Simpson Bay Holiday Rentals

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Check prices for these dates

In two weeks
22 May - 24 May
In two months
3 Jul - 5 Jul
In three months
31 Jul - 2 Aug
In four months
28 Aug - 30 Aug

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, (1,223 reviews)
"This resort is absolutely amazing, our family enjoyed every minute. The pool and swim up bar are great and the private beach was fantastic. Its very centrally located close to airport and bars/restaurants,"
Canada
Curtis
The price is HK$2,191
HK$2,507 total
includes taxes & fees
2 Jun - 3 Jun
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, (157 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$1,057
HK$1,184 total
includes taxes & fees
10 May - 11 May
Simpson Bay Suites
1 bedroom, in-room safe, iron/ironing board, WiFi

D416 – Relaxing apartment with Balcony

D416 – Relaxing apartment with Balcony
Sint Maarten
The price is HK$1,618
HK$2,947 total
includes taxes & fees
11 May - 12 May
D416 – Relaxing apartment with Balcony
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, (4 reviews)
"Great location. Spacious room. "
Canada
Sinisa
Maho Beach House - Spacious 1 Bedroom Suite
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.
The price is HK$1,305
HK$1,485 total
includes taxes & fees
7 May - 8 May
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)
"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$2,376
HK$3,371 total
includes taxes & fees
7 May - 8 May
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
9.4 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
Maho Beach House Ocean Front Garden Studio
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$980
HK$1,474 total
includes taxes & fees
7 May - 8 May
Beach Front 1 Bedroom Flat D3
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$3,330
HK$4,388 total
includes taxes & fees
1 Jun - 2 Jun
Turquoise paradise, directly ON beach, gated w underground parking!
On the beach, sun-loungers, beach towels

front-balcony beach view and the back-balcony main airport View

front-balcony beach view and the back-balcony main airport View
Simpson Bay
front-balcony beach view and the back-balcony main airport 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
Beach Front Studio C3
Pool

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$991
HK$1,156 total
includes taxes & fees
19 May - 20 May
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$901
HK$1,745 total
includes taxes & fees
11 May - 12 May
1 bedroom with pool in Simpson Bay - GENERATOR (1-3B)
Property grounds

Maho Beach House - Petit Studio Océanique - Charmante Vue

Maho Beach House - Petit Studio Océanique - Charmante Vue
Maho, Sint Maarten
9.4 out of 10, Exceptional, (3 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.
Maho Beach House - Petit Studio Océanique - Charmante Vue
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
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
Property grounds

Maho Beach House: Sunset Suite, 1-Bedroom

Maho Beach House: Sunset Suite, 1-Bedroom
Maho
10.0 out of 10, Exceptional, (1 review)
"We had a great stay. Noah and Dwayne were great to work with. They were quick to respond to any questions we had or help we needed. We enjoyed out daily walks and spent time enjoying 3 different beaches within walking distance as well great places to eat, drink and enjoy time in the sun."
United States
Dawn A.
Maho Beach House: Sunset Suite, 1-Bedroom
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 HK$2,813
HK$3,871 total
includes taxes & fees
14 May - 15 May
Beach Front 2 Bed Condon D1.1 with Sea View and Private Pool !!
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
Maho Beach Escape; Sunset Ocean View
Interior

Maho Beach Suite

Maho Beach Suite
Simpson Bay
The price is HK$2,868
HK$3,934 total
includes taxes & fees
26 May - 27 May
Maho Beach Suite
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

The Atrium Beach Resort and Spa, an Ascend Collection Resort

The Atrium Beach Resort and Spa, an Ascend Collection Resort

8/10 Good
"Great experience, friendly staff nice spacious rooms."
John-Ross 7-night trip
Posted 5 hours ago
The Atrium Beach Resort and Spa, an Ascend Collection 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
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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 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 New Listing, Exceptional 3 bed & bath with private pool in Pelican Cove.

How many holiday rentals are there in Simpson Bay?

With 41 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.