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

Little Bay Holiday Rentals

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Little Bay holiday rentals

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

1. MIDTOWN MOTEL SXM

MIDTOWN MOTEL SXM
2.5 star property
Downtown Philipsburg
7.6 out of 10, Good, (75 reviews)
"The place was amazing"
United States
brenton
The price is HK$572
HK$686 total
includes taxes & fees
3 Nov - 4 Nov
MIDTOWN MOTEL SXM
A dining area with a table, chairs, a small potted plant, a framed picture on the wall, and a mounted TV.

2. 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 HK$941
HK$1,174 total
includes taxes & fees
30 Oct - 31 Oct
The Castle f
A compact, white front-loading washer and dryer unit in a corner of a room with a tiled floor and a small potted plant.

3. The Castle ᴴ

The Castle ᴴ
Downtown Philipsburg
8.0 out of 10, Very good, (2 reviews)
"Absolutely great place to stay. Only downside is there is a bird that treats her 2 AM and then a rooster from about 5 AM to 9 AM so make sure you bring your earplugs."
United States
Denise W.
The price is HK$1,059
HK$1,301 total
includes taxes & fees
30 Oct - 31 Oct
The Castle ᴴ
A compact living space with a bed, a dining area, and a kitchenette.

4. The Castle L - Twin Studio

The Castle L - Twin Studio
Downtown Philipsburg
The price is HK$941
HK$1,174 total
includes taxes & fees
30 Oct - 31 Oct
The Castle L - Twin Studio
A living room with a brown sofa, two red pillows, a small white table, and a floor lamp.

5. The Castle ᴳ

The Castle ᴳ
Downtown Philipsburg
The price is HK$941
HK$1,174 total
includes taxes & fees
13 Nov - 14 Nov
The Castle ᴳ
A bedroom with a bed, bedside table, chair, and artwork on the walls.

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 HK$941
HK$1,174 total
includes taxes & fees
31 Oct - 1 Nov
The Castle ᴶ
A clear blue sky, a swimming pool with a view of the sea, and a hillside with buildings.

7. condostmaarten by the sea -Adults Only-

condostmaarten by the sea -Adults Only-
4.0 star property
Indigo Bay
9.2 out of 10, Wonderful, (44 reviews)
"Love love the property was amazing. Will definitely return."
United States
Muneca
The price is HK$3,048
HK$4,316 total
includes taxes & fees
1 Nov - 2 Nov
condostmaarten by the sea -Adults Only-
A bedroom with a red bedspread, white headboard, and two red pillows. There are two paintings on the wall, a closet with a sliding door, and a bathroom visible in the background.

8. The Castle ᴷ

The Castle ᴷ
Downtown Philipsburg
10.0 out of 10, Exceptional, (1 review)
The price is HK$941
HK$1,174 total
includes taxes & fees
30 Oct - 31 Oct
The Castle ᴷ
A hotel room with a bed, a sofa, a small round table, and a chair. There is a bathroom visible through an open door.

9. 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 HK$953
HK$1,001 total
includes taxes & fees
30 Oct - 31 Oct
July Apartments
A resort with a view of sailboats on the water, a beach with palm trees, and a modern building with balconies.

10. 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, (1,324 reviews)
"The staff was very friendly"
United States
Carmelle,
The price is HK$1,127
HK$1,379 total
includes taxes & fees
10 Nov - 11 Nov
Hilton Vacation Club Royal Palm St. Maarten
A high-rise hotel with a view of the sunset over a marina.

11. Simpson Bay Suites

Simpson Bay Suites
3.5 star property
Simpson Bay
7.2 out of 10, Good, (169 reviews)
"Overall good. Location is great."
Canada
Manishkumar
The price is HK$1,059
HK$1,186 total
includes taxes & fees
31 Oct - 1 Nov
Simpson Bay Suites
A modern living room with a large sliding glass door leading to a balcony with a view of a coastal town and mountains.

12. The Hills Residence

The Hills Residence
3.0 star property
Simpson Bay
8.4 out of 10, Very good, (173 reviews)
"My next stay I’ll be a returning guest at the hills …"
United States
Harold
The price is HK$1,500
HK$2,716 total
includes taxes & fees
2 Nov - 3 Nov
The Hills Residence
A bedroom with a bed, a TV mounted on the wall, a small fridge, and a bedside table with a lamp.

13. Philips Scott House Calinago

Philips Scott House Calinago
3.0 star property
Downtown Philipsburg
2.0 out of 10, (1 review)
The price is HK$1,080
HK$1,688 total
includes taxes & fees
31 Oct - 1 Nov
Philips Scott House Calinago
A coastal view with a clear beach, a rocky shoreline, and a hillside with buildings.

14. 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 HK$1,526
HK$3,013 total
includes taxes & fees
2 Nov - 3 Nov
Modern Indigo Bay Studio – 3 Min Walk To Beach!
A modern living room with large windows, a purple sofa, and a view of the beach and ocean.

15. 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 HK$2,008
HK$2,817 total
includes taxes & fees
10 Nov - 11 Nov
Mullet Bay Suites: Your Luxury Stay Awaits
A beach with rows of umbrellas and lounge chairs, a marina with boats, and a cruise ship docked in the background.

16. 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 HK$1,177
HK$1,773 total
includes taxes & fees
1 Nov - 2 Nov
Cozy flat on the boardwalk!
A hallway with a decorative gate, potted plants, and a fire extinguisher.

17. The Castle ᴵ

The Castle ᴵ
Downtown Philipsburg
10.0 out of 10, Exceptional, (1 review)
The price is HK$1,059
HK$1,301 total
includes taxes & fees
22 Nov - 23 Nov
The Castle ᴵ
A balcony with white railings, a bench, and two chairs.

18. 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 HK$900
HK$1,842 total
includes taxes & fees
30 Oct - 31 Oct
Hillside Penthouse spacious 2-bed/bath condo - ideal getaway but still central
A beachfront property with multiple buildings, a beach, and a red arrow pointing to a specific building.

19. 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 HK$840
HK$1,319 total
includes taxes & fees
30 Oct - 31 Oct
Beach Front 1 Bedroom Flat D3
A beachfront property with multiple buildings, a beach, and a red arrow pointing to a specific building.

20. 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 HK$777
HK$1,247 total
includes taxes & fees
30 Oct - 31 Oct
Beach Front Studio C3
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

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

10/10 Excellent
"I love how friendly the staff was. I felt right at home. In fact, I immediately rebooked my trip back in a month!"
Akilah 4-night trip
Posted less than an hour ago
Simpson Bay Resort, Marina & Spa

Find out more about Little Bay

Search for holiday rentals in Little Bay on Expedia! You can easily find your home rentals, villas, holiday apartments in Little Bay using one of the methods below:

  • View our selection of featured holiday rentals in Little Bay
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  • Enter your travel dates to view the best deals on holiday rentals in Little Bay while they last

Look no further and take a look at our great range of rental properties in Little Bay!

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.