Cheap Vacations in Puerto Rico Island

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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
Isla Verde
Save 100% on your flight
Price was $630, price is now $383 per person
$383
per person
Feb 22 - Feb 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
Ola Boutique Hotel

Ola Boutique Hotel

4.5 out of 5
Condado
Price was $1,691, price is now $878 per person
$878
per person
Mar 3 - Mar 7
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
Higuillar
Price was $3,510, price is now $1,912 per person
$1,912
per person
Feb 28 - Mar 6
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
Save 100% on your flight
Price was $1,764, price is now $970 per person
$970
per person
Feb 22 - Feb 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
Enjoy our Luxurious Penthouse in Condado

Enjoy our Luxurious Penthouse in Condado

2 out of 5
Santurce
Price was $2,022, price is now $1,186 per person
$1,186
per person
Feb 24 - Mar 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
Hyatt Vacation Club at Hacienda del Mar, Dorado

Hyatt Vacation Club at Hacienda del Mar, Dorado

3.5 out of 5
Sabana
Save 100% on your flight
Price was $1,234, price is now $739 per person
$739
per person
Mar 3 - Mar 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
Outsite Puerto Rico - Ocean Park

Outsite Puerto Rico - Ocean Park

2 out of 5
Santurce
Save 100% on your flight
Price was $664, price is now $433 per person
$433
per person
Feb 22 - Feb 26
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
Santurce
Save 100% on your flight
Price was $1,417, price is now $938 per person
$938
per person
Mar 5 - Mar 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
Breathtaking 3-Br Beachside Apt

Breathtaking 3-Br Beachside Apt

2 out of 5
Santurce
Price was $1,832, price is now $1,216 per person
$1,216
per person
Feb 24 - Mar 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
El Conquistador Resort

El Conquistador Resort

4 out of 5
Cabezas
Save 100% on your flight
Price was $1,215, price is now $807 per person
$807
per person
Feb 22 - Feb 26
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.
Segovia Studio Units

Segovia Studio Units

3 out of 5
Price was $455, price is now $321 per person
$321
per person
Feb 24 - Feb 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
Ola Boutique Hotel

Ola Boutique Hotel

4.5 out of 5
Price was $610, price is now $345 per person
$345
per person
Feb 24 - Feb 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
Hyatt Vacation Club at Hacienda del Mar, Dorado

Hyatt Vacation Club at Hacienda del Mar, Dorado

3.5 out of 5
Price was $1,143, price is now $710 per person
$710
per person
Feb 26 - Mar 1
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
Save 100% on your flight
Price was $1,484, price is now $977 per person
$977
per person
Feb 17 - Feb 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
Enjoy our Luxurious Penthouse in Condado

Enjoy our Luxurious Penthouse in Condado

2 out of 5
Save 100% on your flight
Price was $1,712, price is now $1,150 per person
$1,150
per person
Mar 12 - Mar 15
found 10 hours 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 $1,533, price is now $1,038 per person
$1,038
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
La Playita

La Playita

3 out of 5
Price was $780, price is now $545 per person
$545
per person
Feb 26 - Mar 1
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
Price was $1,556, price is now $1,098 per person
$1,098
per person
Feb 26 - Mar 1
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 $644, price is now $454 per person
$454
per person
Feb 24 - Feb 27
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 $593, price is now $419 per person
$419
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
Outsite Puerto Rico - Ocean Park

Outsite Puerto Rico - Ocean Park

2 out of 5
Price was $649, price is now $458 per person
$458
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
El Conquistador Resort

El Conquistador Resort

4 out of 5
Price was $958, price is now $681 per person
$681
per person
Feb 26 - Mar 1
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.
Coral by the Sea Hotel

Coral by the Sea Hotel

3 out of 5
Save 100% on your flight
Price was $630, price is now $383 per person
$383
per person
Feb 22 - Feb 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
Ola Boutique Hotel

Ola Boutique Hotel

4.5 out of 5
Price was $1,691, price is now $878 per person
$878
per person
Mar 3 - Mar 7
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 $1,764, price is now $970 per person
$970
per person
Feb 22 - Feb 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
Hyatt Vacation Club at Hacienda del Mar, Dorado

Hyatt Vacation Club at Hacienda del Mar, Dorado

3.5 out of 5
Save 100% on your flight
Price was $1,234, price is now $739 per person
$739
per person
Mar 3 - Mar 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
Enjoy our Luxurious Penthouse in Condado

Enjoy our Luxurious Penthouse in Condado

2 out of 5
Save 100% on your flight
Price was $1,721, price is now $1,096 per person
$1,096
per person
Feb 25 - Mar 1
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to San Juan (SJU)
Outsite Puerto Rico - Ocean Park

Outsite Puerto Rico - Ocean Park

2 out of 5
Save 100% on your flight
Price was $664, price is now $433 per person
$433
per person
Feb 22 - Feb 26
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 $827, price is now $548 per person
$548
per person
Feb 22 - Feb 26
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 $1,215, price is now $807 per person
$807
per person
Feb 22 - Feb 26
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 $1,492, price is now $992 per person
$992
per person
Feb 22 - Feb 26
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
Save 100% on your flight
Price was $1,060, price is now $708 per person
$708
per person
Feb 22 - Feb 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
La Playita

La Playita

3 out of 5
Save 100% on your flight
Price was $784, price is now $524 per person
$524
per person
Feb 22 - Feb 26
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 $1,376, price is now $937 per person
$937
per person
Feb 22 - Feb 26
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
Price was $1,055, price is now $556 per person
$556
per person
Mar 11 - Mar 16
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 $1,208, price is now $584 per person
$584
per person
Mar 11 - Mar 16
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 $3,521, price is now $1,929 per person
$1,929
per person
Mar 11 - Mar 16
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 $1,074, price is now $594 per person
$594
per person
Mar 11 - Mar 16
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 $1,467, price is now $831 per person
$831
per person
Mar 1 - Mar 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
Hyatt Vacation Club at Hacienda del Mar, Dorado

Hyatt Vacation Club at Hacienda del Mar, Dorado

3.5 out of 5
Save 100% on your flight
Price was $1,616, price is now $941 per person
$941
per person
Mar 5 - Mar 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
Enjoy our Luxurious Penthouse in Condado

Enjoy our Luxurious Penthouse in Condado

2 out of 5
Price was $2,022, price is now $1,186 per person
$1,186
per person
Feb 24 - Mar 1
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 $1,362, price is now $809 per person
$809
per person
Mar 14 - Mar 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
Stunning 3-Bedroom Beachside Apartment

Stunning 3-Bedroom Beachside Apartment

2 out of 5
Price was $1,567, price is now $957 per person
$957
per person
Feb 24 - Mar 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
Outsite Puerto Rico - Ocean Park

Outsite Puerto Rico - Ocean Park

2 out of 5
Save 100% on your flight
Price was $1,063, price is now $657 per person
$657
per person
Mar 5 - Mar 10
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 $2,355, price is now $1,459 per person
$1,459
per person
Feb 22 - Feb 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
The Tryst Beachfront Hotel

The Tryst Beachfront Hotel

3.5 out of 5
Price was $1,412, price is now $876 per person
$876
per person
Mar 11 - Mar 16
found 1 day 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.
Segovia Studio Units

Segovia Studio Units

3 out of 5
Save 100% on your flight
Price was $769, price is now $508 per person
$508
per person
Mar 9 - Mar 16
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
Price was $3,510, price is now $1,912 per person
$1,912
per person
Feb 28 - Mar 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
Hyatt Vacation Club at Hacienda del Mar, Dorado

Hyatt Vacation Club at Hacienda del Mar, Dorado

3.5 out of 5
Price was $2,174, price is now $1,248 per person
$1,248
per person
Feb 28 - Mar 7
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 $4,758, price is now $2,985 per person
$2,985
per person
Mar 7 - Mar 14
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to San Juan (SJU)
Hotel Milano

Hotel Milano

2 out of 5
Save 100% on your flight
Price was $2,144, price is now $1,351 per person
$1,351
per person
Mar 7 - Mar 14
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 $1,479, price is now $936 per person
$936
per person
Mar 7 - Mar 14
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 $1,833, price is now $1,203 per person
$1,203
per person
Feb 23 - Mar 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to San Juan (SJU)
Enjoy our Luxurious Penthouse in Condado

Enjoy our Luxurious Penthouse in Condado

2 out of 5
Price was $2,889, price is now $1,897 per person
$1,897
per person
Feb 17 - Feb 24
found 19 hours ago
Roundtrip non-stop 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 $2,455, price is now $1,614 per person
$1,614
per person
Feb 23 - Mar 1
found 1 day ago
Roundtrip non-stop 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 $2,188, price is now $1,454 per person
$1,454
per person
Mar 7 - Mar 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
Stunning 3-Bedroom Beachside Apartment

Stunning 3-Bedroom Beachside Apartment

2 out of 5
Price was $2,196, price is now $1,472 per person
$1,472
per person
Feb 17 - Feb 24
found 19 hours ago
Roundtrip non-stop 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.

Wed, Feb 25 - Tue, Mar 3
MIA
Miami
SJU
San Juan
$100 Roundtrip, found 4 days ago
$100
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Wed, Feb 25 from Miami to San Juan, returning Tue, Mar 3, priced at $100 found 4 days ago
Mon, Feb 2 - Tue, Feb 3
BOS
Boston
SJU
San Juan
$113 Roundtrip, found 3 days ago
$113
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Mon, Feb 2 from Boston to San Juan, returning Tue, Feb 3, priced at $113 found 3 days ago
Tue, Jan 27 - Wed, Jan 28
MCO
Orlando
SJU
San Juan
$124 Roundtrip, found 4 days ago
$124
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Tue, Jan 27 from Orlando to San Juan, returning Wed, Jan 28, priced at $124 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
$503 nightly
The price is $558 total per night
$558 total
Feb 2 - Feb 3
Total with taxes and fees
With a stay at La Concha Resort, Puerto Rico, Autograph Collection in San Juan (Condado), you'll be a 3-minute walk from Casino del Mar at La Concha Resort and 12 minutes by foot from Condado Beach.
Pool
Hot Tub
The Royal Sonesta San Juan

The Royal Sonesta San Juan

4 out of 5
5961 Isla Verde Avenue Carolina
Free Cancellation
Reserve now, pay when you stay
14.06 mi from city center
$570 nightly
The price is $621 total per night
$621 total
Jan 21 - Jan 22
Total with taxes and fees
With a stay at The Royal Sonesta San Juan in Carolina (Isla Verde), you'll be a 4-minute walk from Isla Verde Beach and 6 minutes by foot from Carolina Beach.
Pool
Spa
Condado Vanderbilt Hotel

Condado Vanderbilt Hotel

5 out of 5
1055 Ashford Avenue San Juan
Free Cancellation
Reserve now, pay when you stay
11.22 mi from city center
$635 nightly
The price is $705 total per night
$705 total
Jan 25 - Jan 26
Total with taxes and fees
A stay at Condado Vanderbilt Hotel places you in the heart of San Juan, within a 10-minute walk of Casino del Mar at La Concha Resort and Condado Beach.
Pool
Hot Tub
Don't see what you're looking for?
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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.

^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.