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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Simpson Bay holiday 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, (1,335 reviews)
"It was nice"
United States
Prem
The price is £166
includes taxes & fees
11 Nov - 12 Nov
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 £112
includes taxes & fees
11 Nov - 12 Nov
Simpson Bay Suites
A beachfront property with multiple buildings, a beach, and a red arrow pointing to a specific building.

3. 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 £114
includes taxes & fees
18 Nov - 19 Nov
Beach Front Studio C3
A poolside area with a wooden table, lounge chairs, and a view of the ocean.

4. Blue Sail Apartments - Two-Bedroom Apartments

Blue Sail Apartments - Two-Bedroom Apartments
Pelican Key
6.0 out of 10, (3 reviews)
"Check in was seamless accommodations were exactly as expected and the staff were very friendly. We noticed many things were brand new and we were informed that there was a new owner- appears that they are working hard!"
United States
Heidi
The price is £101
includes taxes & fees
14 Nov - 15 Nov
Blue Sail Apartments - Two-Bedroom Apartments
A beachfront property with multiple buildings, a beach, and a red arrow pointing to a specific building.

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 £121
includes taxes & fees
12 Nov - 13 Nov
Beach Front 1 Bedroom Flat D3
A wooden deck with a staircase leading to a beach view, surrounded by potted plants and colorful beach toys.

6. 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 £171
includes taxes & fees
11 Nov - 12 Nov
Maho Beach House Ocean Front Garden Studio
A pool area with a stone wall, palm trees, and lounge chairs.

7. 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 £152
includes taxes & fees
30 Nov - 1 Dec
1 bedroom with pool in Simpson Bay - GENERATOR (1-3B)
A swimming pool with lounge chairs and a stone wall.

8. 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 £171
includes taxes & fees
16 Nov - 17 Nov
Blue Sky Apt in the middle of Simpson Bay-GENERATOR(1-3A)
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
The price is £161
includes taxes & fees
11 Nov - 12 Nov
5 minutes walking from the beach 1-4B
A wooden deck leading to a beach with clear turquoise water and a rocky shoreline.

10. 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 £192
includes taxes & fees
11 Nov - 12 Nov
Maho Beach House - Spacious 1 Bedroom Suite
A pool area with lounge chairs and a stone wall.

11. Modern apartment with shared pool and generator (2-2B)

Modern apartment with shared pool and generator (2-2B)
Simpson Bay
The price is £162
includes taxes & fees
15 Nov - 16 Nov
Modern apartment with shared pool and generator (2-2B)
A pool area with a dolphin statue, blue lounge chairs, and a stone wall with greenery.

12. Centrally located Simpson bay 1bdr apt (1-2)

Centrally located Simpson bay 1bdr apt (1-2)
Simpson Bay
The price is £175
includes taxes & fees
18 Nov - 19 Nov
Centrally located Simpson bay 1bdr apt (1-2)
A modern living room with a large window offering a view of a city and mountains.

13. B243 - Deluxe 1 Bedroom

B243 - Deluxe 1 Bedroom
Sint Maarten
B243 - Deluxe 1 Bedroom
A modern dining area with a view of a harbor and hills.

14. C335 - Comfortable Lagoon View Apartment

C335 - Comfortable Lagoon View Apartment
Sint Maarten
The price is £229
includes taxes & fees
21 Nov - 22 Nov
C335 - Comfortable Lagoon View Apartment
A swimming pool with wooden deck, surrounded by greenery, overlooking a coastal town and mountains.

15. C352 - Top view with balcony

C352 - Top view with balcony
Simpson Bay
The price is £243
includes taxes & fees
22 Nov - 23 Nov
C352 - Top 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.

16. C344 - Lagoon view with balcony

C344 - Lagoon view with balcony
Simpson Bay
The price is £234
includes taxes & fees
15 Nov - 16 Nov
C344 - Lagoon view with balcony
A rooftop swimming pool with wooden decking, surrounded by potted plants, overlooking a coastal town and hills.

17. A116 - Immersive Simpson Bay Lagoon View

A116 - Immersive Simpson Bay Lagoon View
Sint Maarten
The price is £248
includes taxes & fees
13 Nov - 14 Nov
A116 - Immersive Simpson Bay Lagoon View
A modern interior with a dining area, a large mirror, and a view of a coastal landscape.

18. A135 - Beautiful one bedroom apartment

A135 - Beautiful one bedroom apartment
Cole Bay
A135 - Beautiful one bedroom apartment
A rooftop pool with a wooden deck, surrounded by potted plants.

19. B236 - Homely Apartment with Balcony

B236 - Homely Apartment with Balcony
Sint Maarten
The price is £234
includes taxes & fees
18 Nov - 19 Nov
B236 - Homely Apartment with Balcony
A swimming pool with a view of a marina and mountains.

20. D402 - Beautiful apartment with garden and view

D402 - Beautiful apartment with garden and view
Cole Bay
The price is £248
includes taxes & fees
11 Nov - 12 Nov
D402 - Beautiful apartment with garden and view
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

A balcony with a view of the ocean, a bottle of champagne, two wine glasses, and a book titled "Linda Van Rijn Zoutelande".
La Vista Hotel

La Vista Hotel

La Vista Hotel
Pelican Key

10/10 Excellent

The whole experience is exceptional, we have booked to come straight back.
United Kingdom
Julie
Reviewed January 3, 2026
La Vista Hotel

Find out more about Simpson Bay

Everything you need to know about Simpson Bay holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Simpson Bay holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Simpson Bay holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Simpson Bay holiday rentals we have selected for you start as low as £101 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 holiday 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 holiday.

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 holiday rental in Simpson Bay?

Yes, there are holiday rentals close to the most popular sights in Simpson Bay, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals that Simpson Bay has to offer?

Philips Scott House Calinago: This holiday 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 such as 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 holiday rentals are there in Simpson Bay?

With 38 Expedia holiday rentals, you're guaranteed 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 holiday rental in Simpson Bay like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Simpson Bay. Holiday rentals feature extras such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about cleanliness, a holiday rental can provide a sense of security away from public hotel lifts and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a small group gathering.