
Exclusive Happy Bay Vacation Deals

Happy Bay vacation package deals
Price found within the past 48 hours. Click for updated prices.

Simpson Bay Resort, Marina & Spa
Pelican Key
Price was $1,803, price is now $779 per person
$779
per person
Apr 9 - Apr 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Philipsburg (SXM)
This smoke-free resort features a private beach, a full-service spa, and a marina. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. There's fun for all ages with a children's pool and a playground, and barbecue grills are available on site.

The Villas at Simpson Bay Resort
Pelican Key
Price was $2,774, price is now $1,388 per person
$1,388
per person
Mar 8 - Mar 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
A marina, 3 restaurants, and 6 outdoor pools are all featured at this smoke-free resort. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. There's fun for all ages with a children's pool and a waterslide, and barbecue grills are available on site.

Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
Price was $1,629, price is now $984 per person
$984
per person
Feb 26 - Mar 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Philipsburg (SXM)
This hotel features an outdoor pool and a 24-hour gym. Families will appreciate the waterslide, onsite laundry facilities, and in-room childcare. Guests will appreciate free perks like free self parking and WiFi in public areas.

Panorama Residences at Monte Vista
Point Blanche
Price was $1,541, price is now $946 per person
$946
per person
Feb 26 - Mar 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Philipsburg (SXM)
An outdoor pool, free self parking, and laundry facilities are featured at this aparthotel. WiFi in public areas is free. A terrace, a garden, and a virtual front desk are also on offer.

Oyster Bay Beach Resort
Oyster Pond
Price was $1,152, price is now $802 per person
$802
per person
Mar 8 - Mar 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
This resort features a full-service spa, a marina, and 2 restaurants. Families will appreciate the children's pool, onsite laundry facilities, and in-room childcare. Enjoy the outdoor pool and perks like free WiFi.

Oceans at Divi Little Bay
Price was $1,919, price is now $1,355 per person
$1,355
per person
Feb 26 - Mar 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Philipsburg (SXM)
This hotel's 4 restaurants and 3 outdoor pools are some of the featured amenities. Guests will appreciate free perks like free self parking and WiFi in public areas. Dry cleaning, luggage storage, and concierge services are also on offer.
Frequently asked questions
Top Happy Bay hotel deals
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.
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