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

Orient Bay Vacation Rentals

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Our top choices for Orient Bay vacation rentals

1. STUDIO EVE Residence Adam et Eve

STUDIO EVE Residence Adam et Eve
Baie Orientale
The price is CA $397
CA $413 total
includes taxes & fees
Sep 11 - Sep 12
STUDIO EVE Residence Adam et Eve

2. Studio Avec Mezzanine,

Studio Avec Mezzanine,
saint martin
10.0 out of 10, Exceptional, (1 review)
The price is CA $240
CA $279 total
includes taxes & fees
Sep 20 - Sep 21
Studio Avec Mezzanine,

3. 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 $130
CA $246 total
includes taxes & fees
Sep 12 - Sep 13
Studio Charma Soualiga à Orient Bay

4. Appart "tintamarre" Avec vue sur la Piscine, Situé à 5 Minutes de la Plage !

Appart "tintamarre" Avec vue sur la Piscine, Situé à 5 Minutes de la Plage !
saint martin
The price is CA $216
CA $254 total
includes taxes & fees
Sep 21 - Sep 22
Appart "tintamarre" Avec vue sur la Piscine, Situé à 5 Minutes de la Plage !

5. Detached yellow studio in front of the pool 150m from the beach!

Detached yellow studio in front of the pool 150m from the beach!
saint martin
The price is CA $240
CA $332 total
includes taxes & fees
Sep 21 - Sep 22
Detached yellow studio in front of the pool 150m from the beach!

6. Studio "pinel" Avec Grande Terrasse vue sur Piscine et Accès à Plage à 5 Minutes

Studio "pinel" Avec Grande Terrasse vue sur Piscine et Accès à Plage à 5 Minutes
saint martin
The price is CA $240
CA $341 total
includes taxes & fees
Sep 21 - Sep 22
Studio "pinel" Avec Grande Terrasse vue sur Piscine et Accès à Plage à 5 Minutes

7. Studio Indépendant Devant Piscine et BBQ à Orient Bay à 5 Minutes de la Plage !

Studio Indépendant Devant Piscine et BBQ à Orient Bay à 5 Minutes de la Plage !
saint martin
The price is CA $240
CA $341 total
includes taxes & fees
Sep 21 - Sep 22
Studio Indépendant Devant Piscine et BBQ à Orient Bay à 5 Minutes de la Plage !

8. 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
Sep 17 - Sep 18
The Castle ᴶ

9. The Castle ᴷ

The Castle ᴷ
Downtown Philipsburg
10.0 out of 10, Exceptional, (1 review)
The price is CA $165
CA $206 total
includes taxes & fees
Sep 17 - Sep 18
The Castle ᴷ

10. 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
Sep 17 - Sep 18
The Castle f

11. 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
Sep 21 - Sep 22
The Castle ᴴ

12. View planes, beach & lolos in Grand-Case

View planes, beach & lolos in Grand-Case
Grand-Case
The price is CA $194
CA $223 total
includes taxes & fees
Sep 21 - Sep 22
View planes, beach & lolos in Grand-Case

13. 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
The price is CA $128
CA $134 total
includes taxes & fees
Sep 13 - Sep 14
July Apartments

14. Modern Cozy Condo - Central Location - Near Shops & Beaches

Modern Cozy Condo - Central Location - Near Shops & Beaches
St Martin
The price is CA $130
CA $223 total
includes taxes & fees
Oct 3 - Oct 4
Modern Cozy Condo - Central Location - Near Shops & Beaches

15. The Castle ᴳ

The Castle ᴳ
Downtown Philipsburg
The price is CA $165
CA $206 total
includes taxes & fees
Sep 11 - Sep 12
The Castle ᴳ

16. To complete

To complete
Cul-de-Sac
The price is CA $79
CA $87 total
includes taxes & fees
Oct 6 - Oct 7
To complete

17. 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
The price is CA $867
CA $1,041 total
includes taxes & fees
Sep 25 - Sep 26
Dawn Beach Club Resort Sint Maarten

18. The Castle L - Twin Studio

The Castle L - Twin Studio
Downtown Philipsburg
The price is CA $165
CA $206 total
includes taxes & fees
Sep 17 - Sep 18
The Castle L - Twin Studio

19. To complete

To complete
Cul-de-Sac
The price is CA $79
CA $87 total
includes taxes & fees
Oct 6 - Oct 7
To complete

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

Singh Luxury Apartments With sea View, Apt.2
3.5 star property
Oyster Pond
The price is CA $445
CA $571 total
includes taxes & fees
Sep 17 - Sep 18
Singh Luxury Apartments With sea View, Apt.2
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

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.

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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.

How many vacation rentals are there in Orient Bay?

Expedia has 61 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.