Exclusive Happy Bay Vacation Deals

Happy Bay vacation package deals

Price found within the past 48 hours. Click for updated prices.
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Oyster Pond
Save 100% on your flight
Price was $1,383, price is now $882 per person
$882
per person
Nov 26 - Dec 3
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.
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Save 100% on your flight
Price was $1,665, price is now $964 per person
$964
per person
Oct 12 - Oct 19
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.
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
Save 100% on your flight
Price was $1,489, price is now $896 per person
$896
per person
Nov 26 - Dec 3
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.
Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Downtown Philipsburg
Save 100% on your flight
Price was $2,158, price is now $1,310 per person
$1,310
per person
Nov 26 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
A restaurant and a bar/lounge are featured at this hotel. Dine at the beachfront restaurant and relax with beach umbrellas. WiFi in public areas is free.
Esmeralda Resort

Esmeralda Resort

4 out of 5
Save 100% on your flight
Price was $1,643, price is now $1,043 per person
$1,043
per person
Dec 1 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
This hotel features 15 outdoor pools, a restaurant, and a bar/lounge. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Families will appreciate the playground and onsite laundry facilities.
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Oyster Pond
Price was $1,400, price is now $940 per person
$940
per person
Oct 12 - Oct 19
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.

Frequently asked questions

How much are vacation packages to Happy Bay?
Save a tidy sum on your visit to Happy Bay by combining your flights and hotel into a $882 package. With all that extra cash jangling around in your pocket, why not stay for another night or two and discover even more?
Where can I get the best vacation package deals for Happy Bay?
It's simple — head to Travelocity. With as many as 400 air carriers and 1,000,000 worldwide properties, it's a breeze to find a Happy Bay package deal that fits your budget.
Why should I purchase my Happy Bay vacation package with Travelocity?
We offer round-the-clock support, exceptional service and a Price Match Guarantee. Life is all about the journey — and we have amazing destinations for you to journey to all across the globe. Wander with us and make your hip pocket happy.

Top Happy Bay hotel deals

Lovely room in a nice villa with a big garden, close to Friars bay beach

Lovely room in a nice villa with a big garden, close to Friars bay beach

$97 nightly
The price is $97 total per night
$97 total
Sep 11 - Sep 12
Total with taxes and fees
A terrace and a garden are available at this vacation home.
Air conditioning
Outdoor Space
MAGNIFIQUE VILLA KYLA'S the most beautiful sea view in the Caribbean with POOL

MAGNIFIQUE VILLA KYLA'S the most beautiful sea view in the Caribbean with POOL

A hot tub is featured at this villa, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.
Pool
Hot Tub
ON THE BEACH CONDO WITH PANORAMIC VIEW ON GRAND CASE BEACH

ON THE BEACH CONDO WITH PANORAMIC VIEW ON GRAND CASE BEACH

A rooftop terrace is featured at this condo, along with a terrace and laundry facilities.
Kitchen
Washer
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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.

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