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
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

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, (1,318 reviews)
"The staff was very friendly"
United States
Carmelle,
The price is ￥25,486
￥30,924 total
includes taxes & fees
Nov 5 - Nov 6
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, (168 reviews)
"Overall good. Location is great."
Canada
Manishkumar
The price is ￥21,376
￥23,941 total
includes taxes & fees
Oct 17 - Oct 18
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, (171 reviews)
"Very good"
United States
Alyssia
The price is ￥26,872
￥45,145 total
includes taxes & fees
Oct 21 - Oct 22
The Hills Residence
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 ￥19,115
￥22,301 total
includes taxes & fees
Oct 15 - Oct 16
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 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 ￥15,676
￥25,176 total
includes taxes & fees
Nov 14 - Nov 15
Beach Front Studio C3
A beachfront property with multiple buildings, a beach, and a red arrow pointing to a specific building.

6. Beach Front 1 Bedroom Flat D3

Beach Front 1 Bedroom Flat D3
Simpson Bay
10.0 out of 10, Exceptional, (3 reviews)
The price is ￥19,846
￥29,999 total
includes taxes & fees
Oct 15 - Oct 16
Beach Front 1 Bedroom Flat D3
A beach with clear turquoise waters, a thatched-roof structure, and vibrant pink flowers.

7. 1 BR 1 BA Simpson | Beach Access, Pool & Patio

1 BR 1 BA Simpson | Beach Access, Pool & Patio
Simpson Bay
The price is ￥14,135
￥26,826 total
includes taxes & fees
Oct 29 - Oct 30
1 BR 1 BA Simpson | Beach Access, Pool & Patio
A wooden deck with a staircase leading to a beach view, surrounded by potted plants and colorful beach toys.

8. 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
Maho Beach House Ocean Front Garden Studio
A wooden deck leading to a beach with clear turquoise water and a rocky shoreline.

9. Maho Beach House - Petit Studio Océanique - Charmante Vue

Maho Beach House - Petit Studio Océanique - Charmante Vue
Maho, Sint Maarten
9.4 out of 10, Exceptional, (3 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.
Maho Beach House - Petit Studio Océanique - Charmante Vue
A pool area with a stone wall, palm trees, and lounge chairs.

10. 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 ￥16,419
￥33,263 total
includes taxes & fees
Oct 15 - Oct 16
1 bedroom with pool in Simpson Bay - GENERATOR (1-3B)
A pool area with a dolphin statue, blue lounge chairs, and a stone wall with greenery.

11. 5 minutes walking from the beach 1-4B

5 minutes walking from the beach 1-4B
Simpson Bay
The price is ￥17,331
￥34,378 total
includes taxes & fees
Oct 18 - Oct 19
5 minutes walking from the beach 1-4B
A swimming pool with lounge chairs and a stone wall.

12. 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 ￥18,244
￥35,337 total
includes taxes & fees
Oct 17 - Oct 18
Blue Sky Apt in the middle of Simpson Bay-GENERATOR(1-3A)
A poolside area with outdoor seating and a view of a hotel building and the sea.

13. 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
8.8 out of 10, Excellent, (8 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.
The price is ￥46,704
￥67,010 total
includes taxes & fees
Oct 15 - Oct 16
Beach Front 2 Bed Condon C1.1 with Sea View and Private Pool !!
A beach with clear turquoise water, a sandy shore, and a row of multi-story hotels in the background.

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

The Luxe 1 bedroom apartment with pool - GENERATOR (2-2A)
Simpson Bay
The price is ￥18,244
￥35,337 total
includes taxes & fees
Oct 15 - Oct 16
The Luxe 1 bedroom apartment with pool - GENERATOR (2-2A)
A modern living room with a dining area, a kitchen, and a balcony with a mountain view.

15. D407 – Charming Apartment with Terrace

D407 – Charming Apartment with Terrace
Sint Maarten
The price is ￥29,015
￥56,531 total
includes taxes & fees
Oct 26 - Oct 27
D407 – Charming Apartment with Terrace
A modern living room with a large sliding glass door leading to a balcony with a scenic mountain view.

16. D442 - Apartment with balcony and lagoon view

D442 - Apartment with balcony and lagoon view
Cole Bay
The price is ￥29,015
￥56,372 total
includes taxes & fees
Oct 25 - Oct 26
D442 - Apartment with balcony and lagoon view
A modern living room with a curved sofa, a flat-screen TV, and a dining area with a wooden table and chairs.

17. D402 - Beautiful apartment with garden and view

D402 - Beautiful apartment with garden and view
Cole Bay
D402 - Beautiful apartment with garden and view
A swimming pool with a wooden deck, surrounded by greenery and a hillside.

18. A101 - Outstanding Lagoon View & Garden

A101 - Outstanding Lagoon View & Garden
Sint Maarten
The price is ￥30,887
￥58,571 total
includes taxes & fees
Oct 28 - Oct 29
A101 - Outstanding Lagoon View & Garden
A rooftop pool with a view of a marina and mountains.

19. A107 - Beautiful 2 Bedroom with Garden

A107 - Beautiful 2 Bedroom with Garden
Sint Maarten
The price is ￥39,311
￥71,402 total
includes taxes & fees
Oct 31 - Nov 1
A107 - Beautiful 2 Bedroom with Garden
A modern room with a glass door leading to a balcony with a view of a marina and mountains.

20. D438 – Amazing 2-Bedroom Lagoon View with Balcony

D438 – Amazing 2-Bedroom Lagoon View with Balcony
Sint Maarten
8.0 out of 10, Very good, (1 review)
"Clean room, amazing view!! A little precarious getting up there though- should have more of a description of the challenge of getting to the unit!"
United States
ALLEN
D438 – Amazing 2-Bedroom Lagoon View with Balcony
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
"Rooms and Grounds are clean and well kept. Best location I've ever stayed at and we travel frequently to various islands Beach access and accessibility to various restaurants is steps away!! There's alot to do for Singles, Family and Couples! This is my 3rd time on the island and I give this resort 5 Stars for location, quick check-in, personable staff and cleanliness!!!"
Timber D 5-night trip
Posted 5 hours 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
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  • 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?

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.