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

Upper Prince's Quarter Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Upper Prince's Quarter vacation 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 CA $895
CA $1,074 total
includes taxes & fees
Oct 6 - Oct 7
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 CA $122
CA $185 total
includes taxes & fees
Oct 9 - Oct 10
Lovely Studio Apartment with Pool & Nature Views!
A coastal marina with numerous boats docked, a small island with buildings, and a clear view of the sea.

3. 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 CA $459
CA $589 total
includes taxes & fees
Oct 3 - Oct 4
Singh Luxury Apartments With sea View, Apt.1
A rooftop terrace with a pool, lounge chairs, and a view of the sea.

4. 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 CA $5,278
CA $5,985 total
includes taxes & fees
Oct 3 - Oct 4
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.

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 CA $1,011
CA $1,168 total
includes taxes & fees
Oct 3 - Oct 4
Singh Luxury Apartments With sea View, Apt.3
A multi-story building with a pool, surrounded by hilly terrain.

6. 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 $459
CA $589 total
includes taxes & fees
Oct 3 - Oct 4
Singh Luxury Apartments With sea View, Apt.2
A dining area on a boat with a table set for two, a view of the sea, and a mountainous landscape in the background.

7. UNIQUE EXPERIENCE: OVERNIGHT ON A CATAMARAN WITH DINNER AND BREAKFAST INCLUDED

UNIQUE EXPERIENCE: OVERNIGHT ON A CATAMARAN WITH DINNER AND BREAKFAST INCLUDED
Grand-Case
The price is CA $1,599
CA $1,855 total
includes taxes & fees
Oct 20 - Oct 21
UNIQUE EXPERIENCE: OVERNIGHT ON A CATAMARAN WITH DINNER AND BREAKFAST INCLUDED
A view from inside a building looking out to a beach with clear turquoise water and a distant ship.

8. MIDTOWN MOTEL SXM

MIDTOWN MOTEL SXM
2.5 star property
Downtown Philipsburg
7.4 out of 10, Good, (73 reviews)
"It was a wonderful stay and experience"
United States
Yollanda
The price is CA $94
CA $115 total
includes taxes & fees
Oct 15 - Oct 16
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.

9. 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 $132
CA $138 total
includes taxes & fees
Oct 6 - Oct 7
July Apartments
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, (1,310 reviews)
"The staff was very friendly"
United States
Carmelle,
The price is CA $156
CA $201 total
includes taxes & fees
Oct 11 - Oct 12
Hilton Vacation Club Royal Palm St. Maarten
A beach with rows of umbrellas and lounge chairs, a marina with boats, and a cruise ship docked in the background.

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 CA $213
CA $316 total
includes taxes & fees
Oct 4 - Oct 5
Cozy flat on the boardwalk!
A bedroom with a red bedspread, white headboard, and two red pillows. There are two paintings on the wall, a closet with a sliding door, and a bathroom visible in the background.

12. The Castle ᴷ

The Castle ᴷ
Downtown Philipsburg
10.0 out of 10, Exceptional, (1 review)
The price is CA $171
CA $213 total
includes taxes & fees
Oct 14 - Oct 15
The Castle ᴷ
A hallway with a decorative gate, potted plants, and a fire extinguisher.

13. The Castle ᴵ

The Castle ᴵ
Downtown Philipsburg
10.0 out of 10, Exceptional, (1 review)
The price is CA $192
CA $236 total
includes taxes & fees
Oct 4 - Oct 5
The Castle ᴵ
A living room with a brown sofa, two red pillows, a small white table, and a floor lamp.

14. The Castle ᴳ

The Castle ᴳ
Downtown Philipsburg
The price is CA $171
CA $213 total
includes taxes & fees
Oct 4 - Oct 5
The Castle ᴳ
A dining area with a table, chairs, a small potted plant, a framed picture on the wall, and a mounted TV.

15. 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 $171
CA $213 total
includes taxes & fees
Oct 4 - Oct 5
The Castle f
A bedroom with a bed, bedside table, chair, and artwork on the walls.

16. 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 $171
CA $213 total
includes taxes & fees
Oct 4 - Oct 5
The Castle ᴶ
A compact, white front-loading washer and dryer unit in a corner of a room with a tiled floor and a small potted plant.

17. 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 $192
CA $236 total
includes taxes & fees
Oct 7 - Oct 8
The Castle ᴴ
A bedroom with a bed, a TV mounted on the wall, a small fridge, and a bedside table with a lamp.

18. Philips Scott House Calinago

Philips Scott House Calinago
3.0 star property
Downtown Philipsburg
2.0 out of 10, (1 review)
The price is CA $192
CA $306 total
includes taxes & fees
Oct 12 - Oct 13
Philips Scott House Calinago
A clear blue sky, a swimming pool with a view of the sea, and a hillside with buildings.

19. 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 CA $430
CA $635 total
includes taxes & fees
Oct 14 - Oct 15
condostmaarten by the sea -Adults Only-
A modern living room with a large sliding glass door leading to a balcony with a view of a coastal town and mountains.

20. The Hills Residence

The Hills Residence
3.0 star property
Simpson Bay
8.4 out of 10, Very good, (170 reviews)
"Very good"
United States
Alyssia
The price is CA $241
CA $405 total
includes taxes & fees
Oct 4 - Oct 5
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

Divi Little Bay Beach Resort

Divi Little Bay Beach Resort

10/10 Excellent
"Last year we stayed at Little Debbland we had an ocean view"
Gabreille Lynn 6-night trip
Posted 16 hours ago
Divi Little Bay Beach Resort

Find out more about Upper Prince's Quarter

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 Upper Prince's Quarter. 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.

Frequently asked questions

Are there vacation rentals in Upper Prince's Quarter?

Yes, you can find vacation rentals near the most popular local attractions in Upper Prince's Quarter, or you can go with a more secluded option if you want a relaxing place to stay.

What are some of the best vacation rentals in Upper Prince's Quarter?

LUXURY VILLA! KILLER VIEWS! HIGHEST GUEST RATINGS ON ISLAND!: This highly rated vacation home rental in Upper Prince's Quarter offers an outdoor pool, a balcony, and a barbecue grill 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 you can cook with friends or family. It offers a terrace, a garden, and a selection of games so you can immerse yourself in your vacation. 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 vacation rentals will I find in Upper Prince's Quarter?

Choose from 31 Expedia vacation rentals in Upper Prince's Quarter for a memorable vacation.

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 vacation rentals like in Upper Prince's Quarter?

Vacation rentals are privately owned accommodations you can reserve for several days or more in Upper Prince's Quarter. Vacation rentals offer amenities such as WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, vacation rentals can provide a sense of safety away from public hotel elevators and lobbies packed with people while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive option for a family trip or a small group gathering.