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
8.4 out of 10, Very Good, (72 reviews)
"Good location, walkable area, great views. "
United States
Tiffany
$320 nightly
The price is $334
Jan 26 - Jan 27
Total with taxes and fees
The Hills Residence

Simpson Bay Suites

Simpson Bay Suites
3.5 star property
Simpson Bay
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
Jan 25 - Jan 26
Total with taxes and fees
Simpson Bay Suites

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, (1,173 reviews)
"Room was great, resort was great, staff was great"
Canada
Gisele
$408 nightly
The price is $428
Feb 12 - Feb 13
Total with taxes and fees
Hilton Vacation Club Royal Palm St. Maarten

Beach Front 1 Bedroom Flat D3

Beach Front 1 Bedroom Flat D3
Simpson Bay
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

Beach Front Studio C3

Beach Front Studio C3
Simpson Bay
$159 nightly
The price is $159
Jan 25 - Jan 26
Total with taxes and fees
Beach Front Studio C3

1 bedroom with pool in Simpson Bay - GENERATOR (1-3B)

1 bedroom with pool in Simpson Bay - GENERATOR (1-3B)
Simpson Bay
10.0 out of 10, Exceptional, (2 reviews)
"perfect!!"
United States
jason l.
$312 nightly
The price is $322
Feb 8 - Feb 9
Total with taxes and fees
1 bedroom with pool in Simpson Bay - GENERATOR (1-3B)

Marina Views in the Heart of Simpson Bay

Marina Views in the Heart of Simpson Bay
Simpson Bay
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.
$440 nightly
The price is $459
Jan 25 - Jan 26
Total with taxes and fees
Marina Views in the Heart of Simpson Bay

Ocean View Studio in Maho, Beach Access

Ocean View Studio in Maho, Beach Access
Maho
9.2 out of 10, Wonderful, (7 reviews)
"Awsome location "
United States
todd
$342 nightly
The price is $342
Jan 24 - Jan 25
Total with taxes and fees
Ocean View Studio in Maho, Beach Access

Maho Beach House - Petit Studio Océanique - Charmante Vue

Maho Beach House - Petit Studio Océanique - Charmante Vue
Maho, Sint Maarten
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

D434 - Amazing Apartment with Balcony

D434 - Amazing Apartment with Balcony
Sint Maarten
D434 - Amazing Apartment with Balcony

Modern 2BR Townhome | Walk to Maho & SXM Planes

Modern 2BR Townhome | Walk to Maho & SXM Planes
2.0 star property
Simpson Bay
$625 nightly
The price is $652
Jan 26 - Jan 27
Total with taxes and fees
Modern 2BR Townhome | Walk to Maho & SXM Planes

C344 - Lagoon view with balcony

C344 - Lagoon view with balcony
Simpson Bay
C344 - Lagoon view with balcony

Modern 2BR Villa | Beach Access | Mins to Maho

Modern 2BR Villa | Beach Access | Mins to Maho
2.0 star property
Simpson Bay
$645 nightly
The price is $673
Jan 27 - Jan 28
Total with taxes and fees
Modern 2BR Villa | Beach Access | Mins to Maho

A134 - Panoramic View of the Lagoon

A134 - Panoramic View of the Lagoon
Sint Maarten
$386 nightly
The price is $410
Feb 9 - Feb 10
Total with taxes and fees
A134 - Panoramic View of the Lagoon

2 BR 2 BA, beachfront condo, amazing oceanview, private beach access

2 BR 2 BA, beachfront condo, amazing oceanview, private beach access
Simpson Bay
9.6 out of 10, Exceptional, (17 reviews)
"Great location close to everything I will definitely be back love it."
United States
keenan j.
$484 nightly
The price is $501
Jan 26 - Jan 27
Total with taxes and fees
2 BR 2 BA, beachfront condo, amazing oceanview, private beach access

Beach Front 2 Bed Condon C1.1 with Sea View and Private Pool !!

Beach Front 2 Bed Condon C1.1 with Sea View and Private Pool !!
Simpson Bay
8.0 out of 10, Very Good, (2 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.
$510 nightly
The price is $510
Feb 2 - Feb 3
Total with taxes and fees
Beach Front 2 Bed Condon C1.1 with Sea View and Private Pool !!

B253 - Incredible Top Floor Lagoon Views

B253 - Incredible Top Floor Lagoon Views
Sint Maarten
$349 nightly
The price is $370
Jan 26 - Jan 27
Total with taxes and fees
B253 - Incredible Top Floor Lagoon Views

A116 - Immersive Simpson Bay Lagoon View

A116 - Immersive Simpson Bay Lagoon View
Sint Maarten
$384 nightly
The price is $407
Feb 10 - Feb 11
Total with taxes and fees
A116 - Immersive Simpson Bay Lagoon View

C337 - Charming 2-Bedroom Lagoon View

C337 - Charming 2-Bedroom Lagoon View
Sint Maarten
$490 nightly
The price is $522
Feb 18 - Feb 19
Total with taxes and fees
C337 - Charming 2-Bedroom Lagoon View

A101 - Outstanding Lagoon View & Garden

A101 - Outstanding Lagoon View & Garden
Sint Maarten
$392 nightly
The price is $417
Feb 11 - Feb 12
Total with taxes and fees
A101 - Outstanding Lagoon View & Garden
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
February
$442
Month
Price
January
$406
February
$442
March
$389
April
$381
May
$285
June
$290
July
$305
August
$283
September
$251
October
$265
November
$301
December
$437
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.