Deals on vacations and trips to Little Bay

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Little Bay flight + hotel vacation packages

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 $945, price is now $599 per person
$599
per person
Oct 30 - Nov 2
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.
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
Price was $2,199, price is now $861 per person
$861
per person
Oct 24 - Oct 31
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
Save 100% on your flight
Price was $1,503, price is now $756 per person
$756
per person
Oct 30 - Nov 2
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.
Sonesta Maho Beach All Inclusive Resort Casino & Spa

Sonesta Maho Beach All Inclusive Resort Casino & Spa

4 out of 5
Price was $2,837, price is now $1,808 per person
$1,808
per person
Oct 24 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
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.
The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Save 100% on your flight
Price was $1,364, price is now $923 per person
$923
per person
Oct 30 - Nov 2
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.

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
$207 nightly
The price is $219 total per night
$219 total
Sep 8 - Sep 9
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
$259 nightly
The price is $274 total per night
$274 total
Sep 9 - Sep 10
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
$235 nightly
The price is $245 total per night
$245 total
Sep 7 - Sep 8
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
Sep 8 - Sep 9
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
$512 nightly
The price is $536 total per night
$536 total
Sep 8 - Sep 9
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
$523 nightly
The price is $545 total per night
$545 total
Sep 8 - Sep 9
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
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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.

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 seaside 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 $599. 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.