A beach with clear turquoise water, rows of blue lounge chairs, and a mountain in the background.

Little Bay Vacation Rentals

Q: What are some of the best vacation rentals in Little Bay?

Philips Scott House Calinago : This vacation home rental outside Little Bay is in a shopping district and equipped with air-conditioning and WiFi to help you feel perfectly comfortable in your new surroundings. Amenities like a microwave and free parking are also available for your convenience. Our travelers also rate Private House -GreatBay- Philipsburg - Free Wifi and Free Private Parking. as a favorite home for rent in Little Bay.

Dates

November 2026

December 2026

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Our top choices for Little Bay vacation rentals

A view from inside a building looking out to a beach with clear turquoise water and a distant ship.

1. MIDTOWN MOTEL SXM

Downtown Philipsburg

brenton

CA $122 total

includes taxes & fees

Nov 22 - Nov 23

A swimming pool with clear water, a grassy area, and a view of a coastal landscape with buildings.

2. condostmaarten by the sea -Adults Only-

Indigo Bay

Elouise

CA $777 total

includes taxes & fees

Nov 9 - Nov 10

A resort with a view of sailboats on the water, a beach with palm trees, and a modern building with balconies.

3. Hilton Vacation Club Royal Palm St. Maarten

Simpson Bay

Carmelle,

CA $304 total

includes taxes & fees

Nov 11 - Nov 12

A hotel room with a bed, a sofa, a small round table, and a chair. There is a bathroom visible through an open door.

4. July Apartments

Madame's Estate

JoyAnn Carolyn

CA $173 total

includes taxes & fees

Dec 8 - Dec 9

A high-rise hotel with a view of the sunset over a marina.

5. Simpson Bay Suites

Simpson Bay

Manishkumar

CA $214 total

includes taxes & fees

Nov 9 - Nov 10

A balcony with a view of the sea and a white building in the distance.

6. Modern Indigo Bay Studio – 3 Min Walk To Beach!

Indigo Bay

Joseph K.

CA $537 total

includes taxes & fees

Nov 9 - Nov 10

A bedroom with a bed, a TV mounted on the wall, a small fridge, and a bedside table with a lamp.

7. Philips Scott House Calinago

Downtown Philipsburg

CA $304 total

includes taxes & fees

Nov 9 - Nov 10

A balcony with a view of the sea, a table, and two chairs.

8. Cozy flat on the boardwalk!

Downtown Philipsburg

Robert H.

CA $302 total

includes taxes & fees

Nov 9 - Nov 10

A modern living room with large windows, a purple sofa, and a view of the beach and ocean.

9. Mullet Bay Suites: Your Luxury Stay Awaits

Maho

Kenneth

CA $448 total

includes taxes & fees

Nov 11 - Nov 12

An infinity pool with a clear view of the sea, a wooden table with food and drinks, and a lounge area with a view.

10. Luxury 4BR Villa w/ Private Pool & Ocean Views

Indigo Bay

"This property has a breathtaking view and is in the perfect location—close to stores and just minutes from the beaches.Fritz, the host, was amazing! The island had just gone through a major storm the day before we arrived, and despite the circumstances, Fritz was always available and ready to help with anything we needed. He even offered us an extra day to make up for any inconvenience, which was so thoughtful and appreciated.I would absolutely stay here again and would highly recommend this...

Ms Light T.

CA $2,002 total

includes taxes & fees

Nov 10 - Nov 11

A modern room with a dining area, large windows, and a view of the sea.

11. Villa Solandra – 3BR Oceanfront Sunset w/ Pool

Indigo Bay

Olivia G.

CA $1,449 total

includes taxes & fees

Nov 27 - Nov 28

A hallway with a decorative gate, potted plants, and a fire extinguisher.

12. The Castle ᴵ

Downtown Philipsburg

CA $223 total

includes taxes & fees

Nov 22 - Nov 23

A rooftop pool with a clear view of the sea and distant hills.

13. D443 - One Bedroom with Lagoon view

Cole Bay

CA $430 total

includes taxes & fees

Nov 10 - Nov 11

A large swimming pool surrounded by palm trees and lounge chairs, with a hotel building in the background.

14. Dawn Beach Club Resort Sint Maarten

Oyster Pond

Gavin

CA $1,219 total

includes taxes & fees

Nov 22 - Nov 23

A terrace with wicker furniture, a hanging chair, and a view of boats at a marina.

15. Panoramic Ocean View Flat: St Maarten

Downtown Philipsburg

CA $507 total

includes taxes & fees

Nov 11 - Nov 12

A poolside area with a wooden table, lounge chairs, and a view of the ocean.

16. Blue Sail Apartments - Two-Bedroom Apartments

Pelican Key

Heidi

CA $187 total

includes taxes & fees

Nov 9 - Nov 10

A modern living room with a large sliding glass door leading to a balcony with a view of a coastal town and mountains.

17. B256 - Amazing Top Floor Apartment With Balcony

Sint Maarten

CA $460 total

includes taxes & fees

Nov 17 - Nov 18

A swimming pool with lounge chairs, palm trees, and a mountainous backdrop.

18. Charming studio with the beach at your feet & pool access

Marigot

Brad W.

CA $281 total

includes taxes & fees

Nov 9 - Nov 10

A rooftop swimming pool with wooden decking, surrounded by potted plants, overlooking a coastal town and hills.

19. A116 - Immersive Simpson Bay Lagoon View

Sint Maarten

A balcony with a view of a marina and mountains.

20. B254 - Cozy Apartment in the Heart of Simpson Bay

Sint Maarten

CA $460 total

includes taxes & fees

Nov 9 - Nov 10

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Find vacation rentals that suit your style

Top Little Bay Hotel Reviews

A pool area with a waterfall feature, surrounded by wooden deck chairs and covered seating areas.

Belair Beach Hotel

Belair

10/10 Excellent

The Belair Beach Hotel resort is fairly small, with a smaller but nice beach. The resort assigns beach chairs to your room when you check in and they are reserved for you until check out. The 2 bedroom 2 bathroom kitchenett suite was excellent, all of the sutes have full front ocean views with A full double balcony with all glass walls . The view is indeed spectacular You are literally 30 feet from the beach. The furniture was dated but still comfortable and functional, the beds and bedding were...

Cliff

A resort pool with lounge chairs, palm trees, and a view of the ocean.

Divi Little Bay Beach Resort

Philipsburg

10/10 Excellent

Peter Victor

A glass table with a white mug and a loaf of bread, a decorative vase, and a poolside lounge area with a view of purple flowers and palm trees.

Pomme Cannelle Luxury Suites & Spa

Orient Bay

10/10 Excellent

Wilf

A person sitting at a table with a book, a croissant, and a cup.

Le Martin Boutique Hôtel

Cul de Sac

10/10 Excellent

10/10 experience at Le Martin Hotel. From the hospitality, to the beautiful decor, to the daily breakfast, to the pool oasis - everything was perfect. Marion and her staff go above and beyond to make your stay just perfect. It was peaceful, quiet and the perfect place to relax and recharge. Only note is that it was a bit difficult to find as maps and waze direct you to the wrong spot. I loved the proximity to Pinel Island as well as both Grand Case and Orient Bay beaches

Michelle

A swimming pool with lounge chairs and a table on a wooden deck, surrounded by greenery and a mountain view.

Villa Jwi Lavi Boutique Hotel

Cul de Sac

10/10 Excellent

Dawn

A beach resort with palm trees, a pathway, and a view of the ocean.

Orient Beach Hotel

Orient Bay

10/10 Excellent

We had an incredible week at Orient Beach Hotel. Our immediate first impression was the genuinely warm welcome from the front desk team member, Junior. This positive energy remained through the week and was complemented by the incredible hotel manager, Myriam, and the attentive housekeeping staff. Room and views were exactly as pictured. We couldn’t have planned it any better. Thank you!! We hope to be back.

Luigi

A balcony with a view of the ocean, a bottle of champagne, two wine glasses, and a book titled "Linda Van Rijn Zoutelande".

La Vista Hotel

Pelican Key

10/10 Excellent

I stayed at the property from August 22-29. Great location, very clean, wonderful property and friendly staff. Rooms were cleaned daily, kitchen did not lack any appliances or dishes, plenty of towels daily, super comfortable bed and pillows, wifi worked wonderfully as well as the air conditioners and the pressure in the shower with hot water was amazing. Check in was quick and easy, late check out available as well as a great shower area near the pool with toiletries and towels to get ready...

Marta

A balcony with a view of the sea, a bed with towels, and two white wicker chairs.

Le Temps des Cerises Hotel Beach

Grand Case

10/10 Excellent

Heather

A coastal resort with a swimming pool, beach access, and lush greenery.

Grand Case Beach Club

Grand Case

10/10 Excellent

WAYNE

A beachfront hotel with a pool, palm trees, and a clear blue sky.

Azure Hotel and Art Studio

Simpson Bay

10/10 Excellent

Anonymous traveller

A poolside bar with a view of a pool and lounge chairs.

Hotel L'Esplanade

Grand Case

10/10 Excellent

Great location looking out over Grand Case to the bay, provided you don't want to be right on the beach. A sister property "Le Petit Hotel" is on the beach at the other end of Grand Case. Each day we exercised by walking through Grand Case to Petit Hotel (about 20 min) where L'Esplanade guests can use the beach chairs, towels etc. Then a pleasant walk back along the beach later in the day. Other than beach access the only thing we didn't like about L'Esplanade itself was keeping the heated pool...

Anonymous traveller

A swimming pool with clear blue water, a building with balconies, and palm trees.

Hilton Vacation Club Flamingo Beach St. Maarten

Pelican Key

10/10 Excellent

Positives: Great property!!!! Clean well kept grounds, great room sizes!! Having full kitchen is a bonus!! Personable and attentive staff!! Enjoyed daily activities. Really liked being on beach side. Walking distance to great restaurants! Things to work on: We had beach chairs stacked right in front of our room so view was not the greatest while looking out in our room and deck. (7140) Empty bottles of conditioner and body lotion where in our room upon arrival but quickly replaced when...

Audrey

condostmaarten by the sea -Adults Only-

Indigo Bay

10/10 Excellent

Rozana

A balcony with a view of a beach and ocean.

Holland House Beach Hotel

Downtown Philipsburg

10/10 Excellent

Debra

A balcony with a view of a beach and hotel buildings.

Baker's Suites

Simpson Bay

10/10 Excellent

Anonymous traveller

Find out more about Little Bay

Everything you need to know about Little Bay vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Little Bay vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Little Bay vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Little Bay vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Little Bay. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Little Bay vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Little Bay vacation rentals we have selected for you start as low as CA $100 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Little Bay rentals

At Expedia, we put the best Little Bay vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Little Bay rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Little Bay vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Little Bay. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Are there vacation rentals in Little Bay?

Yes, we give you a choice of vacation rentals near popular points of interest in Little Bay, or you can select a more secluded option if you want a relaxing place to stay.

What are some of the best vacation rentals in Little Bay?

Philips Scott House Calinago: This vacation home rental outside Little Bay is in a shopping district and equipped with air-conditioning and WiFi to help you feel perfectly comfortable in your new surroundings. Amenities like a microwave and free parking are also available for your convenience. Our travelers also rate Private House -GreatBay- Philipsburg - Free Wifi and Free Private Parking. as a favorite home for rent in Little Bay.

How many vacation rentals will I find in Little Bay?

Expedia has 6 vacation rentals for your stay in Little Bay.

What’s there to see and do in Little Bay?

Little Bay Beach and Great Bay Beach are a couple of lovely local spots to get outside and enjoy nature. In the larger area, you’ll find Fort Amsterdam and Maho Beach.

What’s a vacation rental in Little Bay like?

Vacation rentals are private accommodations you can reserve for several days or longer in Little Bay. Vacation rentals offer extras like kitchens and laundry facilities so your stay will be comfortable. If you're concerned about a sanitized environment, vacation rentals can offer a sense of security away from public hotel elevators and busy lobbies while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for a family trip.

Little Bay Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Little Bay vacation rentals

1. MIDTOWN MOTEL SXM

2. condostmaarten by the sea -Adults Only-

3. Hilton Vacation Club Royal Palm St. Maarten

4. July Apartments

5. Simpson Bay Suites

6. Modern Indigo Bay Studio – 3 Min Walk To Beach!

7. Philips Scott House Calinago

8. Cozy flat on the boardwalk!

9. Mullet Bay Suites: Your Luxury Stay Awaits

10. Luxury 4BR Villa w/ Private Pool & Ocean Views

11. Villa Solandra – 3BR Oceanfront Sunset w/ Pool

12. The Castle ᴵ

13. D443 - One Bedroom with Lagoon view

14. Dawn Beach Club Resort Sint Maarten

15. Panoramic Ocean View Flat: St Maarten

16. Blue Sail Apartments - Two-Bedroom Apartments

17. B256 - Amazing Top Floor Apartment With Balcony

18. Charming studio with the beach at your feet & pool access

19. A116 - Immersive Simpson Bay Lagoon View

20. B254 - Cozy Apartment in the Heart of Simpson Bay

Find vacation rentals that suit your style

Top Little Bay Hotel Reviews

Belair Beach Hotel

10/10 Excellent

Find out more about Little Bay

Little Bay vacation rentals: An excellent choice for every season

How to find incredible deals on Little Bay rentals

Frequently Asked Questions

Are there vacation rentals in Little Bay?

What are some of the best vacation rentals in Little Bay?

How many vacation rentals will I find in Little Bay?

What’s there to see and do in Little Bay?

What’s a vacation rental in Little Bay like?