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

Little Bay Vacation Rentals

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Our top choices for Little Bay vacation rentals

1. MIDTOWN MOTEL SXM

MIDTOWN MOTEL SXM
2.5 star property
Downtown Philipsburg
7.4 out of 10, Good, (70 reviews)
"All in all it was a great experience. Close to the beach. Clean environment. Kind staff"
United States
James
The price is CA $98
CA $119 total
includes taxes & fees
Sep 8 - Sep 9
MIDTOWN MOTEL SXM

2. July Apartments

July Apartments
3.0 star property
Madame's Estate
9.0 out of 10, Wonderful, (251 reviews)
"Great stay"
United States
Drunisha
The price is CA $123
CA $130 total
includes taxes & fees
Aug 12 - Aug 13
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, (1,264 reviews)
"It was a great stay"
United States
Shawn
The price is CA $212
CA $259 total
includes taxes & fees
Aug 25 - Aug 26
Hilton Vacation Club Royal Palm St. Maarten

4. The Hills Residence

The Hills Residence
3.0 star property
Simpson Bay
8.4 out of 10, Very good, (162 reviews)
"Comfortable room and ac was a welcome after a hot day."
United States
Maria
The price is CA $220
CA $380 total
includes taxes & fees
Aug 27 - Aug 28
The Hills Residence

5. Simpson Bay Suites

Simpson Bay Suites
3.5 star property
Simpson Bay
7.2 out of 10, Good, (161 reviews)
"AC worked well the room was cleaned daily and the staff was always friendly and made great suggestions for dinning and places to see."
United States
Michael
The price is CA $169
CA $190 total
includes taxes & fees
Aug 9 - Aug 10
Simpson Bay Suites

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 CA $481
CA $694 total
includes taxes & fees
Aug 12 - Aug 13
condostmaarten by the sea -Adults Only-

7. The Castle ᴵ

The Castle ᴵ
Downtown Philipsburg
10.0 out of 10, Exceptional, (1 review)
The price is CA $188
CA $231 total
includes taxes & fees
Aug 12 - Aug 13
The Castle ᴵ

8. Philips Scott House Calinago

Philips Scott House Calinago
3.0 star property
Downtown Philipsburg
The price is CA $207
CA $319 total
includes taxes & fees
Sep 8 - Sep 9
Philips Scott House Calinago

9. 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 CA $209
CA $309 total
includes taxes & fees
Aug 12 - Aug 13
Cozy flat on the boardwalk!

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 CA $231
CA $476 total
includes taxes & fees
Aug 12 - Aug 13
Modern Indigo Bay Studio – 3 Min Walk To Beach!

11. 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 CA $138
CA $222 total
includes taxes & fees
Aug 9 - Aug 10
Beach Front Studio C3

12. 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 CA $167
CA $313 total
includes taxes & fees
Aug 14 - Aug 15
Hillside Penthouse spacious 2-bed/bath condo - ideal getaway but still central

13. 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 CA $174
CA $259 total
includes taxes & fees
Aug 20 - Aug 21
Beach Front 1 Bedroom Flat D3

14. Blue Sail Apartments - Double room

Blue Sail Apartments - Double room
Pelican Key
2.0 out of 10, (1 review)
The price is CA $145
CA $174 total
includes taxes & fees
Aug 14 - Aug 15
Blue Sail Apartments - Double room

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

Charming studio with the beach at your feet & pool access
Marigot
10.0 out of 10, Exceptional, (2 reviews)
"Everything was great"
Canada
Brad W.
The price is CA $229
CA $322 total
includes taxes & fees
Aug 9 - Aug 10
Charming studio with the beach at your feet & pool access

16. 1 bedroom with pool in Simpson Bay - GENERATOR (1-3B)

1 bedroom with pool in Simpson Bay - GENERATOR (1-3B)
Simpson Bay
10.0 out of 10, Exceptional, (2 reviews)
"perfect!!"
United States
jason l.
The price is CA $152
CA $296 total
includes taxes & fees
Aug 13 - Aug 14
1 bedroom with pool in Simpson Bay - GENERATOR (1-3B)

17. Quiet cozy flat in the centre of the island.

Quiet cozy flat in the centre of the island.
Weymouth Hill, Sint Maarten
7.6 out of 10, Good, (5 reviews)
"Amazing view, Very friendly and helpful people. Only 1 thing is a must that's a SUV rental car. And some driving skills. But still a great spot to be spending your holiday."
Netherlands
Tobias
The price is CA $223
CA $301 total
includes taxes & fees
Aug 12 - Aug 13
Quiet cozy flat in the centre of the island.

18. 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, (176 reviews)
"Great stay! Beautiful suite"
United States
Crystal Alana
The price is CA $355
CA $500 total
includes taxes & fees
Aug 9 - Aug 10
Mullet Bay Suites: Your Luxury Stay Awaits

19. Modern apartment with shared pool and generator (2-2B)

Modern apartment with shared pool and generator (2-2B)
Simpson Bay
The price is CA $161
CA $308 total
includes taxes & fees
Aug 10 - Aug 11
Modern apartment with shared pool and generator (2-2B)

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 CA $195
CA $266 total
includes taxes & fees
Aug 15 - Aug 16
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 vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

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 free WiFi to help you feel perfectly comfortable in your new surroundings. Amenities like a microwave and free parking are also available for your convenience.

How many vacation rentals will I find in Little Bay?

Expedia has 7 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.