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

Little Bay Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

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

MIDTOWN MOTEL SXM
2.5 star property
Downtown Philipsburg
7.6 out of 10, Good, (76 reviews)
"The place was amazing"
United States
brenton
$74 nightly
The price is $78
Nov 25 - Nov 26
Total with taxes and fees
MIDTOWN MOTEL SXM
A clear blue sky, a swimming pool with a view of the sea, and a hillside with buildings.

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, (44 reviews)
"Every thing was perfect, clean , quiet,beautiful views, definitely on my list to revisit.The host was very informative about the whole process he was very polite guy"
United States
Elouise
$527 nightly
The price is $550
Nov 15 - Nov 16
Total with taxes and fees
condostmaarten by the sea -Adults Only-
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

Hilton Vacation Club Royal Palm St. Maarten
4.0 star property
Simpson Bay
9.0 out of 10, Wonderful, (1,339 reviews)
"It was nice"
United States
Prem
$227 nightly
The price is $238
Dec 2 - Dec 3
Total with taxes and fees
Hilton Vacation Club Royal Palm St. Maarten
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

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
$122 nightly
The price is $128
Nov 15 - Nov 16
Total with taxes and fees
July Apartments
A high-rise hotel with a view of the sunset over a marina.

5. Simpson Bay Suites

Simpson Bay Suites
3.5 star property
Simpson Bay
7.2 out of 10, Good, (170 reviews)
"Overall good. Location is great."
Canada
Manishkumar
$144 nightly
The price is $151
Nov 15 - Nov 16
Total with taxes and fees
Simpson Bay Suites
A bedroom with a bed, a TV mounted on the wall, a small fridge, and a bedside table with a lamp.

6. Philips Scott House Calinago

Philips Scott House Calinago
3.0 star property
Downtown Philipsburg
2.0 out of 10, (1 review)
$206 nightly
The price is $215
Nov 15 - Nov 16
Total with taxes and fees
Philips Scott House Calinago
A beach with rows of umbrellas and lounge chairs, a marina with boats, and a cruise ship docked in the background.

7. 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.
$203 nightly
The price is $215
Nov 21 - Nov 22
Total with taxes and fees
Cozy flat on the boardwalk!
An infinity pool with a clear view of the sea, a wooden table with food and drinks, and a lounge area with a view.

8. 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.
$1,330 nightly
The price is $1,390
Nov 16 - Nov 17
Total with taxes and fees
Luxury 4BR Villa w/ Private Pool & Ocean Views
A modern room with a dining area, large windows, and a view of the sea.

9. 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.
$1,034 nightly
The price is $1,080
Nov 16 - Nov 17
Total with taxes and fees
Villa Solandra – 3BR Oceanfront Sunset w/ Pool
A beach with rows of sun loungers and umbrellas, a pier with a large ship, and a sailboat in the water.

10. Panoramic Ocean View Flat: St Maarten

Panoramic Ocean View Flat: St Maarten
Downtown Philipsburg
$337 nightly
The price is $359
Nov 15 - Nov 16
Total with taxes and fees
Panoramic Ocean View Flat: St Maarten
A modern living room with a large window, a sofa, a coffee table, and a wicker chair.

11. B221 - Beautiful Cosy 2 Bedroom

B221 - Beautiful Cosy 2 Bedroom
Sint Maarten
$368 nightly
The price is $388
Nov 17 - Nov 18
Total with taxes and fees
B221 - Beautiful Cosy 2 Bedroom
A hallway with a decorative gate, potted plants, and a fire extinguisher.

12. The Castle ᴵ

The Castle ᴵ
Downtown Philipsburg
10.0 out of 10, Exceptional, (1 review)
$147 nightly
The price is $158
Nov 22 - Nov 23
Total with taxes and fees
The Castle ᴵ
A modern living room with large windows, a purple sofa, and a view of the beach and ocean.

13. 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, (186 reviews)
"Breakfast was good. Some of the staff were ok, others were fantastic!"
Canada
Susan
$305 nightly
The price is $317
Nov 21 - Nov 22
Total with taxes and fees
Mullet Bay Suites: Your Luxury Stay Awaits
A modern living room with a large window overlooking a marina and hills.

14. B225 - Incredible Lagoon View

B225 - Incredible Lagoon View
Sint Maarten
B225 - Incredible Lagoon View
A covered balcony with a view of trees and a tiled floor.

15. SXM Hillside Retreat large 3-bed/bath condo, tucked in the hills but central

SXM Hillside Retreat large 3-bed/bath condo, tucked in the hills but central
South Reward
$290 nightly
The price is $290
Nov 20 - Nov 21
Total with taxes and fees
SXM Hillside Retreat large 3-bed/bath condo, tucked in the hills but central
A pool area with two lounge chairs, a door, and a stone-tiled floor.

16. 4bed Condo - Sleeps 8 - Pool, Bbq, Views, Parking

4bed Condo - Sleeps 8 - Pool, Bbq, Views, Parking
3.5 star property
St. Peters
$586 nightly
The price is $612
Nov 16 - Nov 17
Total with taxes and fees
4bed Condo - Sleeps 8 - Pool, Bbq, Views, Parking
A pool area with lounge chairs and a stone wall.

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

Modern apartment with shared pool and generator (2-2B)
Simpson Bay
$210 nightly
The price is $216
Nov 15 - Nov 16
Total with taxes and fees
Modern apartment with shared pool and generator (2-2B)
A modern living room with a large window offering a view of a coastal town and mountains.

18. D417 - One Bedroom Apartment with Lagoon View

D417 - One Bedroom Apartment with Lagoon View
Cole Bay
D417 - One Bedroom Apartment with Lagoon View
A white SUV parked in a covered area with a view of the ocean.

19. 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.
$200 nightly
The price is $200
Nov 21 - Nov 22
Total with taxes and fees
Beautiful spacious Studio with spectacular view
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
$151 nightly
The price is $151
Nov 15 - Nov 16
Total with taxes and fees
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

Oyster Bay Beach Resort

Oyster Bay Beach Resort

10/10 Excellent
"Awesome time, staff was great food was awesome and beaches were beautiful"
Derrick 7-night trip
Posted less than an hour ago
Oyster Bay Beach Resort

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Little Bay in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $78 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.