Roosevelt Roads Vacation Packages 2026 from $598

Roosevelt Roads flight + hotel vacation packages

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

Urbana Hotel

San Juan Antiguo

Save 100% on your flight

$598

per person

Feb 11 - Feb 18

found 1 day ago

Roundtrip 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.

Hotel Puerto Valdes

San Juan Antiguo

$1,128

per person

Feb 11 - Feb 18

found 1 day ago

Roundtrip flight included

Hartford (BDL) 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.

The Oliver Hotel

San Juan Antiguo

Save 100% on your flight

$729

per person

Jan 28 - Feb 4

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.

Romeo Gay Hotel

San Juan Antiguo

Save 100% on your flight

$657

per person

Feb 11 - Feb 18

found 1 day ago

Roundtrip flight included

Hartford (BDL) 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.

Aire de O:live

Isla Verde

$1,492

per person

Jan 28 - Feb 4

found 1 day ago

Roundtrip non-stop flight included

Hartford (BDL) to San Juan (SJU)

This smoke-free hotel includes 2 restaurants, an outdoor pool, and a gym. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi.

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

$513 nightly

$560 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.

El Conquistador Resort

1000 Conquistador Avenue Fajardo

$414 nightly

$451 total

Jan 14 - Jan 15, 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.

Wyndham Grand Rio Mar Rainforest Beach and Golf Resort

6000 Rio Mar Boulevard Río Grande

Free Cancellation

Reserve now, pay when you stay

$891 nightly

$989 total

Jan 20 - Jan 21, 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.

Wyndham Palmas Beach and Golf Boutique Resort

170 Candelero Drive, Palmas del Mar Humacao

Free Cancellation

Reserve now, pay when you stay

$329 nightly

$359 total

Jan 8 - Jan 9, 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.

Fairfield by Marriott Luquillo Beach

3KM 36.0 MATA DE PLATANO Luquillo

Free Cancellation

Reserve now, pay when you stay

$277 nightly

$307 total

Jan 19 - Jan 20, 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

Sea Gate Hotel

Route 989 Km .04 Vieques

$116 nightly

$126 total

Dec 31 - Jan 1, 2026

Total with 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 $598. 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.