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Upper Prince's Quarter Holiday Rentals

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Upper Prince's Quarter holiday rentals

Terrace/patio

1. Villa de 10 Chambres les Pieds Dans L'eau à Guana Bay

Villa de 10 Chambres les Pieds Dans L'eau à Guana Bay
Sint Maarten
10.0 out of 10, Exceptional, (2 reviews)
The price is NZ$7,184
includes taxes & fees
15 Sept - 16 Sept
Villa de 10 Chambres les Pieds Dans L'eau à Guana Bay
Pool

2. Lovely Studio Apartment with Pool & Nature Views!

Lovely Studio Apartment with Pool & Nature Views!
Oyster Pond
9.4 out of 10, Exceptional, (3 reviews)
"The feature of the unit is the view! For the price it’s a great deal - especially if you have a car. The unit is clean - but the shower only runs really hot. "
United States
Jennifer
The price is NZ$237
includes taxes & fees
13 Sept - 14 Sept
Lovely Studio Apartment with Pool & Nature Views!
Infinity pool

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
The price is NZ$1,279
includes taxes & fees
20 Aug - 21 Aug
Dawn Beach Club Resort Sint Maarten
Outdoor dining

4. 1-Bedroom Loft Apartment in Point Blanche

1-Bedroom Loft Apartment in Point Blanche
Point Blanche
The price is NZ$273
includes taxes & fees
27 Aug - 28 Aug
1-Bedroom Loft Apartment in Point Blanche
Beach

5. 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)
The price is NZ$1,391
includes taxes & fees
20 Aug - 21 Aug
Singh Luxury Apartments With sea View, Apt.3
Beach

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

Singh Luxury Apartments With sea View, Apt.1
3.0 star property
Oyster Pond
The price is NZ$701
includes taxes & fees
20 Aug - 21 Aug
Singh Luxury Apartments With sea View, Apt.1
Exterior

7. 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 NZ$701
includes taxes & fees
20 Aug - 21 Aug
Singh Luxury Apartments With sea View, Apt.2
Interior

8. 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 NZ$253
includes taxes & fees
20 Aug - 21 Aug
The Castle f
Room

9. 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 NZ$253
includes taxes & fees
20 Aug - 21 Aug
The Castle ᴶ
Room

10. 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 NZ$281
includes taxes & fees
20 Aug - 21 Aug
The Castle ᴴ
Room

11. The Castle ᴳ

The Castle ᴳ
Downtown Philipsburg
The price is NZ$253
includes taxes & fees
20 Aug - 21 Aug
The Castle ᴳ
Deluxe Double Room

12. July Apartments

July Apartments
3.0 star property
Madame's Estate
9.0 out of 10, Wonderful, (252 reviews)
"The property was no frills and the staff super helpful. Would stay again!"
United States
JoyAnn Carolyn
The price is NZ$159
includes taxes & fees
4 Sept - 5 Sept
July Apartments
Comfort Room, 1 King Bed, Non Smoking, Ocean View

13. MIDTOWN MOTEL SXM

MIDTOWN MOTEL SXM
2.5 star property
Downtown Philipsburg
7.4 out of 10, Good, (71 reviews)
"Good rooms at a great location"
United States
Asheed
The price is NZ$152
includes taxes & fees
21 Aug - 22 Aug
MIDTOWN MOTEL SXM
Terrace/patio

14. Simpson Bay Suites

Simpson Bay Suites
3.5 star property
Simpson Bay
7.2 out of 10, Good, (163 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 NZ$231
includes taxes & fees
20 Aug - 21 Aug
Simpson Bay Suites
Interior

15. The Castle ᴵ

The Castle ᴵ
Downtown Philipsburg
10.0 out of 10, Exceptional, (1 review)
The price is NZ$281
includes taxes & fees
20 Aug - 21 Aug
The Castle ᴵ
Beach

16. 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 NZ$373
includes taxes & fees
25 Aug - 26 Aug
Cozy flat on the boardwalk!
Deluxe Apartment, Courtyard View

17. Philips Scott House Calinago

Philips Scott House Calinago
3.0 star property
Downtown Philipsburg
The price is NZ$396
includes taxes & fees
20 Aug - 21 Aug
Philips Scott House Calinago
Outdoor dining

18. 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 NZ$212
includes taxes & fees
20 Aug - 21 Aug
Lovely room in a nice villa , close to Friars bay and happy bay
Terrace/patio

19. 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 NZ$393
includes taxes & fees
20 Aug - 21 Aug
Hillside Penthouse spacious 2-bed/bath condo - ideal getaway but still central
Amazing Top Floor Apartment | Balcony

20. The Hills Residence

The Hills Residence
3.0 star property
Simpson Bay
8.4 out of 10, Very good, (164 reviews)
"Comfortable room and ac was a welcome after a hot day."
United States
Maria
The price is NZ$462
includes taxes & fees
20 Aug - 21 Aug
The Hills Residence
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 Upper Prince's Quarter Hotel Reviews

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

10/10 Excellent
"No complaints at all"
DeQuan 4-night trip
Posted 5 hours ago
Simpson Bay Resort, Marina & Spa

Find out more about Upper Prince's Quarter

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Upper Prince's Quarter holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Upper Prince's Quarter. 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 Upper Prince's Quarter. Seeing all the best attractions is bound to make you fall in love with Upper Prince's Quarter. Who knows, you may even be tempted to extend your 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 holiday 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 Upper Prince's Quarter short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Upper Prince's Quarter?

Yes, there are holiday rentals close to the most popular sights in Upper Prince's Quarter, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Upper Prince's Quarter has to offer?

LUXURY VILLA! HIGHEST GUEST RATINGS ON ISLAND! DISCOUNTED SUMMER RATES!: This highly rated holiday home rental in Upper Prince's Quarter offers an outdoor pool, a balcony and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a terrace, a garden and a selection of games so that you can immerse yourself in your holiday. Some other top choices in Upper Prince's Quarter are Charming 2-bedrooms Dream Cottage tranquil retreat in Pointe Blanche and Villa Flagrantia, Paradise at your pleasure.

How many holiday rentals will I find in Upper Prince's Quarter?

Choose from 30 Expedia holiday rentals in Upper Prince's Quarter for a memorable holiday.

What can I see and do in Upper Prince's Quarter?

Dawn Beach and Guana Bay Beach are a couple of lovely local spots to get outside and enjoy nature. While here, Oyster Bay Marina and Front Street District are other places worth a visit.

What are holiday rentals like in Upper Prince's Quarter?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Upper Prince's Quarter. Holiday rentals provide amenities such as WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of security away from public hotel lifts and busy concierge desks while still allowing you to travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for a family trip or a small group gathering.