Roosevelt Roads Vacation Packages 2025 from $386

Roosevelt Roads flight + hotel vacation packages

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

San Agustin Apartments

San Juan Antiguo

Save 100% on your flight

per person

Aug 17 - Aug 20

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to San Juan (SJU)

This apartment features express check-in, laundry facilities, and free self parking. Business travelers can take advantage of the business center. Express check-out and luggage storage are also provided.

Ola Boutique Hotel

Condado

per person

Aug 7 - Aug 10

found 1 day ago

Roundtrip flight included

Atlanta (ATL) 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.

Villa Azure Ocean Suites

Santurce

per person

Aug 11 - Aug 14

found 1 day ago

Roundtrip flight included

New York (JFK) to San Juan (SJU)

An outdoor pool is featured at this guesthouse, along with free WiFi in public areas and a terrace. A picnic area, express check-out, and concierge services are also on offer.

El Colonial - Adults Only

Old San Juan

per person

Jul 10 - Jul 14

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to San Juan (SJU)

This hotel features a bar/lounge, free WiFi in public areas, and a terrace. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. The front desk is staffed around-the-clock and concierge services are on offer.

Ciqala Suites Hotel

Santurce

Save 100% on your flight

per person

Aug 16 - Aug 21

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to San Juan (SJU)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Enjoy the a rooftop terrace and free perks like cooked-to-order breakfast and free self parking.

Top Roosevelt Roads hotels deals

Hyatt Regency Grand Reserve Puerto Rico

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

Free Cancellation

Reserve now, pay when you stay

$306 nightly

$333 total

Jun 12 - Jun 13

Total includes taxes and fees

This smoke-free 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

El Conquistador Resort

1000 Conquistador Avenue, Fajardo

Free Cancellation

Reserve now, pay when you stay

$343 nightly

$374 total

Jun 22 - Jun 23

Total includes taxes and fees

This Mediterranean hotel features a private beach, a golf course, and free water park access. Relax with free beach cabanas and sun loungers, and cool off with a drink at the beachside bar. Bring the family and enjoy the lazy river, children's pool, and waterslide.

On private beach

Pool

Wyndham Grand Rio Mar Rainforest Beach and Golf Resort

6000 Rio Mar Boulevard, Río Grande

Free Cancellation

Reserve now, pay when you stay

$310 nightly

$344 total

Jun 12 - Jun 13

Total includes taxes and fees

This smoke-free resort features a golf course, a casino, and a full-service spa. Relax with beach cabanas and sun loungers, and enjoy a drink at one of the 2 beachside bars. There's fun for all ages with a children's pool and a waterslide.

Pool

Hot Tub

Wyndham Palmas Beach and Golf Boutique Resort

170 Candelero Drive, Palmas del Mar, Humacao

$186 nightly

$202 total

Jun 9 - Jun 10

Total includes taxes and fees

A marina, 5 restaurants, and 2 outdoor pools are all featured at this smoke-free resort. Traveling on business? Take advantage of the 4 conference rooms, free WiFi in public areas, and express check-out. Unwind with drinks at one of the 2 bars/lounges or the poolside bar and make the most of the 15 outdoor tennis courts.

Pool

Hot Tub

Fairfield by Marriott Luquillo Beach

3KM 36.0 MATA DE PLATANO, Luquillo

Free Cancellation

Reserve now, pay when you stay

$183 nightly

$203 total

Jun 15 - Jun 16

Total includes taxes and fees

A casino, a 24-hour gym, and a restaurant are all featured at this hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the outdoor pool and free full breakfast each morning.

Pool

Breakfast included

Sea Gate Hotel

Route 989 Km .04, Vieques

$87 nightly

$95 total

Jun 18 - Jun 19

Total includes taxes and fees

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Bring the family and enjoy the children's pool, along with horse riding/rentals. Business travelers can take advantage of the laundry service.

Pool

Pet friendly

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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.

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Frequently asked questions

How much are vacation packages to Roosevelt Roads?

With Travelocity vacation packages, you can live the high life in Roosevelt Roads for a mere $386. Hotels, adventures and flights — we’ve got it all. You’re bound to save loads just by combining your bookings together. With all of that taken care of before you set off, you won’t have to worry about a thing.

Where can I get the best vacation package deals for Roosevelt Roads?

You’ll find a terrific selection of Roosevelt Roads package deals on Travelocity. With no less than 400 air carriers and 1,000,000 worldwide properties, putting together your ideal getaway will be a breeze.

Why should I book my Roosevelt Roads vacation package with Travelocity?

We offer destinations for every kind of traveler, superb service and customer support available 24/7. And the icing on the cake is we’ll match any lower price you come across with our Price Match Guarantee.

Can I save money on my Roosevelt Roads car rental if I bundle it with my hotel or flight?

Combining your bookings into a Roosevelt Roads vacation package will save you a tidy sum. You can book a flight and car; a flight, car and hotel; or a car and hotel. There’s no better way to discover the greater Roosevelt Roads area than from the comfort of your own rental car. You can also add activities and experiences to your Travelocity package.