Deals on vacations and trips to Playa

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Playa flight + hotel 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
Save 100% on your flight
Price was $1,075, price is now $607 per person
$607
per person
Mar 11 - Mar 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to San Juan (SJU)
A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. Luggage storage is provided and the front desk is staffed around-the-clock.
Ola Boutique Hotel

Ola Boutique Hotel

4.5 out of 5
Condado
Price was $1,846, price is now $783 per person
$783
per person
Mar 11 - Mar 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to San Juan (SJU)
This luxury hotel features a full-service spa and a restaurant. Enjoy the a rooftop terrace and free perks like continental breakfast and WiFi in public areas. There's a bar/lounge on site, and a 24-hour front desk and laundry facilities are also provided.
OLV Fifty Five - Adults Only

OLV Fifty Five - Adults Only

4.5 out of 5
Condado
Price was $2,531, price is now $1,366 per person
$1,366
per person
Feb 25 - Mar 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
This luxury hotel features 2 restaurants, a bar/lounge, and an outdoor pool. Enjoy the a rooftop terrace and perks like free WiFi. Valet parking, limo/town car service, and dry cleaning are also offered.
Isla Verde Beachfront Retreat With Parking

Isla Verde Beachfront Retreat With Parking

2 out of 5
Isla Verde
Save 100% on your flight
Price was $1,796, price is now $1,003 per person
$1,003
per person
Mar 13 - Mar 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to San Juan (SJU)
A gym is featured at this apartment, along with free WiFi in public areas.
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
Condado
Save 100% on your flight
Price was $2,281, price is now $1,288 per person
$1,288
per person
Feb 25 - Mar 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
This hotel features a restaurant, an indoor pool, and a bar/lounge. WiFi in public areas is free. Valet parking is offered and multilingual staff can provide around-the-clock assistance.

Top Playa hotels 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
Free Cancellation
Reserve now, pay when you stay
$354 nightly
The price is $386 total per night
$386 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
A marina, 5 restaurants, and 2 outdoor pools are all featured at this smoke-free resort. Traveling on business? Take advantage of the 5 conference rooms, free WiFi in public areas, and express check-out. Unwind with drinks at one of the 2 bars/lounges or the poolside bar and make the most of the 15 outdoor tennis courts.
Pool
Hot Tub
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
Free Cancellation
Reserve now, pay when you stay
$316 nightly
The price is $350 total per night
$350 total
Jan 25 - Jan 26, 2026
Total with taxes and fees
A casino, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. There's fun for all ages with a children's pool and a waterslide, and families will appreciate the onsite laundry facilities. Enjoy the outdoor pool and perks like free WiFi.
Pool
Free WiFi
Park Royal Homestay Club Cala Puerto Rico

Park Royal Homestay Club Cala Puerto Rico

3.5 out of 5
50 Club Cala Drive Humacao
$326 nightly
The price is $349 total per night
$349 total
Jan 21 - Jan 22, 2026
Total with taxes and fees
This hotel features 2 outdoor pools and a poolside bar. Families will appreciate the children's pool and onsite laundry facilities. Self parking, a 24-hour business center, and a coffee shop are also offered.
Pool
Air conditioning
Parador MaunaCaribe

Parador MaunaCaribe

3 out of 5
901 Panoramic Road, Km. 1.9 Maunabo
$165 nightly
The price is $175 total per night
$175 total
Dec 29 - Dec 30
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the gym and perks like free self parking and free WiFi. There's a poolside bar on site, and laundry facilities and wedding services are also provided.
Pool
Parking included
RainForest House by Otium

RainForest House by Otium

2.5 out of 5
133 Cam Rio Abajo Ceiba Ceiba
$93 nightly
The price is $99 total per night
$99 total
Dec 27 - Dec 28
Total with taxes and fees
This apartment features a virtual front desk.
Kitchen
Free WiFi
Casa Parcha

Casa Parcha

3.5 out of 5
Carr 191 km 27.9 Naguabo Naguabo
$185 nightly
The price is $197 total per night
$197 total
Dec 31 - Jan 1, 2026
Total with taxes and fees
This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a communal living room are also on offer.
Kitchen
Parking included
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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.

Frequently asked questions

How much are vacation packages to Playa?
Get ready to be surprised — you can recharge your batteries in Playa for only $607. Allow Travelocity to save you time and stress with our awesome vacation package deals. With flights, hotels and tours all in one place, why put it off?
Where can I get the best vacation package deals for Playa?
It's hard to beat Travelocity when it comes to finding your Playa package deal. There are at least 400 air carriers and 1,000,000 properties around the world to choose from. Book your trip now and get ready to cross another exciting place off your must-visit list.
Why should I purchase my Playa vacation package via Travelocity?
With exceptional service, customer support available 24/7 and some of the most incredible escapes imaginable, you'll never roam alone. And if you find a cheaper price, we'll match it. That's our Price Match Guarantee.
Can I save money on my Playa car rental if I book it with my hotel or flight?
Certainly — and if you also add an experience or a tour to your Playa vacation package, you'll save some more. With an affordable package from Travelocity, you can find things to do in the area that are just right for you. Then, jump in your rental car and work your way through the list. The Baths is one renowned attraction to key into your GPS. You'll find it 95 mi from Playa.

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