A coastal town with a beach, a mountain, and a clear blue sky.

Little Bay Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Little Bay holiday rentals

1. MIDTOWN MOTEL SXM

MIDTOWN MOTEL SXM
2.5 star property
Downtown Philipsburg
7.6 out of 10, Good, (74 reviews)
"It was a wonderful stay and experience"
United States
Yollanda
The price is NZ$143
includes taxes & fees
14 Oct - 15 Oct
MIDTOWN MOTEL SXM

2. condostmaarten by the sea -Adults Only-

condostmaarten by the sea -Adults Only-
4.0 star property
Indigo Bay
9.2 out of 10, Wonderful, (43 reviews)
"Love love the property was amazing. Will definitely return."
United States
Muneca
The price is NZ$796
includes taxes & fees
14 Oct - 15 Oct
condostmaarten by the sea -Adults Only-

3. Hilton Vacation Club Royal Palm St. Maarten

Hilton Vacation Club Royal Palm St. Maarten
4.0 star property
Simpson Bay
9.0 out of 10, Wonderful, (1,318 reviews)
"The staff was very friendly"
United States
Carmelle,
The price is NZ$315
includes taxes & fees
22 Oct - 23 Oct
Hilton Vacation Club Royal Palm St. Maarten

4. July Apartments

July Apartments
3.0 star property
Madame's Estate
9.0 out of 10, Wonderful, (254 reviews)
"The property was no frills and the staff super helpful. Would stay again!"
United States
JoyAnn Carolyn
The price is NZ$173
includes taxes & fees
13 Oct - 14 Oct
July Apartments

5. The Castle f

The Castle f
Downtown Philipsburg
8.0 out of 10, Very good, (1 review)
"After a bit of confusion about checking in, we arrived and after that everything was great. It was a surprise to find the window was onto a corridor, but the air con was good so no need to open a window, and also helped to make the room quiet."
United Kingdom
Pat R.
The price is NZ$266
includes taxes & fees
19 Oct - 20 Oct
The Castle f

6. The Castle ᴶ

The Castle ᴶ
Downtown Philipsburg
10.0 out of 10, Exceptional, (1 review)
"Host was welcoming and the apartment was very clean and inviting. We will Definitely stay here again when we come back. "
United States
Neil C.
The price is NZ$266
includes taxes & fees
13 Oct - 14 Oct
The Castle ᴶ

7. The Hills Residence

The Hills Residence
3.0 star property
Simpson Bay
8.4 out of 10, Very good, (171 reviews)
"Very good"
United States
Alyssia
The price is NZ$507
includes taxes & fees
14 Oct - 15 Oct
The Hills Residence

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

Modern Indigo Bay Studio – 3 Min Walk To Beach!
Indigo Bay
9.0 out of 10, Wonderful, (2 reviews)
"Beautiful unit, great view, everything fantastic!"
United States
Joseph K.
The price is NZ$630
includes taxes & fees
13 Oct - 14 Oct
Modern Indigo Bay Studio – 3 Min Walk To Beach!

9. Simpson Bay Suites

Simpson Bay Suites
3.5 star property
Simpson Bay
7.2 out of 10, Good, (168 reviews)
"Overall good. Location is great."
Canada
Manishkumar
The price is NZ$269
includes taxes & fees
15 Oct - 16 Oct
Simpson Bay Suites

10. Philips Scott House Calinago

Philips Scott House Calinago
3.0 star property
Downtown Philipsburg
2.0 out of 10, (1 review)
The price is NZ$400
includes taxes & fees
14 Oct - 15 Oct
Philips Scott House Calinago

11. Mullet Bay Suites: Your Luxury Stay Awaits

Mullet Bay Suites: Your Luxury Stay Awaits
4.0 star property
Maho
9.6 out of 10, Exceptional, (185 reviews)
"This place was amazing. Perfect experience"
United States
Kenneth
The price is NZ$585
includes taxes & fees
20 Oct - 21 Oct
Mullet Bay Suites: Your Luxury Stay Awaits

12. Cozy flat on the boardwalk!

Cozy flat on the boardwalk!
Downtown Philipsburg
10.0 out of 10, Exceptional, (2 reviews)
"Host was very accommodating and helpful. Amenities were abundant."
United States
Robert H.
The price is NZ$388
includes taxes & fees
22 Oct - 23 Oct
Cozy flat on the boardwalk!

13. Hillside Penthouse spacious 2-bed/bath condo - ideal getaway but still central

Hillside Penthouse spacious 2-bed/bath condo - ideal getaway but still central
South Reward
10.0 out of 10, Exceptional, (3 reviews)
"Home away from home "
United States
Trevayne
The price is NZ$405
includes taxes & fees
13 Oct - 14 Oct
Hillside Penthouse spacious 2-bed/bath condo - ideal getaway but still central

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

Luxury 4BR Villa w/ Private Pool & Ocean Views
Indigo Bay
10.0 out of 10, Exceptional, (1 review)
"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...
United States
Ms Light T.
The price is NZ$2,239
includes taxes & fees
13 Oct - 14 Oct
Luxury 4BR Villa w/ Private Pool & Ocean Views

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

Villa Solandra – 3BR Oceanfront Sunset w/ Pool
Indigo Bay
10.0 out of 10, Exceptional, (1 review)
"Our stay at Villa Solandra was nothing short of amazing. The check in process was seamless, the communication with the host was always smooth and timely, the villa itself was beautiful. It was clean, great location, and the view is insane. This place was part of the reason we had such a memorable time in St. Maarten. "
United States
Olivia G.
The price is NZ$1,535
includes taxes & fees
27 Oct - 28 Oct
Villa Solandra – 3BR Oceanfront Sunset w/ Pool

16. Panoramic Ocean View Flat: St Maarten

Panoramic Ocean View Flat: St Maarten
Downtown Philipsburg
The price is NZ$470
includes taxes & fees
13 Oct - 14 Oct
Panoramic Ocean View Flat: St Maarten

17. Beach Front Studio C3

Beach Front Studio C3
Simpson Bay
8.8 out of 10, Excellent, (5 reviews)
"Really cool place and the location was prime. The cleaning lady was the nicest person there could be as well. "
Canada
Benjamin
The price is NZ$283
includes taxes & fees
13 Oct - 14 Oct
Beach Front Studio C3

18. Charming studio with splendid Caribbean Sea view & pool/beach access

Charming studio with splendid Caribbean Sea view & pool/beach access
Marigot
9.4 out of 10, Exceptional, (3 reviews)
"Beautiful view and the host was very welcoming."
United States
Dasha A.
The price is NZ$407
includes taxes & fees
13 Oct - 14 Oct
Charming studio with splendid Caribbean Sea view & pool/beach access

19. Blue Sail Apartments - Two bedroom apartments

Blue Sail Apartments - Two bedroom apartments
Pelican Key
6.0 out of 10, (3 reviews)
"Check in was seamless accommodations were exactly as expected and the staff were very friendly. We noticed many things were brand new and we were informed that there was a new owner- appears that they are working hard!"
United States
Heidi
The price is NZ$251
includes taxes & fees
13 Oct - 14 Oct
Blue Sail Apartments - Two bedroom apartments

20. Beach Front 1 Bedroom Flat D3

Beach Front 1 Bedroom Flat D3
Simpson Bay
10.0 out of 10, Exceptional, (3 reviews)
"Great location near Simpson Bay restaurants and nightlife. Accommodations were exactly as pictured with modern furnishings. Car rental is recommended to fully enjoy the island. "
United States
Christopher
The price is NZ$330
includes taxes & fees
13 Oct - 14 Oct
Beach Front 1 Bedroom Flat D3
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Little Bay Hotel Reviews

Find out more about Little Bay

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Little Bay holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Little Bay. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Little Bay. Seeing all the best attractions is bound to make you fall in love with Little Bay. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Little Bay short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Little Bay?

Yes, there are holiday rentals close to the most popular sights in Little Bay, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Little Bay has to offer?

Philips Scott House Calinago: This holiday 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 such as a microwave and free parking are also available for your convenience. Our travellers also rate Private House -GreatBay- Philipsburg - Free Wifi and Free Private Parking. as a favourite home for rent in Little Bay.

How many holiday rentals will I find in Little Bay?

Expedia has 6 holiday 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 wider area, you’ll find Fort Amsterdam and Maho Beach.

What’s a holiday rental in Little Bay like?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Little Bay. Holiday rentals offer extras such as WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a clean environment, a holiday rental can offer a sense of privacy away from public hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive option for a small group gathering.