Simpson Bay Holiday Rentals

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Check prices for these dates

In two weeks
13 Feb - 15 Feb
In two months
27 Mar - 29 Mar
In three months
24 Apr - 26 Apr
In four months
22 May - 24 May

Our top choices for Simpson Bay holiday rentals

Balcony

The Hills Residence

The Hills Residence
3.0 star property
Simpson Bay
8.4 out of 10, Very good, (76 reviews)
"Great staff, would stay again!"
United States
Maimuna
The Hills Residence
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, (1,173 reviews)
"Room was great, resort was great, staff was great"
Canada
Gisele
The price is HK$2,687
HK$3,026 total
includes taxes & fees
12 Feb - 13 Feb
Hilton Vacation Club Royal Palm St. Maarten
Beach

Beach Front Studio C3

Beach Front Studio C3
Simpson Bay
10.0 out of 10, Exceptional, (2 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$772
HK$1,240 total
includes taxes & fees
6 Feb - 7 Feb
Beach Front Studio C3
Beach nearby, white sand, sun-loungers, beach umbrellas

Simpson Bay Suites

Simpson Bay Suites
3.5 star property
Simpson Bay
7.0 out of 10, Good, (132 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$1,318
HK$1,476 total
includes taxes & fees
8 Feb - 9 Feb
Simpson Bay Suites
Living area

Blue Sail Apartments - Double room

Blue Sail Apartments - Double room
Pelican Key
Blue Sail Apartments - Double room
Pool

Blue Sail Apartments - 1 bedroom apartments

Blue Sail Apartments - 1 bedroom apartments
Pelican Key
The price is HK$830
HK$996 total
includes taxes & fees
31 Jan - 1 Feb
Blue Sail Apartments - 1 bedroom apartments
Beach

Beach Front 1 Bedroom Flat D3

Beach Front 1 Bedroom Flat D3
Simpson Bay
10.0 out of 10, Exceptional, (1 review)
"Great spot! Clean, comfortable and well equipped. "
United States
Jill
The price is HK$975
HK$1,474 total
includes taxes & fees
5 Feb - 6 Feb
Beach Front 1 Bedroom Flat D3
Terrace/patio

Blue Sail Apartments - Two bedroom apartments

Blue Sail Apartments - Two bedroom apartments
Pelican Key
The price is HK$996
HK$1,162 total
includes taxes & fees
31 Jan - 1 Feb
Blue Sail Apartments - Two bedroom apartments
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$1,569
HK$2,513 total
includes taxes & fees
8 Feb - 9 Feb
1 bedroom with pool in Simpson Bay - GENERATOR (1-3B)
Smart TV, stereo, offices

Marina Views in the Heart of Simpson Bay

Marina Views in the Heart of Simpson Bay
Simpson Bay
10.0 out of 10, Exceptional, (1 review)
"We loved this place so much we bought it! The location is to die for. Right in the heart of Simpson Bay, there is soooo much to see and do right around you. The beach is literally a four minute walk and the water is calm and beautiful. We can’t wait to come back again and again! Also, Kayla, the manager is the best to work with. Sweet and helpful."
United States
Trish S.
Marina Views in the Heart of Simpson Bay
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$2,012
HK$2,651 total
includes taxes & fees
23 Feb - 24 Feb
Maho Beach House - Petit Studio Océanique - Charmante Vue
Exterior

Maho Beach Modern 1-Bedroom, Ocean Level

Maho Beach Modern 1-Bedroom, Ocean Level
Maho
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$2,294
HK$2,590 total
includes taxes & fees
29 Jan - 30 Jan
Maho Beach Modern 1-Bedroom, Ocean Level
Pool

A112 - Extraordinary Lagoon View with Balcony

A112 - Extraordinary Lagoon View with Balcony
Sint Maarten
A112 - Extraordinary Lagoon View with Balcony
Pool

B253 - Incredible Top Floor Lagoon Views

B253 - Incredible Top Floor Lagoon Views
Sint Maarten
B253 - Incredible Top Floor Lagoon Views
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
8.0 out of 10, Very good, (2 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$3,267
HK$4,343 total
includes taxes & fees
1 Feb - 2 Feb
Beach Front 2 Bed Condon C1.1 with Sea View and Private Pool !!
A heated pool

A101 - Outstanding Lagoon View & Garden

A101 - Outstanding Lagoon View & Garden
Sint Maarten
A101 - Outstanding Lagoon View & Garden
Pool

A116 - Immersive Simpson Bay Lagoon View

A116 - Immersive Simpson Bay Lagoon View
Sint Maarten
The price is HK$2,062
HK$3,176 total
includes taxes & fees
10 Feb - 11 Feb
A116 - Immersive Simpson Bay Lagoon View
Interior

C344 - Lagoon view with balcony

C344 - Lagoon view with balcony
Simpson Bay
The price is HK$2,116
HK$3,281 total
includes taxes & fees
9 Feb - 10 Feb
C344 - Lagoon view with balcony
Property grounds

2 BR 2 BA, beachfront condo, amazing oceanview, private beach access

2 BR 2 BA, beachfront condo, amazing oceanview, private beach access
Simpson Bay
9.6 out of 10, Exceptional, (17 reviews)
"Great location close to everything I will definitely be back love it."
United States
keenan j.
The price is HK$2,737
HK$3,989 total
includes taxes & fees
10 Feb - 11 Feb
2 BR 2 BA, beachfront condo, amazing oceanview, private beach access
Pool

A134 - Panoramic View of the Lagoon

A134 - Panoramic View of the Lagoon
Sint Maarten
A134 - Panoramic View of the Lagoon
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
"Nice room, helpful staff, good restaurants, convenient location, nice beach and amenities."
Silvana 7-night trip
Posted 1 day ago
Simpson Bay Resort, Marina & Spa

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?

Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool : This highly rated holiday home rental in Simpson Bay is located on the beach, and has an outdoor pool, a patio and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Other favourite homes for rent in Simpson Bay are New Listing, Exceptional 3 bed & bath with private pool in Pelican Cove and White Sands Retreat - Beachside at Beacon Hill.

How many holiday rentals are there in Simpson Bay?

With 39 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.