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

Simpson Bay Vacation Rentals

Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

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, (1,323 reviews)
"The staff was very friendly"
United States
Carmelle,
$184 nightly
The price is $194
Nov 5 - Nov 6
Total with taxes and fees
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
$144 nightly
The price is $151
Oct 26 - Oct 27
Total with taxes and fees
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, (172 reviews)
"Very good"
United States
Alyssia
$337 nightly
The price is $346
Nov 6 - Nov 7
Total with taxes and fees
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
$159 nightly
The price is $159
Oct 26 - Oct 27
Total with taxes and fees
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
$168 nightly
The price is $168
Oct 27 - Oct 28
Total with taxes and fees
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 - 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
$141 nightly
The price is $141
Oct 26 - Oct 27
Total with taxes and fees
Blue Sail Apartments - Two-Bedroom Apartments
A balcony with two white chairs and a view of the ocean.

7. 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.
$230 nightly
The price is $230
Oct 26 - Oct 27
Total with taxes and fees
Maho Beach House - Petit Studio Océanique - Charmante Vue
A pool area with a dolphin statue, blue lounge chairs, and a stone wall with greenery.

8. 5 minutes walking from the beach 1-4B

5 minutes walking from the beach 1-4B
Simpson Bay
$211 nightly
The price is $217
Oct 26 - Oct 27
Total with taxes and fees
5 minutes walking from the beach 1-4B
A poolside area with outdoor seating and a view of a hotel building and the sea.

9. 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.
$302 nightly
The price is $302
Oct 26 - Oct 27
Total with taxes and fees
Beach Front 2 Bed Condon C1.1 with Sea View and Private Pool !!
A table with two wine glasses and a bucket of ice, set against a scenic mountain view.

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

The Luxe 1 bedroom apartment with pool - GENERATOR (2-2A)
Simpson Bay
$217 nightly
The price is $223
Oct 26 - Oct 27
Total with taxes and fees
The Luxe 1 bedroom apartment with pool - GENERATOR (2-2A)
A swimming pool with lounge chairs and a stone wall.

11. 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
$217 nightly
The price is $223
Oct 26 - Oct 27
Total with taxes and fees
Blue Sky Apt in the middle of Simpson Bay-GENERATOR(1-3A)
A pool area with a stone wall, palm trees, and lounge chairs.

12. 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.
$205 nightly
The price is $210
Oct 26 - Oct 27
Total with taxes and fees
1 bedroom with pool in Simpson Bay - GENERATOR (1-3B)
A rooftop pool with a wooden deck, surrounded by lush greenery and a view of a town and hills in the distance.

13. C342 - Glorious Lagoon View Apartment with Balcony

C342 - Glorious Lagoon View Apartment with Balcony
Sint Maarten
$325 nightly
The price is $340
Nov 8 - Nov 9
Total with taxes and fees
C342 - Glorious Lagoon View Apartment with Balcony
A modern kitchen with a dining area, large windows with a view of a marina and hills.

14. D428 - Spacious 2-Bedroom Lagoon View with Balcony

D428 - Spacious 2-Bedroom Lagoon View with Balcony
Sint Maarten
7.0 out of 10, Good, (2 reviews)
"The location, view and hotel were very beautiful. But getting towels was extremely difficult, the home was not equipped with things like dustpan, bowls and things. I would stay again but I recommend an easier way of contacting the front desk for necessities. "
United Kingdom
Kaylin W.
$387 nightly
The price is $387
Nov 12 - Nov 13
Total with taxes and fees
D428 - Spacious 2-Bedroom Lagoon View with Balcony
A white building with a pool, surrounded by a garden with pink flowers and a view of the sea.

15. Blue Sail Apartments - Double Room

Blue Sail Apartments - Double Room
Pelican Key
2.0 out of 10, (1 review)
$121 nightly
The price is $121
Oct 26 - Oct 27
Total with taxes and fees
Blue Sail Apartments - Double Room
A multi-story hotel with balconies, a beach in front, and palm trees.

16. 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
$262 nightly
The price is $262
Oct 26 - Oct 27
Total with taxes and fees
Maho Beach House - Spacious 1 Bedroom Suite
A poolside area with a wooden table, lounge chairs, and a view of the ocean.

17. Blue Sail Apartments - 1-Bedroom Apartments

Blue Sail Apartments - 1-Bedroom Apartments
Pelican Key
$196 nightly
The price is $196
Oct 26 - Oct 27
Total with taxes and fees
Blue Sail Apartments - 1-Bedroom Apartments
A swimming pool with a view of a beach and a hotel in the background.

18. 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
$357 nightly
The price is $357
Oct 26 - Oct 27
Total with taxes and fees
Beach Front 2 Bed Condon D1.1 with Sea View and Private Pool !!
A beach view with a wooden structure in the foreground, clear turquoise water, and a distant boat.

19. Maho Beach House: Studio Getaway, Oceanfront Vibe

Maho Beach House: Studio Getaway, Oceanfront Vibe
Maho, Sint Maarten
10.0 out of 10, Exceptional, (2 reviews)
"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.
$243 nightly
The price is $243
Oct 26 - Oct 27
Total with taxes and fees
Maho Beach House: Studio Getaway, Oceanfront Vibe
A clear blue pool with a view of a marina and buildings in the background.

20. Beach Front 4 Bed Condon D2.1 with Sea View and Private Pool !!

Beach Front 4 Bed Condon D2.1 with Sea View and Private Pool !!
Simpson Bay
2.0 out of 10, (1 review)
$583 nightly
The price is $583
Oct 27 - Oct 28
Total with taxes and fees
Beach Front 4 Bed Condon D2.1 with Sea View and Private Pool !!
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 Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

8/10 Good
"I had a wonderful stay at this hotel! The room was clean and comfortable, the staff were friendly and welcoming, and the service was excellent. The atmosphere was pleasant and relaxing, making the entire experience enjoyable. I would definitely recommend this hotel and look forward to staying here again!"
Cislyn 3-night trip
Posted 1 hour ago
The Villas at Simpson Bay Resort

Price trends for vacation rentals in Simpson Bay

Less expensive
More expensive
Next month
October
February
$293
Month
Price
January
$523
February
$539
March
$419
April
$392
May
$304
June
$268
July
$256
August
$277
September
$281
October
$243
November
$293
December
$482
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 $141 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.

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.