Roosevelt Roads Vacation Packages 2025/2026 from $364

Roosevelt Roads flight + hotel vacation packages

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

Lazy Parrot Inn

$364

per person

Jan 11 - Jan 16

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.

Hotel Puerto Valdes

San Juan Antiguo

Save 100% on your flight

$557

per person

Jan 3 - Jan 6

found 1 day ago

Roundtrip flight included

Atlanta (ATL) 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.

Ola Boutique Hotel

Condado

Save 100% on your flight

$470

per person

Jan 10 - Jan 13

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.

San Agustin Apartments

San Juan Antiguo

Save 100% on your flight

$385

per person

Jan 10 - Jan 13

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.

Casa Ciana

Santurce

Save 100% on your flight

$841

per person

Jan 7 - Jan 12

found 1 day ago

Roundtrip flight included

Boston (BOS) to San Juan (SJU)

This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the laundry service. Luggage storage is also provided.

Top Roosevelt Roads hotels deals

Hyatt Regency Grand Reserve Puerto Rico

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

$326 nightly

$355 total

Nov 3 - Nov 4

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

Free Cancellation

Reserve now, pay when you stay

$354 nightly

$386 total

Oct 28 - Oct 29

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

$475 nightly

$527 total

Nov 23 - Nov 24

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

Fairfield by Marriott Luquillo Beach

3KM 36.0 MATA DE PLATANO, Luquillo

$178 nightly

$198 total

Nov 9 - Nov 10

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

Anchors Hotel

PR 987 BO, Fajardo, Fajardo

Free Cancellation

Reserve now, pay when you stay

$180 nightly

$196 total

Oct 28 - Oct 29

Total with taxes and fees

An outdoor pool is featured at this hotel, along with free self parking. WiFi in public areas is free. Staff at the 24-hour front desk can provide around-the-clock assistance.

Pool

Parking included

Fajardo Inn

52 Parcelas Beltran, Puerto Real, Fajardo

Free Cancellation

Reserve now, pay when you stay

$157 nightly

$171 total

Nov 3 - Nov 4

Total with taxes and fees

This hotel features 2 outdoor pools, an outdoor tennis court, and a restaurant. Enjoy the gym and perks like free self parking and free WiFi. There's a bar/lounge on site, and laundry facilities and concierge services are also provided.

Pool

Parking included

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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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3.5/5(109 reviews)

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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 $364. 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.