Upper Prince's Quarter Vacation Rentals

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Check prices for these dates

In two weeks
Jun 5 - Jun 7
In two months
Jul 17 - Jul 19
In three months
Aug 14 - Aug 16
In four months
Sep 11 - Sep 13

Our top choices for Upper Prince's Quarter vacation rentals

Exterior

Singh Luxury Apartments With sea View, Apt.2

Singh Luxury Apartments With sea View, Apt.2
3.5 star property
Oyster Pond
$392 nightly
The price is $409
Jun 6 - Jun 7
Total with taxes and fees
Singh Luxury Apartments With sea View, Apt.2
Outdoor pool

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
$655 nightly
The price is $687
May 29 - May 30
Total with taxes and fees
Dawn Beach Club Resort Sint Maarten
Pool

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
$126 nightly
The price is $130
May 31 - Jun 1
Total with taxes and fees
Lovely Studio Apartment with Pool & Nature Views!
Terrace/patio

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)
$4,373 nightly
The price is $4,373
May 25 - May 26
Total with taxes and fees
Villa de 10 Chambres les Pieds Dans L'eau à Guana Bay
Outdoor dining

1-Bedroom Loft Apartment in Point Blanche

1-Bedroom Loft Apartment in Point Blanche
Point Blanche
$187 nightly
The price is $194
May 28 - May 29
Total with taxes and fees
1-Bedroom Loft Apartment in Point Blanche
Outdoor pool

Luxurious Waterfront Townhome @ CORAL BEACH CLUB

Luxurious Waterfront Townhome @ CORAL BEACH CLUB
Oyster Pond
$472 nightly
The price is $494
May 25 - May 26
Total with taxes and fees
Luxurious Waterfront Townhome @ CORAL BEACH CLUB
Beach

Singh Luxury Apartments With sea View, Apt.1

Singh Luxury Apartments With sea View, Apt.1
3.0 star property
Oyster Pond
$392 nightly
The price is $409
Jun 6 - Jun 7
Total with taxes and fees
Singh Luxury Apartments With sea View, Apt.1
Beach

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)
$743 nightly
The price is $779
May 25 - May 26
Total with taxes and fees
Singh Luxury Apartments With sea View, Apt.3
Interior

Your half-day cruise with scenic Zephyr and water activities

Your half-day cruise with scenic Zephyr and water activities
Collectivité de Saint-Martin
$1,668 nightly
The price is $1,668
Jun 7 - Jun 8
Total with taxes and fees
Your half-day cruise with scenic Zephyr and water activities
Outdoor dining

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

UNIQUE EXPERIENCE: OVERNIGHT ON A CATAMARAN WITH DINNER AND BREAKFAST INCLUDED
Grand-Case
$994 nightly
The price is $1,029
Jun 7 - Jun 8
Total with taxes and fees
UNIQUE EXPERIENCE: OVERNIGHT ON A CATAMARAN WITH DINNER AND BREAKFAST INCLUDED
Outdoor dining

Unusual night in catamaran with dinner

Unusual night in catamaran with dinner
Grand-Case
$1,171 nightly
The price is $1,171
Jun 7 - Jun 8
Total with taxes and fees
Unusual night in catamaran with dinner
Deluxe Apartment, Courtyard View | Blackout drapes, free WiFi

Philips Scott House Calinago

Philips Scott House Calinago
3.0 star property
Downtown Philipsburg
$212 nightly
The price is $222
May 30 - May 31
Total with taxes and fees
Philips Scott House Calinago
Beach nearby, sun loungers, beach towels

Charming studio with the beach at your feet & pool access

Charming studio with the beach at your feet & pool access
Marigot
10.0 out of 10, Exceptional, (2 reviews)
"Everything was great"
Canada
Brad W.
$176 nightly
The price is $181
May 31 - Jun 1
Total with taxes and fees
Charming studio with the beach at your feet & pool access
On the beach, sun loungers, beach towels

Charming studio with splendid Caribbean Sea view & pool/beach access

Charming studio with splendid Caribbean Sea view & pool/beach access
Marigot
9.0 out of 10, Wonderful, (2 reviews)
"Beautiful view and the host was very welcoming."
United States
Dasha A.
$193 nightly
The price is $198
May 25 - May 26
Total with taxes and fees
Charming studio with splendid Caribbean Sea view & pool/beach access
Outdoor pool

condostmaarten by the sea -Adults Only-

condostmaarten by the sea -Adults Only-
4.0 star property
Indigo Bay
9.2 out of 10, Wonderful, (40 reviews)
"We loved everything about this spot and the staff. We will definitely stay here again. The property is very clean, safe and comfortable."
Canada
Rozana
$328 nightly
The price is $343
Jun 2 - Jun 3
Total with taxes and fees
condostmaarten by the sea -Adults Only-
Terrace/patio

Hillside Penthouse

Hillside Penthouse
South Reward
10.0 out of 10, Exceptional, (3 reviews)
"The host was very welcoming and kind. The apartment was very clean, it has very large bedrooms, kitchen and living room space. I will definitely book this place again on my next trip to St. Maarten. "
Canada
Diana M.
$256 nightly
The price is $256
May 27 - May 28
Total with taxes and fees
Hillside Penthouse
Comfort Room, 1 King Bed, Non Smoking, Ocean View | Iron/ironing board, free WiFi

MIDTOWN MOTEL SXM

MIDTOWN MOTEL SXM
2.5 star property
Downtown Philipsburg
7.4 out of 10, Good, (61 reviews)
"Good rooms at a great location"
United States
Asheed
$80 nightly
The price is $84
Jun 4 - Jun 5
Total with taxes and fees
MIDTOWN MOTEL SXM
On the beach, sun loungers, beach towels

Beachside Retreat: Balcony, Pools, and Direct Ocean Access and Peloton!

Beachside Retreat: Balcony, Pools, and Direct Ocean Access and Peloton!
Maho
$461 nightly
The price is $461
May 25 - May 26
Total with taxes and fees
Beachside Retreat: Balcony, Pools, and Direct Ocean Access and Peloton!
Outdoor dining

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

Lovely room in a nice villa , close to Friars bay and happy bay
Saint-martin
9.0 out of 10, Wonderful, (11 reviews)
"Great place to stay. Will definitely be staying again next year! "
United States
Kurt
$96 nightly
The price is $96
May 26 - May 27
Total with taxes and fees
Lovely room in a nice villa , close to Friars bay and happy bay
On the beach, sun loungers, beach towels

Oceanfront Paradise: Luxurious Penthouse with Spectacular Pools and Peloton

Oceanfront Paradise: Luxurious Penthouse with Spectacular Pools and Peloton
Maho
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful space, great location, communicative host. Would definitely recommend and would love to stay again. "
United States
Kara K.
$436 nightly
The price is $436
May 25 - May 26
Total with taxes and fees
Oceanfront Paradise: Luxurious Penthouse with Spectacular Pools and Peloton
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

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

10/10 Excellent
"Really enjoyed my stay at the villas. The beach is beautiful, really nice views. Walking distance to stores and restaurants."
Alena 3-night trip
Posted 4 hours ago
The Villas at Simpson Bay Resort

Price trends for vacation rentals in Upper Prince's Quarter

Less expensive
More expensive
Next month
February
April
$508
Month
Price
January
$578
February
$467
March
$491
April
$752
May
$599
June
$508
July
$530
August
$638
September
$542
October
$624
November
$645
December
$714
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 $82 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?

Philips Scott House Calinago: This vacation home rental outside Upper Prince's Quarter is in a shopping district and equipped with air-conditioning and WiFi to help you feel perfectly comfortable in your new surroundings. Amenities like a microwave and free parking are also available for your convenience. Some other homes for rent in Upper Prince's Quarter include LUXURY VILLA! HIGHEST GUEST RATINGS ON ISLAND! DISCOUNTED SUMMER RATES! and Villa Flagrantia, Paradise at your pleasure.

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

Choose from 30 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 are a couple of lovely local spots to get outside and enjoy nature. While here, Oyster Bay Marina and Front Street District 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.