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Roosevelt Roads Vacation Packages

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An aerial view of a tropical island with clear turquoise waters and a sandy beach.

Roosevelt Roads
Puerto Rico
Caribbean
Hotwire.com

Roosevelt Roads Flight + Hotel Packages

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

Picuas Village

3 out of 5

Save 100% on your flight

Price was $773, price is now $510 per person

$510

per person

Dec 5 - Dec 9

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to San Juan (SJU)

Book a stay at this beach villa in Río Grande. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Luquillo Beach and Wyndham Rio Mar Golf Course are located nearby.

Ola Boutique Hotel

4.5 out of 5

Save 100% on your flight

Price was $1,182, price is now $633 per person

$633

per person

Nov 26 - Nov 30

found 2 days ago

Roundtrip flight included

Atlanta (ATL) to San Juan (SJU)

Book a stay at this luxury hotel in San Juan. Enjoy free WiFi, a full-service spa, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Casino del Mar at La Concha Resort and Condado Beach are located nearby.

Hotel Puerto Valdes

4 out of 5

Save 100% on your flight

Price was $1,118, price is now $648 per person

$648

per person

Jan 4 - Jan 8

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to San Juan (SJU)

Book a stay at this business-friendly hotel in San Juan. Enjoy free WiFi, free parking, and a rooftop terrace. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Port of San Juan and Condado Beach are located nearby.

The staff were extremely helpful during this stay! The apartment was clean and in a close location to Old Town centre (approx 15 mins walk). We didn't eat at the restaurant but it looked lovely. All on all a very nice stay.

Reviewed on Oct 19, 2026

Villa Gaviota with private pool by Otium

3 out of 5

Save 100% on your flight

Price was $1,672, price is now $1,017 per person

$1,017

per person

Nov 30 - Dec 4

found 17 hours ago

Roundtrip flight included

Philadelphia (PHL) to San Juan (SJU)

Stay at this villa in Río Grande. Enjoy free WiFi, free parking, and a garden. Popular attractions Luquillo Beach and Wyndham Rio Mar Golf Course are located nearby.

Signature Collection at Rio Mar

5 out of 5

Save 100% on your flight

Price was $10,025, price is now $6,233 per person

$6,233

per person

Dec 25 - Dec 30

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to San Juan (SJU)

Book a stay at this luxury aparthotel in Río Grande. Enjoy free WiFi, 5 outdoor pools, and a full-service spa. Popular attractions Luquillo Beach and Wyndham Rio Mar Golf Course are located nearby.

Everything is 10 times more expensive compare to any other place I visites

Reviewed on Aug 8, 2026

Casa Condado Hotel & Residences

3 out of 5

Save 100% on your flight

Price was $1,479, price is now $963 per person

$963

per person

Dec 1 - Dec 5

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to San Juan (SJU)

Stay at this hotel in San Juan. Enjoy free WiFi, parking (surcharge), and cable TV channels. Popular attractions Casino del Mar at La Concha Resort and Condado Beach are located nearby.

Don Rafa Boutique Hotel & Residences

4 out of 5

Save 100% on your flight

Price was $1,267, price is now $832 per person

$832

per person

Nov 26 - Nov 30

found 2 days ago

Roundtrip flight included

Atlanta (ATL) to San Juan (SJU)

Stay at this hotel in San Juan. Enjoy free breakfast, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Condado Beach and Casino del Mar at La Concha Resort are located nearby.