Roosevelt Roads Vacation Packages 2026 from $559

Roosevelt Roads flight + hotel vacation packages

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

Lazy Parrot Inn

Save 100% on your flight

$559

per person

Apr 24 - Apr 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to San Juan (SJU)

This resort features a restaurant, an outdoor pool, and a poolside bar. There's fun for all ages with a children's pool and an arcade/game room, and families will appreciate the onsite laundry facilities. Enjoy the hot tub and perks like free WiFi.

Ola Boutique Hotel

Condado

$1,925

per person

Apr 19 - Apr 24

found 1 day ago

Roundtrip flight included

Boston (BOS) 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.

Urbana Hotel

San Juan Antiguo

Save 100% on your flight

$648

per person

Apr 24 - Apr 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to San Juan (SJU)

This hotel features luggage storage, concierge services, and free self parking. Staff at the 24-hour front desk can provide around-the-clock assistance.

Hotel Puerto Valdes

San Juan Antiguo

Save 100% on your flight

$601

per person

Apr 24 - Apr 28

found 1 day ago

Roundtrip flight included

Boston (BOS) to San Juan (SJU)

A restaurant and a 24-hour gym are featured at this hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the a rooftop terrace and perks like free self parking and a free area shuttle.

Romeo Gay Hotel

San Juan Antiguo

Save 100% on your flight

$681

per person

Apr 24 - Apr 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to San Juan (SJU)

An outdoor pool, free self parking, and laundry facilities are featured at this aparthotel. A grocery/convenience store, luggage storage, and concierge services are also on offer.

Top Roosevelt Roads hotels deals

El Conquistador Resort

1000 Conquistador Avenue Fajardo

Free Cancellation

Reserve now, pay when you stay

$434 nightly

$473 total

Mar 1 - Mar 2

Total with 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

Hyatt Regency Grand Reserve Puerto Rico

200 Coco Beach Blvd. Highway 955-I Río Grande

Free Cancellation

Reserve now, pay when you stay

$498 nightly

$543 total

Feb 26 - Feb 27

Total with taxes and fees

This Mediterranean 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

Wyndham Grand Rio Mar Rainforest Beach and Golf Resort

6000 Rio Mar Boulevard Río Grande

Free Cancellation

Reserve now, pay when you stay

$670 nightly

$743 total

Mar 15 - Mar 16

Total with taxes and fees

This smoke-free resort features a golf course, free water park access, and a casino. Relax with beach cabanas and sun loungers, and enjoy a drink at one of the 3 beachside bars. There's fun for all ages with a children's club and a children's pool, and in-room childcare is an added bonus.

Pool

Hot Tub

Wyndham Palmas Beach and Golf Boutique Resort

170 Candelero Drive, Palmas del Mar Humacao

$268 nightly

$293 total

Mar 1 - Mar 2

Total with taxes and fees

This smoke-free resort features a golf course, a marina, and 5 restaurants. Take the free beach shuttle and relax with beach cabanas and sun loungers. Bring the family and enjoy the children's club, children's pool, and kid-friendly dining.

Pool

Hot Tub

Fairfield by Marriott Luquillo Beach

3KM 36.0 MATA DE PLATANO Luquillo

Free Cancellation

Reserve now, pay when you stay

$307 nightly

$340 total

Feb 22 - Feb 23

Total with 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

Las Casitas Village at El Conquistador

1000 Avenida El Conquistador Fajardo

Free Cancellation

Reserve now, pay when you stay

$520 nightly

$567 total

Feb 26 - Feb 27

Total with taxes and fees

This smoke-free hotel features a golf course, free water park access, and a marina. There's fun for all ages with a lazy river and a waterslide, and families will appreciate the convenience store. Enjoy a meal in one of the 10 restaurants and perks like free WiFi.

Pool

Spa

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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 $559. 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.