Deals on vacations and trips to Little Bay

Save when you book Little Bay package deals

Choose two or more items and save on your trip:

Little Bay flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
Price was $2,563, price is now $1,009 per person
$1,009
per person
Oct 11 - Oct 18
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

The Villas at Simpson Bay Resort

4 out of 5
Pelican Key
Price was $3,256, price is now $1,220 per person
$1,220
per person
Oct 10 - Oct 17
found 1 day ago
Roundtrip 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.
The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Save 100% on your flight
Price was $2,673, price is now $1,503 per person
$1,503
per person
Oct 11 - Oct 18
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 resort. Enjoy the gym and perks like free valet parking and a free airport shuttle. There's a bar/lounge on site, and concierge services and free newspapers are also provided.
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 $1,796, price is now $1,013 per person
$1,013
per person
Oct 11 - Oct 18
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.
La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Save 100% on your flight
Price was $1,723, price is now $1,069 per person
$1,069
per person
Oct 12 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. Families will appreciate the onsite laundry facilities and in-room childcare.

Top Little Bay hotels deals

Divi Little Bay Beach Resort

Divi Little Bay Beach Resort

4 out of 5
Little Bay Road Philipsburg
Free Cancellation
Reserve now, pay when you stay
$252 nightly
The price is $267 total per night
$267 total
Aug 26 - Aug 27
Total with taxes and fees
A full-service spa, 5 restaurants, and 3 outdoor pools are all featured at this resort. Relax with free beach cabanas, sun loungers, and beach umbrellas. Relax with a drink at one of the 4 bars/lounges and enjoy free perks like free self parking and WiFi in public areas.
Pool
Spa
Oceans at Divi Little Bay

Oceans at Divi Little Bay

4 out of 5
Little Bay Road Philipsburg St. Maarten
Free Cancellation
Reserve now, pay when you stay
$294 nightly
The price is $311 total per night
$311 total
Aug 27 - Aug 28
Total with taxes and fees
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.
Pool
Spa
Belair Beach Hotel

Belair Beach Hotel

3 out of 5
Little Bay Philipsburg
$238 nightly
The price is $248 total per night
$248 total
Jul 29 - Jul 30
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Families will appreciate the onsite laundry facilities and babysitting. Guests will appreciate free perks like free self parking and WiFi in public areas.
Pool
Parking included
L'Esperance Hotel

L'Esperance Hotel

2.5 out of 5
4 Tiger Road Philipsburg
$132 nightly
The price is $139 total per night
$139 total
Aug 26 - Aug 27
Total with taxes and fees
An outdoor pool, free self parking, and barbecue grills are featured at this hotel. WiFi in public areas is free. A terrace, a garden, and a library are also on offer.
Pool
Parking included
The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
2 Beacon Hill Road Simpson Bay
Free Cancellation
Reserve now, pay when you stay
$506 nightly
The price is $528 total per night
$528 total
Aug 20 - Aug 21
Total with taxes and fees
A full-service spa, an outdoor pool, and a restaurant are all featured at this resort. Enjoy the gym and perks like free valet parking and a free airport shuttle. There's a bar/lounge on site, and concierge services and free newspapers are also provided.
Pool
Spa
Sonesta Maho Beach All Inclusive Resort Casino & Spa

Sonesta Maho Beach All Inclusive Resort Casino & Spa

4 out of 5
1 Rhine Road Lowlands
$473 nightly
The price is $493 total per night
$493 total
Aug 24 - Aug 25
Total with taxes and fees
This property features free water park access, a casino, and a full-service spa. 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 free kid's club and a children's pool, and free supervised childcare is an added bonus.
Pool
Spa
Don't see what you're looking for?
See all available properties in Little Bay
View all properties
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.

Stay near popular Little Bay attractions

Fort Amsterdam

8.8/10 (245 reviews)
You can find out about the history of Little Bay with a stop at Fort Amsterdam. Stroll along the beautiful beaches in this romantic area, or check out its top-notch restaurants.
See properties

Frequently asked questions

How much are vacation packages to Little Bay?
With a Travelocity vacation package, you can be living it up in Little Bay from just $1,009. Hotels, adventures and flights — we've got it covered. You'll save a bunch just for combining your bookings. And with all of that taken care of before you leave, you won't have a care in the world.
Where can I get the best vacation package deals for Little Bay?
You can pick up fantastic Little Bay package deals with Travelocity. Pick and choose from 400 air carriers and 1,000,000 worldwide properties and turn those vacation dreams into reality.
Why should I book my Little Bay vacation bundle via Travelocity?
Travel should be about making fantastic new memories and leaving all your stresses behind — which is why we provide you with a friendly team of customer service experts available 24/7 should you need them. On top of that, our Price Match Guarantee ensures you'll always get the best deal available on our terrific range of vacation destinations. So what are you waiting for? There's no time like the present to secure the vacation you've always dreamed of.
Will I save money on my Little Bay car rental if I bundle it with a hotel or flight?
Booking a Little Bay vacation package with Travelocity is a simple way to save your hard-earned money. You can combine a flight, hotel and car, or any combination of them, and score awesome discounts. You might also like to add in some experiences and tours. Once you've picked up the keys to the rental car, venture out of the neighborhood and find out what this place has to offer. Approximately 100 mi from Little Bay, Dickenson Bay Beach is certainly worth a road trip.

Photos of local treasures

Browse Little Bay vacation photos for more inspiration

A coastal town with a beach, a mountain, and a clear blue sky.
A coastal landscape with turquoise waters, a cruise ship, and a mountainous backdrop.
A beach with clear turquoise water, a ship in the distance, and a wooden fence in the foreground.
A stone wall, a mountain, and a body of water with boats.
A beach with white umbrellas, lounge chairs, and a clear blue sky.