Upper Prince's Quarter Holiday Rentals

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Check prices for these dates

In two weeks
12 Sept - 14 Sept
In one month
26 Sept - 28 Sept
In two months
24 Oct - 26 Oct
In three months
21 Nov - 23 Nov

Holiday Rentals in Upper Prince's Quarter

Dawn Beach Club Resort Sint Maarten
Sundeck

Dawn Beach Club Resort Sint Maarten

4.0 star property
8.8 out of 10, Excellent, (21)
"Wonderful vacation spot in st maarten"
Dawn Beach Club Resort Sint Maarten
Luxury Villa, Walk to beach, BRAND NEW 55KW BACKUP GENERATOR
On the beach, sun-loungers, beach towels

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

10.0 out of 10, Exceptional, (104)
"The property was perfect for our family of five, my parents and a sister. Beautiful property!"
Luxury Villa, Walk to beach, BRAND NEW 55KW BACKUP GENERATOR
LUXURY VILLA! Resort Amenities, Stunning Views, Beach Access! GENERATOR
Interior

LUXURY VILLA! Resort Amenities, Stunning Views, Beach Access! GENERATOR

10.0 out of 10, Exceptional, (151)
"We LOVED our stay at this beautiful estate. We will definitely be back. "
LUXURY VILLA! Resort Amenities, Stunning Views, Beach Access! GENERATOR
LITERALLY OCEANFRONT VILLA ALABASTER, DAWN BEACH w private pool ~ Owners' site
Outdoor pool

LITERALLY OCEANFRONT VILLA ALABASTER, DAWN BEACH w private pool ~ Owners' site

9.8 out of 10, Exceptional, (90)
"Location was wonderful, beach was beautiful, everyone was lovely. "
LITERALLY OCEANFRONT VILLA ALABASTER, DAWN BEACH w private pool ~ Owners' site
Direct Beachfront 6 BDR/en-suite /maid included. Excellent service. Rare gem (J)
Outdoor dining

Direct Beachfront 6 BDR/en-suite /maid included. Excellent service. Rare gem (J)

10.0 out of 10, Exceptional, (3)
"Beautiful property and location. Chris was awesome and very attentive to our needs. "
Direct Beachfront 6 BDR/en-suite /maid included. Excellent service. Rare gem (J)
FantaSea beachfront, every bedroom facing ocean! Remodeled 2024
Property grounds

FantaSea beachfront, every bedroom facing ocean! Remodeled 2024

9.8 out of 10, Exceptional, (61)
"The place was amazing and had everything we needed. It was very quiet here and was great for relaxing. Our family enjoyed this location very much. "
FantaSea beachfront, every bedroom facing ocean! Remodeled 2024
Direct Beachfront 6 BDR/en-suite /maid included. Excellent service. Rare gem (O)
Outdoor pool

Direct Beachfront 6 BDR/en-suite /maid included. Excellent service. Rare gem (O)

10.0 out of 10, Exceptional, (23)
"The property is Wonderfull. Plenty of space, The Pool Beautiful, and convince to the beach is great. Chris the property manager was very easy to work with and gave great advice for places to go and Things to do!!!"
Direct Beachfront 6 BDR/en-suite /maid included. Excellent service. Rare gem (O)
Luxury Villa w Spectacular Ocean Views, private pool/Hottub, Walk to Beach
Outdoor pool

Luxury Villa w Spectacular Ocean Views, private pool/Hottub, Walk to Beach

10.0 out of 10, Exceptional, (134)
"Had a wonderful experience at the villa with beautiful scenery and plenty of entertainment for all ages in our family. "
Luxury Villa w Spectacular Ocean Views, private pool/Hottub, Walk to Beach
Cozy one-bedroom & mezzanine apartment
Standard Apartment, 2 Bedrooms | Balcony

Cozy one-bedroom & mezzanine apartment

3.0 star property
9.6 out of 10, Exceptional, (18)
"The host was incredibly communicative throughout our entire stay, from pre-arrival to departure. The location was perfect, with supermarkets and shopping centers nearby, and just a 12-minute walk to the town center. The apartment was beautifully presented, featuring a lovely shared pool and equipped with everything we needed. We'll definitely be staying here again on our next visit. "
Cozy one-bedroom & mezzanine apartment
Villa Angelina with Amazing Panoramic Views. Enjoy the quiet at Oyster Pond
Pool

Villa Angelina with Amazing Panoramic Views. Enjoy the quiet at Oyster Pond

9.6 out of 10, Exceptional, (55)
"This house has the best views on the island, without question! My wife and I personally loved this house. We felt like we were at our own home, that was relocated to paradise! The management company is extremely attentive and informative. I would stay here again anytime we are able to visit the island! Thoroughly enjoyed this house, location, and the wonderful staff!"
Villa Angelina with Amazing Panoramic Views. Enjoy the quiet at Oyster Pond
Alizee by Island Properties Online
Outdoor dining

Alizee by Island Properties Online

3.5 star property
Alizee by Island Properties Online
Villa de 10 Chambres les Pieds Dans L'eau à Guana Bay
Pool

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

The price is AU$6,777
includes taxes & fees
1 Sept - 2 Sept
Villa de 10 Chambres les Pieds Dans L'eau à Guana Bay
Gorgeous ocean views! Spend your days in pure bliss at a perfect paradise!
Pool

Gorgeous ocean views! Spend your days in pure bliss at a perfect paradise!

10.0 out of 10, Exceptional, (172)
"We stayed at the Jewel for a week with 4 adults and 4 young kids. We had the best time, if not for the adults wanting to explore the island the kids would have been fine swimming and hanging out at the house. The view is incredible, the house provides everything you could need, and Ursula was so kind making us a meal for the evening we arrived, pina coladas, muffins for the kids. We will only stay at the Jewel when we return. "
Gorgeous ocean views! Spend your days in pure bliss at a perfect paradise!
Singh Luxury Apartments With sea View, Apt.3
Beach

Singh Luxury Apartments With sea View, Apt.3

3.0 star property
2.0 out of 10, (1)
The price is AU$1,255
includes taxes & fees
31 Aug - 1 Sept
Singh Luxury Apartments With sea View, Apt.3
Direct Beachfront 6 BDR/en-suite /maid included. Excellent service. Rare gem (H)
Outdoor pool

Direct Beachfront 6 BDR/en-suite /maid included. Excellent service. Rare gem (H)

10.0 out of 10, Exceptional, (22)
"We were more than pleased with our stay at Villa Hibiscus! This was our first trip to Sint Maarten and we could not have picked a better spot. The host, Chris, was very accommodating and helpful during our stay. He made the whole process of arrival and departure so easy and was available to help throughout our entire vacation! We hope to return again and stay at Villa Hibiscus!"
Direct Beachfront 6 BDR/en-suite /maid included. Excellent service. Rare gem (H)
The Waves; Oceanfront 2 Bedroom. Gorgeous Sunrises. Relax With The Wave Rythyms
Dining

The Waves; Oceanfront 2 Bedroom. Gorgeous Sunrises. Relax With The Wave Rythyms

9.0 out of 10, Wonderful, (18)
"Interesting stay. The ambiance of the waves outside was amazing. But we had a few other problems while staying there...including bathroom doors that wouldn't close (half our stay), leaks in the kitchen and bedroom, and some bugs upon arrival. Otherwise, nice stay next to a secluded beach."
The Waves; Oceanfront 2 Bedroom. Gorgeous Sunrises. Relax With The Wave Rythyms
Singh Luxury Apartments With sea View, Apt.2
Outdoor pool

Singh Luxury Apartments With sea View, Apt.2

3.5 star property
The price is AU$633
includes taxes & fees
31 Aug - 1 Sept
Singh Luxury Apartments With sea View, Apt.2
Fourteen at Mullet Bay
Deluxe Condo, 1 Bedroom, Balcony, Beach View | Terrace/patio

Fourteen at Mullet Bay

3.5 star property
9.2 out of 10, Wonderful, (338)
"Great location "
Fourteen at Mullet Bay
Hilton Vacation Club Royal Palm St. Maarten
Outdoor pool, pool loungers

Hilton Vacation Club Royal Palm St. Maarten

4.0 star property
9.0 out of 10, Wonderful, (1102)
"Most convenient hotel to stay, due to an array of shopping and dinning options near the property."
The price is AU$200
includes taxes & fees
21 Sept - 22 Sept
Hilton Vacation Club Royal Palm St. Maarten
The Hills Residence
Amazing Top Floor Apartment | Balcony

The Hills Residence

3.0 star property
9.0 out of 10, Wonderful, (40)
"Love the view first of all. Property was in a great location. "
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

Find out more about Upper Prince's Quarter

Find out more about Upper Prince's Quarter

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

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

Upper Prince's Quarter holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Upper Prince's Quarter holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Upper Prince's Quarter holiday rentals we have selected for you start as low as AU$200 per night. Entering your travel dates in the search wizard might find you even better deals!

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

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

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 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. Some other homes for rent in Upper Prince's Quarter include LUXURY VILLA! Resort Amenities, Stunning Views, Beach Access! GENERATOR and DawnBeach Club 4 Bed/4Bath Villa With Swimming Pool, Beach and Resorts Access. .

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

Choose from 30 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, Oyster Bay Marina and Guana Bay 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.