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
Jul 17 - Jul 19
In two months
Aug 28 - Aug 30
In three months
Sep 25 - Sep 27
In four months
Oct 23 - Oct 25

Our top choices for Simpson Bay vacation rentals

Terrace/patio

Simpson Bay Suites

Simpson Bay Suites
3.5 star property
Simpson Bay
7.2 out of 10, Good, (159 reviews)
"AC worked well the room was cleaned daily and the staff was always friendly and made great suggestions for dinning and places to see."
United States
Michael
$130 nightly
The price is $136
Jul 6 - Jul 7
Total with taxes and fees
Simpson Bay Suites
Property grounds

Blue Sail Apartments - Double room

Blue Sail Apartments - Double room
Pelican Key
2.0 out of 10, (1 review)
$124 nightly
The price is $124
Jul 6 - Jul 7
Total with taxes and fees
Blue Sail Apartments - Double room
Interior

Maho Beach Suite

Maho Beach Suite
Simpson Bay
$525 nightly
The price is $525
Jul 7 - Jul 8
Total with taxes and fees
Maho Beach Suite
Property grounds

Turquoise paradise, directly ON beach, gated w underground parking!

Turquoise paradise, directly ON beach, gated w underground parking!
Simpson Bay
9.8 out of 10, Exceptional, (22 reviews)
"This is the perfect place to stay location wise and with the beach views! Also there is a/c in each room which is super nice! "
United States
Rachel S.
$526 nightly
The price is $526
Jul 7 - Jul 8
Total with taxes and fees
Turquoise paradise, directly ON beach, gated w underground parking!
Pool

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
$506 nightly
The price is $506
Jul 6 - Jul 7
Total with taxes and fees
Beach Front 2 Bed Condon D1.1 with Sea View and Private Pool !!
TV

B225 - Incredible Lagoon View

B225 - Incredible Lagoon View
Sint Maarten
$340 nightly
The price is $356
Jul 7 - Jul 8
Total with taxes and fees
B225 - Incredible Lagoon View
Pool

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
$216 nightly
The price is $222
Jul 17 - Jul 18
Total with taxes and fees
Blue Sky Apt in the middle of Simpson Bay-GENERATOR(1-3A)
Beach

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
$189 nightly
The price is $189
Jul 6 - Jul 7
Total with taxes and fees
Beach Front 1 Bedroom Flat D3
Amazing Top Floor Apartment | Balcony

The Hills Residence

The Hills Residence
3.0 star property
Simpson Bay
8.4 out of 10, Very Good, (154 reviews)
"We had a great stay definitely will be back!!"
United States
Lornella
$247 nightly
The price is $258
Jul 7 - Jul 8
Total with taxes and fees
The Hills Residence
Beach

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
Jul 6 - Jul 7
Total with taxes and fees
Beach Front Studio C3
On the beach, sun loungers, beach umbrellas, beach towels

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, (1,249 reviews)
"Great staff.. Great location..Great property"
United States
Wilbert
$155 nightly
The price is $162
Jul 18 - Jul 19
Total with taxes and fees
Hilton Vacation Club Royal Palm St. Maarten
Interior

Maho Beach Escape; Sunset Ocean View

Maho Beach Escape; Sunset Ocean View
Maho, Sint Maarten
10.0 out of 10, Exceptional, (4 reviews)
"Self check in and out was a nice experience "
United States
Kelva
$257 nightly
The price is $257
Jul 7 - Jul 8
Total with taxes and fees
Maho Beach Escape; Sunset Ocean View
Pool

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.
$210 nightly
The price is $216
Jul 7 - Jul 8
Total with taxes and fees
1 bedroom with pool in Simpson Bay - GENERATOR (1-3B)
Pool

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, (6 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.
$422 nightly
The price is $422
Jul 6 - Jul 7
Total with taxes and fees
Beach Front 2 Bed Condon C1.1 with Sea View and Private Pool !!
Pool

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)
$932 nightly
The price is $932
Jul 7 - Jul 8
Total with taxes and fees
Beach Front 4 Bed Condon D2.1 with Sea View and Private Pool !!
Outdoor dining

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
$144 nightly
The price is $144
Jul 6 - Jul 7
Total with taxes and fees
Blue Sail Apartments - Two bedroom apartments
Outdoor dining

Blue Sail Apartments - 1 bedroom apartments

Blue Sail Apartments - 1 bedroom apartments
Pelican Key
$200 nightly
The price is $200
Jul 6 - Jul 7
Total with taxes and fees
Blue Sail Apartments - 1 bedroom apartments
Pool

Beach Front 4 Bed Condon C2.1 with Sea View and Private Pool !!

Beach Front 4 Bed Condon C2.1 with Sea View and Private Pool !!
Simpson Bay
10.0 out of 10, Exceptional, (4 reviews)
$879 nightly
The price is $879
Jul 30 - Jul 31
Total with taxes and fees
Beach Front 4 Bed Condon C2.1 with Sea View and Private Pool !!
Interior

The Castle f

The Castle f
Downtown Philipsburg
8.0 out of 10, Very Good, (1 review)
"After a bit of confusion about checking in, we arrived and after that everything was great. It was a surprise to find the window was onto a corridor, but the air con was good so no need to open a window, and also helped to make the room quiet."
United Kingdom
Pat R.
$140 nightly
The price is $150
Jul 6 - Jul 7
Total with taxes and fees
The Castle f
Interior

The Castle ᴷ

The Castle ᴷ
Downtown Philipsburg
10.0 out of 10, Exceptional, (1 review)
$140 nightly
The price is $150
Jul 6 - Jul 7
Total with taxes and fees
The Castle ᴷ
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

8/10 Good
"I had a really good experience, but what took my score from 5 to a 4 was that my bathroom sink, the floor wasn’t clean, and the shower also wasn’t cleaned well because I saw hairs on the wall. I was able to rinse them off easily, so I felt like it wasn’t cleaned either. I always bring items to clean my room for instances like this, but I’ve never experienced a cleanliness issue like this. How did I know the bathroom sink wasn’t clean? I saw sandlike debris like someone washed their swimsuit in the sink. Other than that, everyone was kind and the grounds were maintained well. I ate at the restaurant everyday for breakfast and ate the Caribbean plate. The location was great for me. It was far enough from the main street that it was quiet at night. If you are located by the pool, you will hear everything during the day. That didn’t bother me since during the day I wasn’t in my room. When it was quiet at night and early mornings, I could hear the ocean crashing. It was a beautiful relaxing sound."
Jena 4-night trip
Posted 1 hour ago
Hilton Vacation Club Flamingo Beach St. Maarten

Price trends for vacation rentals in Simpson Bay

Less expensive
More expensive
This month
Next month
October
February
$256
$277
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 $89 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 lively bars and top-notch restaurants.

What are some of the best vacation home rentals that Simpson Bay has to offer?

Philips Scott House Calinago: This vacation home rental outside 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. Some other homes for rent in Simpson Bay include New Listing, Exceptional 3 bed & bath with private pool in Pelican Cove and Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool .

How many vacation rentals are there in Simpson Bay?

With 46 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.