Parrot Inn

Save 100% on your flight

$439

per person

Dec 12 - Dec 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to San Juan (SJU)

This resort features a restaurant, an outdoor pool, and a poolside bar. There's fun for all ages with a children's pool and an arcade/game room, and families will appreciate the onsite laundry facilities. Enjoy the hot tub and perks like free WiFi.

Dorado Beach 5 Bedroom Villa

Higuillar

$574

per person

Nov 15 - Nov 19

found 1 day ago

Roundtrip flight included

Boston (BOS) to San Juan (SJU)

This villa features a private beach, a golf course, and a casino. Relax with sun loungers and enjoy a refreshing drink at one of the 2 beach bars. Bring the family and enjoy the water park, lazy river, and children's club.

Ola Boutique Hotel

Condado

$506

per person

Nov 30 - Dec 4

found 1 day ago

Roundtrip flight included

Boston (BOS) to San Juan (SJU)

This luxury hotel features a full-service spa and a restaurant. Enjoy the a rooftop terrace and free perks like continental breakfast and WiFi in public areas. There's a bar/lounge on site, and a 24-hour front desk and laundry facilities are also provided.

The Oliver Hotel

San Juan Antiguo

Save 100% on your flight

$619

per person

Dec 13 - Dec 18

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to San Juan (SJU)

A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. Luggage storage is provided and the front desk is staffed around-the-clock.

The Emerald

Santurce

Save 100% on your flight

$547

per person

Dec 4 - Dec 9

found 1 day ago

Roundtrip flight included

Boston (BOS) to San Juan (SJU)

This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and luggage storage are also on offer.

Top Puerto Rico Island hotels deals

The Royal Sonesta San Juan

5961 Isla Verde Avenue, Carolina

Free Cancellation

Reserve now, pay when you stay

$289 total

per night

Oct 5 - Oct 6

A full-service spa, 6 restaurants, and an outdoor pool are all featured at this smoke-free resort. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Traveling on business? Take advantage of the express check-out, conference space, and valet parking.

Pool

Spa

Condado Vanderbilt Hotel

1055 Ashford Avenue, San Juan

Free Cancellation

Reserve now, pay when you stay

$244 total

per night

Sep 30 - Oct 1

A full-service spa, 3 restaurants, and 4 outdoor pools are all featured at this luxury hotel. Enjoy beachfront dining and relax with beach cabanas and sun loungers. Families will appreciate the children's pool, complimentary bicycles, and babysitting.

Pool

Hot Tub

La Concha Resort, Puerto Rico, Autograph Collection

1077 Ashford Ave Condado, San Juan

Free Cancellation

Reserve now, pay when you stay

$319 total

per night

Oct 26 - Oct 27

This Art Deco resort features a casino, a full-service spa, and a nightclub. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Enjoy the 3 outdoor pools and perks like free WiFi.

Pool

Hot Tub

Fairmont El San Juan Hotel

6063 Isla Verde Avenue, Carolina

Free Cancellation

Reserve now, pay when you stay

$412 total

per night

Sep 27 - Sep 28

This eco-certified resort features a casino, a full-service spa, and a nightclub. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Enjoy a meal in one of the 6 restaurants and perks like free WiFi.

Pool

Spa

Embassy Suites by Hilton San Juan Hotel & Casino

8000 Tartak Street, Carolina

Free Cancellation

Reserve now, pay when you stay

$217 total

per night

Sep 29 - Sep 30

A casino, a 24-hour gym, and a restaurant are all featured at this smoke-free resort. There's fun for all ages with a children's pool and a playground, and barbecue grills are available on site. Enjoy the outdoor pool and free perks like cooked-to-order breakfast and WiFi in public areas.

Pool

Hot Tub

Hyatt Regency Grand Reserve Puerto Rico

200 Coco Beach Blvd. Highway 955-I, Río Grande

Free Cancellation

Reserve now, pay when you stay

$333 total

per night

Sep 28 - Sep 29

This Mediterranean resort features a golf course, a full-service spa, and 4 restaurants. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. Enjoy the 3 outdoor pools and perks like free WiFi.

Pool

Hot Tub

Don't see what you're looking for?

See all available properties in Puerto Rico Island

View all properties

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.

Popular places to visit

La Guancha

La Guancha is just one of the places to see in Playa, so why not enjoy the other things to explore during your travels? Amble around the area's seaside or attend a sporting event.

Puerto Rico Convention Center

During your trip, find out what's happening at Puerto Rico Convention Center, a top convention center in San Juan. Amble around this vibrant area's beautiful beaches or experience its acclaimed art scene.

Casino del Mar at La Concha Resort

Why not try your luck with a visit to Casino del Mar at La Concha Resort during your time in San Juan? Stroll along the seaside in this vibrant area, or check out its top-notch restaurants.

Frequently asked questions

How much are vacation packages to Puerto Rico Island?

You might be pleasantly surprised — you can find yourself in Puerto Rico Island for as little as $439. Here at Travelocity, we save you time and stress with our excellent vacation packages. With hotels, flights and experiences all in one place, why wait?

Where can I get the best vacation package deals for Puerto Rico Island?

There are fantastic Puerto Rico Island package deals to score with Travelocity. Did you know we partner with 400 airlines and 1,000,000 worldwide properties? Keep that in mind the next time you're ready to tick another place off your bucket list.

Why should I book my Puerto Rico Island vacation bundle via Travelocity?

From our 24/7 customer support to our range of fantastic destinations, we are committed to fulfilling your vacation dreams. All you'll have to do is to click and book — our Price Match Guarantee will ensure you lock in the lowest price.

Will I save money on my Puerto Rico Island car rental if I combine it with a hotel or flight?

Combining your bookings into a Puerto Rico Island vacation package will certainly save you money. Choose a car and flight; a car, hotel and flight; or a car and hotel. You won't find a better way to explore the greater Puerto Rico Island region than from the comfort of your own rental car. You can also add tours and experiences to your Travelocity package.