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
13 Mar - 15 Mar
In two months
24 Apr - 26 Apr
In three months
22 May - 24 May
In four months
19 Jun - 21 Jun

Our top choices for Simpson Bay holiday rentals

On the beach, sun-loungers, beach umbrellas, beach towels

Aparthotel in Simpson Bay

Hilton Vacation Club Royal Palm St. Maarten
4.0 star property
9.0 out of 10, Wonderful, (1,184 reviews)
"Great staff, location and amenities."
United States
Deon Oliver
The price is HK$2,696
HK$3,036 total
includes taxes & fees
15 Mar - 16 Mar
Hilton Vacation Club Royal Palm St. Maarten
Balcony

Aparthotel in Simpson Bay

The Hills Residence
3.0 star property
8.6 out of 10, Excellent, (92 reviews)
"Great staff, would stay again!"
United States
Maimuna
The Hills Residence
Beach nearby, white sand, sun-loungers, beach umbrellas

Aparthotel in Simpson Bay

Simpson Bay Suites
3.5 star property
7.0 out of 10, Good, (138 reviews)
"Room was clean. Had a full living room and kitchen incl microwave. Convenient to kim-sha beach. "
United States
Dale
The price is HK$1,322
HK$1,481 total
includes taxes & fees
29 Mar - 30 Mar
Simpson Bay Suites
Exterior

Condo in Maho

Maho Beach Modern 1-Bedroom, Ocean Level
9.4 out of 10, Exceptional, (3 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.
The price is HK$2,258
HK$2,547 total
includes taxes & fees
2 Mar - 3 Mar
Maho Beach Modern 1-Bedroom, Ocean Level
Property grounds

Condo in Maho, Sint Maarten

Maho Beach House: Studio Getaway, Oceanfront Vibe
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.
The price is HK$2,910
HK$3,747 total
includes taxes & fees
18 Mar - 19 Mar
Maho Beach House: Studio Getaway, Oceanfront Vibe
Pool

Apartment in Simpson Bay

Oasis Apartment in Simpson bay (2-3)
The price is HK$1,799
HK$3,000 total
includes taxes & fees
2 Mar - 3 Mar
Oasis Apartment in Simpson bay (2-3)
Pool

Condo in Pelican Key

Blue Sail Apartments - Double room
The price is HK$739
HK$906 total
includes taxes & fees
1 Apr - 2 Apr
Blue Sail Apartments - Double room
Pool

Apartment in Simpson Bay

Beach Front 2 Bed Condon C1.1 with Sea View and Private Pool !!
8.4 out of 10, Very good, (5 reviews)
"Very good place. Service very good. Keep up the good work lisa"
United States
Carlos
The price is HK$3,122
HK$4,185 total
includes taxes & fees
5 Mar - 6 Mar
Beach Front 2 Bed Condon C1.1 with Sea View and Private Pool !!
WiFi, bed sheets

Apartment in Simpson Bay

Seafront Studio C4
10.0 out of 10, Exceptional, (3 reviews)
"My stay was amazing. Room was nice and cozy, located on strip near buccaneer beach. Everything was walking distance and the host was very kind and helpful and even gave me a gift. I traveled alone and felt extremely safe at this property. I will be returning!!"
United States
sacoya f.
The price is HK$696
HK$1,087 total
includes taxes & fees
2 Mar - 3 Mar
Seafront Studio C4
Property grounds

Condo in Simpson Bay

Maho Beach House: Elegant 1-Bedroom, Beach Level
The price is HK$2,582
HK$3,309 total
includes taxes & fees
17 Mar - 18 Mar
Maho Beach House: Elegant 1-Bedroom, Beach Level
Beach

Apartment in Simpson Bay

Beach Front 1 Bedroom Flat D3
10.0 out of 10, Exceptional, (1 review)
"Great spot! Clean, comfortable and well equipped. "
United States
Jill
The price is HK$979
HK$1,472 total
includes taxes & fees
12 Mar - 13 Mar
Beach Front 1 Bedroom Flat D3
A heated pool

Apartment in Sint Maarten

B242 - Glorious Lagoon View Apartment with Balcony
The price is HK$1,979
HK$3,104 total
includes taxes & fees
19 Mar - 20 Mar
B242 - Glorious Lagoon View Apartment with Balcony
Pool

Apartment in Simpson Bay

Modern apartment with shared pool and generator (2-2B)
The price is HK$1,574
HK$2,553 total
includes taxes & fees
9 Mar - 10 Mar
Modern apartment with shared pool and generator (2-2B)
Interior

Condo in Maho, Sint Maarten

Maho Beach Escape; Sunset Ocean View
10.0 out of 10, Exceptional, (4 reviews)
"Self check in and out was a nice experience "
United States
Kelva
The price is HK$2,065
HK$2,730 total
includes taxes & fees
2 Mar - 3 Mar
Maho Beach Escape; Sunset Ocean View
Pool

Apartment in Simpson Bay

Beach Front 2 Bed Condon D1.1 with Sea View and Private Pool !!
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$3,122
HK$4,185 total
includes taxes & fees
14 Mar - 15 Mar
Beach Front 2 Bed Condon D1.1 with Sea View and Private Pool !!
Property grounds

Condo in Maho, Sint Maarten

Maho Beach House: Sand Bar Suite, 2-Bedroom
The price is HK$3,586
HK$4,705 total
includes taxes & fees
23 Mar - 24 Mar
Maho Beach House: Sand Bar Suite, 2-Bedroom
Interior

Condo in Simpson Bay

Maho Beach Suite
The price is HK$4,741
HK$6,024 total
includes taxes & fees
3 Mar - 4 Mar
Maho Beach Suite
Beach

Apartment in Simpson Bay

Beach Front Studio C3
8.8 out of 10, Excellent, (3 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$775
HK$1,244 total
includes taxes & fees
10 Mar - 11 Mar
Beach Front Studio C3
Pool

Condo in Pelican Key

Blue Sail Apartments - 1 bedroom apartments
The price is HK$1,386
HK$1,589 total
includes taxes & fees
1 Apr - 2 Apr
Blue Sail Apartments - 1 bedroom apartments
Pool

Apartment in Simpson Bay

Beach Front 4 Bed Condon C2.1 with Sea View and Private Pool !!
10.0 out of 10, Exceptional, (3 reviews)
"Great location! a two minute walk to the beach. The host was very responsive and Lisa the caretaker was great! Property was like new very clean and well equipped"
United States
Janice A.
The price is HK$6,016
HK$8,105 total
includes taxes & fees
1 Apr - 2 Apr
Beach Front 4 Bed Condon C2.1 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.
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

Travel Inn Hotel

Travel Inn Hotel

10/10 Excellent
"Perfect for a stopover. Next to lots of restaurants and stores. Staff very helpful, thank you."
Andrew 1-night trip
Posted 10 hours ago
Travel Inn Hotel

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 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 Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool and White Sands Retreat - Beachside at Beacon Hill.

How many holiday rentals are there in Simpson Bay?

With 33 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.