Upper Prince's Quarter Holiday Rentals

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Holiday Rentals in Upper Prince's Quarter

Dawn Beach Club Resort Sint Maarten
Sundeck
Dawn Beach Club Resort Sint Maarten
4.0 star property
8.6 out of 10, Excellent, (14)
"Nice property, but far away from the airport and party area"
The price is NZ$1,219
includes taxes & fees
17 Jun - 18 Jun
Dawn Beach Club Resort Sint Maarten
LITERALLY OCEANFRONT VILLA ALABASTER, DAWN BEACH w private pool ~ Owners' site
Outdoor pool
LITERALLY OCEANFRONT VILLA ALABASTER, DAWN BEACH w private pool ~ Owners' site
10.0 out of 10, Exceptional, (67)
"From the moment we walked out of the airport everything was amazing. The resort had transportation waiting for us. There was no real check-in like most resorts, the taxi driver walked us right to our villa and vacation began. On this trip we chose not to rent a car so we hired Claudette Fritz to take us everywhere we wanted to go which was much cheaper than car rental. The house was amazing to say the least. The pool was very well kept and only a couple steps from the beautiful white sand. We...
LITERALLY OCEANFRONT VILLA ALABASTER, DAWN BEACH w private pool ~ Owners' site
FantaSea beachfront, Survived the hurricane, low low prices take advantage!
Beach/ocean view
FantaSea beachfront, Survived the hurricane, low low prices take advantage!
10.0 out of 10, Exceptional, (53)
"This stay was a mixed bag for our group of 4 kids aged 6-15 and 5 adults. Our check in process was not smooth but the owner was apologetic and tried to make it right. And I feel for the owners because I am sure the issues are not so much neglect as not completing repairs after the hurricane. Still, the pictures do not reflect the current state of the home. It feels warn down. Pros The house is spacious with room for a big group. Direct beach access is a great feature. Views from the house and...
FantaSea beachfront, Survived the hurricane, low low prices take advantage!
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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, (116)
"We stayed at Villa Valhalla with our 3 teenage kids and another family of 4. The house was beautiful, clean, well stocked with stunning views! Plenty of room for us all. It’s located in a safe and quiet neighborhood overlooking Dawn Beach. Everything was as stated from the website, except the kitchen has been updated and looks great. We had excellent communication before and during the trip. We were able to walk to the beach, and had dinner at the new JW Marriott. It was nice to have a close...
Luxury Villa w Spectacular Ocean Views, private pool/Hottub, Walk to Beach
The Waves; Oceanfront 2 Bedroom. Gorgeous Sunrises. Relax With The Wave Rythyms
Beach/ocean view
The Waves; Oceanfront 2 Bedroom. Gorgeous Sunrises. Relax With The Wave Rythyms
8.8 out of 10, Excellent, (15)
"On the water quiet area. Close to the main areas we wanted. Went out every day hit the places we wanted and only took a half a tank of gas for the week. Frank was great with any question."
The Waves; Oceanfront 2 Bedroom. Gorgeous Sunrises. Relax With The Wave Rythyms
Direct on the beach/6 BDR/en-suite /maid included. Excellent service. Rare gem.
Outdoor pool
Direct on the beach/6 BDR/en-suite /maid included. Excellent service. Rare gem.
10.0 out of 10, Exceptional, (17)
"We were traveling with three families ages 9 to 63. Property is in an extremely secure and beautiful area. Our host Chris exceeded all of our expectations, and the staff was very friendly and attentive to our needs. The beach is beautiful and we had it to ourselves most days. A car is recommended to see the island and facilitate provisioning and adventuring. House is secluded away from the hustle and bustle of the port. All of our questions, and needs were quickly attended to. The kitchen is...
Direct on the beach/6 BDR/en-suite /maid included. Excellent service. Rare gem.
Oceanfront 2 Bedroom Villa in Guana Bay Sint Maarten; Ocnfrt Deck
Outdoor dining
Oceanfront 2 Bedroom Villa in Guana Bay Sint Maarten; Ocnfrt Deck
9.4 out of 10, Exceptional, (29)
"Casa Leone is a little private paradise. The view of St. Barts and Guana bay are the best. The property is very private even though your neighbors and the pool are only a few steps away. The accommodations are not perfect having weathered numerous hurricanes and the relentless wind and tide, but they are well cared for and perfectly functional. We appreciated the brand new A/C units, dual bathrooms, and an additional bedroom suit that would easily accommodate another couple or a small family if...
Oceanfront 2 Bedroom Villa in Guana Bay Sint Maarten; Ocnfrt Deck
Sea-Renity
Family Apartment | Private kitchen
Sea-Renity
3.0 star property
2.0 out of 10, (1)
Sea-Renity
Fourteen at Mullet Bay
Deluxe Condo, 1 Bedroom, Balcony, Beach View | Terrace/patio
Fourteen at Mullet Bay
3.5 star property
9.6 out of 10, Exceptional, (126)
"Definitely will be returning. "
Fourteen at Mullet Bay
July Apartments
Front of property
July Apartments
3.0 star property
9.2 out of 10, Wonderful, (73)
"Probably one of the easiest parking on the island! Front desk staff is always present and very helpful and friendly. Easy to get to and a nice, clean stay."
The price is NZ$131
includes taxes & fees
21 Jun - 22 Jun
July Apartments
Villa Little Paradise - BIG DISCOUNT MARCH - APRIL !!
Sun-loungers, beach towels
Villa Little Paradise - BIG DISCOUNT MARCH - APRIL !!
10.0 out of 10, Exceptional, (8)
"The house was just as listed and the area was perfect. We enjoyed our stay and would recommend and will return!"
Villa Little Paradise - BIG DISCOUNT MARCH - APRIL !!
The Horny Toad Guesthouse
Orchid | View from room
The Horny Toad Guesthouse
3.0 star property
9.4 out of 10, Exceptional, (51)
"Deb & Doug are accommodating and great to talk to to get ideas of things to do. Perfect place to stay!"
The price is NZ$359
includes taxes & fees
7 Jun - 8 Jun
The Horny Toad Guesthouse
The Hotel Porto Cupecoy
Beach nearby, white sand, sun-loungers, beach umbrellas
The Hotel Porto Cupecoy
3.5 star property
9.6 out of 10, Exceptional, (31)
"Great and safe property. Big rooms"
The price is NZ$871
includes taxes & fees
7 Jun - 8 Jun
The Hotel Porto Cupecoy
Villa Bahia Blue - Four Bedroom Villa, Sleeps 8
Pool
Villa Bahia Blue - Four Bedroom Villa, Sleeps 8
10.0 out of 10, Exceptional, (12)
"2 familes each with 2 kids had a great time. Very close to baie rouge. Pool was nice. Hot tub water seemed bad so we didnt use it. Housekeeper and concierge were really nice. Rented a car and drove all over the small island. Would recommend and would stay again"
Villa Bahia Blue - Four Bedroom Villa, Sleeps 8
Tradewinds at Simpson Bay
Exterior
Tradewinds at Simpson Bay
3.5 star property
8.6 out of 10, Excellent, (10)
"The room was spacious and spotless . The staff were attentive and went out of their way to ensure that we were comfortable. Nothing was too much trouble.Will be back excellent stay "
Tradewinds at Simpson Bay
One Hundred Million Dollar Yacht On Land 5 star Villa Namaste
Outdoor pool, an infinity pool
One Hundred Million Dollar Yacht On Land 5 star Villa Namaste
10.0 out of 10, Exceptional, (66)
""We had an incredible stay at Villa Namaste! The property is gorgeous, with every room beautifully appointed. The view from the patio is breathtaking—worth every penny. Sitting in the infinity edge pool, looking out over the bluest Caribbean waters while watching mega yachts sail by, was a highlight of our days. The villa is also conveniently located close to many cool restaurants, some even within walking distance, which was perfect for our evenings out. The staff, particularly Olive and...
One Hundred Million Dollar Yacht On Land 5 star Villa Namaste
Simpson Bay Suites
Beach nearby, white sand, sun-loungers, beach umbrellas
Simpson Bay Suites
3.5 star property
6.8 out of 10, (100)
"Convenient location with the requisite amenities for local stay and business. Water pressure could be improved. Though clean and tidy furniture could be modernized. "
The price is NZ$220
includes taxes & fees
9 Jun - 10 Jun
Simpson Bay Suites
Beachfront villa with pool in Cul de Sac
Property grounds
Beachfront villa with pool in Cul de Sac
9.8 out of 10, Exceptional, (60)
"We lucked out on selecting this place since we've never been. The french side is the place to stay. The airport, the cruise ships and all the tourist shops are on the dutch side ands its packed all the time. On the french side its beautiful, less touristy an A"
Beachfront villa with pool in Cul de Sac
Beautiful Ocean Front Penthouse/New Furnishings/Stunning View/Private Beach!
Beach
Beautiful Ocean Front Penthouse/New Furnishings/Stunning View/Private Beach!
10.0 out of 10, Exceptional, (66)
"This was our first time in St. Martin. I fell in love with the pictures of this unit. The pictures cannot capture how wonderful this place is. The unit was spotless. The beds were very comfortable. But the VIEW!!!! Oh my gosh!!! The view from the balcony and the private terrace cannot be described!!!! Absolutely breathtaking!!!! The pools were fantastic. Our own private beach! Communication with Susan, the owner, was immediate. She also was so helpful in suggesting places for us to eat and...
Beautiful Ocean Front Penthouse/New Furnishings/Stunning View/Private Beach!
Perfect beach front condo in Simpson Bay Beach🌴 2 bedroom+ Loft, 2.5 Baths.
Beach
Perfect beach front condo in Simpson Bay Beach🌴 2 bedroom+ Loft, 2.5 Baths.
10.0 out of 10, Exceptional, (24)
"Our family of 5 (2-10yr old boys, 1-14yr old girl) were very pleased with the condo. The location was prime in Simpson Bay. Within walking distance to a few beach bars and walked over to Maho Beach too a few times. The pool was nice (warm) and had plenty of seating, always a few seats available. There are beach chairs, toys on the porch along with a beach umbrella. The kitchen was well equipped and left us not needing anything. Bath linens could use a refresh but was sufficient. The only...
Perfect beach front condo in Simpson Bay Beach🌴 2 bedroom+ Loft, 2.5 Baths.
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See all available properties in Upper Prince's Quarter
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.

Other types of properties in Upper Prince's Quarter you may be interested in

JW Marriott St. Maarten Beach Resort & Spa
Outdoor pool, pool cabanas (surcharge), pool umbrellas
JW Marriott St. Maarten Beach Resort & Spa
5.0 star property
9.0 out of 10, Wonderful, (36)
"The pool area is fantastic! Beautiful layout and pool. The door staff were extremely friendly and the rooms were kept tidy. The smoke alarm going off twice in the night I could definitely do without. Not sure it's worthy of the JW rating, it doesn't have the flare of a JW, maybe more of a regular Marriott."
The price is NZ$513
includes taxes & fees
11 Jun - 12 Jun
JW Marriott St. Maarten Beach Resort & Spa
Oyster Bay Beach Resort
Outdoor pool, pool umbrellas, pool loungers
Oyster Bay Beach Resort
4.0 star property
8.4 out of 10, Very good, (734)
"Need more options in menu restaurants"
The price is NZ$312
includes taxes & fees
7 Jun - 8 Jun
Oyster Bay Beach Resort
Princess Heights Luxury Boutique Condo Hotel
Outdoor pool, pool umbrellas, pool loungers
Princess Heights Luxury Boutique Condo Hotel
3.5 star property
9.2 out of 10, Wonderful, (784)
"Great place to stay. Clean, quiet, great view. We had a large studio with a kitchenette. It was perfect. Nice large bathroom too. We were there during shoulder season and the price was fantastic. The pool is huge and was very clean. We pretty much had it to ourselves. It's a few flights of stairs down to the pool, or you can drive. A flight of stairs down from the office and a short walk around the JW Marriott and you're at the beach. I would say you probably want to rent a car as most things...
The price is NZ$268
includes taxes & fees
12 Jun - 13 Jun
Princess Heights Luxury Boutique Condo Hotel
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Upper Prince's Quarter holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Upper Prince's Quarter. 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 Upper Prince's Quarter. 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 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 holiday 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 Upper Prince's Quarter short-term rentals, that won’t be hard to do.

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.

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

Choose from 33 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.

Recent reviews of Upper Prince's Quarter properties
Expedia verified reviews

Oyster Bay Beach Resort

Oyster Bay Beach Resort

5/5 Excellent
"Best birthday vacation ever "
A verified traveller stayed at Oyster Bay Beach Resort
Posted 6 days ago
Oyster Bay Beach Resort