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

Little Bay Holiday Rentals

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Our top choices for Little Bay holiday rentals

1. MIDTOWN MOTEL SXM

MIDTOWN MOTEL SXM
2.5 star property
Downtown Philipsburg
7.4 out of 10, Good, (71 reviews)
"Good rooms at a great location"
United States
Asheed
The price is NZ$151
includes taxes & fees
4 Sept - 5 Sept
MIDTOWN MOTEL SXM

2. July Apartments

July Apartments
3.0 star property
Madame's Estate
9.0 out of 10, Wonderful, (253 reviews)
"The property was no frills and the staff super helpful. Would stay again!"
United States
JoyAnn Carolyn
The price is NZ$160
includes taxes & fees
5 Sept - 6 Sept
July Apartments

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, (1,273 reviews)
"It was a great stay"
United States
Shawn
The price is NZ$283
includes taxes & fees
19 Sept - 20 Sept
Hilton Vacation Club Royal Palm St. Maarten

4. Simpson Bay Suites

Simpson Bay Suites
3.5 star property
Simpson Bay
7.2 out of 10, Good, (163 reviews)
"It was good value for money."
United States
Tirichmir
The price is NZ$229
includes taxes & fees
29 Aug - 30 Aug
Simpson Bay Suites

5. The Hills Residence

The Hills Residence
3.0 star property
Simpson Bay
8.4 out of 10, Very good, (167 reviews)
"View"
United States
Enuska
The price is NZ$450
includes taxes & fees
30 Aug - 31 Aug
The Hills Residence

6. 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$750
includes taxes & fees
1 Sept - 2 Sept
condostmaarten by the sea -Adults Only-

7. Philips Scott House Calinago

Philips Scott House Calinago
3.0 star property
Downtown Philipsburg
The price is NZ$385
includes taxes & fees
5 Sept - 6 Sept
Philips Scott House Calinago

8. 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$370
includes taxes & fees
29 Aug - 30 Aug
Cozy flat on the boardwalk!

9. The Castle ᴵ

The Castle ᴵ
Downtown Philipsburg
10.0 out of 10, Exceptional, (1 review)
The price is NZ$278
includes taxes & fees
30 Aug - 31 Aug
The Castle ᴵ

10. 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$556
includes taxes & fees
30 Aug - 31 Aug
Modern Indigo Bay Studio – 3 Min Walk To Beach!

11. 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$390
includes taxes & fees
30 Aug - 31 Aug
Hillside Penthouse spacious 2-bed/bath condo - ideal getaway but still central

12. Cosy (Apt7) - Patio, Sea View and pool

Cosy (Apt7) - Patio, Sea View and pool
Indigo Bay
The price is NZ$608
includes taxes & fees
11 Sept - 12 Sept
Cosy (Apt7) - Patio, Sea View and pool

13. 1-Bedroom Loft Apartment in Point Blanche

1-Bedroom Loft Apartment in Point Blanche
Point Blanche
The price is NZ$271
includes taxes & fees
29 Aug - 30 Aug
1-Bedroom Loft Apartment in Point Blanche

14. Delight (Apt4) - Amazing Sea View # 1 bedroom

Delight (Apt4) - Amazing Sea View # 1 bedroom
Indigo Bay
The price is NZ$778
includes taxes & fees
24 Sept - 25 Sept
Delight (Apt4) - Amazing Sea View # 1 bedroom

15. 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$313
includes taxes & fees
29 Aug - 30 Aug
Beach Front 1 Bedroom Flat D3

16. 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$267
includes taxes & fees
23 Sept - 24 Sept
Beach Front Studio C3

17. Blue Sail Apartments - Double room

Blue Sail Apartments - Double room
Pelican Key
2.0 out of 10, (1 review)
The price is NZ$212
includes taxes & fees
29 Aug - 30 Aug
Blue Sail Apartments - Double room

18. Blue Sky Apt in the middle of Simpson Bay-GENERATOR(1-3A)

Blue Sky Apt in the middle of Simpson Bay-GENERATOR(1-3A)
Simpson Bay
The price is NZ$362
includes taxes & fees
25 Sept - 26 Sept
Blue Sky Apt in the middle of Simpson Bay-GENERATOR(1-3A)

19. D416 – Relaxing apartment with Balcony

D416 – Relaxing apartment with Balcony
Sint Maarten
D416 – Relaxing apartment with Balcony

20. Beautiful spacious Studio with spectacular view

Beautiful spacious Studio with spectacular view
Pelican Key
8.6 out of 10, Excellent, (4 reviews)
"The property is quaint with a beautiful view! "
United States
Linda H.
The price is NZ$321
includes taxes & fees
1 Sept - 2 Sept
Beautiful spacious Studio with spectacular view
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.
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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?

Private House -GreatBay- Philipsburg - Free Wifi and Free Private Parking.: This highly rated holiday home rental in Little Bay is located on the waterfront, and offers a selection of books, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

How many holiday rentals will I find in Little Bay?

Expedia has 7 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.