A wooden pier extending into calm waters with sailboats anchored nearby.

Simpson Bay Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Simpson Bay vacation rentals

Beach

1. 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, (1,274 reviews)
"It was a great stay"
United States
Shawn
The price is ￥21,644
￥26,928 total
includes taxes & fees
Sep 19 - Sep 20
Hilton Vacation Club Royal Palm St. Maarten
Amazing Top Floor Apartment | Balcony

2. The Hills Residence

The Hills Residence
3.0 star property
Simpson Bay
8.4 out of 10, Very Good, (167 reviews)
"View"
United States
Enuska
The price is ￥23,085
￥40,334 total
includes taxes & fees
Sep 9 - Sep 10
The Hills Residence
Terrace/patio

3. Simpson Bay Suites

Simpson Bay Suites
3.5 star property
Simpson Bay
7.2 out of 10, Good, (163 reviews)
"It was good value for money."
United States
Tirichmir
The price is ￥19,362
￥21,687 total
includes taxes & fees
Aug 30 - Aug 31
Simpson Bay Suites
702: Grand Apartment, 1 Queen Bed, Balcony, Sea View | Living area

4. Mullet Bay Suites: Your Luxury Stay Awaits

Mullet Bay Suites: Your Luxury Stay Awaits
4.0 star property
Maho
9.6 out of 10, Exceptional, (180 reviews)
"All together beautiful will stay again"
United States
Kentorrie
The price is ￥38,868
￥55,115 total
includes taxes & fees
Aug 31 - Sep 1
Mullet Bay Suites: Your Luxury Stay Awaits
Comfort Room, 1 King Bed, Non Smoking, Ocean View

5. MIDTOWN MOTEL SXM

MIDTOWN MOTEL SXM
2.5 star property
Downtown Philipsburg
7.4 out of 10, Good, (72 reviews)
"It was a wonderful stay and experience"
United States
Yollanda
The price is ￥11,828
￥14,280 total
includes taxes & fees
Sep 5 - Sep 6
MIDTOWN MOTEL SXM
Deluxe Double Room

6. July Apartments

July Apartments
3.0 star property
Madame's Estate
9.0 out of 10, Wonderful, (253 reviews)
"The property was no frills and the staff super helpful. Would stay again!"
United States
JoyAnn Carolyn
The price is ￥13,208
￥13,950 total
includes taxes & fees
Sep 29 - Sep 30
July Apartments
Pool

7. condostmaarten by the sea -Adults Only-

condostmaarten by the sea -Adults Only-
4.0 star property
Indigo Bay
9.2 out of 10, Wonderful, (43 reviews)
"Love love the property was amazing. Will definitely return."
United States
Muneca
The price is ￥48,387
￥71,512 total
includes taxes & fees
Sep 1 - Sep 2
condostmaarten by the sea -Adults Only-
Deluxe Apartment, Courtyard View

8. Philips Scott House Calinago

Philips Scott House Calinago
3.0 star property
Downtown Philipsburg
The price is ￥24,382
￥37,226 total
includes taxes & fees
Sep 1 - Sep 2
Philips Scott House Calinago
Infinity pool

9. Dawn Beach Club Resort Sint Maarten

Dawn Beach Club Resort Sint Maarten
4.0 star property
Oyster Pond
8.8 out of 10, Excellent, (33 reviews)
"Large rooms with great ocean views! Helpful staff and good beach access!"
United States
Gavin
The price is ￥100,713
￥120,856 total
includes taxes & fees
Aug 30 - Aug 31
Dawn Beach Club Resort Sint Maarten
Beach

10. 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 ￥51,451
￥65,976 total
includes taxes & fees
Sep 2 - Sep 3
Singh Luxury Apartments With sea View, Apt.1
Villa | Living area

11. Avenue du lagon

Avenue du lagon
Oyster Pond
The price is ￥231,072
￥312,027 total
includes taxes & fees
Sep 1 - Sep 2
Avenue du lagon
Exterior

12. 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 ￥51,451
￥65,976 total
includes taxes & fees
Sep 10 - Sep 11
Singh Luxury Apartments With sea View, Apt.2
Beach

13. 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 ￥113,221
￥130,834 total
includes taxes & fees
Sep 10 - Sep 11
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

Hilton Vacation Club Flamingo Beach St. Maarten

Hilton Vacation Club Flamingo Beach St. Maarten

10/10 Excellent
"Centrally located near food, nightlife and beach access."
Shamira 4-night trip
Posted 1 hour ago
Hilton Vacation Club Flamingo Beach St. Maarten

Find out more about Simpson Bay

Search for holiday rentals in Simpson Bay on Expedia! You can easily find your home rentals, villas, holiday apartments in Simpson Bay using one of the methods below:

  • View our selection of featured holiday rentals in Simpson Bay
  • Use the map to find apartments and other holiday homes in the Simpson Bay neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Simpson Bay while they last

Look no further and take a look at our great range of rental properties in Simpson Bay!

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 45 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.