
Roosevelt Roads Vacations from $649
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The Latest Roosevelt Roads Vacation Packages
Price found within the past 48 hours. Click for updated prices.

Ola Boutique Hotel
Condado
Save 100% on your flight
Price was $1,085, price is now $649 per person
$649
per person
Jun 16 - Jun 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
9/10 Wonderful! (758 reviews)
Elliott was the star at our hotel stay. He made us breakfast and was super friendly and helpful. This hotel has no gym, swimming pool, there is no spa in property. There is no a la carte restaurant. The common area is nice and relaxing and there is one pool table. The rooms are tiny and there is no door for the toilet, no privacy, and the shower water goes everywhere. It IS close to everything, 2 24 hour supermarkets, pharmacy, beach, pick up for excursions, easy to uber to old San Juan and to Piñones. Tons of restaurants nearby.
Reviewed on Apr 9, 2026

Lazy Parrot Inn
Save 100% on your flight
Price was $1,438, price is now $780 per person
$780
per person
Jun 23 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to San Juan (SJU)
9.2/10 Wonderful! (1,003 reviews)
This is an incredible place with an amazing staff. The Manager kept going above and beyond, I will be returning!
Reviewed on Apr 7, 2026

Hotel Puerto Valdes
San Juan Antiguo
Save 100% on your flight
Price was $1,417, price is now $798 per person
$798
per person
Jun 25 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to San Juan (SJU)
8.8/10 Excellent! (623 reviews)
Great customer service the receptionist were awesome. Very comfortable place.
Reviewed on Apr 8, 2026


Aire de O:live
Isla Verde
Save 100% on your flight
Price was $1,537, price is now $934 per person
$934
per person
Jun 25 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to San Juan (SJU)
9.2/10 Wonderful! (498 reviews)
Love my stay at Aire De Olive. A chic oasis just a few footsteps from the beach.
The room was a dream as well, we had an ocean view. The shower was the star of the show, the steam and water pressure felt like you were at the spa. Housekeeping came everyday to clean and the staff were readily available to support with any of our needs.
Make sure to grab a drink at AWWA and lay out on the cabanas at the pool on the 2nd floor.
In terms of the area, it was just minutes from the airport and had lots of stores and food at a walkable nearby. It was also easily accessible to the more bustling areas of the island.
If you’re looking for a relaxing getaway with elevated amenities, don’t hesitate to book.
Reviewed on Apr 9, 2026
Find the Best Roosevelt Roads Vacation Packages
Roosevelt Roads Essential Information
Language | Spanish |
|---|---|
Currency | U.S dollars |
Local Welcome | ¡Hola! |
Local Goodbye | Adiós |
Closest Airport | Luis Munoz Marin Intl. Airport (SJU) |
Roosevelt Roads Hotel Deals

El Conquistador Resort
1000 Conquistador Avenue Fajardo
Fully refundableReserve now, pay when you stay
9/10 Wonderful! (3,353 reviews)
Second time staying and is the only place to stay in PR!! Loved all of it!
Reviewed on Apr 9, 2026

Hyatt Regency Grand Reserve Puerto Rico
200 Coco Beach Blvd. Highway 955-I Río Grande
9/10 Wonderful! (2,959 reviews)
The resort is beautiful and the food in the restaurants is top notch. It’s a large expansive property but the staff is always willing to pick you up in golf carts to get you around property.
Reviewed on Apr 9, 2026

Wyndham Grand Rio Mar Rainforest Beach and Golf Resort
6000 Rio Mar Boulevard Río Grande
Fully refundableReserve now, pay when you stay
8.6/10 Excellent! (2,216 reviews)
Everything is pricey. Good was ok buffet for breakfast for 3 was 125
Reviewed on Apr 8, 2026
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.
Discover the most popular places to visit in Roosevelt Roads
Ceiba Ferry Terminal
Explore the waterfront in Machos with a trip to Ceiba Ferry Terminal.
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