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

Simpson Bay Holiday Rentals

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Check prices for these dates

In two weeks
24 Jul - 26 Jul
In two months
4 Sept - 6 Sept
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

Our top choices for Simpson Bay holiday 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
The price is HK$953
HK$1,067 total
includes taxes & fees
10 Jul - 11 Jul
Simpson Bay Suites
Property grounds

Blue Sail Apartments - Double room

Blue Sail Apartments - Double room
Pelican Key
2.0 out of 10, (1 review)
The price is HK$808
HK$969 total
includes taxes & fees
9 Jul - 10 Jul
Blue Sail Apartments - Double room
Interior

Maho Beach Suite

Maho Beach Suite
Simpson Bay
The price is HK$3,388
HK$4,541 total
includes taxes & fees
14 Jul - 15 Jul
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.
The price is HK$3,098
HK$4,125 total
includes taxes & fees
14 Jul - 15 Jul
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
The price is HK$2,886
HK$3,968 total
includes taxes & fees
9 Jul - 10 Jul
Beach Front 2 Bed Condon D1.1 with Sea View and Private Pool !!
TV

B225 - Incredible Lagoon View

B225 - Incredible Lagoon View
Sint Maarten
The price is HK$1,434
HK$2,795 total
includes taxes & fees
16 Jul - 17 Jul
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
The price is HK$902
HK$1,747 total
includes taxes & fees
7 Aug - 8 Aug
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
The price is HK$981
HK$1,483 total
includes taxes & fees
15 Jul - 16 Jul
Beach Front 1 Bedroom Flat D3
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
The price is HK$1,328
HK$2,232 total
includes taxes & fees
19 Jul - 20 Jul
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
The price is HK$776
HK$1,247 total
includes taxes & fees
8 Aug - 9 Aug
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
The price is HK$1,423
HK$1,700 total
includes taxes & fees
31 Jul - 1 Aug
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
The price is HK$1,365
HK$1,969 total
includes taxes & fees
9 Jul - 10 Jul
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.
The price is HK$857
HK$1,692 total
includes taxes & fees
9 Jul - 10 Jul
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.
The price is HK$2,598
HK$3,641 total
includes taxes & fees
12 Jul - 13 Jul
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)
The price is HK$5,223
HK$7,309 total
includes taxes & fees
12 Jul - 13 Jul
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
The price is HK$969
HK$1,131 total
includes taxes & fees
9 Jul - 10 Jul
Blue Sail Apartments - Two bedroom apartments
Outdoor dining

Blue Sail Apartments - 1 bedroom apartments

Blue Sail Apartments - 1 bedroom apartments
Pelican Key
The price is HK$1,373
HK$1,562 total
includes taxes & fees
9 Jul - 10 Jul
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)
"Location worked out well close to airport. We were able to walk to beach and restaurants "
United States
Dominick C.
The price is HK$5,223
HK$7,309 total
includes taxes & fees
14 Jul - 15 Jul
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.
The price is HK$941
HK$1,173 total
includes taxes & fees
15 Jul - 16 Jul
The Castle f
Interior

The Castle ᴷ

The Castle ᴷ
Downtown Philipsburg
10.0 out of 10, Exceptional, (1 review)
The price is HK$941
HK$1,173 total
includes taxes & fees
15 Jul - 16 Jul
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

10/10 Excellent
"Villas were too far away to be comfortably walkable to common areas. Transport via golf cart should have been provided."
Anna Elizabeth 4-night trip
Posted 3 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 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 lively bars and top-notch restaurants.

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

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

With 46 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. Simpson Bay Beach and Hollywood Casino 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.