A hillside residential area with houses, a swimming pool, and mountains in the background.

Orient Bay Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Orient Bay vacation rentals

A hotel room with a bed, a sofa, a small round table, and a chair. There is a bathroom visible through an open door.

1. 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
$93 nightly
The price is $97
Sep 30 - Oct 1
Total with taxes and fees
July Apartments
A view from inside a building looking out to a beach with clear turquoise water and a distant ship.

2. MIDTOWN MOTEL SXM

MIDTOWN MOTEL SXM
2.5 star property
Downtown Philipsburg
7.4 out of 10, Good, (73 reviews)
"It was a wonderful stay and experience"
United States
Yollanda
$77 nightly
The price is $80
Oct 15 - Oct 16
Total with taxes and fees
MIDTOWN MOTEL SXM
A large swimming pool surrounded by palm trees and lounge chairs, with a hotel building in the background.

3. Dawn Beach Club Resort Sint Maarten

Dawn Beach Club Resort Sint Maarten
4.0 star property
Oyster Pond
8.8 out of 10, Excellent, (33 reviews)
"Large rooms with great ocean views! Helpful staff and good beach access!"
United States
Gavin
$723 nightly
The price is $755
Sep 30 - Oct 1
Total with taxes and fees
Dawn Beach Club Resort Sint Maarten
A rooftop terrace with a pool, lounge chairs, and a table with a drink.

4. Avenue du lagon

Avenue du lagon
Oyster Pond
$1,883 nightly
The price is $1,958
Sep 30 - Oct 1
Total with taxes and fees
Avenue du lagon
A multi-story building with a pool, surrounded by hilly terrain.

5. Singh Luxury Apartments With sea View, Apt.2

Singh Luxury Apartments With sea View, Apt.2
3.5 star property
Oyster Pond
$398 nightly
The price is $414
Sep 30 - Oct 1
Total with taxes and fees
Singh Luxury Apartments With sea View, Apt.2
A high-rise hotel with a view of the sunset over a marina.

6. Simpson Bay Suites

Simpson Bay Suites
3.5 star property
Simpson Bay
7.2 out of 10, Good, (166 reviews)
"Overall good. Location is great."
Canada
Manishkumar
$130 nightly
The price is $136
Sep 30 - Oct 1
Total with taxes and fees
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.

7. The Hills Residence

The Hills Residence
3.0 star property
Simpson Bay
8.4 out of 10, Very good, (170 reviews)
"Very good"
United States
Alyssia
$273 nightly
The price is $285
Oct 4 - Oct 5
Total with taxes and fees
The Hills Residence
A modern living room with large windows, a purple sofa, and a view of the beach and ocean.

8. 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, (184 reviews)
"This place was amazing. Perfect experience"
United States
Kenneth
$346 nightly
The price is $359
Oct 6 - Oct 7
Total with taxes and fees
Mullet Bay Suites: Your Luxury Stay Awaits
A resort with a view of sailboats on the water, a beach with palm trees, and a modern building with balconies.

9. 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, (1,308 reviews)
"The property was very conveniently located. The rooms were exactly like the pictures and the staff were very lovely."
United States
Erika
$135 nightly
The price is $141
Oct 11 - Oct 12
Total with taxes and fees
Hilton Vacation Club Royal Palm St. Maarten
A clear blue sky, a swimming pool with a view of the sea, and a hillside with buildings.

10. 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
$428 nightly
The price is $447
Oct 14 - Oct 15
Total with taxes and fees
condostmaarten by the sea -Adults Only-
A bedroom with a bed, a TV mounted on the wall, a small fridge, and a bedside table with a lamp.

11. Philips Scott House Calinago

Philips Scott House Calinago
3.0 star property
Downtown Philipsburg
2.0 out of 10, (1 review)
$224 nightly
The price is $234
Sep 30 - Oct 1
Total with taxes and fees
Philips Scott House Calinago
A coastal marina with numerous boats docked, a small island with buildings, and a clear view of the ocean.

12. Singh Luxury Apartments With sea View, Apt.3

Singh Luxury Apartments With sea View, Apt.3
3.0 star property
Oyster Pond
2.0 out of 10, (1 review)
$785 nightly
The price is $821
Sep 30 - Oct 1
Total with taxes and fees
Singh Luxury Apartments With sea View, Apt.3
A coastal marina with numerous boats docked, a small island with buildings, and a clear view of the sea.

13. Singh Luxury Apartments With sea View, Apt.1

Singh Luxury Apartments With sea View, Apt.1
3.0 star property
Oyster Pond
$398 nightly
The price is $414
Sep 30 - Oct 1
Total with taxes and fees
Singh Luxury Apartments With sea View, Apt.1
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 Orient Bay Hotel Reviews

Palm Court Residence & Hotel at Orient Beach

Palm Court Residence & Hotel at Orient Beach

10/10 Excellent
"The staff was so courteous, the location was excellent, and we had such an excellent trip. I wish we had found this property earlier!"
David Brent 6-night trip
Posted 5 days ago
Palm Court Residence & Hotel at Orient Beach

Find out more about Orient Bay

Everything you need to know about Orient 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 Orient 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 Orient Bay vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Orient Bay vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Orient 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 Orient 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 $174 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 Orient Bay rentals

At Expedia, we put the best Orient 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 Orient 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 Orient 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 Orient 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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Orient Bay?

Yes, we have vacation rentals close to well known points of interest in Orient Bay, or you can go with a more remote option if you're looking for relaxation. Visitors to Orient Bay speak positively about the popular beaches and top-notch restaurants in this destination. While you're in the area, grab a bite or have a drink at the lively bars and cafes.

What's the top vacation rental that Orient Bay has to offer?

Philips Scott House Calinago: You might want to consider this Orient Bay vacation home rental for your stay. It 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 Villa Coquelicot - 2 Bedrooms, Beach and Garden as a favorite home for rent in Orient Bay.

How many vacation rentals are there in Orient Bay?

Expedia has 59 vacation rentals for your stay in Orient Bay.

What’s there to see and do in Orient Bay?

Orient Bay and Mont Vernon are a couple of lovely local spots to get outside and enjoy nature. Coconut Grove Beach and Fish Pond are other places to visit while you're in town.

What’s a vacation rental in Orient Bay like?

Vacation rentals are privately owned properties you can stay in for a few weeks or just a few days in Orient Bay. Vacation rentals offer extras such as WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you to travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental a great option for small groups.