Roosevelt Roads Vacation Packages 2025/2026 from $481

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

$481

per person

Nov 17 - Nov 24

found 1 day ago

Roundtrip non-stop 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

$590

per person

Nov 17 - Nov 24

found 1 day ago

Roundtrip non-stop 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.

WALD HAUS by DW

Save 100% on your flight

$2,346

per person

Nov 8 - Nov 14

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to San Juan (SJU)

An outdoor pool, free self parking, and laundry facilities are featured at this villa. WiFi in public areas is free. A terrace, a garden, and express check-in are also on offer.

Dorado Beach 5 Bedroom Villa

Higuillar

Save 100% on your flight

$1,278

per person

Nov 1 - Nov 5

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to San Juan (SJU)

This villa features a private beach, a golf course, and a casino. Relax with sun loungers and enjoy a refreshing drink at one of the 2 beach bars. Bring the family and enjoy the water park, lazy river, and children's club.

VILLA JOYUDA

Save 100% on your flight

$2,135

per person

Dec 4 - Dec 7

found 1 day ago

Roundtrip flight included

New York (NYC) to San Juan (SJU)

An outdoor pool is featured at this villa, along with free WiFi in public areas and a terrace. A picnic area, laundry facilities, and barbecue grills are also on offer.

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

Sep 9 - Sep 10

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.

Wyndham Grand Rio Mar Rainforest Beach and Golf Resort

6000 Rio Mar Boulevard, Río Grande

Free Cancellation

Reserve now, pay when you stay

$511 nightly

$567 total

Oct 1 - Oct 2

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.

El Conquistador Resort

1000 Conquistador Avenue, Fajardo

Free Cancellation

Reserve now, pay when you stay

$384 nightly

$419 total

Oct 1 - Oct 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

Fajardo Inn

52 Parcelas Beltran, Puerto Real, Fajardo

Free Cancellation

Reserve now, pay when you stay

$130 nightly

$141 total

Sep 14 - Sep 15

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.

Fairfield by Marriott Luquillo Beach

3KM 36.0 MATA DE PLATANO, Luquillo

Free Cancellation

Reserve now, pay when you stay

$173 nightly

$192 total

Sep 21 - Sep 22

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.

Wyndham Palmas Beach and Golf Boutique Resort

170 Candelero Drive, Palmas del Mar, Humacao

Free Cancellation

Reserve now, pay when you stay

$233 nightly

$254 total

Sep 14 - Sep 15

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.

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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 $481. 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.