Title: Upper Prince's Quarter Vacation Rentals from CA $583: Short-Term Rentals for 2026 | Expedia.ca

[Upper Prince's Quarter Travel Guide](https://expedia.ca/Upper-Princes-Quarter.dx553248635976384612)[Hotels in Upper Prince's Quarter](https://expedia.ca/Upper-Princes-Quarter-Hotels.d553248635976384612.Travel-Guide-Hotels)[Upper Prince's Quarter Car Rentals](https://expedia.ca/Car-Rentals-In-Upper-Princes-Quarter.d553248635976384612.Car-Rental-Guide)[Upper Prince's Quarter Vacation Packages](https://expedia.ca/Upper-Princes-Quarter.d553248635976384612.Destination-Travel-Guides)

![Dawn Beach featuring landscape views, a coastal town and a beach](https://images.trvl-media.com/place/6079641/685f5a02-e71f-490e-a4c0-5bac3d7028e2.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/6079641/685f5a02-e71f-490e-a4c0-5bac3d7028e2.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=553248635976384612&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=553248635976384612&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 8 - May 10](https://www.expedia.ca/Hotel-Search?regionId=553248635976384612&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 5 - Jun 7](https://www.expedia.ca/Hotel-Search?regionId=553248635976384612&startDate=2026-06-05&endDate=2026-06-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Upper Prince's Quarter vacation rentals

![Exterior](https://images.trvl-media.com/lodging/43000000/42580000/42572500/42572423/a646e56c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/43000000/42580000/42572500/42572423/f6e90987.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment (2 Bedrooms) | Private kitchen](https://images.trvl-media.com/lodging/43000000/42580000/42572500/42572423/0f678586.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/43000000/42580000/42572500/42572423/cca8955c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Oyster-Pond-Hotels-Singh-Luxury-Apartments-With-Sea-View.h42572423.Hotel-Information)

Oyster Pond

CA $616

CA $749 total

includes taxes & fees

Feb 16 - Feb 17

[](https://www.expedia.ca/Oyster-Pond-Hotels-Singh-Luxury-Apartments-With-Sea-View.h42572423.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/119000000/118720000/118712800/118712750/216bd5a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/119000000/118720000/118712800/118712750/107af700.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/119000000/118720000/118712800/118712750/d5a638e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118720000/118712800/118712750/4912b13f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lovely Studio Apartment with Pool & Nature Views!

[](https://www.expedia.ca/Oyster-Pond-Hotels-Lovely-Studio-Apartment-With-Pool-Nature-Views.h118712750.Hotel-Information)

Oyster Pond

9.0/10

Wonderful

(2 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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jennifer

CA $129

CA $190 total

includes taxes & fees

Mar 5 - Mar 6

[](https://www.expedia.ca/Oyster-Pond-Hotels-Lovely-Studio-Apartment-With-Pool-Nature-Views.h118712750.Hotel-Information)

![Outdoor pool](https://images.trvl-media.com/lodging/69000000/68050000/68048500/68048492/ff3c051d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Panoramic Condo, 3 Bedrooms, Ocean View](https://images.trvl-media.com/lodging/69000000/68050000/68048500/68048492/404bd561.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Panoramic Condo, 3 Bedrooms, Ocean View | Living area](https://images.trvl-media.com/lodging/69000000/68050000/68048500/68048492/e971fa52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/69000000/68050000/68048500/68048492/919c3a50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Dawn Beach Club Resort Sint Maarten

[](https://www.expedia.ca/Oyster-Pond-Hotels-Dawn-Beach-Club-Resort-Sint-Maarten.h68048492.Hotel-Information)

Oyster Pond

8.4/10

Very good

(25 reviews)

"Beautiful condo with large balcony"

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Mary Colleen

CA $779

CA $951 total

includes taxes & fees

Feb 23 - Feb 24

[](https://www.expedia.ca/Oyster-Pond-Hotels-Dawn-Beach-Club-Resort-Sint-Maarten.h68048492.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/102000000/101230000/101228000/101227999/8652af97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/102000000/101230000/101228000/101227999/229816e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/102000000/101230000/101228000/101227999/0d674b2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/102000000/101230000/101228000/101227999/218fb176.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa de 10 Chambres les Pieds Dans L'eau à Guana Bay

[](https://www.expedia.ca/Philipsburg-Hotels-Villa-De-10-Chambres-Les-Pieds-Dans-Leau-A-Guana-Bay.h101227999.Hotel-Information)

Sint Maarten

CA $5,332

CA $6,054 total

includes taxes & fees

Feb 16 - Feb 17

[](https://www.expedia.ca/Philipsburg-Hotels-Villa-De-10-Chambres-Les-Pieds-Dans-Leau-A-Guana-Bay.h101227999.Hotel-Information)

![Living area](https://images.trvl-media.com/lodging/100000000/99270000/99269600/99269588/w1024h569x0y57-e5616ee6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99270000/99269600/99269588/w1024h570x0y57-e8144bf2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels, soap](https://images.trvl-media.com/lodging/100000000/99270000/99269600/99269588/w1024h570x0y56-cf4beec2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99270000/99269600/99269588/e2ccb1de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### SunThan Rentals. Unit # 1

[](https://www.expedia.ca/Philipsburg-Hotels-SunThan-Rentals-Unit-1.h99269588.Hotel-Information)

Point Blanche

2.0/10

(1 review)

"We chose this property by the advertising photos. When we arrived our taxi driver was unable to find the building. Eventually with the help he found it. The apartment although was nice the whole complex was a health and safety issue it was still under construction. It was built on an industrial estate also where the cruise ships keep there containers. We actually did not stay because of issues going on. Having said this I think once the building work is finished it would be a nice complex just...

![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg)

Heather J.

CA $299

CA $343 total

includes taxes & fees

Feb 16 - Feb 17

[](https://www.expedia.ca/Philipsburg-Hotels-SunThan-Rentals-Unit-1.h99269588.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/43000000/42580000/42572500/42572437/8ab47aa8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/43000000/42580000/42572500/42572437/1b11d50e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/43000000/42580000/42572500/42572437/3eac326a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment (2 Bedrooms) | Private kitchen](https://images.trvl-media.com/lodging/43000000/42580000/42572500/42572437/126fd89c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Singh Luxury Apartments With sea View, Apt.1

[](https://www.expedia.ca/Oyster-Pond-Hotels-Singh-Luxury-Apartments-With-Sea-View.h42572437.Hotel-Information)

Oyster Pond

CA $616

CA $749 total

includes taxes & fees

Feb 22 - Feb 23

[](https://www.expedia.ca/Oyster-Pond-Hotels-Singh-Luxury-Apartments-With-Sea-View.h42572437.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/43000000/42580000/42572500/42572432/2d76e223.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/43000000/42580000/42572500/42572432/2be5a019.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/43000000/42580000/42572500/42572432/12039fee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment (4 Bedrooms) | Private kitchen](https://images.trvl-media.com/lodging/43000000/42580000/42572500/42572432/af33cdf8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Singh Luxury Apartments With sea View, Apt.3

[](https://www.expedia.ca/Oyster-Pond-Hotels-Singh-Luxury-Apartments-With-Sea-View.h42572432.Hotel-Information)

Oyster Pond

2.0/10

(1 review)

CA $1,142

CA $1,301 total

includes taxes & fees

Feb 16 - Feb 17

[](https://www.expedia.ca/Oyster-Pond-Hotels-Singh-Luxury-Apartments-With-Sea-View.h42572432.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/113000000/112720000/112711000/112710908/d71c7292.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/113000000/112720000/112711000/112710908/02272588.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/113000000/112720000/112711000/112710908/bc362754.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/113000000/112720000/112711000/112710908/5ce29989.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Grand-Case-Hotels-Unique-Experience-Overnight-On-A-Catamaran-Cruise-With-Dinner-And-Breakfast.h112710908.Hotel-Information)

Grand-Case

CA $1,422

CA $1,681 total

includes taxes & fees

Mar 1 - Mar 2

[](https://www.expedia.ca/Grand-Case-Hotels-Unique-Experience-Overnight-On-A-Catamaran-Cruise-With-Dinner-And-Breakfast.h112710908.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/107000000/106380000/106372700/106372666/3751d8e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Aerial view](https://images.trvl-media.com/lodging/107000000/106380000/106372700/106372666/d75114c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/107000000/106380000/106372700/106372666/6ec6a1d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, oven, cookware/dishes/utensils](https://images.trvl-media.com/lodging/107000000/106380000/106372700/106372666/fd2c1d88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Unusual night in catamaran with dinner

[](https://www.expedia.ca/Grand-Case-Hotels-Unusual-Night-In-Catamaran-With-Dinner.h106372666.Hotel-Information)

Grand-Case

CA $1,630

CA $1,630 total

includes taxes & fees

Mar 1 - Mar 2

[](https://www.expedia.ca/Grand-Case-Hotels-Unusual-Night-In-Catamaran-With-Dinner.h106372666.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/102000000/101550000/101544000/101543997/60ab3508.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/102000000/101550000/101544000/101543997/8a9112cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/102000000/101550000/101544000/101543997/3ee35220.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/102000000/101550000/101544000/101543997/d01a75e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Your half-day cruise with scenic Zephyr and water activities

[](https://www.expedia.ca/Grand-Case-Hotels-Your-Half-Day-Cruise-With-Scenic-Zephyr-And-Water-Activities.h101543997.Hotel-Information)

Collectivité de Saint-Martin

CA $2,323

CA $2,323 total

includes taxes & fees

Mar 1 - Mar 2

[](https://www.expedia.ca/Grand-Case-Hotels-Your-Half-Day-Cruise-With-Scenic-Zephyr-And-Water-Activities.h101543997.Hotel-Information)

![Iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/118000000/117900000/117899500/117899490/6922e499.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 1 Queen Bed, Non Smoking, Beach View](https://images.trvl-media.com/lodging/118000000/117900000/117899500/117899490/6bacd041.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Comfort Room, 1 King Bed, Non Smoking, Ocean View](https://images.trvl-media.com/lodging/118000000/117900000/117899500/117899490/w1917h1080x0y0-8739faf9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Comfort Single Room](https://images.trvl-media.com/lodging/118000000/117900000/117899500/117899490/6727cc11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### MIDTOWN MOTEL SXM

[](https://www.expedia.ca/Philipsburg-Hotels-MIDTOWN-MOTEL-SXM.h117899490.Hotel-Information)

Downtown Philipsburg

7.0/10

Good

(20 reviews)

"I had an absolutely wonderful stay,the room was spotless, comfortable,for the price that we pay was very good we planing to go back and staying at same place ."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ana

CA $101

CA $122 total

includes taxes & fees

Feb 15 - Feb 16

[](https://www.expedia.ca/Philipsburg-Hotels-MIDTOWN-MOTEL-SXM.h117899490.Hotel-Information)

![Deluxe Apartment, Courtyard View](https://images.trvl-media.com/lodging/126000000/125100000/125096600/125096555/799a8d9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Apartment, Courtyard View](https://images.trvl-media.com/lodging/126000000/125100000/125096600/125096555/9f89af05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Apartment, Courtyard View | Bathroom](https://images.trvl-media.com/lodging/126000000/125100000/125096600/125096555/2783b5a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Apartment, Courtyard View](https://images.trvl-media.com/lodging/126000000/125100000/125096600/125096555/4a7f45bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Philips Scott House Calinago

[](https://www.expedia.ca/Philipsburg-Hotels-Philips-Scott-House-Calinago.h125096555.Hotel-Information)

Downtown Philipsburg

CA $231

CA $346 total

includes taxes & fees

Feb 24 - Feb 25

[](https://www.expedia.ca/Philipsburg-Hotels-Philips-Scott-House-Calinago.h125096555.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/45000000/44550000/44548100/44548053/835c2e93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/45000000/44550000/44548100/44548053/cb923536.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/45000000/44550000/44548100/44548053/e00367b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, towels, soap, shampoo](https://images.trvl-media.com/lodging/45000000/44550000/44548100/44548053/e3aad0d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lovely room in a nice villa , close to Friars bay and happy bay

[](https://www.expedia.ca/Grand-Case-Hotels-Lovely-Room-In-A-Nice-Villa-With-A-Big-Garden.h44548053.Hotel-Information)

Saint-martin

8.8/10

Excellent

(10 reviews)

"Great place to stay. Will definitely be staying again next year! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kurt

CA $105

CA $134 total

includes taxes & fees

Mar 9 - Mar 10

[](https://www.expedia.ca/Grand-Case-Hotels-Lovely-Room-In-A-Nice-Villa-With-A-Big-Garden.h44548053.Hotel-Information)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121350000/121340500/121340435/0785874b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121350000/121340500/121340435/4cd7f1f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels, soap](https://images.trvl-media.com/lodging/122000000/121350000/121340500/121340435/724759dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/122000000/121350000/121340500/121340435/57fb8155.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Castle L - Twin Studio

[](https://www.expedia.ca/Philipsburg-Hotels-The-Castle-L-Twin-Studio.h121340435.Hotel-Information)

Downtown Philipsburg

CA $163

CA $204 total

includes taxes & fees

Feb 17 - Feb 18

[](https://www.expedia.ca/Philipsburg-Hotels-The-Castle-L-Twin-Studio.h121340435.Hotel-Information)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121350000/121340100/121340015/1d1b00e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/122000000/121350000/121340100/121340015/080844a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/122000000/121350000/121340100/121340015/464a2491.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/122000000/121350000/121340100/121340015/62030d08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Castle ᴳ

[](https://www.expedia.ca/Philipsburg-Hotels-The-Castle-G.h121340015.Hotel-Information)

Downtown Philipsburg

CA $163

CA $204 total

includes taxes & fees

Feb 17 - Feb 18

[](https://www.expedia.ca/Philipsburg-Hotels-The-Castle-G.h121340015.Hotel-Information)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121350000/121340100/121340008/7153b056.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/122000000/121350000/121340100/121340008/659f226a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/122000000/121350000/121340100/121340008/e43a02af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/122000000/121350000/121340100/121340008/d9517569.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Castle ᴶ

[](https://www.expedia.ca/Philipsburg-Hotels-The-Castle-J.h121340008.Hotel-Information)

Downtown Philipsburg

CA $163

CA $204 total

includes taxes & fees

Feb 24 - Feb 25

[](https://www.expedia.ca/Philipsburg-Hotels-The-Castle-J.h121340008.Hotel-Information)

![Beach nearby, white sand, sun loungers, beach umbrellas](https://images.trvl-media.com/lodging/4000000/4000000/3991200/3991146/e9e59cb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![LCD TV, books](https://images.trvl-media.com/lodging/4000000/4000000/3991200/3991146/e4f7011a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 3 Bedrooms | In-room dining](https://images.trvl-media.com/lodging/4000000/4000000/3991200/3991146/b5064e61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/4000000/4000000/3991200/3991146/b00cd486.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Simpson Bay Suites

[](https://www.expedia.ca/Simpson-Bay-Hotels-Simpson-Bay-Suites.h3991146.Hotel-Information)

Simpson Bay

7.0/10

Good

(133 reviews)

"Room was clean. Had a full living room and kitchen incl microwave. Convenient to kim-sha beach. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Dale

CA $230

CA $258 total

includes taxes & fees

Mar 17 - Mar 18

[](https://www.expedia.ca/Simpson-Bay-Hotels-Simpson-Bay-Suites.h3991146.Hotel-Information)

![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/124000000/123640000/123631300/123631240/w906h683x59y0-4f0b4000.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/124000000/123640000/123631300/123631240/9c649cb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/124000000/123640000/123631300/123631240/w905h683x60y0-aa3a6f2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/124000000/123640000/123631300/123631240/fc02d217.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming studio with the beach at your feet & pool access

[](https://www.expedia.ca/Marigot-Hotels-Charming-Studio-With-The-Beach-At-Your-Feet-Pool-Access.h123631240.Hotel-Information)

Marigot

CA $196

CA $233 total

includes taxes & fees

Feb 21 - Feb 22

[](https://www.expedia.ca/Marigot-Hotels-Charming-Studio-With-The-Beach-At-Your-Feet-Pool-Access.h123631240.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/125000000/124520000/124511600/124511587/6a42c3fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels, soap](https://images.trvl-media.com/lodging/125000000/124520000/124511600/124511587/74dc8a9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, internet, bed sheets](https://images.trvl-media.com/lodging/125000000/124520000/124511600/124511587/d421e7fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/125000000/124520000/124511600/124511587/0ce6dcf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Appartement 1 Chambre face a l'ile de Pinel

[](https://www.expedia.ca/Bouvet-Island-Hotels-Appartement-1-Chambre-Face-A-Lile-De-Pinel.h124511587.Hotel-Information)

Cul-de-Sac

CA $103

CA $229 total

includes taxes & fees

Feb 24 - Feb 25

[](https://www.expedia.ca/Bouvet-Island-Hotels-Appartement-1-Chambre-Face-A-Lile-De-Pinel.h124511587.Hotel-Information)

![Deluxe Double Room](https://images.trvl-media.com/lodging/85000000/84060000/84052400/84052377/396a0e49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/85000000/84060000/84052400/84052377/2d70ac82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/85000000/84060000/84052400/84052377/456bc93c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Triple Room](https://images.trvl-media.com/lodging/85000000/84060000/84052400/84052377/b935451f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### July Apartments

[](https://www.expedia.ca/Philipsburg-Hotels-July-Apartments.h84052377.Hotel-Information)

Madame's Estate

9.2/10

Wonderful

(189 reviews)

"Clean rooms and very friendly staff!"

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Christina

CA $110

CA $116 total

includes taxes & fees

Feb 23 - Feb 24

[](https://www.expedia.ca/Philipsburg-Hotels-July-Apartments.h84052377.Hotel-Information)

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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2026-02-28&endDate=2026-03-01&regionId=553248635976384612&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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## Find vacation rentals that suit your style

Private vacation homes

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Villas

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Aparthotels

[](https://www.expedia.ca/Hotel-Search?destination=Upper+Prince%27s+Quarter%2C+Philipsburg%2C+Sint+Maarten&regionId=553248635976384612&latLong=18.032379%2C-63.029476&adults=2&startDate=2026-05-14&d1=2026-05-14&endDate=2026-05-17&d2=2026-05-17&lodging=APART_HOTEL)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Upper+Prince%27s+Quarter%2C+Philipsburg%2C+Sint+Maarten&regionId=553248635976384612&latLong=18.032379%2C-63.029476&adults=2&startDate=2026-05-14&d1=2026-05-14&endDate=2026-05-17&d2=2026-05-17&lodging=APARTMENT)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Upper+Prince%27s+Quarter%2C+Philipsburg%2C+Sint+Maarten&regionId=553248635976384612&latLong=18.032379%2C-63.029476&adults=2&startDate=2026-05-14&d1=2026-05-14&endDate=2026-05-17&d2=2026-05-17&lodging=CONDO)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Upper+Prince%27s+Quarter%2C+Philipsburg%2C+Sint+Maarten&regionId=553248635976384612&latLong=18.032379%2C-63.029476&adults=2&startDate=2026-05-14&d1=2026-05-14&endDate=2026-05-17&d2=2026-05-17&lodging=COTTAGE)

Houseboats

[](https://www.expedia.ca/Hotel-Search?destination=Upper+Prince%27s+Quarter%2C+Philipsburg%2C+Sint+Maarten&regionId=553248635976384612&latLong=18.032379%2C-63.029476&adults=2&startDate=2026-05-14&d1=2026-05-14&endDate=2026-05-17&d2=2026-05-17&lodging=HOUSE_BOAT)

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## Top Upper Prince's Quarter Hotel Reviews

![Hilton Vacation Club Flamingo Beach St. Maarten](https://images.trvl-media.com/lodging/1000000/800000/796500/796441/67b50717_y.jpg)

### Hilton Vacation Club Flamingo Beach St. Maarten

10/10 Excellent

"Everything was great "

[](https://expedia.ca/Simpson-Bay-Hotels-Flamingo-Beach-Resort-By-Diamond-Resorts.h796441.Hotel-Information)

![Princess Heights Luxury Boutique Condo Hotel](https://images.trvl-media.com/lodging/1000000/570000/561400/561365/3eb207bd_y.jpg)

### Princess Heights Luxury Boutique Condo Hotel

10/10 Excellent

"Very nice rooms, pool and workout room. Staff was very nice, friendly and accommodating."

[](https://expedia.ca/Oyster-Pond-Hotels-Princess-Heights-Luxury-Boutique-Condo-Hotel.h561365.Hotel-Information)

![Simpson Bay Resort, Marina & Spa](https://images.trvl-media.com/lodging/2000000/1260000/1256900/1256868/30f27be9_y.jpg)

### Simpson Bay Resort, Marina & Spa

10/10 Excellent

"We will be back"

[](https://expedia.ca/Simpson-Bay-Hotels-Simpson-Bay-Resort.h1256868.Hotel-Information)

![Fourteen at Mullet Bay](https://images.trvl-media.com/lodging/83000000/82870000/82868300/82868222/7de7c76b_y.jpg)

### Fourteen at Mullet Bay

10/10 Excellent

"Room as beautiful, literally steps from everything. Very convenient we didn't rent a car and honestly didn't need to. Concierge Dre and Isael helped with everything you can think of from taxi service to restaurant recommendations & Lets not forget for the excursion booking We definitely will be back."

[](https://expedia.ca/Lowlands-Hotels-Fourteen-At-Mullet-Bay.h82868222.Hotel-Information)

![The Morgan Resort Spa Village](https://images.trvl-media.com/lodging/18000000/17530000/17525000/17524915/bf19cc27_y.jpg)

### The Morgan Resort Spa Village

10/10 Excellent

"Absolutely beautiful resort. Great service, friendly staff. Our 2nd time staying at the resort and we would go there again!"

[](https://expedia.ca/Simpson-Bay-Hotels-The-Morgan-Resort-Spa-Village.h17524915.Hotel-Information)

![Panorama Residences at Monte Vista](https://images.trvl-media.com/lodging/121000000/120450000/120440200/120440175/89140f9f_y.jpg)

### Panorama Residences at Monte Vista

10/10 Excellent

"Like others have stated I was hesitant to book at first with it being a new property and limited reviews but we are glad we did. The whole complex is very modern, secure and as beautiful as the pictures show. The view from the location is amazing. The pool was great and got sun all day, most of the time we had the pool to ourselves. You will definitely want a car as its a 5 minute drive down the hill to any restaurants or stores. Communication could have been better and being a new place there is a lack of kitchen supplies if you are planning to cook in a lot. Overall it was a great stay and we would stay here again."

[](https://expedia.ca/Philipsburg-Hotels-Panorama-Residences-At-Monte-Vista.h120440175.Hotel-Information)

![Oyster Bay Beach Resort](https://images.trvl-media.com/lodging/2000000/1100000/1095400/1095348/00eb22aa_y.jpg)

### Oyster Bay Beach Resort

10/10 Excellent

"The room, the views, the accommodations… it was all super great!"

[](https://expedia.ca/Oyster-Pond-Hotels-Oyster-Bay-Beach-Resort.h1095348.Hotel-Information)

![Sonesta Maho Beach All Inclusive Resort Casino & Spa](https://images.trvl-media.com/lodging/1000000/570000/565700/565666/45414036_y.jpg)

### Sonesta Maho Beach All Inclusive Resort Casino & Spa

10/10 Excellent

"We were a family of four visiting for the first time. The resort was clean, the staff was very accommodating. Few things we noticed not a whole lot of an activities at night. Wish the pool wouldn’t close so early 6:00 pm. Overall, we would stay again. The location was great for watching the planes."

[](https://expedia.ca/Lowlands-Hotels-Sonesta-Maho-Beach-All-Inclusive-Resort-Casino-Spa.h565666.Hotel-Information)

![Luxury Villa, Walk to beach, BRAND NEW 55KW BACKUP GENERATOR](https://images.trvl-media.com/lodging/39000000/38360000/38358600/38358580/6e794716_y.jpg)

### Luxury Villa, Walk to beach, BRAND NEW 55KW BACKUP GENERATOR

10/10 Excellent

"Villa Fantome was amazing! Our group of 9 had a fantastic stay. There were great personal touches, like sending someone to meet us at the airport and guide us to the villa, special welcome gifts, and attentive service from the always available house manager Nataesha. The house was absolutely spotless, and the housekeeping team was great. They serviced the house twice during our week-long stay. The villa provided a useful guide for places to visit and restaurant recommendations all around the island. The careful renovations that were completed at this villa were well done. They also recommended caterers and we enjoyed 3 different chef-catered meals- a grazing table/ appetizers meal, a plated served dinner party and a brunch feast. While we had hope to dine outside, we happened to catch a windy week and we were happier taking meals indoors, which worked out great. We also had the recommended Steel Pan Drum musician and that was a highlight of the trip! So much fun! It was so helpful to have a set of vetted vendors so we didn't have to sort through the options on our own. Gabi the owner was always super helpful by email as well. Special shout out to the Lilly Pulitzer home accents- loved it! Seriously- no complaints about this place. You'll need to know there are stairs to get to the pool level, the studio suite if using, and the upstairs primary suite. The kitchen was equipped with everything we needed and more. "

[](https://expedia.ca/Oyster-Pond-Hotels-Luxury-Villa.h38358580.Hotel-Information)

## Price trends for vacation rentals in Upper Prince's Quarter

| Less expensive | More expensive | This month | Next month |
| -------------- | -------------- | ---------- | ---------- |
| July           | February       | CA $837    | CA $545    |

| Month     | Price   |
| --------- | ------- |
| January   | CA $542 |
| February  | CA $837 |
| March     | CA $545 |
| April     | CA $539 |
| May       | CA $440 |
| June      | CA $440 |
| July      | CA $436 |
| August    | CA $437 |
| September | CA $439 |
| October   | CA $446 |
| November  | CA $518 |
| December  | CA $609 |

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

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.   

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## Frequently asked questions

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