Roosevelt Roads Vacation Packages 2026 from $476

Roosevelt Roads flight + hotel vacation packages

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

The Oliver Hotel

San Juan Antiguo

Save 100% on your flight

$476

per person

Mar 9 - Mar 13

found 1 day ago

Roundtrip non-stop flight included

Hartford (BDL) to San Juan (SJU)

A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. Luggage storage is provided and the front desk is staffed around-the-clock.

Ola Boutique Hotel

Condado

$547

per person

Mar 9 - Mar 13

found 1 day ago

Roundtrip non-stop flight included

Hartford (BDL) 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.

Placid Suites

Condado

$736

per person

Feb 3 - Feb 10

found 1 day ago

Roundtrip non-stop flight included

Hartford (BDL) to San Juan (SJU)

A rooftop terrace is featured at this guesthouse, along with free WiFi in public areas and concierge services.

Isla Verde Beachfront Retreat With Parking

Isla Verde

Save 100% on your flight

$1,258

per person

Mar 9 - Mar 16

found 1 day ago

Roundtrip non-stop flight included

Hartford (BDL) to San Juan (SJU)

A gym is featured at this apartment, along with free WiFi in public areas.

Urbana Hotel

San Juan Antiguo

Save 100% on your flight

$714

per person

Mar 9 - Mar 16

found 1 day ago

Roundtrip non-stop flight included

Hartford (BDL) 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.

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

$505 nightly

$550 total

Jan 6 - Jan 7, 2026

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

El Conquistador Resort

1000 Conquistador Avenue Fajardo

$414 nightly

$451 total

Jan 7 - Jan 8, 2026

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

Wyndham Grand Rio Mar Rainforest Beach and Golf Resort

6000 Rio Mar Boulevard Río Grande

Free Cancellation

Reserve now, pay when you stay

$854 nightly

$948 total

Jan 30 - Jan 31, 2026

Total with 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

$342 nightly

$372 total

Jan 12 - Jan 13, 2026

Total with 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 5 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

$281 nightly

$312 total

Jan 18 - Jan 19, 2026

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

$536 nightly

$585 total

Jan 6 - Jan 7, 2026

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 $476. 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.