Simpson Bay Holiday Rentals

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sept - 20 Sept
In four months
16 Oct - 18 Oct

Our top choices for Simpson Bay holiday rentals

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, (1,245 reviews)
"Great staff.. Great location..Great property"
United States
Wilbert
The price is HK$1,016
HK$1,273 total
includes taxes & fees
18 Jul - 19 Jul
Hilton Vacation Club Royal Palm St. Maarten
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$952
HK$1,067 total
includes taxes & fees
4 Jul - 5 Jul
Simpson Bay Suites
Balcony

The Hills Residence

The Hills Residence
3.0 star property
Simpson Bay
8.4 out of 10, Very good, (151 reviews)
"We had a great stay definitely will be back!!"
United States
Lornella
The price is HK$1,328
HK$2,231 total
includes taxes & fees
4 Jul - 5 Jul
The Hills Residence
Interior

Maho Beach Suite

Maho Beach Suite
Simpson Bay
Maho Beach Suite
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 HK$1,364
HK$2,053 total
includes taxes & fees
24 Jun - 25 Jun
Maho Beach House - Spacious 1 Bedroom 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$3,097
HK$4,124 total
includes taxes & fees
7 Jul - 8 Jul
Turquoise paradise, directly ON beach, gated w underground parking!
Property grounds

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
The price is HK$1,223
HK$1,803 total
includes taxes & fees
24 Jun - 25 Jun
Maho Beach House Ocean Front Garden Studio
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$2,308
HK$3,311 total
includes taxes & fees
25 Jun - 26 Jun
Beach Front 2 Bed Condon C1.1 with Sea View and Private Pool !!
TV

D416 – Relaxing apartment with Balcony

D416 – Relaxing apartment with Balcony
Sint Maarten
The price is HK$1,434
HK$2,731 total
includes taxes & fees
28 Jun - 29 Jun
D416 – Relaxing apartment with Balcony
Pool

B201 - Wonderfull Apartment with terrasse

B201 - Wonderfull Apartment with terrasse
Sint Maarten
The price is HK$1,758
HK$3,217 total
includes taxes & fees
6 Jul - 7 Jul
B201 - Wonderfull Apartment with terrasse
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$968
HK$1,129 total
includes taxes & fees
24 Jun - 25 Jun
Blue Sail Apartments - Two bedroom apartments
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$1,475 total
includes taxes & fees
24 Jun - 25 Jun
Beach Front 1 Bedroom Flat D3
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$1,746 total
includes taxes & fees
24 Jun - 25 Jun
Blue Sky Apt in the middle of Simpson Bay-GENERATOR(1-3A)
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
24 Jun - 25 Jun
Beach Front Studio C3
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$856
HK$1,699 total
includes taxes & fees
7 Jul - 8 Jul
1 bedroom with pool in Simpson Bay - GENERATOR (1-3B)
Exterior

Maho Beach Modern 1-Bedroom, Ocean Level

Maho Beach Modern 1-Bedroom, Ocean Level
Maho
9.6 out of 10, Exceptional, (4 reviews)
"The Maho was very clean, quiet and close to the airport. I recommend for people passing through or for a few days on St. Martins."
United States
David V.
Maho Beach Modern 1-Bedroom, Ocean Level
TV

B225 - Incredible Lagoon View

B225 - Incredible Lagoon View
Sint Maarten
The price is HK$2,174
HK$3,640 total
includes taxes & fees
1 Jul - 2 Jul
B225 - Incredible Lagoon View
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.
Sunset Beach View - Luxury Studio next to The Morgan Resort
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$1,458
HK$2,070 total
includes taxes & fees
30 Jun - 1 Jul
Maho Beach Escape; Sunset Ocean View
Outdoor dining

Blue Sail Apartments - 1 bedroom apartments

Blue Sail Apartments - 1 bedroom apartments
Pelican Key
The price is HK$1,371
HK$1,568 total
includes taxes & fees
24 Jun - 25 Jun
Blue Sail Apartments - 1 bedroom apartments
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
"Best choice in Simpson Bay"
Viktor 8-night trip
Posted 2 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 White Sands Retreat - Beachside at Beacon Hill and New Listing, Exceptional 3 bed & bath with private pool in Pelican Cove.

How many holiday rentals are there in Simpson Bay?

With 47 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.