Orient Bay Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Orient Bay vacation rentals

Studio Charma Soualiga à Orient Bay

Studio Charma Soualiga à Orient Bay
Collectivité de Saint-Martin
9.6 out of 10, Exceptional, (4 reviews)
"The place is small (but we knew that coming in) but well appointed and in great shape. Fantastic location!"
United States
William S.
The price is CA $124
CA $241 total
includes taxes & fees
Apr 15 - Apr 16
Studio Charma Soualiga à Orient Bay

Charm and sea, large studio designed by architect

Charm and sea, large studio designed by architect
Baie-Orientale
9.4 out of 10, Exceptional, (6 reviews)
""Appartement très bien équipé avec climatisation et wifi indispensables pour nous. La localisation avec la possibilité d''''aller à la plage d''''Orient bay à pied (ou à la piscine de la résidence juste à côté) est très agréable. Mais plus généralement l''''emplacement est très bien pour rayonner dans cette partie de l''''île. Il y a des supermarchés à 5 minutes en voiture. La vue n''''est pas sur l''''océan mais sur un étang à côté, du coup le balcon reste abrité même s''''il y a du vent et de...
France
Gérard B.
The price is CA $219
CA $381 total
includes taxes & fees
Apr 26 - Apr 27
Charm and sea, large studio designed by architect

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 CA $165
CA $206 total
includes taxes & fees
Apr 17 - Apr 18
The Castle ᴶ

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 CA $165
CA $206 total
includes taxes & fees
Apr 15 - Apr 16
The Castle f

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 CA $186
CA $229 total
includes taxes & fees
Apr 17 - Apr 18
The Castle ᴴ

Philips Scott House Calinago

Philips Scott House Calinago
3.0 star property
Downtown Philipsburg
The price is CA $234
CA $350 total
includes taxes & fees
Apr 17 - Apr 18
Philips Scott House Calinago

The Hill Top Cottage

The Hill Top Cottage
Collectivity of Saint Martin
10.0 out of 10, Exceptional, (1 review)
"Getting up the hill was tough in a small car but everything else was great, especially the hosts!"
Canada
Ian
The price is CA $146
CA $181 total
includes taxes & fees
Apr 15 - Apr 16
The Hill Top Cottage

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, (1 review)
"Everything was great"
Canada
Brad W.
The price is CA $168
CA $252 total
includes taxes & fees
May 1 - May 2
Charming studio with the beach at your feet & pool access

MIDTOWN MOTEL SXM

MIDTOWN MOTEL SXM
2.5 star property
Downtown Philipsburg
7.2 out of 10, Good, (54 reviews)
"Good rooms at a great location"
United States
Asheed
The price is CA $117
CA $143 total
includes taxes & fees
May 6 - May 7
MIDTOWN MOTEL SXM

Lovely room in a nice villa , close to Friars bay and happy bay

Lovely room in a nice villa , close to Friars bay and happy bay
Saint-martin
9.0 out of 10, Wonderful, (11 reviews)
"Great place to stay. Will definitely be staying again next year! "
United States
Kurt
The price is CA $105
CA $135 total
includes taxes & fees
Apr 20 - Apr 21
Lovely room in a nice villa , close to Friars bay and happy bay

The Castle ᴳ

The Castle ᴳ
Downtown Philipsburg
The price is CA $165
CA $206 total
includes taxes & fees
Apr 19 - Apr 20
The Castle ᴳ

Hillside Penthouse

Hillside Penthouse
South Reward
10.0 out of 10, Exceptional, (2 reviews)
"The host was very welcoming and kind. The apartment was very clean, it has very large bedrooms, kitchen and living room space. I will definitely book this place again on my next trip to St. Maarten. "
Canada
Diana M.
The price is CA $169
CA $347 total
includes taxes & fees
May 7 - May 8
Hillside Penthouse

Mullet Bay Suites: Your Luxury Stay Awaits

Mullet Bay Suites: Your Luxury Stay Awaits
4.0 star property
Maho
9.8 out of 10, Exceptional, (141 reviews)
"Amazing place ! Impeccable service ! Great location ! Would definitely come back here . "
Canada
Aleisha
The price is CA $328
CA $468 total
includes taxes & fees
Apr 25 - Apr 26
Mullet Bay Suites: Your Luxury Stay Awaits

Charming studio with splendid Caribbean Sea view & pool/beach access

Charming studio with splendid Caribbean Sea view & pool/beach access
Marigot
9.0 out of 10, Wonderful, (2 reviews)
"Beautiful view and the host was very welcoming."
United States
Dasha A.
The price is CA $211
CA $302 total
includes taxes & fees
May 2 - May 3
Charming studio with splendid Caribbean Sea view & pool/beach access

Quiet cozy flat in the centre of the island.

Quiet cozy flat in the centre of the island.
Weymouth Hill, Sint Maarten
7.0 out of 10, Good, (4 reviews)
"Large. Great views, welcoming. Just the internet doesn’t work very well."
Canada
Aayan S.
The price is CA $221
CA $296 total
includes taxes & fees
Apr 17 - Apr 18
Quiet cozy flat in the centre of the island.

Oceanfront Paradise: Luxurious Penthouse with Spectacular Pools and Peloton

Oceanfront Paradise: Luxurious Penthouse with Spectacular Pools and Peloton
Maho
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful space, great location, communicative host. Would definitely recommend and would love to stay again. "
United States
Kara K.
The price is CA $365
CA $653 total
includes taxes & fees
May 12 - May 13
Oceanfront Paradise: Luxurious Penthouse with Spectacular Pools and Peloton

The Forest

The Forest
4.0 star property
Anse Marcel
10.0 out of 10, Exceptional, (25 reviews)
"Very happy with our stay, especially the location in Anse Marcel! Breakfast is great and included"
United States
Chi Yan Jane
The price is CA $483
CA $504 total
includes taxes & fees
Apr 15 - Apr 16
The Forest

condostmaarten by the sea -Adults Only-

condostmaarten by the sea -Adults Only-
4.0 star property
Indigo Bay
9.0 out of 10, Wonderful, (36 reviews)
"Everything was so perfect from the parking to the view, the staff was very welcoming and professional overall i will definitely stay here again. "
United States
Rose
The price is CA $347
CA $533 total
includes taxes & fees
Apr 16 - Apr 17
condostmaarten by the sea -Adults Only-

Beachside Retreat: Balcony, Pools, and Direct Ocean Access and Peloton!

Beachside Retreat: Balcony, Pools, and Direct Ocean Access and Peloton!
Maho
The price is CA $372
CA $662 total
includes taxes & fees
Apr 22 - Apr 23
Beachside Retreat: Balcony, Pools, and Direct Ocean Access and Peloton!

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 $207
CA $330 total
includes taxes & fees
Apr 19 - Apr 20
Cozy flat on the boardwalk!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Orient Bay Hotel Reviews

Find out more about Orient 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 Orient 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

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 lively bars in this destination. While you're in the area, grab a bite or have a drink at the top-notch restaurants and cafes.

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

Philips Scott House Calinago: You might want to consider this vacation rental near Orient Bay, which 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 C&S Home; Spacious 4 BDR 2.5 BTHR with Sea View as a favorite home for rent in Orient Bay.

How many vacation rentals are there in Orient Bay?

Expedia has 62 vacation rentals for your stay in Orient Bay.

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

Orient Bay and Coconut Grove Beach are a couple of lovely local spots to get outside and enjoy nature. Mont Vernon and Maho Beach are a couple of places you'll find in the larger area.

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.