
Roosevelt Roads Holidays from AU$2,477
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The Latest Roosevelt Roads Holiday Deals
Price found within the past 48 hours. Click for updated prices.

DREAMCATCHER by DW - ADULTS ONLY
Santurce
Price was AU$3,151, price is now AU$2,477 per person
AU$2,477
per person
29 Dec - 1 Jan
found 1 day ago
Return direct flight included
Las Vegas (LAS) to San Juan (SJU)
9.4/10 Exceptional! (950 reviews)
Boho style boutique hotel.. we’ll be staying here again when back in the area
Reviewed on 4 Oct 2025

OLV Fifty Five - Adults Only
Condado
Save 100% on your flight
Price was AU$4,493, price is now AU$2,845 per person
AU$2,845
per person
29 Dec - 1 Jan
found 1 day ago
Return direct flight included
Las Vegas (LAS) to San Juan (SJU)
8.8/10 Excellent! (545 reviews)
This hotel is very beautiful yet the cleaning staff only makes the bed. I’ve complained numerous times about the cleanliness of my room. The staff was amazing the manager Jay was very accommodating and the staff were all helpful and nice.
Reviewed on 13 Oct 2025

Aire de O:live
Isla Verde
Price was AU$4,096, price is now AU$2,851 per person
AU$2,851
per person
29 Dec - 1 Jan
found 1 day ago
Return direct flight included
Las Vegas (LAS) to San Juan (SJU)
9/10 Wonderful! (266 reviews)
I loved everything about this hotel and our stay. The beach is very nice and the hotel is ON the beach. You go downstairs and exit the lobby to the beach. No drive. The hotel provides beach towls, loungers, and umbrellas at no extra charge. There is also beach service from the restaurant. This is perfect for families with young children.
The pool service is the absolute best. The restaurant Awwa is the restaurant by the pool. The menu is top notch. The food is quite good. My 4 year old loved the fish tacos and the wagu sliders. The upstairs restaurant Kumo is awesome we enjoyed their breakfast and dinner.
The room is amazing. We loved it plus the view of the beach was ideal.
The staff is very accomodating, personable, and polite. We highly recommend this hotel.
Reviewed on 11 Oct 2025

Olive Boutique Hotel, A Small Luxury Hotel of the World (Adults Only)
Condado
Price was AU$3,582, price is now AU$2,594 per person
AU$2,594
per person
29 Dec - 1 Jan
found 1 day ago
Return direct flight included
Las Vegas (LAS) to San Juan (SJU)
9/10 Wonderful! (640 reviews)
This has to be my #1 hotel experience ever. The staff was so great, environment very private and just awesome place and views. I will be back.,
Reviewed on 15 Sept 2025
Roosevelt Roads Holiday
Roosevelt Roads Essential Information
Language | Spanish |
---|---|
Currency | U.S dollars |
Local Welcome | ¡Hola! |
Local Goodbye | Adiós |
Closest Airport | Luis Munoz Marin Intl. Airport (SJU) |
Top Sights | Playa Blanca, Playa Los Machos and Playa Medio Mundo |
Our pick of the best Roosevelt Roads Hotel Deals

Hyatt Regency Grand Reserve Puerto Rico
200 Coco Beach Blvd. Highway 955-I, Río Grande
Fully refundableReserve now, pay when you stay
The price is AU$530 per night from 3 Nov to 4 Nov
AU$530
3 Nov - 4 Nov
includes taxes & fees
8.8/10 Excellent! (2,694 reviews)
"Need to add microwave in the rooms"
Reviewed on 13 Oct 2025

El Conquistador Resort
1000 Conquistador Avenue, Fajardo
Fully refundableReserve now, pay when you stay
9/10 Wonderful! (3,192 reviews)
"Great property and amazing staff. Lots to do!"
Reviewed on 9 Oct 2025

Wyndham Grand Rio Mar Rainforest Beach and Golf Resort
6000 Rio Mar Boulevard, Río Grande
Fully refundableReserve now, pay when you stay
The price is AU$960 per night from 14 Oct to 15 Oct
AU$960
14 Oct - 15 Oct
includes taxes & fees
8.4/10 Very Good! (2,194 reviews)
"Coqui frog serenade at night is one of a kind. Staff was very friendly. Paying to park kinda sucks."
Reviewed on 9 Oct 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.
Explore a world of travel with Expedia
Lodging
- Aguas Claras Hotels
- Hotels near Black Sand Beach
- Ceiba Hotels
- Hotels near El Conquistador Golf Course
- Hotels near El Yunque National Forest
- Hotels near Esperanza Malecon
- Esperanza Hotels
- Fajardo Hotels
- Flamenco Hotels
- Florencio Hotels
- Lgbt Welcoming Hotels in Florida
- Florida Hotels
- Resort in Florida
- Humacao Hotels
- Isabel II Hotels
- Luxury Hotels in Juncos
- Las Piedras Hotels
- Loiza Hotels
- Inns in Loiza
- Resort in Loiza
- Apartments in Luquillo
- Luxury Hotels in Luquillo
- Luquillo Hotels
- B&B in Mabu
- Mabu Hotels
- Resort in Mabu
- Villas in Mabu
- Mata de Plátano Hotels
- Naguabo Hotels
- Hotels near Palmas del Mar Beach
- Lgbt Welcoming Hotels in Puerto Diablo
- Lgbt Welcoming Hotels in Puerto Ferro
- Lgbt Welcoming Hotels in Puerto Real
- Puerto Real Hotels
- All Inclusive Hotels in Punta Santiago
- Resort in Quebrada Fajardo
- Río Grande Hotels
- Cheap Hotels in San Lorenzo
- San Lorenzo Hotels
- Luxury Hotels in Santillana del Mar
- Sector Los Ramos Hotels
- Hotels near Sun Bay
- B&B in Vieques
- Hostels in Vieques
- Vieques Hotels
- Holiday Homes in Vieques Island
- Vieques Island Hotels
- Hotels near Wyndham Rio Mar Casino
Flights
- Flights to Ceiba
- Flights to Florida
- Flights to Humacao
- Flights to Juan Martín
- Flights to Mabu
- Flights to Playa
- Flights to Punta Arenas
- Flights to Punta Santiago
- Flights to Río Grande
- Flights to Río
- Flights to Santa Cruz
- Flights to Santiago y Lima
- Flights to Vieques Island
- Flights to Vieques
- Flights from Ceiba
- Flights from San Lorenzo
Packages
- Bioluminescent Bay
- Caracas Beach
- Castillo San Felipe del Morro
- Coco Beach Golf and Country Club
- Condado Beach
- El Yunque National Forest
- Escambron Beach
- Esperanza Holidays
- Fajardo Holidays
- Florida Holidays
- La Coca Falls
- La Fortaleza
- La Mina Falls
- Las Cabezas de San Juan Nature Reserve
- Las Paylas
- Luquillo Beach
- Pan American Pier
- Plaza de Armas
- Puerto Rico Island Holidays
- Puerto Rico Holidays
- Visit Río Grande
- San Juan Holidays
- Sea Glass Beach
- Visit Yabucoa
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.