Cheap Vacations in Puerto Rico Island

Choose two or more items and save on your trip:

Puerto Rico Island vacations

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

Casamares

3 out of 5
Save 100% on your flight
Price was $518, price is now $325 per person
$325
per person
Apr 11 - Apr 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
Coral by the Sea Hotel

Coral by the Sea Hotel

3 out of 5
Isla Verde
Price was $963, price is now $548 per person
$548
per person
Mar 25 - Mar 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
Olimpo Court by Otium

Olimpo Court by Otium

2 out of 5
Santurce
Price was $1,165, price is now $728 per person
$728
per person
Mar 25 - Mar 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
Janer House

Janer House

3 out of 5
Río Piedras
Price was $851, price is now $554 per person
$554
per person
Mar 25 - Mar 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
Hyatt Regency Grand Reserve Puerto Rico

Hyatt Regency Grand Reserve Puerto Rico

4 out of 5
Zarzal
Price was $2,533, price is now $1,656 per person
$1,656
per person
Apr 6 - Apr 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
OLV Fifty Five - Adults Only

OLV Fifty Five - Adults Only

4.5 out of 5
Condado
Price was $2,467, price is now $1,614 per person
$1,614
per person
Mar 25 - Mar 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
El Conquistador Resort

El Conquistador Resort

4 out of 5
Cabezas
Price was $2,277, price is now $1,498 per person
$1,498
per person
Apr 6 - Apr 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
Aire de O:live

Aire de O:live

4 out of 5
Isla Verde
Price was $2,588, price is now $1,761 per person
$1,761
per person
Mar 25 - Mar 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)

3-night Puerto Rico Island vacations

Price found within the past 48 hours. Click for updated prices.
Coral by the Sea Hotel

Coral by the Sea Hotel

3 out of 5
Price was $589, price is now $428 per person
$428
per person
Apr 1 - Apr 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
Hotel Puerto Valdes

Hotel Puerto Valdes

4 out of 5
Save 100% on your flight
Price was $1,217, price is now $685 per person
$685
per person
Apr 11 - Apr 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
OLV Fifty Five - Adults Only

OLV Fifty Five - Adults Only

4.5 out of 5
Price was $1,597, price is now $1,092 per person
$1,092
per person
Apr 10 - Apr 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
Dorado Beach 5 Bedroom Villa

Dorado Beach 5 Bedroom Villa

3.5 out of 5
Save 100% on your flight
Price was $1,866, price is now $1,303 per person
$1,303
per person
Mar 30 - Apr 2
found 18 hours ago
Roundtrip flight included
New York (NYC) to San Juan (SJU)
Aire de O:live

Aire de O:live

4 out of 5
Price was $1,250, price is now $876 per person
$876
per person
Apr 1 - Apr 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
Olive Boutique Hotel, A Small Luxury Hotel of the World (Adults Only)

Olive Boutique Hotel, A Small Luxury Hotel of the World (Adults Only)

4 out of 5
Save 100% on your flight
Price was $1,141, price is now $819 per person
$819
per person
Apr 6 - Apr 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
Fortaleza Suites

Fortaleza Suites

3.5 out of 5
Price was $845, price is now $614 per person
$614
per person
Apr 9 - Apr 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
Casa Elena by Otium

Casa Elena by Otium

3 out of 5
Price was $839, price is now $617 per person
$617
per person
Apr 10 - Apr 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
The Condado Plaza Hotel

The Condado Plaza Hotel

4 out of 5
Price was $1,184, price is now $874 per person
$874
per person
Apr 10 - Apr 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)

4-night Puerto Rico Island vacations

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

Casamares

3 out of 5
Save 100% on your flight
Price was $518, price is now $325 per person
$325
per person
Apr 11 - Apr 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
Isla Verde Beachfront Retreat With Parking

Isla Verde Beachfront Retreat With Parking

2 out of 5
Save 100% on your flight
Price was $1,364, price is now $748 per person
$748
per person
Apr 11 - Apr 15
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to San Juan (SJU)
Ola Boutique Hotel

Ola Boutique Hotel

4.5 out of 5
Save 100% on your flight
Price was $1,117, price is now $617 per person
$617
per person
Apr 11 - Apr 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
Hotel Puerto Valdes

Hotel Puerto Valdes

4 out of 5
Price was $1,396, price is now $861 per person
$861
per person
Apr 18 - Apr 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
La Playita

La Playita

3 out of 5
Price was $825, price is now $549 per person
$549
per person
Apr 9 - Apr 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
Coral by the Sea Hotel

Coral by the Sea Hotel

3 out of 5
Price was $830, price is now $564 per person
$564
per person
Apr 2 - Apr 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
Romeo Gay Hotel

Romeo Gay Hotel

4 out of 5
Price was $1,004, price is now $700 per person
$700
per person
Mar 26 - Mar 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
Urbana Hotel

Urbana Hotel

2 out of 5
Price was $989, price is now $692 per person
$692
per person
Mar 26 - Mar 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
Hyatt Regency Grand Reserve Puerto Rico

Hyatt Regency Grand Reserve Puerto Rico

4 out of 5
Price was $1,598, price is now $1,124 per person
$1,124
per person
Apr 9 - Apr 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
Olive Boutique Hotel, A Small Luxury Hotel of the World (Adults Only)

Olive Boutique Hotel, A Small Luxury Hotel of the World (Adults Only)

4 out of 5
Price was $2,105, price is now $1,488 per person
$1,488
per person
Apr 17 - Apr 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
OLV Fifty Five - Adults Only

OLV Fifty Five - Adults Only

4.5 out of 5
Save 100% on your flight
Price was $1,494, price is now $1,057 per person
$1,057
per person
Mar 26 - Mar 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)

5-night Puerto Rico Island vacations

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

Urbana Hotel

2 out of 5
Save 100% on your flight
Price was $973, price is now $655 per person
$655
per person
Apr 10 - Apr 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
Isla Verde Beachfront Retreat With Parking

Isla Verde Beachfront Retreat With Parking

2 out of 5
Save 100% on your flight
Price was $1,779, price is now $933 per person
$933
per person
Apr 15 - Apr 20
found 20 hours ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
Hotel Puerto Valdes

Hotel Puerto Valdes

4 out of 5
Save 100% on your flight
Price was $2,052, price is now $1,312 per person
$1,312
per person
Apr 18 - Apr 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
El Conquistador Resort

El Conquistador Resort

4 out of 5
Save 100% on your flight
Price was $1,877, price is now $1,211 per person
$1,211
per person
Apr 3 - Apr 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
Aire de O:live

Aire de O:live

4 out of 5
Save 100% on your flight
Price was $2,259, price is now $1,458 per person
$1,458
per person
Apr 18 - Apr 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
Fortaleza Suites

Fortaleza Suites

3.5 out of 5
Save 100% on your flight
Price was $1,140, price is now $764 per person
$764
per person
Apr 10 - Apr 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
El Colonial - Adults Only

El Colonial - Adults Only

3.5 out of 5
Save 100% on your flight
Price was $1,103, price is now $763 per person
$763
per person
Apr 10 - Apr 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
Olive Boutique Hotel, A Small Luxury Hotel of the World (Adults Only)

Olive Boutique Hotel, A Small Luxury Hotel of the World (Adults Only)

4 out of 5
Price was $1,810, price is now $1,255 per person
$1,255
per person
Mar 29 - Apr 3
found 8 hours ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
Casa Elena by Otium

Casa Elena by Otium

3 out of 5
Save 100% on your flight
Price was $1,025, price is now $718 per person
$718
per person
Apr 9 - Apr 14
found 7 hours ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)

6-7 night Puerto Rico Island vacations

Price found within the past 48 hours. Click for updated prices.
Coral by the Sea Hotel

Coral by the Sea Hotel

3 out of 5
Price was $963, price is now $548 per person
$548
per person
Mar 25 - Mar 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
Isla Verde Beachfront Retreat With Parking

Isla Verde Beachfront Retreat With Parking

2 out of 5
Price was $2,284, price is now $1,103 per person
$1,103
per person
Mar 31 - Apr 7
found 19 hours ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
Hotel Puerto Valdes

Hotel Puerto Valdes

4 out of 5
Price was $2,086, price is now $1,086 per person
$1,086
per person
Apr 15 - Apr 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
The Oliver Hotel

The Oliver Hotel

3 out of 5
Price was $1,188, price is now $668 per person
$668
per person
Apr 4 - Apr 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
Olive Boutique Hotel, A Small Luxury Hotel of the World (Adults Only)

Olive Boutique Hotel, A Small Luxury Hotel of the World (Adults Only)

4 out of 5
Price was $2,421, price is now $1,365 per person
$1,365
per person
Apr 12 - Apr 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
Mata e' Platano Guesthouse

Mata e' Platano Guesthouse

3 out of 5
Save 100% on your flight
Price was $1,442, price is now $825 per person
$825
per person
Apr 9 - Apr 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
Placid Suites

Placid Suites

3 out of 5
Save 100% on your flight
Price was $1,279, price is now $772 per person
$772
per person
Apr 10 - Apr 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
El Colonial - Adults Only

El Colonial - Adults Only

3.5 out of 5
Save 100% on your flight
Price was $1,254, price is now $781 per person
$781
per person
Apr 10 - Apr 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
Olimpo Court by Otium

Olimpo Court by Otium

2 out of 5
Price was $1,165, price is now $728 per person
$728
per person
Mar 25 - Mar 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
Casa Elena by Otium

Casa Elena by Otium

3 out of 5
Price was $1,352, price is now $862 per person
$862
per person
Apr 6 - Apr 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
La Playita

La Playita

3 out of 5
Price was $1,121, price is now $716 per person
$716
per person
Apr 4 - Apr 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
Old San Juan Rentals

Old San Juan Rentals

3.5 out of 5
Price was $1,129, price is now $730 per person
$730
per person
Apr 4 - Apr 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)

Flight deals to Puerto Rico Island

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Sat, Mar 7 - Sat, Mar 7
MCO
Orlando
PSE
Ponce
$114 Roundtrip, found 5 days ago
$114
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, Mar 7 from Orlando to Ponce, returning Sat, Mar 7, priced at $114 found 5 days ago
Thu, Mar 26 - Wed, Apr 15
MCO
Orlando
BQN
Aguadilla
$114 Roundtrip, found 6 days ago
$114
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Thu, Mar 26 from Orlando to Aguadilla, returning Wed, Apr 15, priced at $114 found 6 days ago
Fri, May 1 - Mon, May 4
FLL
Fort Lauderdale
SJU
San Juan
$120 Roundtrip, found 4 days ago
$120
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Fri, May 1 from Fort Lauderdale to San Juan, returning Mon, May 4, priced at $120 found 4 days ago

Top rated hotels for your Puerto Rico Island vacation

La Concha Resort, Puerto Rico, Autograph Collection

La Concha Resort, Puerto Rico, Autograph Collection

4 out of 5
1077 Ashford Ave Condado San Juan
Free Cancellation
Reserve now, pay when you stay
11.29 mi from city center
$534 nightly
The price is $593 total per night
$593 total
Mar 1 - Mar 2
Total with taxes and fees
With a stay at La Concha Resort, Puerto Rico, Autograph Collection in San Juan (Condado), you'll be steps from Casino del Mar at La Concha Resort and 12 minutes by foot from Condado Beach.
Pool
Hot Tub
El Conquistador Resort

El Conquistador Resort

4 out of 5
1000 Conquistador Avenue Fajardo
38.81 mi from city center
$434 nightly
The price is $473 total per night
$473 total
Mar 5 - Mar 6
Total with taxes and fees
Located in Fajardo (Cabezas), El Conquistador Resort is within a 15-minute drive of Laguna Grande and Cayo Icacos.
On private beach
Pool
Embassy Suites by Hilton San Juan Hotel & Casino

Embassy Suites by Hilton San Juan Hotel & Casino

3.5 out of 5
8000 Tartak Street Carolina
Free Cancellation
Reserve now, pay when you stay
13.84 mi from city center
$371 nightly
The price is $412 total per night
$412 total
Mar 3 - Mar 4
Total with taxes and fees
With a stay at Embassy Suites by Hilton San Juan Hotel & Casino in Carolina (Isla Verde), you'll be a 3-minute drive from Isla Verde Beach and 7 minutes from Condado Beach.
Pool
Hot Tub
Don't see what you're looking for?
See all available properties in Puerto Rico Island
View all properties
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.

^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.