Little Bay Vacation Packages 2025/2026 from $721

Little Bay flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

The Villas at Simpson Bay Resort

Save 100% on your flight

$721

per person

Nov 13 - Nov 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.

Simpson Bay Resort, Marina & Spa

Pelican Key

Save 100% on your flight

$756

per person

Nov 28 - Dec 4

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

Downtown Philipsburg

Save 100% on your flight

$1,129

per person

Nov 28 - Dec 4

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.

Princess Heights Luxury Boutique Condo Hotel

Oyster Pond

Save 100% on your flight

$800

per person

Nov 28 - Dec 4

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.

Divi Little Bay Beach Resort

Save 100% on your flight

$1,010

per person

Nov 28 - Dec 4

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

A full-service spa, 3 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 2 bars/lounges and enjoy free perks like free self parking and WiFi in public areas.

Top Little Bay hotels deals

Divi Little Bay Beach Resort

Little Bay Road, Philipsburg

Free Cancellation

Reserve now, pay when you stay

$292 nightly

$307 total

Sep 11 - Sep 12

Total with taxes and fees

A full-service spa, 3 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 2 bars/lounges and enjoy free perks like free self parking and WiFi in public areas.

Oceans at Divi Little Bay

Little Bay Road, Philipsburg, St. Maarten

Free Cancellation

Reserve now, pay when you stay

$272 nightly

$285 total

Sep 11 - Sep 12

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.

Belair Beach Hotel

Little Bay, Philipsburg

$195 nightly

$203 total

Sep 11 - Sep 12

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.

L'Esperance Hotel

4 Tiger Road, Cay Hill, Philipsburg

Get rates

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

Sonesta Maho Beach All Inclusive Resort Casino & Spa

1 Rhine Road, Maho Bay, Lowlands

$215 nightly

$224 total

Sep 11 - Sep 12

Total with taxes and fees

This all-inclusive 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.

Simpson Bay Resort, Marina & Spa

Billy Folly Road 37, Simpson Bay

Free Cancellation

Reserve now, pay when you stay

$95 nightly

$99 total

Sep 25 - Sep 26

Total with taxes and fees

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.

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.

Popular places to visit

Great Bay Beach

If a restful vacation is part of your travel plans, Great Bay Beach might be the perfect place to seek out during your trip to Philipsburg. Check out the shops and top-notch restaurants in this romantic area.

Philipsburg Boardwalk

Philipsburg Boardwalk is just one of the places to see in Philipsburg, so why not enjoy the other things to explore during your travels? Stroll along the area's beaches or simply enjoy its restaurants.

Fort Amsterdam

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.

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 $721. 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.