Upper Prince's Quarter Holiday Rentals

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Check prices for these dates

In two weeks
23 Jan - 25 Jan
In two months
6 Mar - 8 Mar
In three months
3 Apr - 5 Apr
In four months
1 May - 3 May

Our top choices for Upper Prince's Quarter holiday rentals

Outdoor pool
Dawn Beach Club Resort Sint Maarten

Condo resort in Oyster Pond

Dawn Beach Club Resort Sint Maarten
4.0 star property
8.6 out of 10, Excellent, (23)
"Housing was good. To be able to use JW Marriott is excellent "
United States
Shana
Dawn Beach Club Resort Sint Maarten
Exterior
Singh Luxury Apartments With sea View, Apt.2

Apartment in Oyster Pond

Singh Luxury Apartments With sea View, Apt.2
3.5 star property
The price is S$704
includes taxes & fees
13 Jan - 14 Jan
Singh Luxury Apartments With sea View, Apt.2
Beach
Singh Luxury Apartments With sea View, Apt.1

Apartment in Oyster Pond

Singh Luxury Apartments With sea View, Apt.1
3.0 star property
The price is S$704
includes taxes & fees
17 Jan - 18 Jan
Singh Luxury Apartments With sea View, Apt.1
Beach
Singh Luxury Apartments With sea View, Apt.3

Apartment in Oyster Pond

Singh Luxury Apartments With sea View, Apt.3
3.0 star property
2.0 out of 10, (1)
The price is S$1,224
includes taxes & fees
14 Jan - 15 Jan
Singh Luxury Apartments With sea View, Apt.3
Living area
Mullet Bay Suites: Your Luxury Stay Awaits

Apartment in Maho

Mullet Bay Suites: Your Luxury Stay Awaits
4.0 star property
9.8 out of 10, Exceptional, (120)
"Great apartment and great location!"
United States
Miljan
The price is S$503
includes taxes & fees
18 Jan - 19 Jan
Mullet Bay Suites: Your Luxury Stay Awaits
On the beach, sun-loungers, beach umbrellas, beach towels
Hilton Vacation Club Royal Palm St. Maarten

Aparthotel in Simpson Bay

Hilton Vacation Club Royal Palm St. Maarten
4.0 star property
9.0 out of 10, Wonderful, (1168)
"Room was great, resort was great, staff was great"
Canada
Gisele
The price is S$549
includes taxes & fees
15 Jan - 16 Jan
Hilton Vacation Club Royal Palm St. Maarten
Balcony
The Hills Residence

Aparthotel in Simpson Bay

The Hills Residence
3.0 star property
8.6 out of 10, Excellent, (66)
"Good location, walkable area, great views. "
United States
Tiffany
The price is S$414
includes taxes & fees
2 Feb - 3 Feb
The Hills Residence
Outdoor pool
condostmaarten by the sea -Adults Only-

Apartment in Indigo Bay

condostmaarten by the sea -Adults Only-
4.0 star property
9.4 out of 10, Exceptional, (24)
"Good location easy access to a private beach "
United States
All About
The price is S$661
includes taxes & fees
21 Jan - 22 Jan
condostmaarten by the sea -Adults Only-
Beach nearby, white sand, sun-loungers, beach umbrellas
Simpson Bay Suites

Aparthotel in Simpson Bay

Simpson Bay Suites
3.5 star property
7.0 out of 10, Good, (131)
"It is 'value priced', has a convenient location and the AC works :) But be realistic in your expectations, this is not competing with the Hiltons and Morgans on the island. Great for an overnight layover. Huge rooms - Really it's a full sized apartment with all the amenities. "
United States
Roger
The price is S$242
includes taxes & fees
12 Jan - 13 Jan
Simpson Bay Suites
Down duvets, free WiFi, bed sheets
July Apartments

Aparthotel in Madame's Estate

July Apartments
3.0 star property
9.2 out of 10, Wonderful, (162)
"Amazing place. "
United States
Cristina
July Apartments
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

Hilton Vacation Club Flamingo Beach St. Maarten

Hilton Vacation Club Flamingo Beach St. Maarten

10/10 Excellent
"We were at this hotel for 10 days (end of November 2025). The room was very clean. The room location was great as we faced the beach. We were on the second level which made it very convenient/walkable between the beach and the room. The kitchen in the room included everything that you need including paper towels, dishwasher soap, cleaning sponges , salt, pepper, dishes, pots and pans..etc. Hotel location was great (walking distance to many restaurants). Ample parking spaces (not sure why others said it was limited, they may have not known the parking under the hotel). Staff were amazing (both at the front desk and cleaning staff-not sure why some visitors had issues with the front desk as they were very courteous and professional-Tessy was the best). Our room was cleaned every 3 days (witout having to request the cleaning unlike some of the other reviews hear). The hotel staff communicated via text message so it would be helpful to have a phone plan to use at the island. The beaches at the hotel was just awesome. Waters were always calm. There is sand in the water so no need for rock shoes. Great snorkeling within the bay at the hotel as well as further out where you can find sea turtles and sting rays. This hotel, location and staff make it a 10/10 place to visit. We will be visiting again!"
Jacek Pawel 10-night trip
Posted 3 days ago
Hilton Vacation Club Flamingo Beach St. Maarten

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?

Villa Amalia: This highly rated holiday home rental in Upper Prince's Quarter is located near the beach, and has an outdoor pool, a balcony and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a full-sized fridge, a dishwasher and an oven. You and your friends and family can relax into your holiday with amenities such as a terrace.

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

Choose from 28 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, Guana Bay 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.