Puerto Rico Island Vacations from $354

Book a Hotel + Flight or Car together to unlock savings

Plan, book, travel with confidence

Better together

Save up to $1,045 when you book a flight and hotel together*

Find the right fit

With over 300,000 hotels worldwide, it's easy to create a perfect package

Rest easy

Plan, book, and manage your trip all in one place

The Latest Puerto Rico Island Vacation Packages

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

Jan 30 - Feb 4
San Agustin Apartments
San Juan Antiguo
3.0 star property
9.2 Wonderful (438)
"En general todo la estadia fue buena. El área bastante tranquila. Camas comodas, algunos ruidos de los pisos de arriba pero nada para no descansar. En general las amenidades que prestan segun fotos. Area de parqueo. Y a 800 metros de la entrada del viejo San Juan"
Roundtrip • Boston (BOS) - San Juan (SJU)
BOS - SJU • Nonstop SJU - BOS • Nonstop
Save 100% on your flight
~~$675~~
$354
per traveler
found 2 days ago
San Agustin Apartments
Feb 16 - Feb 22
Ola Boutique Hotel
Condado
4.5 star property
9.2 Wonderful (631)
"Very welcoming & clean "
Roundtrip • Boston (BOS) - San Juan (SJU)
BOS - SJU • 1 stop SJU - BOS • 1 stop
~~$2,548~~
$1,049
per traveler
found 2 days ago
Ola Boutique Hotel
Feb 16 - Feb 22
The Oliver Hotel
San Juan Antiguo
3.0 star property
8.8 Excellent (55)
"Centrico, comodo, perfecto para estar cerca de todo y tener tranquilidad"
Roundtrip • Boston (BOS) - San Juan (SJU)
BOS - SJU • 1 stop SJU - BOS • 1 stop
Save 100% on your flight
~~$1,877~~
$972
per traveler
found 2 days ago
The Oliver Hotel
Jan 17 - Jan 22
OLV Fifty Five - Adults Only
Condado
4.5 star property
8.6 Excellent (584)
"Very beautiful place . Classy and sexy environment . I LOVED the room with the barn door I felt rich or something and don’t get me started on the shower in there. I could not get my man out of there he loves the amenities so much LOL. Def in a good location close to shopping areas and the strip . I would def book again. "
Roundtrip • Boston (BOS) - San Juan (SJU)
BOS - SJU • Nonstop SJU - BOS • Nonstop
~~$1,985~~
$1,049
per traveler
found 2 days ago
OLV Fifty Five - Adults Only
Feb 17 - Feb 21
Hotel Puerto Valdes
San Juan Antiguo
4.0 star property
9.0 Wonderful (511)
"Really nice apartment with a great view, we could live there. 5-10 minute walk to old town shops and restaurants, as well as cruise terminal. "
Roundtrip • Boston (BOS) - San Juan (SJU)
BOS - SJU • 1 stop SJU - BOS • 1 stop
Save 100% on your flight
~~$1,605~~
$869
per traveler
found 2 days ago
Hotel Puerto Valdes