A white gate, a stone wall, and a pink building.

Upper Prince's Quarter Holiday Rentals

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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Upper Prince's Quarter holiday rentals

A large swimming pool surrounded by palm trees and lounge chairs, with a hotel building in the background.

1. 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 AU$1,054
includes taxes & fees
3 Sept - 4 Sept
Dawn Beach Club Resort Sint Maarten
A view through a window with a pool and a mountainous landscape.

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 AU$184
includes taxes & fees
8 Sept - 9 Sept
Lovely Studio Apartment with Pool & Nature Views!
A covered outdoor area with a pool, chairs, and a table.

3. 1-Bedroom Loft Apartment in Point Blanche

1-Bedroom Loft Apartment in Point Blanche
Point Blanche
The price is AU$228
includes taxes & fees
15 Sept - 16 Sept
1-Bedroom Loft Apartment in Point Blanche
A coastal marina with numerous boats docked, a small island with buildings, and a clear view of the sea.

4. 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 AU$578
includes taxes & fees
3 Sept - 4 Sept
Singh Luxury Apartments With sea View, Apt.1
A rooftop terrace with a pool, lounge chairs, and a view of the sea.

5. 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 AU$5,943
includes taxes & fees
3 Sept - 4 Sept
Villa de 10 Chambres les Pieds Dans L'eau à Guana Bay
A coastal marina with numerous boats docked, a small island with buildings, and a clear view of the ocean.

6. 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 AU$1,146
includes taxes & fees
3 Sept - 4 Sept
Singh Luxury Apartments With sea View, Apt.3
A multi-story building with a pool, surrounded by hilly terrain.

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 AU$578
includes taxes & fees
3 Sept - 4 Sept
Singh Luxury Apartments With sea View, Apt.2
A hotel room with a bed, a sofa, a small round table, and a chair. There is a bathroom visible through an open door.

8. 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 AU$131
includes taxes & fees
3 Sept - 4 Sept
July Apartments
A view from inside a building looking out to a beach with clear turquoise water and a distant ship.

9. MIDTOWN MOTEL SXM

MIDTOWN MOTEL SXM
2.5 star property
Downtown Philipsburg
7.4 out of 10, Good, (72 reviews)
"It was a wonderful stay and experience"
United States
Yollanda
The price is AU$127
includes taxes & fees
26 Sept - 27 Sept
MIDTOWN MOTEL SXM
A resort with a view of sailboats on the water, a beach with palm trees, and a modern building with balconies.

10. 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, (1,277 reviews)
"Fantastic location. Great little beach right next to hotel"
United States
Kevin
The price is AU$188
includes taxes & fees
9 Sept - 10 Sept
Hilton Vacation Club Royal Palm St. Maarten
A bedroom with a bed, bedside table, chair, and artwork on the walls.

11. 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 AU$212
includes taxes & fees
3 Sept - 4 Sept
The Castle ᴶ
A high-rise hotel with a view of the sunset over a marina.

12. Simpson Bay Suites

Simpson Bay Suites
3.5 star property
Simpson Bay
7.2 out of 10, Good, (163 reviews)
"It was good value for money."
United States
Tirichmir
The price is AU$190
includes taxes & fees
3 Sept - 4 Sept
Simpson Bay Suites
A bedroom with a bed, a dining table with chairs, a sofa, and a window with curtains.

13. The Castle ᴷ

The Castle ᴷ
Downtown Philipsburg
10.0 out of 10, Exceptional, (1 review)
The price is AU$212
includes taxes & fees
17 Sept - 18 Sept
The Castle ᴷ
A modern living room with a large sliding glass door leading to a balcony with a view of a coastal town and mountains.

14. The Hills Residence

The Hills Residence
3.0 star property
Simpson Bay
8.4 out of 10, Very good, (168 reviews)
"View"
United States
Enuska
The price is AU$374
includes taxes & fees
3 Sept - 4 Sept
The Hills Residence
A bedroom with a bed, nightstands, a ceiling fan, and a large mirror.

15. 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 AU$234
includes taxes & fees
3 Sept - 4 Sept
The Castle ᴴ
A bedroom with a bed, a sofa, a ceiling fan, a window with curtains, a floor lamp, and a wall with two framed pictures.

16. 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 AU$212
includes taxes & fees
3 Sept - 4 Sept
The Castle f
A beach with rows of umbrellas and lounge chairs, a marina with boats, and a cruise ship docked in the background.

17. 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 AU$313
includes taxes & fees
3 Sept - 4 Sept
Cozy flat on the boardwalk!
A hallway with a decorative gate, potted plants, and a fire extinguisher.

18. The Castle ᴵ

The Castle ᴵ
Downtown Philipsburg
10.0 out of 10, Exceptional, (1 review)
The price is AU$234
includes taxes & fees
22 Sept - 23 Sept
The Castle ᴵ
A hotel room with two beds, a dining table, and a ceiling fan.

19. The Castle L - Twin Studio

The Castle L - Twin Studio
Downtown Philipsburg
The price is AU$212
includes taxes & fees
3 Sept - 4 Sept
The Castle L - Twin Studio
A bedroom with a large bed, red curtains, a nightstand, a lamp, and two paintings on the wall.

20. The Castle ᴳ

The Castle ᴳ
Downtown Philipsburg
The price is AU$212
includes taxes & fees
3 Sept - 4 Sept
The Castle ᴳ
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

Sonesta Maho Beach All Inclusive Resort Casino & Spa

Sonesta Maho Beach All Inclusive Resort Casino & Spa

10/10 Excellent
"Very fun place to visit"
Steven 5-night trip
Posted 4 hours ago
Sonesta Maho Beach All Inclusive Resort Casino & Spa

Find out more about Upper Prince's Quarter

Everything you need to know about Upper Prince's Quarter holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Upper Prince's Quarter holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 Upper Prince's Quarter holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Upper Prince's Quarter holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Upper Prince's Quarter. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Upper Prince's Quarter holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Upper Prince's Quarter holiday rentals we have selected for you start as low as AU$127 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Upper Prince's Quarter rentals

At Expedia, we put the best Upper Prince's Quarter holiday 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 Upper Prince's Quarter 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 Upper Prince's Quarter holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Upper Prince's Quarter. 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 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?

Charming 2-bedrooms Dream Cottage tranquil retreat in Pointe Blanche: This highly rated holiday home rental in Upper Prince's Quarter is located near the beach, and has an outdoor pool, a garden and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as a selection of books. Some other top choices in Upper Prince's Quarter are LUXURY VILLA! KILLER VIEWS! HIGHEST GUEST RATINGS ON ISLAND! and Tropical Oasis in St. Martin 5 min to beach! Huge private pool+panoramic views!!.

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

Choose from 31 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.