Simpson Bay Vacation Rentals

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Our top choices for Simpson Bay vacation rentals

4.0 star property
9.0 out of 10, Wonderful, (1164)
"One of my favorite places to stay."
United States
Carlos
$408 nightly
The price is $428
Jan 6 - Jan 7, 2026
Total with taxes and fees
Hilton Vacation Club Royal Palm St. Maarten

Aparthotel in Simpson Bay

Simpson Bay Suites
3.5 star property
6.8 out of 10, (125)
"No issues. Staff were very welcoming and accommodating. Was a pleasant stay. "
United States
Sharmain
$181 nightly
The price is $189
Dec 25 - Dec 26
Total with taxes and fees
Simpson Bay Suites

Aparthotel in Simpson Bay

The Hills Residence
3.0 star property
8.8 out of 10, Excellent, (55)
"Enjoyed my stay "
United States
Shakia
$265 nightly
The price is $277
Dec 24 - Dec 25
Total with taxes and fees
The Hills Residence

Aparthotel in Pelican Key

FLAMINGO BEACH
3.5 star property
$461 nightly
The price is $482
Jan 17 - Jan 18, 2026
Total with taxes and fees
FLAMINGO BEACH

Condo resort in Oyster Pond

Dawn Beach Club Resort Sint Maarten
4.0 star property
8.8 out of 10, Excellent, (21)
"Wonderful vacation spot in st maarten"
United States
Debasis
$642 nightly
The price is $673
Jan 23 - Jan 24, 2026
Total with taxes and fees
Dawn Beach Club Resort Sint Maarten

Villa in Oyster Pond

Avenue du lagon
$2,233 nightly
The price is $2,322
Jan 19 - Jan 20, 2026
Total with taxes and fees
Avenue du lagon
3.5 star property
$527 nightly
The price is $550
Dec 28 - Dec 29
Total with taxes and fees
Singh Luxury Apartments With sea View, Apt.2

Aparthotel in Anse Marcel

The Forest
4.0 star property
10.0 out of 10, Exceptional, (15)
"Great boutique hotel in anse Marcel. Owners are hands on and very pleasant. Look forward to going again. "
Canada
Nadalina
$408 nightly
The price is $427
Jan 15 - Jan 16, 2026
Total with taxes and fees
The Forest
4.0 star property
9.6 out of 10, Exceptional, (23)
"Good location easy access to a private beach "
United States
All About
$495 nightly
The price is $516
Dec 28 - Dec 29
Total with taxes and fees
condostmaarten by the sea -Adults Only-
4.0 star property
9.8 out of 10, Exceptional, (113)
"Fantastic place to stay. Clean, great views, excellent amenities"
Canada
Oleksii
$314 nightly
The price is $329
Dec 26 - Dec 27
Total with taxes and fees
Mullet Bay Suites: Your Luxury Stay Awaits

Aparthotel in Downtown Philipsburg

Sea Palace
3.0 star property
8.6 out of 10, Excellent, (111)
"Great staff. Excellent room. Awesome views. The young lady with the glasses at the front desk is the best ever. Didn't get her name unfortunately. "
United States
Elizabeth
$215 nightly
The price is $226
Jan 1 - Jan 2, 2026
Total with taxes and fees
Sea Palace

Aparthotel in Downtown Philipsburg

MIDTOWN MOTEL SXM
2.5 star property
8.0 out of 10, Very Good, (1)
"The staff was extremely helpful "
United States
Joycelyn
$81 nightly
The price is $85
Dec 27 - Dec 28
Total with taxes and fees
MIDTOWN MOTEL SXM

Aparthotel in Madame's Estate

July Apartments
3.0 star property
9.2 out of 10, Wonderful, (156)
"Amazing place. "
United States
Cristina
$99 nightly
The price is $104
Dec 28 - Dec 29
Total with taxes and fees
July Apartments
3.0 star property
$527 nightly
The price is $550
Dec 24 - Dec 25
Total with taxes and fees
Singh Luxury Apartments With sea View, Apt.1
3.0 star property
2.0 out of 10, (1)
$914 nightly
The price is $956
Dec 24 - Dec 25
Total with taxes and fees
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
October
December
$387
Month
Price
January
$387
February
$366
March
$374
April
$358
May
$292
June
$281
July
$287
August
$281
September
$212
October
$188
November
$271
December
$421
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

Everything you need to know about Simpson Bay 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 Simpson Bay 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 Simpson Bay vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Simpson Bay vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Simpson Bay. 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 Simpson Bay 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 $189 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 Simpson Bay rentals

At Expedia, we put the best Simpson Bay 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 Simpson Bay 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 Simpson Bay 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 Simpson Bay. 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

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 lively bars and top-notch restaurants.

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

Caribbean Sea Studio next to The Morgan Resort: Visitors like this Simpson Bay vacation home rental. It is located on the beach and has an outdoor pool, a patio, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Kick off your shoes and enjoy yourself with a garden and a hot tub. Other favorite homes for rent in Simpson Bay are Charming 3BR Villa w Private Pool in Pelican Key and White Sands Retreat - Beachside at Beacon Hill.

How many vacation rentals are there in Simpson Bay?

With 41 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. Simpson Bay Beach and Hollywood Casino 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.