Simpson Bay Vacation Rentals

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Vacation Rentals in Simpson Bay

Hilton Vacation Club Royal Palm St. Maarten

4.0 star property
Simpson Bay
9.0 out of 10, Wonderful, (1154)
"Beautiful vacation "
Canada
alonzo
$161 nightly
The price is $169
Dec 17 - Dec 18
Total with taxes and fees
Hilton Vacation Club Royal Palm St. Maarten

The Hills Residence

3.0 star property
Simpson Bay
9.0 out of 10, Wonderful, (49)
"This apartment was nice, clean, modern, walking distance to restaurants and shops. "
United States
Lionel
$261 nightly
The price is $273
Dec 8 - Dec 9
Total with taxes and fees
The Hills Residence

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

Simpson Bay
10.0 out of 10, Exceptional, (1)
"Communication with the host was very easy. The location is outstanding and the facility has every amenity. You can imagine. I highly recommend this property and can’t wait to visit again."
United States
Richard S.
$217 nightly
The price is $223
Nov 25 - Nov 26
Total with taxes and fees
1 bedroom with pool in Simpson Bay - GENERATOR (1-3B)

Simpson Bay Suites

3.5 star property
Simpson Bay
6.8 out of 10, (125)
"No issues. Staff were very welcoming and accommodating. Was a pleasant stay. "
United States
Sharmain
$130 nightly
The price is $136
Nov 24 - Nov 25
Total with taxes and fees
Simpson Bay Suites

Marina Views in the Heart of Simpson Bay

Simpson Bay
10.0 out of 10, Exceptional, (1)
"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.
$327 nightly
The price is $342
Nov 24 - Nov 25
Total with taxes and fees
Marina Views in the Heart of Simpson Bay

Maho Beach House: Sunset Suite, 1-Bedroom

Maho
10.0 out of 10, Exceptional, (1)
"We had a great stay. Noah and Dwayne were great to work with. They were quick to respond to any questions we had or help we needed. We enjoyed out daily walks and spent time enjoying 3 different beaches within walking distance as well great places to eat, drink and enjoy time in the sun."
United States
Dawn A.
$301 nightly
The price is $301
Nov 25 - Nov 26
Total with taxes and fees
Maho Beach House: Sunset Suite, 1-Bedroom

Maho Beach House: Studio Getaway, Oceanfront Vibe

Maho, Sint Maarten
10.0 out of 10, Exceptional, (2)
"Nothing fancy just a nice clean place to stay. Great location. Lots of restaurants nearby. Dwayne was a great communicator and very accommodating."
United States
Colleen M.
$284 nightly
The price is $284
Nov 24 - Nov 25
Total with taxes and fees
Maho Beach House: Studio Getaway, Oceanfront Vibe

Oceanview Escape in Sint Maarten

Pelican Key
$468 nightly
The price is $489
Nov 24 - Nov 25
Total with taxes and fees
Oceanview Escape in Sint Maarten

Sunny Days at Simpson Bay Yacht Club

Simpson Bay
10.0 out of 10, Exceptional, (2)
"This is a great location to come to: comfortable central location lots to do around restaurant everything you would need in a getaway I will definitely here again"
United States
JEROME J.
$511 nightly
The price is $533
Nov 24 - Nov 25
Total with taxes and fees
Sunny Days at Simpson Bay Yacht Club

Caribbean Sea Studio next to The Morgan Resort

Maho, Sint Maarten
8.0 out of 10, Very Good, (1)
$237 nightly
The price is $237
Nov 24 - Nov 25
Total with taxes and fees
Caribbean Sea Studio next to The Morgan Resort

A116 - Immersive Simpson Bay Lagoon View

Sint Maarten
$279 nightly
The price is $294
Dec 17 - Dec 18
Total with taxes and fees
A116 - Immersive Simpson Bay Lagoon View

C323 – Elegant apartment with glass wall

Sint Maarten
$288 nightly
The price is $304
Dec 8 - Dec 9
Total with taxes and fees
C323 – Elegant apartment with glass wall

A117 - Lovely 2 Bedroom with Lagoon View

2.0 star property
Sint Maarten
$342 nightly
The price is $342
Dec 2 - Dec 3
Total with taxes and fees
A117 - Lovely 2 Bedroom with Lagoon View

Maho Beach House: Elegant 1-Bedroom, Beach Level

Simpson Bay
$271 nightly
The price is $271
Nov 24 - Nov 25
Total with taxes and fees
Maho Beach House: Elegant 1-Bedroom, Beach Level

Turquoise paradise, directly ON beach, gated w underground parking!

Simpson Bay
9.8 out of 10, Exceptional, (20)
"This is the perfect place to stay location wise and with the beach views! Also there is a/c in each room which is super nice! "
United States
Rachel S.
$519 nightly
The price is $519
Nov 24 - Nov 25
Total with taxes and fees
Turquoise paradise, directly ON beach, gated w underground parking!

Beacon Hill Hideaway: Luxury Condo in Simpson Bay

Simpson Bay
$521 nightly
The price is $544
Dec 3 - Dec 4
Total with taxes and fees
Beacon Hill Hideaway: Luxury Condo in Simpson Bay

A101 - Outstanding Lagoon View & Garden

Sint Maarten
$309 nightly
The price is $326
Dec 2 - Dec 3
Total with taxes and fees
A101 - Outstanding Lagoon View & Garden

A111 - Condo with amazing view

Sint Maarten
$406 nightly
The price is $431
Dec 23 - Dec 24
Total with taxes and fees
A111 - Condo with amazing view

A114 - Beautiful Lagoon View & Balcony

Sint Maarten
$432 nightly
The price is $459
Dec 23 - Dec 24
Total with taxes and fees
A114 - Beautiful Lagoon View & Balcony

Charming 3BR Villa w Private Pool in Pelican Key

Pelican Key
$663 nightly
The price is $722
Nov 27 - Nov 28
Total with taxes and fees
Charming 3BR Villa w Private Pool in Pelican Key
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
$429
Month
Price
January
$435
February
$438
March
$381
April
$302
May
$280
June
$279
July
$256
August
$228
September
$157
October
$204
November
$240
December
$429
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 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 White Sands Retreat - Beachside at Beacon Hill and Charming 3BR Villa w Private Pool in Pelican Key.

How many vacation rentals are there in Simpson Bay?

With 37 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. In the larger area, you’ll find popular places like Maho Beach and Orient Bay Beach.

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.