Roosevelt Roads Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ￥109,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Find the Best Roosevelt Roads Vacation Packages

Roosevelt Roads Hotel Deals

Hyatt Regency Grand Reserve Puerto Rico

Hyatt Regency Grand Reserve Puerto Rico

4 out of 5
200 Coco Beach Blvd. Highway 955-I Río Grande
Fully refundableReserve now, pay when you stay
The price is ￥41,875 per night from Jul 19 to Jul 20
￥41,875
￥53,861 total
Jul 19 - Jul 20
includes taxes & fees
9/10 Wonderful! (3,054 reviews)
"This property is absolutely picturesque and in an amazing location!! The staff members were all very kind and helpful, and the whole resort has been maintained very well. However, there are some improvements needed with the restaurant quality and availability of food options. We never received a ..."

Reviewed on Jul 13, 2026

Hyatt Regency Grand Reserve Puerto Rico
Wyndham Grand Rio Mar Rainforest Beach and Golf Resort

Wyndham Grand Rio Mar Rainforest Beach and Golf Resort

5 out of 5
6000 Rio Mar Boulevard Río Grande
Fully refundableReserve now, pay when you stay
The price is ￥60,145 per night from Jul 16 to Jul 17
￥60,145
￥82,783 total
Jul 16 - Jul 17
includes taxes & fees
8.6/10 Excellent! (2,192 reviews)
"Ana at the front desk was terrible. Her attitude was unprofessional, she didn’t make me feel welcomed because I didn’t speak Spanish. Also, I paid extra for an ocean view room and I got a rainforest view room. I’m disappointed and won’t be returning. The roots breakfast buffet was DISGUSTING and ..."

Reviewed on Jul 12, 2026

Wyndham Grand Rio Mar Rainforest Beach and Golf Resort
El Conquistador Resort

El Conquistador Resort

4 out of 5
1000 Conquistador Avenue Fajardo
Fully refundableReserve now, pay when you stay
The price is ￥52,239 per night from Aug 9 to Aug 10
￥52,239
￥68,395 total
Aug 9 - Aug 10
includes taxes & fees
9/10 Wonderful! (3,526 reviews)
"We loved everything about this property is always our number one to when we travel to Puerto Rico!! Specially Melanie Lopez she always makes us feel at home she is a great asset to your team!!"

Reviewed on Jul 11, 2026

El Conquistador Resort
See all 2,209 properties in Roosevelt Roads
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.

Stay near popular Roosevelt Roads attractions

Playa Blanca

6.6/10 (4 reviews)
Why not spend a lazy afternoon at Playa Blanca during your trip to Guayacán?
See properties

Frequently asked questions

How much does a Roosevelt Roads vacation package cost?
Be ready to book, because a getaway to Roosevelt Roads starts from an affordable . When you bundle your flights, hotels and car rentals into a package, you'll pick up the biggest bargains.
How do I get a cheap travel package to Roosevelt Roads?
Imagine all the wonderful things you could do in Roosevelt Roads with a wad of extra cash in your wallet. Watch your savings stack up when you combine your flights and hotel into a Roosevelt Roads vacation package. You have loads of choice when it comes to booking with Expedia too. In fact, you can pick from over 550 airlines and 1,000,000 hotel options throughout the world. Whether you're taking a vacation with the whole family or traveling with someone special, organizing a trip to Roosevelt Roads is better with a package.
What are the top hotels in Roosevelt Roads?
People traveling to Roosevelt Roads often book Vistaazulpenthouse or Cbrava Apartment With Ocean View/ Pool. You'll find them in Machos. Another interesting neighborhood is Guayacán. Exclusive Villas, Hidden Paradise Near Beaches and Escape Half The World are well-liked options in this part of town.
How far in advance should I book my Roosevelt Roads vacation?
Savvy travelers often book early. You can generally compare international airfares on Expedia up to a year before your intended flight. If you're late to book, there's no need to worry. Discounted prices occasionally occur just weeks before departure.
What does an Expedia Roosevelt Roads travel package include?
It all comes down to what type of trip you're thinking about. Roosevelt Roads vacation deals can include hotels, car rentals and flights. You can mix and match to find the travel package that suits you. You can also add on experiences and activities after you've booked to pick up even bigger discounts.
What should I know before booking a Roosevelt Roads travel package?
Locking in all the parts of your vacation together is a simple way to save. Combine your airfares, rental cars and hotels into a tidy little package. But hotels aren't your only option. Expedia has all kinds of properties, including vacation rentals like oceanfront condos and short-term homes. You've got loads of choices!
Can I choose my airline with a Roosevelt Roads Expedia vacation package?
Yes, so take your pick! Expedia has access to more than 550 airlines throughout the world, so you can customize your Roosevelt Roads adventure according to your needs and budget.
If I'm not able to travel, can I cancel my Roosevelt Roads vacation package?
It's difficult to predict what tomorrow might bring, so it's good to know that you can change or cancel your Roosevelt Roads vacation package. If your booking was made in the last 24 hours, you may be eligible for a refund. If your booking is older, your hotel, airline or car rental company may charge a fee. Visit our Customer Service Portal for more information.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.