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
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

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 NZ$1,325
includes taxes & fees
26 Oct - 27 Oct
Dawn Beach Club Resort Sint Maarten
A multi-story building with a pool, surrounded by hilly terrain.

2. 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$726
includes taxes & fees
26 Oct - 27 Oct
Singh Luxury Apartments With sea View, Apt.2
A view through a window with a pool and a mountainous landscape.

3. 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$245
includes taxes & fees
17 Nov - 18 Nov
Lovely Studio Apartment with Pool & Nature Views!
A covered outdoor area with a pool, chairs, and a table.

4. 1-Bedroom Loft Apartment in Point Blanche

1-Bedroom Loft Apartment in Point Blanche
Point Blanche
The price is NZ$425
includes taxes & fees
28 Oct - 29 Oct
1-Bedroom Loft Apartment in Point Blanche
A multi-story hotel with a pool, set against a mountainous backdrop.

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$1,441
includes taxes & fees
26 Oct - 27 Oct
Singh Luxury Apartments With sea View, Apt.3
A multi-story hotel with a pool, set against a mountainous backdrop.

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$726
includes taxes & fees
26 Oct - 27 Oct
Singh Luxury Apartments With sea View, Apt.1
A view from inside a building looking out to a beach with clear turquoise water and a distant ship.

7. MIDTOWN MOTEL SXM

MIDTOWN MOTEL SXM
2.5 star property
Downtown Philipsburg
7.6 out of 10, Good, (75 reviews)
"The place was amazing"
United States
brenton
The price is NZ$141
includes taxes & fees
28 Oct - 29 Oct
MIDTOWN MOTEL SXM
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, (254 reviews)
"The property was no frills and the staff super helpful. Would stay again!"
United States
JoyAnn Carolyn
The price is NZ$197
includes taxes & fees
26 Oct - 27 Oct
July Apartments
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, (1,323 reviews)
"The staff was very friendly"
United States
Carmelle,
The price is NZ$340
includes taxes & fees
5 Nov - 6 Nov
Hilton Vacation Club Royal Palm St. Maarten
A swimming pool with clear water, a grassy area, and a view of a coastal landscape 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
The price is NZ$874
includes taxes & fees
26 Oct - 27 Oct
condostmaarten by the sea -Adults Only-
A balcony with a view of the sea, a table, and two chairs.

11. 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$390
includes taxes & fees
26 Oct - 27 Oct
Cozy flat on the boardwalk!
A rooftop terrace with a pool, lounge chairs, and a table with a drink.

12. Avenue du lagon

Avenue du lagon
Oyster Pond
The price is NZ$3,436
includes taxes & fees
29 Oct - 30 Oct
Avenue du lagon
A modern living room with a large sliding glass door leading to a balcony with a view of a coastal town and mountains.

13. The Hills Residence

The Hills Residence
3.0 star property
Simpson Bay
8.4 out of 10, Very good, (172 reviews)
"Very good"
United States
Alyssia
The price is NZ$607
includes taxes & fees
6 Nov - 7 Nov
The Hills Residence
A high-rise hotel with a view of the sunset over a marina.

14. Simpson Bay Suites

Simpson Bay Suites
3.5 star property
Simpson Bay
7.2 out of 10, Good, (168 reviews)
"Overall good. Location is great."
Canada
Manishkumar
The price is NZ$265
includes taxes & fees
26 Oct - 27 Oct
Simpson Bay Suites
A bedroom with a bed, a TV mounted on the wall, a small fridge, and a bedside table with a lamp.

15. Philips Scott House Calinago

Philips Scott House Calinago
3.0 star property
Downtown Philipsburg
2.0 out of 10, (1 review)
The price is NZ$383
includes taxes & fees
1 Nov - 2 Nov
Philips Scott House Calinago
A modern living room with large windows, a purple sofa, and a view of the beach and ocean.

16. 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, (185 reviews)
"This place was amazing. Perfect experience"
United States
Kenneth
The price is NZ$554
includes taxes & fees
1 Nov - 2 Nov
Mullet Bay Suites: Your Luxury Stay Awaits
A balcony with white railings, a bench, and two chairs.

17. 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$408
includes taxes & fees
26 Oct - 27 Oct
Hillside Penthouse spacious 2-bed/bath condo - ideal getaway but still central
A spacious living room with a large flat-screen TV, a ceiling fan, and a modern sofa.

18. 4bed Condo - Sleeps 8 - Pool, Bbq, Views, Parking

4bed Condo - Sleeps 8 - Pool, Bbq, Views, Parking
3.5 star property
St. Peters
The price is NZ$1,121
includes taxes & fees
1 Nov - 2 Nov
4bed Condo - Sleeps 8 - Pool, Bbq, Views, Parking
A terrace with wicker furniture, a hanging chair, and a view of boats at a marina.

19. Panoramic Ocean View Flat: St Maarten

Panoramic Ocean View Flat: St Maarten
Downtown Philipsburg
The price is NZ$495
includes taxes & fees
27 Oct - 28 Oct
Panoramic Ocean View Flat: St Maarten
A modern kitchen with a dining area, a grey sofa, and a TV.

20. A View of Airplanes, the Beach, and Lolos in Grand-Case

A View of Airplanes, the Beach, and Lolos in Grand-Case
Grand-Case
The price is NZ$273
includes taxes & fees
26 Oct - 27 Oct
A View of Airplanes, the Beach, and Lolos in Grand-Case
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

Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

10/10 Excellent
"Super clean, beautiful location. Friendly staff. Safe place. Will book again"
Dinnae Nessa 3-night trip
Posted 1 hour ago
Panorama Residences at Monte Vista

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! KILLER VIEWS! HIGHEST GUEST RATINGS ON ISLAND!: 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 Villa Flagrantia, Paradise at your pleasure and 1-Bedroom Loft Apartment in Point Blanche.

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, Front Street District and Oyster Bay Marina 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.