Roosevelt Roads Holidays from £905

Book a Hotel + Flight or Car together to unlock savings

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  • Plan, book, travel with confidence

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    Better together

    Save up to £335 when you book a flight and hotel together*
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    Find the right fit

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

    Packages with flights are ATOL protected

Top Roosevelt Roads Flight + Hotel Deals

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

Hotel Puerto Valdes

4 out of 5
San Juan Antiguo
Save 100% on your flight
per person
22 Sept - 29 Sept
found 12 hours ago
Return direct flight included
London (LON) to San Juan (SJU)
8.8/10 Excellent! (446 reviews)
Very clean and close distance to old San Juan

Reviewed on 31 Jul 2025

Ola Boutique Hotel

Ola Boutique Hotel

4.5 out of 5
Condado
Save 100% on your flight
per person
22 Sept - 29 Sept
found 12 hours ago
Return direct flight included
London (LON) to San Juan (SJU)
9/10 Wonderful! (429 reviews)
For my first time in Puerto Rico this hotel was perfect! The location was amazing and was walking distance to a lot of places like the beach and many good restaurants! Additionally, the hotel staff were super nice and made sure we had everything we needed! Would definitely stay here again!

Reviewed on 31 Jul 2025

OLV Fifty Five - Adults Only

OLV Fifty Five - Adults Only

4 out of 5
Condado
Save 100% on your flight
per person
22 Sept - 29 Sept
found 12 hours ago
Return direct flight included
London (LON) to San Juan (SJU)
8.8/10 Excellent! (500 reviews)
Omg that bed will have u sleep in

Reviewed on 29 Jul 2025

Fairmont El San Juan Hotel

Fairmont El San Juan Hotel

5 out of 5
Isla Verde
Save 100% on your flight
per person
22 Sept - 29 Sept
found 12 hours ago
Return direct flight included
London (LON) to San Juan (SJU)
8.4/10 Very Good! (1,795 reviews)
Great place to stay

Reviewed on 31 Jul 2025

Aire de O:live

Aire de O:live

4 out of 5
Isla Verde
Save 100% on your flight
per person
22 Sept - 29 Sept
found 12 hours ago
Return direct flight included
London (LON) to San Juan (SJU)
9.2/10 Wonderful! (193 reviews)
Beautiful hotel, the new pool on 2nd floor is awesome , food on the rooftop as well , beautifully decorated

Reviewed on 31 Jul 2025

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 hotels in Roosevelt Roads

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 £251 per night from 25 Aug to 26 Aug
£251
25 Aug - 26 Aug
includes taxes & fees
8.8/10 Excellent! (2,433 reviews)
"Parking too much"

Reviewed on 31 Jul 2025

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 £265 per night from 24 Aug to 25 Aug
£265
24 Aug - 25 Aug
includes taxes & fees
8.6/10 Excellent! (2,111 reviews)
"We had a nice time, the beach wasn’t as nice as I thought it would be. Overall my wife and I had a great time."

Reviewed on 30 Jul 2025

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 £297 per night from 24 Aug to 25 Aug
£297
24 Aug - 25 Aug
includes taxes & fees
9/10 Wonderful! (3,122 reviews)
"Gorgeous, clean and beautiful view."

Reviewed on 29 Jul 2025

El Conquistador Resort
See all 2,110 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Roosevelt Roads travel package cost?
From as little as £905. Yes, you read that correctly. Our Roosevelt Roads packages are the best way to stretch your budget. Bundle your favourite hotels, flights and rental car and get out and see this popular destination.
If I'm not able to travel, can I cancel my Roosevelt Roads travel package?
We totally understand that life sometimes gets in the way of your plans. If you've locked in a Roosevelt Roads travel package and need to cancel or amend it, we're here to help. We recommend having a look at our Customer Service Portal first for information. But generally speaking, if you've taken out your package in the last 24 hours, you may be able to change your itinerary for free. If it's more than 24 hours, your airline, hotel or car rental company may impose a charge.
How do I get a cheap travel package to Roosevelt Roads?
One of the simplest ways to save cash (and time) is to bundle your bookings with Expedia. Flights, hotels, rental cars and activities — we've got them all. Pick a combination that best suits you and watch your savings stack up. We know a travel package is never one-size-fits-all. That's why Expedia offers over 550 partner airlines and 1,000,000 hotel options worldwide, which lets you customize your Roosevelt Roads holiday.
Does Expedia offer Book Now, Pay Later Roosevelt Roads holidays?
We certainly do. Expedia has joined forces with online lender Klarna to help you easily pay for your holiday in instalments. Simply pick the payment plan that suits you best during checkout and take the stress out of budgeting for your trip. Be sure to bundle your flights, car hire and accommodation with Expedia to get the biggest bang for your travel buck. Consider these flexible payment options below:

  • Pay monthly holidays: Klarna offers easy monthly payment plans that suit all budgets, so you can take that well-earned holiday sooner.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it possible to pay for your holiday across multiple transactions.
  • Low deposit holidays: If paying a small percentage of your getaway (rather than the full total upfront) makes it easier to click that "book now" button, go for a low deposit holiday payment plan from Klarna.

How far in advance should I book my Roosevelt Roads holiday?
To bag discount prices, book as early as you can. Air carriers usually release flight tickets, along with some of the lowest fares, around 12 months prior to departure. Hotels, experiences and car rental should also be booked well in advance so you can have the pick of the bunch. If you've decided on a last-minute getaway in Roosevelt Roads, there are always plenty of great deals to be had on Expedia. Book your escape today!
What does an Expedia Roosevelt Roads travel package include?
It comes down to what you're after. If you're travelling by yourself, you might decide to bundle hotels and flights. Taking the whole crew to Roosevelt Roads? A travel package including hotels, flights and rental cars might be a better fit. Expedia gives you the flexibility and freedom to customize your travel package.
What should I know before booking a Roosevelt Roads travel package?
Tailor deals that match your budget with an Expedia package. Airfares, hotels, rental cars — we have them all. You'll save loads just for combining your bookings. Whether you're embarking on a snow and ski adventure or drinking cocktails on a beach, your dream getaway is only a few clicks away.
Can I choose my airline with a Roosevelt Roads Expedia travel package?
Yes, you're in control. We offer more than 550 partner airlines throughout the world, so you can design your Roosevelt Roads getaway according to your needs and budget.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.