Simpson Bay Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
17 Apr - 19 Apr
In two months
29 May - 31 May
In three months
26 Jun - 28 Jun
In four months
24 Jul - 26 Jul

Our top choices for Simpson Bay holiday rentals

Balcony

The Hills Residence

The Hills Residence
3.0 star property
Simpson Bay
8.6 out of 10, Excellent, (106 reviews)
"Clean rooms, amazing views, and responsive staff! Will be staying again next time. "
United States
Nicole
The price is HK$1,220
HK$2,152 total
includes taxes & fees
7 Apr - 8 Apr
The Hills Residence
Terrace/patio

Simpson Bay Suites

Simpson Bay Suites
3.5 star property
Simpson Bay
7.0 out of 10, Good, (151 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$1,325
HK$1,484 total
includes taxes & fees
8 Apr - 9 Apr
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, (1,199 reviews)
"rooms were spacious and very nice staff"
United States
Morgan
The price is HK$3,755
HK$4,149 total
includes taxes & fees
30 Apr - 1 May
Hilton Vacation Club Royal Palm St. Maarten
Property grounds

Maho Beach House - Petit Studio Océanique - Charmante Vue

Maho Beach House - Petit Studio Océanique - Charmante Vue
Maho, Sint Maarten
9.0 out of 10, Wonderful, (2 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.
The price is HK$1,928
HK$2,571 total
includes taxes & fees
5 Apr - 6 Apr
Maho Beach House - Petit Studio Océanique - Charmante Vue
Outdoor dining

Coco Beachside Duplex

Coco Beachside Duplex
Simpson Bay
9.4 out of 10, Exceptional, (17 reviews)
"Right on the beach with beautiful view, very spacious living and sleeping quarters, clean and abundantly equipped."
United States
Carla
The price is HK$2,845
HK$3,237 total
includes taxes & fees
21 Apr - 22 Apr
Coco Beachside Duplex
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
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)
"Very good place. Service very good. Keep up the good work lisa"
United States
Carlos
Beach Front 2 Bed Condon C1.1 with Sea View and Private Pool !!
Property grounds

Maho Beach House Ocean Front Garden Studio

Maho Beach House Ocean Front Garden Studio
Maho, Sint Maarten
9.0 out of 10, Wonderful, (2 reviews)
"The location was very good. Located right by the Sunset Beach Bar and the arrival of the planes. The unit, itself, was great. Roomy for two. Nice patio area to watch the planes. The people that work in the building were very obliging and hospitable."
United States
Robin P.
The price is HK$1,486
HK$2,097 total
includes taxes & fees
14 Apr - 15 Apr
Maho Beach House Ocean Front Garden Studio
Pool

Blue Sail Apartments - Two bedroom apartments

Blue Sail Apartments - Two bedroom apartments
Pelican Key
8.0 out of 10, Very good, (2 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$1,090
HK$1,254 total
includes taxes & fees
1 May - 2 May
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, (2 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
Beach Front 1 Bedroom Flat D3
Pool

A116 - Immersive Simpson Bay Lagoon View

A116 - Immersive Simpson Bay Lagoon View
Sint Maarten
The price is HK$1,619
HK$2,917 total
includes taxes & fees
9 Apr - 10 Apr
A116 - Immersive Simpson Bay Lagoon View
Beach

Beach Front Studio C3

Beach Front Studio C3
Simpson Bay
8.8 out of 10, Excellent, (5 reviews)
"Clean and modern. Need a door for the bathroom. Check in was easy and Lisa was there to help us get checked in. She even provided 2 cold water and 2 cold beers"
United States
Norman
The price is HK$776
HK$1,246 total
includes taxes & fees
2 May - 3 May
Beach Front Studio C3
Pool

C321 - Spectacular Apartment with Lagoon Views

C321 - Spectacular Apartment with Lagoon Views
Sint Maarten
C321 - Spectacular Apartment with Lagoon Views
Pool

B236 - Homely Apartment with Balcony

B236 - Homely Apartment with Balcony
Sint Maarten
B236 - Homely Apartment with Balcony
Living area

B204 - Amazing 1 Bedroom with terrace

B204 - Amazing 1 Bedroom with terrace
Sint Maarten
The price is HK$1,665
HK$3,014 total
includes taxes & fees
16 Apr - 17 Apr
B204 - Amazing 1 Bedroom with terrace
Interior

C307 – Incredible 2 Bedroom with Terrace

C307 – Incredible 2 Bedroom with Terrace
Sint Maarten
The price is HK$2,127
HK$3,627 total
includes taxes & fees
16 Apr - 17 Apr
C307 – Incredible 2 Bedroom with Terrace
A heated pool

B246 - Breathtaking Lagoon View with Balcony

B246 - Breathtaking Lagoon View with Balcony
Sint Maarten
The price is HK$1,619
HK$2,916 total
includes taxes & fees
13 Apr - 14 Apr
B246 - Breathtaking Lagoon View with Balcony
Property grounds

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.
Maho Beach House: Studio Getaway, Oceanfront Vibe
TV

C347 – Stylish 2 Bedroom

C347 – Stylish 2 Bedroom
Sint Maarten
C347 – Stylish 2 Bedroom
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.
1 bedroom with pool in Simpson Bay - GENERATOR (1-3B)
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Simpson Bay Hotel Reviews

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

10/10 Excellent
"Clean room helpful staff, helped you with getting taxi. Nice pool and room and air condition rooms"
Dion 4-night trip
Posted 3 hours ago
The Villas at Simpson Bay Resort

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
  • Use the map to find apartments and other holiday homes in the Simpson Bay neighbourhood you prefer
  • 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 top-notch restaurants and lively bars.

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 Dream Beachfront Home : Stunning sea views, private pool and walking distance .

How many holiday rentals are there in Simpson Bay?

With 40 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. Hollywood Casino and Simpson Bay Beach 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.