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

Sapphire Beach Club Resort
Maho
Price was $1,187, price is now $808 per person
$808
per person
Dec 24 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
A full-service spa, an outdoor pool, and a restaurant are all featured at this smoke-free resort. Enjoy the gym and perks like free self parking and free WiFi. There's a bar/lounge on site, and a 24-hour front desk and laundry facilities are also provided.

Simpson Bay Resort, Marina & Spa
Pelican Key
Price was $3,040, price is now $1,327 per person
$1,327
per person
Dec 31 - Jan 7
found 1 day ago
Roundtrip non-stop 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
Price was $2,158, price is now $1,083 per person
$1,083
per person
Jan 5 - Jan 9
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.

Oceans at Divi Little Bay
Save 100% on your flight
Price was $3,260, price is now $2,103 per person
$2,103
per person
Dec 24 - Dec 28
found 1 day ago
Roundtrip non-stop 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.

Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
Save 100% on your flight
Price was $1,655, price is now $1,076 per person
$1,076
per person
Dec 24 - Dec 28
found 1 day ago
Roundtrip non-stop 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.
Frequently asked questions
Top Happy Bay hotel deals

Lovely room in a nice villa with a big garden, close to Friars bay beach
$96 nightly
The price is $96 total per night
$96 total
Nov 4 - Nov 5
Total with taxes and fees
A terrace and a garden are available at this vacation home.
Air conditioning
Outdoor Space
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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