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
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Simpson Bay vacation rentals

A resort with a view of sailboats on the water, a beach with palm trees, and a modern building with balconies.

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, (1,325 reviews)
"The staff was very friendly"
United States
Carmelle,
The price is CA $201
CA $246 total
includes taxes & fees
Nov 10 - Nov 11
Hilton Vacation Club Royal Palm St. Maarten
A high-rise hotel with a view of the sunset over a marina.

2. Simpson Bay Suites

Simpson Bay Suites
3.5 star property
Simpson Bay
7.2 out of 10, Good, (169 reviews)
"Overall good. Location is great."
Canada
Manishkumar
The price is CA $189
CA $211 total
includes taxes & fees
Nov 10 - Nov 11
Simpson Bay Suites
A modern living room with a large sliding glass door leading to a balcony with a view of a coastal town and mountains.

3. The Hills Residence

The Hills Residence
3.0 star property
Simpson Bay
8.4 out of 10, Very good, (173 reviews)
"My next stay I’ll be a returning guest at the hills …"
United States
Harold
The price is CA $267
CA $484 total
includes taxes & fees
Nov 2 - Nov 3
The Hills Residence
A compact living space with a kitchenette, a dining area, and a sofa.

4. Beach Front Studio C3

Beach Front Studio C3
Simpson Bay
8.8 out of 10, Excellent, (5 reviews)
"Really cool place and the location was prime. The cleaning lady was the nicest person there could be as well. "
Canada
Benjamin
The price is CA $138
CA $201 total
includes taxes & fees
Nov 3 - Nov 4
Beach Front Studio C3
A modern bathroom with wooden cabinetry, a glass shower enclosure, and a black floor lamp.

5. Beach Front 1 Bedroom Flat D3

Beach Front 1 Bedroom Flat D3
Simpson Bay
10.0 out of 10, Exceptional, (3 reviews)
"Great location near Simpson Bay restaurants and nightlife. Accommodations were exactly as pictured with modern furnishings. Car rental is recommended to fully enjoy the island. "
United States
Christopher
The price is CA $150
CA $224 total
includes taxes & fees
Nov 1 - Nov 2
Beach Front 1 Bedroom Flat D3
A poolside area with a wooden table, lounge chairs, and a view of the ocean.

6. Blue Sail Apartments - 1-Bedroom Apartments

Blue Sail Apartments - 1-Bedroom Apartments
Pelican Key
The price is CA $239
CA $248 total
includes taxes & fees
Nov 3 - Nov 4
Blue Sail Apartments - 1-Bedroom Apartments
A wooden deck with a staircase leading to a beach view, surrounded by potted plants and colorful beach toys.

7. Maho Beach House Ocean Front Garden Studio

Maho Beach House Ocean Front Garden Studio
Maho, Sint Maarten
9.4 out of 10, Exceptional, (3 reviews)
"Perfect location for us! We wanted easy access to see the planes coming in and it could not have been more perfect. Close to taxis and buses. Hosts were excellent at communicating. Friendly staff, would recommend!! "
United States
Laura
The price is CA $218
CA $306 total
includes taxes & fees
Nov 1 - Nov 2
Maho Beach House Ocean Front Garden Studio
A multi-story hotel with balconies, a beach in front, and palm trees.

8. Maho Beach House - Spacious 1 Bedroom Suite

Maho Beach House - Spacious 1 Bedroom Suite
Maho, Sint Maarten
9.6 out of 10, Exceptional, (5 reviews)
"Great location. Spacious room. "
Canada
Sinisa
The price is CA $243
CA $348 total
includes taxes & fees
Nov 1 - Nov 2
Maho Beach House - Spacious 1 Bedroom Suite
A pool area with a dolphin statue, blue lounge chairs, and a stone wall with greenery.

9. 5 minutes walking from the beach 1-4B

5 minutes walking from the beach 1-4B
Simpson Bay
5 minutes walking from the beach 1-4B
A swimming pool with lounge chairs and a stone wall.

10. Blue Sky Apt in the middle of Simpson Bay-GENERATOR(1-3A)

Blue Sky Apt in the middle of Simpson Bay-GENERATOR(1-3A)
Simpson Bay
The price is CA $161
CA $295 total
includes taxes & fees
Nov 7 - Nov 8
Blue Sky Apt in the middle of Simpson Bay-GENERATOR(1-3A)
A pool area with a stone wall, palm trees, and lounge chairs.

11. 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.
The price is CA $145
CA $276 total
includes taxes & fees
Nov 2 - Nov 3
1 bedroom with pool in Simpson Bay - GENERATOR (1-3B)
A table with two wine glasses and a bucket of ice, set against a scenic mountain view.

12. The Luxe 1 bedroom apartment with pool - GENERATOR (2-2A)

The Luxe 1 bedroom apartment with pool - GENERATOR (2-2A)
Simpson Bay
The Luxe 1 bedroom apartment with pool - GENERATOR (2-2A)
A pool area with clear blue water, wooden deck, and a view of a marina with boats and a hilly landscape in the background.

13. C314 - Stunning 1 Bedroom Apartment

C314 - Stunning 1 Bedroom Apartment
Sint Maarten
The price is CA $239
CA $456 total
includes taxes & fees
Nov 2 - Nov 3
C314 - Stunning 1 Bedroom Apartment
A swimming pool with wooden deck, surrounded by greenery, overlooking a coastal town and mountains.

14. C352 - Top view with balcony

C352 - Top view with balcony
Simpson Bay
The price is CA $239
CA $477 total
includes taxes & fees
Nov 16 - Nov 17
C352 - Top view with balcony
A coastal hotel with multiple balconies overlooking the sea, a beach area with palm trees, and a clear view of the ocean.

15. Maho Beach Modern 1-Bedroom, Ocean Level

Maho Beach Modern 1-Bedroom, Ocean Level
Maho
9.6 out of 10, Exceptional, (4 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.
The price is CA $340
CA $389 total
includes taxes & fees
Nov 1 - Nov 2
Maho Beach Modern 1-Bedroom, Ocean Level
A modern living room with a large TV, a wooden coffee table, a sofa, and a sliding glass door leading to an outdoor patio with a view of mountains.

16. C301 - Beautiful Lagoon View Apartment

C301 - Beautiful Lagoon View Apartment
Cole Bay
The price is CA $239
CA $455 total
includes taxes & fees
Nov 9 - Nov 10
C301 - Beautiful Lagoon View Apartment
A rooftop pool with wooden decking and potted plants, overlooking a coastal cityscape.

17. B226 - Amazing Lagoon View with Balcony

B226 - Amazing Lagoon View with Balcony
Sint Maarten
B226 - Amazing Lagoon View with Balcony
A balcony with a view of a coastal city and mountains. There are two wicker chairs and a small table with a vase of flowers.

18. C344 - Lagoon view with balcony

C344 - Lagoon view with balcony
Simpson Bay
The price is CA $239
CA $455 total
includes taxes & fees
Nov 9 - Nov 10
C344 - Lagoon view with balcony
A swimming pool with a view of a beach and a hotel in the background.

19. Beach Front 2 Bed Condon D1.1 with Sea View and Private Pool !!

Beach Front 2 Bed Condon D1.1 with Sea View and Private Pool !!
Simpson Bay
10.0 out of 10, Exceptional, (1 review)
"Incredible property. Views for days, great location. Had a wonderful stay and Lisa was great also. Very secure condo and clean. Loved the pool and so many dining options close by. "
United States
Camelo
The price is CA $416
CA $566 total
includes taxes & fees
Nov 8 - Nov 9
Beach Front 2 Bed Condon D1.1 with Sea View and Private Pool !!
A swimming pool with a view of a marina and mountains.

20. D418 - Beautiful two-bedroom apartment

D418 - Beautiful two-bedroom apartment
Cole Bay
D418 - Beautiful two-bedroom apartment
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

The Morgan Resort Spa Village

The Morgan Resort Spa Village

10/10 Excellent
"The entire stay was great. Easy and quick pick up from the airport. Welcome drink upon arrival. They were able to get all of our rooms close together (girl’s trip). The restaurant was conveniently located. Free prosecco on Thursdays. The breakfast was good, fast and tasty. The room was well decorated and clean. Any requests were met quickly and efficiently. The grounds were beautiful and walkable to nearby Maho beach and shopping. No critiques."
Alexandria Nykole 4-night trip
Posted 2 hours ago
The Morgan Resort Spa Village

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, cottages, cabins, villas... 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Simpson Bay vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Simpson Bay vacation rentals we have selected for you start as low as CA $175 per night. Entering your travel dates in the search wizard 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. 

Explore a world of travel with Expedia

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?

Philips Scott House Calinago: This vacation home rental outside of Simpson Bay is in a shopping district and equipped with air-conditioning and WiFi to help you feel perfectly comfortable in your new surroundings. Amenities like a microwave and free parking are also available for your convenience. Another good choice for your trip to Simpson Bay is Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool .

How many vacation rentals are there in Simpson Bay?

With 38 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. Hollywood Casino and Simpson Bay Beach 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.