Simpson Bay Vacation Rentals

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Our top choices for Simpson Bay vacation rentals

Aparthotel in Simpson Bay

The Hills Residence
3.0 star property
8.4 out of 10, Very Good, (76 reviews)
"Great staff, would stay again!"
United States
Maimuna
$331 nightly
The price is $347
Feb 20 - Feb 21
Total with taxes and fees
The Hills Residence
4.0 star property
9.0 out of 10, Wonderful, (1,173 reviews)
"Room was great, resort was great, staff was great"
Canada
Gisele
$408 nightly
The price is $428
Mar 1 - Mar 2
Total with taxes and fees
Hilton Vacation Club Royal Palm St. Maarten

Apartment in Simpson Bay

Beach Front Studio C3
10.0 out of 10, Exceptional, (2 reviews)
"Clean and modern. Need a door for the bathroom. Check in was easy and Lisa was there to help us get checked in. She even provided 2 cold water and 2 cold beers"
United States
Norman
$159 nightly
The price is $159
Feb 6 - Feb 7
Total with taxes and fees
Beach Front Studio C3

Aparthotel in Simpson Bay

Simpson Bay Suites
3.5 star property
7.0 out of 10, Good, (132 reviews)
"Room was clean. Had a full living room and kitchen incl microwave. Convenient to kim-sha beach. "
United States
Dale
$181 nightly
The price is $189
Feb 11 - Feb 12
Total with taxes and fees
Simpson Bay Suites
$108 nightly
The price is $108
Jan 31 - Feb 1
Total with taxes and fees
Blue Sail Apartments - Double room
$129 nightly
The price is $129
Jan 31 - Feb 1
Total with taxes and fees
Blue Sail Apartments - 1 bedroom apartments

Apartment in Simpson Bay

Beach Front 1 Bedroom Flat D3
10.0 out of 10, Exceptional, (1 review)
"Great spot! Clean, comfortable and well equipped. "
United States
Jill
$189 nightly
The price is $189
Feb 5 - Feb 6
Total with taxes and fees
Beach Front 1 Bedroom Flat D3
$151 nightly
The price is $151
Jan 31 - Feb 1
Total with taxes and fees
Blue Sail Apartments - Two bedroom apartments
10.0 out of 10, Exceptional, (2 reviews)
"perfect!!"
United States
jason l.
$311 nightly
The price is $321
Feb 12 - Feb 13
Total with taxes and fees
1 bedroom with pool in Simpson Bay - GENERATOR (1-3B)
10.0 out of 10, Exceptional, (1 review)
"We loved this place so much we bought it! The location is to die for. Right in the heart of Simpson Bay, there is soooo much to see and do right around you. The beach is literally a four minute walk and the water is calm and beautiful. We can’t wait to come back again and again! Also, Kayla, the manager is the best to work with. Sweet and helpful."
United States
Trish S.
$452 nightly
The price is $471
Feb 1 - Feb 2
Total with taxes and fees
Marina Views in the Heart of Simpson Bay
9.0 out of 10, Wonderful, (2 reviews)
"Very close to the sunset bar and interesting views of approaching aircraft. Excellent sunset views from the Sunset bar or the Morgan resort on the other side of the unit. Morgan resort also had excellent dining area and bar facilities open to the public."
United States
Roy N.
$340 nightly
The price is $340
Feb 23 - Feb 24
Total with taxes and fees
Maho Beach House - Petit Studio Océanique - Charmante Vue
9.4 out of 10, Exceptional, (3 reviews)
"The Maho was very clean, quiet and close to the airport. I recommend for people passing through or for a few days on St. Martins."
United States
David V.
$332 nightly
The price is $332
Feb 2 - Feb 3
Total with taxes and fees
Maho Beach Modern 1-Bedroom, Ocean Level
A112 - Extraordinary Lagoon View with Balcony
B253 - Incredible Top Floor Lagoon Views
8.8 out of 10, Excellent, (3 reviews)
"Great place to stay with a lot of privacy and walkable to stores and restaurants. Amazing views! Lisa is so friendly and keeps the place amazing!"
United States
Alaciel S.
$463 nightly
The price is $463
Feb 1 - Feb 2
Total with taxes and fees
Beach Front 2 Bed Condon C1.1 with Sea View and Private Pool !!
$392 nightly
The price is $417
Feb 11 - Feb 12
Total with taxes and fees
A101 - Outstanding Lagoon View & Garden
$384 nightly
The price is $407
Feb 10 - Feb 11
Total with taxes and fees
A116 - Immersive Simpson Bay Lagoon View

Vacation Home in Simpson Bay

C344 - Lagoon view with balcony
$396 nightly
The price is $421
Feb 9 - Feb 10
Total with taxes and fees
C344 - Lagoon view with balcony
9.6 out of 10, Exceptional, (17 reviews)
"Great location close to everything I will definitely be back love it."
United States
keenan j.
$509 nightly
The price is $527
Feb 10 - Feb 11
Total with taxes and fees
2 BR 2 BA, beachfront condo, amazing oceanview, private beach access

Apartment in Sint Maarten

A134 - Panoramic View of the Lagoon
$386 nightly
The price is $410
Feb 9 - Feb 10
Total with taxes and fees
A134 - Panoramic View of the Lagoon
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
February
$414
Month
Price
January
$411
February
$414
March
$389
April
$371
May
$281
June
$279
July
$285
August
$286
September
$270
October
$258
November
$279
December
$405
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 top-notch restaurants and lively bars.

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

Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool : Visitors like this Simpson Bay vacation home rental. It is located on the beach and has an outdoor pool, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Other favorite homes for rent in Simpson Bay are New Listing, Exceptional 3 bed & bath with private pool in Pelican Cove and White Sands Retreat - Beachside at Beacon Hill.

How many vacation rentals are there in Simpson Bay?

With 39 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.