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 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

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
$723 nightly
The price is $755
Oct 7 - Oct 8
Total with taxes and fees
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
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
$398 nightly
The price is $414
Oct 7 - Oct 8
Total with taxes and fees
Singh Luxury Apartments With sea View, Apt.1
A coastal marina with numerous boats docked, a small island with buildings, and a clear view of the ocean.

4. 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)
$785 nightly
The price is $821
Oct 7 - Oct 8
Total with taxes and fees
Singh Luxury Apartments With sea View, Apt.3
A multi-story building with a pool, surrounded by hilly terrain.

5. Singh Luxury Apartments With sea View, Apt.2

Singh Luxury Apartments With sea View, Apt.2
3.5 star property
Oyster Pond
$398 nightly
The price is $414
Oct 7 - Oct 8
Total with taxes and fees
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.

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

UNIQUE EXPERIENCE: OVERNIGHT ON A CATAMARAN WITH DINNER AND BREAKFAST INCLUDED
Grand-Case
$1,265 nightly
The price is $1,309
Oct 20 - Oct 21
Total with taxes and fees
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.

7. 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
$77 nightly
The price is $80
Oct 15 - Oct 16
Total with taxes and fees
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, (253 reviews)
"The property was no frills and the staff super helpful. Would stay again!"
United States
JoyAnn Carolyn
$93 nightly
The price is $97
Oct 7 - Oct 8
Total with taxes and fees
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, (1,311 reviews)
"The staff was very friendly"
United States
Carmelle,
$141 nightly
The price is $148
Oct 11 - Oct 12
Total with taxes and fees
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.

10. 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.
$195 nightly
The price is $206
Oct 7 - Oct 8
Total with taxes and fees
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.

11. The Castle ᴷ

The Castle ᴷ
Downtown Philipsburg
10.0 out of 10, Exceptional, (1 review)
$140 nightly
The price is $150
Oct 12 - Oct 13
Total with taxes and fees
The Castle ᴷ
A hallway with a decorative gate, potted plants, and a fire extinguisher.

12. The Castle ᴵ

The Castle ᴵ
Downtown Philipsburg
10.0 out of 10, Exceptional, (1 review)
The Castle ᴵ
A living room with a brown sofa, two red pillows, a small white table, and a floor lamp.

13. The Castle ᴳ

The Castle ᴳ
Downtown Philipsburg
$140 nightly
The price is $150
Oct 7 - Oct 8
Total with taxes and fees
The Castle ᴳ
A dining area with a table, chairs, a small potted plant, a framed picture on the wall, and a mounted TV.

14. 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.
$140 nightly
The price is $150
Oct 7 - Oct 8
Total with taxes and fees
The Castle f
A bedroom with a bed, bedside table, chair, and artwork on the walls.

15. 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.
$140 nightly
The price is $150
Oct 13 - Oct 14
Total with taxes and fees
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.

16. 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.
$155 nightly
The price is $166
Oct 7 - Oct 8
Total with taxes and fees
The Castle ᴴ
A bedroom with a bed, a TV mounted on the wall, a small fridge, and a bedside table with a lamp.

17. Philips Scott House Calinago

Philips Scott House Calinago
3.0 star property
Downtown Philipsburg
2.0 out of 10, (1 review)
$213 nightly
The price is $223
Oct 15 - Oct 16
Total with taxes and fees
Philips Scott House Calinago
A clear blue sky, a swimming pool with a view of the sea, and a hillside with buildings.

18. 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
$428 nightly
The price is $447
Oct 14 - Oct 15
Total with taxes and fees
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.

19. 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
$273 nightly
The price is $285
Oct 7 - Oct 8
Total with taxes and fees
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

Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

10/10 Excellent
"Amazing stay"
labrietta 4-night trip
Posted 2 hours ago
Panorama Residences at Monte Vista

Price trends for vacation rentals in Upper Prince's Quarter

Less expensive
More expensive
This month
Next month
September
December
$696
$735
Month
Price
January
$582
February
$505
March
$839
April
$779
May
$678
June
$514
July
$529
August
$542
September
$502
October
$696
November
$735
December
$868
Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed vacation rentals in Upper Prince's Quarter. Select dates and complete search for nightly totals inclusive of taxes and fees.

Find out more about Upper Prince's Quarter

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

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

Upper Prince's Quarter vacation 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 low season months. For more hustle and bustle, you may prefer to visit Upper Prince's Quarter in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $80 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

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

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

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 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.