Playa Vacations from $581

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Your Playa Vacation

Lock in a Playa vacation package and prepare to experience everything this city has to offer. Think about staying in the neighborhood of Calzada, which is great for watersports, families and history. Any trip to Playa needs a well-crafted itinerary. Fill yours with attractions like Palmas del Mar Beach, Palmas Del Mar Golf Club and Playa El Cocal. That dream Playa vacation is only clicks away. Explore airfares, hotels and more on Expedia for a trip that's tailored to suit your travel style.

The Latest Playa vacation packages

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

The Oliver Hotel

3 out of 5
San Juan Antiguo
Price was $1,294, price is now $581 per person
$581
per person
Dec 4 - Dec 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to San Juan (SJU)
9/10 Wonderful! (36 reviews)
Everything very nice and clean. There is no permanent staff manning the front desk, but they are a call and a couple of minutes away. The area, Puerta de Tierra, is very safe and within walkable distance to El Viejo San Juan. Only complaint: at arriving, on Thursday, I let the front desk to know that it was my wife birthday the following Saturday, and ask for their help to prepare a small surprise for my wife (that I was going to pay for). The following day I was told that the owners, due to their religion, do not celebrate birthdays. I found that a weird reason. It is their religion, not mine, and I didn’t want them to celebrate anything, I was the one celebrating my wife birthday.

Reviewed on Sep 28, 2025

Dorado Beach 5 Bedroom Villa

Dorado Beach 5 Bedroom Villa

3.5 out of 5
Higuillar
Price was $2,520, price is now $844 per person
$844
per person
Dec 14 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to San Juan (SJU)
No reviews
Ola Boutique Hotel

Ola Boutique Hotel

4.5 out of 5
Condado
Price was $1,417, price is now $652 per person
$652
per person
Dec 4 - Dec 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to San Juan (SJU)
9/10 Wonderful! (498 reviews)
Had an excellent stay at Ola boutique- I can not say enough about the hospitality we received. We would absolutely stay again !

Reviewed on Oct 1, 2025

Hotel Puerto Valdes

Hotel Puerto Valdes

4 out of 5
San Juan Antiguo
Price was $1,442, price is now $702 per person
$702
per person
Dec 4 - Dec 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to San Juan (SJU)
9/10 Wonderful! (485 reviews)
Beautiful intimate hotel in a great location. Staff was great and super helpful at all times. Definitely would stay here again.

Reviewed on Sep 10, 2025

OLV Fifty Five - Adults Only

OLV Fifty Five - Adults Only

4.5 out of 5
Condado
Price was $1,956, price is now $965 per person
$965
per person
Dec 4 - Dec 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to San Juan (SJU)
8.8/10 Excellent! (545 reviews)
Beautiful rooms. Grsat amenities. Amazing hot tub

Reviewed on Sep 25, 2025

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Playa Hotel Deals

Wyndham Palmas Beach and Golf Boutique Resort

Wyndham Palmas Beach and Golf Boutique Resort

4 out of 5
170 Candelero Drive, Palmas del Mar, Humacao
Fully refundableReserve now, pay when you stay
$233 nightly
The price is $254 total per night from Oct 5 to Oct 6
$254 total
Oct 5 - Oct 6
Total with taxes and fees
8.2/10 Very Good! (636 reviews)
"No breakfast and the parking lot is too far."

Reviewed on Sep 15, 2025

Wyndham Palmas Beach and Golf Boutique Resort
Four Points by Sheraton Caguas Real Hotel & Casino

Four Points by Sheraton Caguas Real Hotel & Casino

3.5 out of 5
500 Alhambra En Granada Boulevard, Caguas
Fully refundableReserve now, pay when you stay
$227 nightly
The price is $252 total per night from Oct 12 to Oct 13
$252 total
Oct 12 - Oct 13
Total with taxes and fees
8.6/10 Excellent! (1,015 reviews)
"Excellent stay! The staff was welcoming, the room spotless and comfortable, and the location perfect. I highly recommend this hotel and would definitely return."

Reviewed on Sep 23, 2025

Four Points by Sheraton Caguas Real Hotel & Casino
Park Royal Homestay Club Cala Puerto Rico

Park Royal Homestay Club Cala Puerto Rico

3.5 out of 5
50 Club Cala Drive, Humacao
$227 nightly
The price is $242 total per night from Nov 1 to Nov 2
$242 total
Nov 1 - Nov 2
Total with taxes and fees
8.4/10 Very Good! (431 reviews)
"The property was great had everything we needed from markets and dinning option it had beautiful sights and so quite"

Reviewed on Sep 15, 2025

Park Royal Homestay Club Cala Puerto Rico
See all 684 properties in Playa
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.

Playa Essential Information

Language
Spanish
Currency
U.S dollars
Local Welcome
¡Hola!
Local Goodbye
Adiós
Closest Airport
Luis Munoz Marin Intl. Airport (SJU)
Population
2,200
Top Sights
Lucia Beach, Playa Guayanés and Playa El Cocal

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Frequently asked questions

How much does a Playa vacation package cost?
Offering great value package deals from $581 on Expedia, you'll be pleasantly surprised at how much a vacation to Playa costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Playa?
You're likely to find lower prices and better availability in September, October and December. Take a look at our cheap Playa vacation packages and you could score some great off-season discounts.
How many days is enough for Playa?
Generally, a handful of days is enough to go to the main sights during your Playa vacation. But if you want to have more time to kick back or go on day trips, think about extending your itinerary.
How to find the best Playa package deals?
Use Expedia's filter tool to find some of the best Playa package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your escape for midweek, or browse for Playa package deals in the off-season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to lock in your vacation package as soon as possible.
Is it cheaper to book a Playa vacation as a package?
An Expedia vacation package could land you considerable savings when compared to arranging hotels and flights separately. Better still, you can tailor your Playa getaway to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Playa?
Score incredible discounts by booking your flights ahead of time with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for an impromptu Playa trip.
Does Expedia offer Book Now, Pay Later Playa vacation packages?
If you're like us, you love going away but are not a fan of the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the total cost of your Playa break over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.