Simpson Bay Vacation Rentals

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Our top choices for Simpson Bay vacation rentals

The Hills Residence

The Hills Residence
3.0 star property
Simpson Bay
8.6 out of 10, Excellent, (100 reviews)
"Clean rooms, amazing views, and responsive staff! Will be staying again next time. "
United States
Nicole
The price is CA $214
CA $380 total
includes taxes & fees
Apr 5 - Apr 6
The Hills Residence

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, (1,196 reviews)
"Went for a family vacation, everything was so convenient pool beach, shopping restaurants cabs easy to get to visit anywhere to visit we loved it ."
United States
Cynthia
The price is CA $532
CA $595 total
includes taxes & fees
Apr 3 - Apr 4
Hilton Vacation Club Royal Palm St. Maarten

Simpson Bay Suites

Simpson Bay Suites
3.5 star property
Simpson Bay
7.0 out of 10, Good, (150 reviews)
"Room was great and also the staff"
United States
Shevlin
The price is CA $235
CA $263 total
includes taxes & fees
Apr 6 - Apr 7
Simpson Bay Suites

The Forest

The Forest
4.0 star property
Anse Marcel
10.0 out of 10, Exceptional, (24 reviews)
"We had very peaceful and relaxed vacation Staff extremely caring and accommodating Karaoke night with fun and beautiful singing Clean and comfortable rooms, beautiful vegetation all around Location is close to Anse Marcel beach and Casa Grande restaurants for dinner - car is needed"
United States
Artur
The price is CA $486
CA $507 total
includes taxes & fees
Mar 31 - Apr 1
The Forest

Philips Scott House Calinago

Philips Scott House Calinago
3.0 star property
Downtown Philipsburg
The price is CA $236
CA $353 total
includes taxes & fees
Mar 30 - Mar 31
Philips Scott House Calinago

Dawn Beach Club Resort Sint Maarten

Dawn Beach Club Resort Sint Maarten
4.0 star property
Oyster Pond
8.8 out of 10, Excellent, (32 reviews)
"Large rooms with great ocean views! Helpful staff and good beach access!"
United States
Gavin
The price is CA $869
CA $1,069 total
includes taxes & fees
Apr 4 - Apr 5
Dawn Beach Club Resort Sint Maarten

condostmaarten by the sea -Adults Only-

condostmaarten by the sea -Adults Only-
4.0 star property
Indigo Bay
9.0 out of 10, Wonderful, (34 reviews)
"Everything was so perfect from the parking to the view, the staff was very welcoming and professional overall i will definitely stay here again. "
United States
Rose
The price is CA $420
CA $621 total
includes taxes & fees
Apr 16 - Apr 17
condostmaarten by the sea -Adults Only-

Avenue du lagon

Avenue du lagon
Oyster Pond
The price is CA $2,014
CA $2,720 total
includes taxes & fees
Apr 2 - Apr 3
Avenue du lagon

Mullet Bay Suites: Your Luxury Stay Awaits

Mullet Bay Suites: Your Luxury Stay Awaits
4.0 star property
Maho
9.8 out of 10, Exceptional, (140 reviews)
"Beautiful view. Pool was lovely.great atmosphere love the place.."
United States
Rene
The price is CA $296
CA $434 total
includes taxes & fees
Apr 9 - Apr 10
Mullet Bay Suites: Your Luxury Stay Awaits

Singh Luxury Apartments With sea View, Apt.2

Singh Luxury Apartments With sea View, Apt.2
3.5 star property
Oyster Pond
The price is CA $449
CA $575 total
includes taxes & fees
Apr 25 - Apr 26
Singh Luxury Apartments With sea View, Apt.2

MIDTOWN MOTEL SXM

MIDTOWN MOTEL SXM
2.5 star property
Downtown Philipsburg
7.0 out of 10, Good, (47 reviews)
"Good rooms at a great location"
United States
Asheed
The price is CA $115
CA $142 total
includes taxes & fees
Apr 6 - Apr 7
MIDTOWN MOTEL SXM

July Apartments

July Apartments
3.0 star property
Madame's Estate
9.2 out of 10, Wonderful, (219 reviews)
"Friendly and helpful staff, very clean environment. You get value for your money, I'll definitely stay there again 💯 "
United States
Irma
The price is CA $113
CA $118 total
includes taxes & fees
Apr 4 - Apr 5
July Apartments

Singh Luxury Apartments With sea View, Apt.1

Singh Luxury Apartments With sea View, Apt.1
3.0 star property
Oyster Pond
The price is CA $449
CA $575 total
includes taxes & fees
Apr 25 - Apr 26
Singh Luxury Apartments With sea View, Apt.1

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)
The price is CA $948
CA $1,102 total
includes taxes & fees
Apr 26 - Apr 27
Singh Luxury Apartments With sea View, Apt.3
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 Simpson Bay Hotel Reviews

Price trends for vacation rentals in Simpson Bay

Less expensive
More expensive
Next month
September
January
CA $315
Month
Price
January
CA $516
February
CA $472
March
CA $457
April
CA $315
May
CA $261
June
CA $252
July
CA $240
August
CA $224
September
CA $200
October
CA $283
November
CA $295
December
CA $485
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 Simpson Bay. Select dates and complete search for nightly totals inclusive of taxes and fees.

Find out more about Simpson Bay

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 Simpson Bay. 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.

Frequently asked questions

Can I find a vacation rental in Simpson Bay?

Yes, we give you a choice of vacation rentals near top attractions in Simpson Bay, or you can choose a secluded option if you'd like a relaxing place to stay. Visitors like the array of shops and popular beaches in Simpson Bay. While you're here, grab a bite or have a drink at the top-notch restaurants and lively bars.

What are some of the best vacation home rentals that Simpson Bay has to offer?

Philips Scott House Calinago: This vacation home rental outside Simpson Bay 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 Simpson Bay include White Sands Retreat - Beachside at Beacon Hill and Dream Beachfront Home : Stunning sea views, private pool and walking distance .

How many vacation rentals are there in Simpson Bay?

With 40 Expedia vacation rentals, you're sure to find just the right place for your Simpson Bay stay.

What’s there to see and do in Simpson Bay?

Kim Sha Beach and Flamingo Beach are a couple of lovely local spots to get outside and enjoy nature. Hollywood Casino and Simpson Bay Beach are other places to visit while you're in town.

What’s a vacation rental in Simpson Bay like?

A vacation rental is a private property where you can stay for a few weeks or just a few days in Simpson Bay. Vacation rentals offer amenities such as patios, hot tubs, and fire pits so you'll have all the conveniences of home. If you're concerned about cleanliness, vacation rentals can offer a sense of security away from public hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great choice for families.