Simpson Bay Vacation Rentals

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Vacation Rentals in Simpson Bay

Hilton Vacation Club Royal Palm St. Maarten

4.0 star property
Simpson Bay
9.0 out of 10, Wonderful, (1152)
"Beautiful vacation "
Canada
alonzo
$161 nightly
The price is $169
Dec 17 - Dec 18
Total with taxes and fees
Hilton Vacation Club Royal Palm St. Maarten

The Hills Residence

3.0 star property
Simpson Bay
9.0 out of 10, Wonderful, (49)
"This apartment was nice, clean, modern, walking distance to restaurants and shops. "
United States
Lionel
$249 nightly
The price is $261
Dec 19 - Dec 20
Total with taxes and fees
The Hills Residence

Tradewinds at Simpson Bay

3.5 star property
Simpson Bay
9.4 out of 10, Exceptional, (30)
"This place is amazing. Great price. Super helpful and flexible owner and staff. They truly did everything to help and make my stay perfect. The room was clean. The bed was very comfortable. There's beautiful sunset view from this property. Great seafood restaurant next door. I'll definitely be back. 10 out of 10"
United States
hanan
Tradewinds at Simpson Bay

Simpson Bay Suites

3.5 star property
Simpson Bay
6.8 out of 10, (125)
"No issues. Staff were very welcoming and accommodating. Was a pleasant stay. "
United States
Sharmain
$130 nightly
The price is $136
Nov 20 - Nov 21
Total with taxes and fees
Simpson Bay Suites

Oceanfront amazing 2 BR Villa - 2 min from the beach

Beacon Hill
9.4 out of 10, Exceptional, (96)
"Good stay nice place property is comfortable, quiet, private, easily accessible, amenities worked well, kitchen very well equipment. Enjoyed my stay so did my group."
United States
Nicolas C.
Oceanfront amazing 2 BR Villa - 2 min from the beach

Maho Beach House - Spacious 1 Bedroom Suite

Maho, Sint Maarten
10.0 out of 10, Exceptional, (3)
"I booked this very last minute for a short (2 night) stay. They were very quick to reply and confirm. It was a big place for a one bedroom on a island. It was very clean, well decorated and with a nice view of the ocean and planes coming in to land. The air-conditioning worked well and I was happy to find the bedroom had a ceiling fan. The location worked well for me, there was a charge for parking, but it is gated and guarded. When I had an issue logging onto the wifi I sent a msg via the VRBO...
United States
Ben B.
Maho Beach House - Spacious 1 Bedroom Suite

Beachfront Ultra Luxury - New Modern 2 Bed/2.5 Bath

Simpson Bay
9.6 out of 10, Exceptional, (14)
"Was very clean and close to the beach and D's Beach Bar."
United States
Ray
Beachfront Ultra Luxury - New Modern 2 Bed/2.5 Bath

The Horny Toad Guesthouse

3.0 star property
Simpson Bay
9.4 out of 10, Exceptional, (53)
"We like it being beachfront, wide verandas, spacious unit, host and staff were excellent!"
United States
Melanie Pacoli
The Horny Toad Guesthouse

Oceanfront amazing 2 bedrooms Condo

Beacon Hill
9.6 out of 10, Exceptional, (60)
"Kitchen set up was good, clean and so nice set up very spacious, Very very responsive, respectful and so welcoming."
Canada
Ion
Oceanfront amazing 2 bedrooms Condo

Turquoise paradise, directly ON beach, gated w underground parking!

Simpson Bay
9.8 out of 10, Exceptional, (20)
"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.
$519 nightly
The price is $519
Nov 20 - Nov 21
Total with taxes and fees
Turquoise paradise, directly ON beach, gated w underground parking!

Sunny Days at Simpson Bay Yacht Club

Simpson Bay
10.0 out of 10, Exceptional, (2)
"This is a great location to come to: comfortable central location lots to do around restaurant everything you would need in a getaway I will definitely here again"
United States
JEROME J.
$483 nightly
The price is $504
Nov 20 - Nov 21
Total with taxes and fees
Sunny Days at Simpson Bay Yacht Club

Anchor House - Direct Oceanfront - Luxury & Modern Style

Cupecoy
10.0 out of 10, Exceptional, (146)
"You know you are in the right place as soon as you enter the courtyard of the property. The view is absolutely breathtaking. We found it hard to leave for some of the fun activities we took part in. Always happy to return to this beautiful spot in the sun."
United States
Nancy J.
Anchor House - Direct Oceanfront - Luxury & Modern Style

4 bedroom Pelican Key Private Luxury Villa, Panoramic View Of The Caribbean Sea

Pelican Key
9.6 out of 10, Exceptional, (49)
"Amazing property! Amazing experience with Michael and peaches! Would recommend the property to anyone wanting a nice place to stay in Sint Maarten."
Canada
Andre D.
4 bedroom Pelican Key Private Luxury Villa, Panoramic View Of The Caribbean Sea

1 bedroom with pool in Simpson Bay - GENERATOR (1-3B)

Simpson Bay
10.0 out of 10, Exceptional, (1)
"Communication with the host was very easy. The location is outstanding and the facility has every amenity. You can imagine. I highly recommend this property and can’t wait to visit again."
United States
Richard S.
$217 nightly
The price is $223
Nov 20 - Nov 21
Total with taxes and fees
1 bedroom with pool in Simpson Bay - GENERATOR (1-3B)

Newly Renovated Pelican Key Studio, near the beach. The best area on Dutch side!

Pelican Key
Newly Renovated Pelican Key Studio, near the beach. The best area on Dutch side!

Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool

Simpson Bay
10.0 out of 10, Exceptional, (3)
"This was an excellent place to bring our family to ! The beautiful house was spacious with multiple bedrooms and a large living area. The outside space was also great with a really nice pool for adults and kids and lots of outdoor seating . There is also access to the beach! We really enjoyed our stay and the view was spectacular !! Eli was always available to answer questions and help to make our stay memorable !"
Canada
Janet M.
Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool

Large WATERFRONT 1BR/1Bath Apt in Beautiful St Martin in Simpson Bay

Simpson Bay
10.0 out of 10, Exceptional, (11)
"Will stay again. "
United States
Ruslan
Large WATERFRONT 1BR/1Bath Apt in Beautiful St Martin in Simpson Bay

One Hundred Million Dollar Yacht On Land 5 star Villa Namaste on the Ocean

Pelican Key
9.8 out of 10, Exceptional, (77)
"Great property, the amenities were first rate and the pool and lounge area were fantastic. Everything one would need like restaurants, food markets, with adult beverages and a bakery are close by."
United States
Norman T.
One Hundred Million Dollar Yacht On Land 5 star Villa Namaste on the Ocean

Pirates Booty - Beach Bar Studio next to The Morgan Resort

Simpson Bay
8.6 out of 10, Excellent, (4)
"Welcoming love the area we will be coming back thank you so much "
United States
Juan D.
$239 nightly
The price is $239
Nov 20 - Nov 21
Total with taxes and fees
Pirates Booty - Beach Bar Studio next to The Morgan Resort

Cliff House

3.5 star property
Simpson Bay
8.8 out of 10, Excellent, (3)
"Amazing location. Views of the bay and the ocean on each side. Walkable to Maho restaurants and grocery. Would stay again"
United States
Cami
Cliff House
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

Price trends for vacation rentals in Simpson Bay

Less expensive
More expensive
Next month
September
January
$410
Month
Price
January
$444
February
$405
March
$391
April
$296
May
$245
June
$256
July
$169
August
$170
September
$155
October
$166
November
$242
December
$410
Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed vacation rentals in Simpson Bay. Select dates and complete search for nightly totals inclusive of taxes and fees.

Find out more about Simpson Bay

Everything you need to know about Simpson Bay vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Simpson Bay vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Simpson Bay vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Simpson Bay vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Simpson Bay. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Simpson Bay in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $136 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Simpson Bay rentals

At Expedia, we put the best Simpson Bay vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Simpson Bay rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Simpson Bay vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Simpson Bay. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a vacation rental in Simpson Bay?

Yes, we give you a choice of vacation rentals near top attractions in Simpson Bay, or you can choose a secluded option if you'd like a relaxing place to 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 vacation home rentals that Simpson Bay has to offer?

Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool : Visitors like this Simpson Bay vacation home rental. It is located on the beach and has an outdoor pool, a patio, and a barbecue grill 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 you can cook with friends or family. Other favorite homes for rent in Simpson Bay are White Sands Retreat - Beachside at Beacon Hill and Charming 3BR Villa w Private Pool in Pelican Key.

How many vacation rentals are there in Simpson Bay?

With 37 Expedia vacation rentals, you're sure 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. In the larger area, you’ll find popular places like Maho Beach and Orient Bay Beach.

What’s a vacation rental in Simpson Bay like?

A vacation rental is a private property where you can stay for a few weeks or just a few days in Simpson Bay. Vacation rentals offer amenities such as patios, hot tubs, and fire pits so you'll have all the conveniences of home. If you're concerned about cleanliness, vacation rentals can offer a sense of security away from public hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great choice for families.