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

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
The price is SAR 456
SAR 511 total
includes taxes & fees
5 Jul - 6 Jul
Simpson Bay Suites
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, (1,248 reviews)
"Great staff.. Great location..Great property"
United States
Wilbert
The price is SAR 487
SAR 610 total
includes taxes & fees
18 Jul - 19 Jul
Hilton Vacation Club Royal Palm St. Maarten
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
The price is SAR 585
SAR 1,018 total
includes taxes & fees
6 Jul - 7 Jul
The Hills Residence
Property grounds

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 SAR 654
SAR 984 total
includes taxes & fees
2 Jul - 3 Jul
Maho Beach House - Spacious 1 Bedroom Suite
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 SAR 1,106
SAR 1,586 total
includes taxes & fees
2 Jul - 3 Jul
Beach Front 2 Bed Condon C1.1 with Sea View and Private Pool !!
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 SAR 372
SAR 597 total
includes taxes & fees
2 Jul - 3 Jul
Beach Front Studio C3
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 SAR 470
SAR 710 total
includes taxes & fees
2 Jul - 3 Jul
Beach Front 1 Bedroom Flat D3
Interior

Maho Beach Suite

Maho Beach Suite
Simpson Bay
The price is SAR 1,465
SAR 1,998 total
includes taxes & fees
7 Jul - 8 Jul
Maho Beach Suite
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 SAR 463
SAR 541 total
includes taxes & fees
2 Jul - 3 Jul
Blue Sail Apartments - Two bedroom apartments
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 SAR 1,484
SAR 1,976 total
includes taxes & fees
7 Jul - 8 Jul
Turquoise paradise, directly ON beach, gated w underground parking!
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 SAR 410
SAR 810 total
includes taxes & fees
7 Jul - 8 Jul
1 bedroom with pool in Simpson Bay - GENERATOR (1-3B)
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 SAR 432
SAR 833 total
includes taxes & fees
17 Jul - 18 Jul
Blue Sky Apt in the middle of Simpson Bay-GENERATOR(1-3A)
TV

B225 - Incredible Lagoon View

B225 - Incredible Lagoon View
Sint Maarten
The price is SAR 687
SAR 1,331 total
includes taxes & fees
1 Aug - 2 Aug
B225 - Incredible Lagoon View
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 SAR 699
SAR 991 total
includes taxes & fees
7 Jul - 8 Jul
Maho Beach Escape; Sunset Ocean View
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 SAR 1,383
SAR 1,901 total
includes taxes & fees
2 Jul - 3 Jul
Beach Front 2 Bed Condon D1.1 with Sea View and Private Pool !!
Pool

Sunset Beach View - Luxury Studio next to The Morgan Resort

Sunset Beach View - Luxury Studio next to The Morgan Resort
Maho, Sint Maarten
7.4 out of 10, Good, (3 reviews)
"Great unit. Exceeded all expectations. Beautiful view. Close to almost everything you might need. Staff support was over and above Would recommend this property and host to all"
United States
RAYMOND S.
The price is SAR 699
SAR 1,014 total
includes taxes & fees
2 Jul - 3 Jul
Sunset Beach View - Luxury Studio next to The Morgan Resort
Property grounds

Blue Sail Apartments - Double room

Blue Sail Apartments - Double room
Pelican Key
2.0 out of 10, (1 review)
The price is SAR 386
SAR 463 total
includes taxes & fees
2 Jul - 3 Jul
Blue Sail Apartments - Double room
Outdoor dining

Blue Sail Apartments - 1 bedroom apartments

Blue Sail Apartments - 1 bedroom apartments
Pelican Key
The price is SAR 656
SAR 751 total
includes taxes & fees
2 Jul - 3 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 SAR 2,326
SAR 3,303 total
includes taxes & fees
30 Jul - 31 Jul
Beach Front 4 Bed Condon C2.1 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 SAR 2,501
SAR 3,500 total
includes taxes & fees
2 Jul - 3 Jul
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

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

10/10 Excellent
"Room was clean and enough room for my wife and I and our two girls (6 and 10). Pullout bed was plenty comfortable. Room was a little warm, as the mini split wall unit didn’t seem strong enough to cool the room adequately, but there were two strong ceiling fans. Kids enjoyed the shallower pools. Bartenders were great. Pool bar service can be a little slow because there was only one bartender at a time when we were there, but great 2 for 1 drink specials daily at happy hour and friendly bartenders. Beach waters were typically clear and you could see fish, even when not snorkeling. Also a good location to plenty of restaurants within walking distance. We didn’t drive to dinner a single night during our 5 night stay. All in all a great spot and I would go back."
Kenneth 5-night trip
Posted 10 hours ago
Simpson Bay Resort, Marina & Spa

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 White Sands Retreat - Beachside at Beacon Hill and New Listing, Exceptional 3 bed & bath with private pool in Pelican Cove.

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. 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.