Simpson Bay Vacation Rentals

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Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Vacation Rentals in Simpson Bay

Outdoor pool, sun loungers
Hilton Vacation Club Royal Palm St. Maarten

Aparthotel in Simpson Bay

4.0 star property
9.0 out of 10, Wonderful, (1157)
"Beautiful vacation "
Canada
alonzo
$206 nightly
The price is $216
Dec 18 - Dec 19
Total with taxes and fees
Hilton Vacation Club Royal Palm St. Maarten
Amazing Top Floor Apartment | Balcony
The Hills Residence

Aparthotel in Simpson Bay

3.0 star property
8.8 out of 10, Excellent, (51)
"Enjoyed my stay "
United States
Shakia
$256 nightly
The price is $268
Dec 8 - Dec 9
Total with taxes and fees
The Hills Residence
Exterior
Tradewinds at Simpson Bay

Condo in Simpson Bay

3.5 star property
9.4 out of 10, Exceptional, (31)
"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
Beach nearby, white sand, sun loungers, beach umbrellas
Simpson Bay Suites

Aparthotel in Simpson Bay

3.5 star property
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
Dec 4 - Dec 5
Total with taxes and fees
Simpson Bay Suites
Outdoor pool
Oceanfront amazing 2 BR Villa - 2 min from the beach

Villa in Beacon Hill

9.4 out of 10, Exceptional, (96)
"Overall the location was great, the property manager Stacey was super friendly and very responsive to our needs. The only negative thing i will say is that the property is a little dated and is in need of a minor touch up."
United States
Ella M.
Oceanfront amazing 2 BR Villa - 2 min from the beach
Property grounds
Maho Beach House - Spacious 1 Bedroom Suite

Condo in 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.
$288 nightly
The price is $288
Dec 4 - Dec 5
Total with taxes and fees
Maho Beach House - Spacious 1 Bedroom Suite
Pool
Sunny Days at Simpson Bay Yacht Club

Condo in 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.
Sunny Days at Simpson Bay Yacht Club
On the beach
Beachfront Ultra Luxury - New Modern 2 Bed/2.5 Bath

Condo in Simpson Bay

9.6 out of 10, Exceptional, (14)
"The stay was very wonderful , property very clean as describe in the pictures 100% , Lisa was very helpful and responsive as well I will be booking again !"
United States
Dija T.
Beachfront Ultra Luxury - New Modern 2 Bed/2.5 Bath
Orchid | View from room
The Horny Toad Guesthouse

Apartment in Simpson Bay

3.0 star property
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
Property grounds
Turquoise paradise, directly ON beach, gated w underground parking!

Apartment in 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.
$632 nightly
The price is $632
Dec 4 - Dec 5
Total with taxes and fees
Turquoise paradise, directly ON beach, gated w underground parking!
Outdoor dining
Large WATERFRONT 1BR/1Bath Apt in Beautiful St Martin in Simpson Bay

Condo in 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
Property grounds
Oceanfront amazing 2 bedrooms Condo

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

Apartment in 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.
$231 nightly
The price is $237
Dec 4 - Dec 5
Total with taxes and fees
1 bedroom with pool in Simpson Bay - GENERATOR (1-3B)
On the beach, beach towels
One Hundred Million Dollar Yacht On Land 5 star Villa Namaste on the Ocean

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

Apartment in Pelican Key

Newly Renovated Pelican Key Studio, near the beach. The best area on Dutch side!
Outdoor pool
4 bedroom Pelican Key Private Luxury Villa, Panoramic View Of The Caribbean Sea

Villa in 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
On the beach
Gorgeous Beachfront Ground Floor 2 Bedroom 2 Bath Condo

Condo in Philipsburg

10.0 out of 10, Exceptional, (14)
"Can't beat this location and view."
United States
Tyler M.
Gorgeous Beachfront Ground Floor 2 Bedroom 2 Bath Condo
Terrace/patio
Anchor House - Direct Oceanfront - Luxury & Modern Style

Condo in Cupecoy

10.0 out of 10, Exceptional, (146)
"Anchor House is a truly spectacular. The home is spacious and beautifully decorated. Our family’s favorite activity was spending time in the pool overlooking the ocean and relaxing on the deck. The views are amazing. Any issues that arose were quickly addressed. It is helpful to rent a car to get around. We had a fabulous vacation and highly recommend this property!"
United States
Jill C.
Anchor House - Direct Oceanfront - Luxury & Modern Style
Beach
Pirates Booty - Beach Bar Studio next to The Morgan Resort

Condo in 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.
$243 nightly
The price is $243
Dec 4 - Dec 5
Total with taxes and fees
Pirates Booty - Beach Bar Studio next to The Morgan Resort
Pool
Beach Front 2 Bed Condon C1.1 with Sea View and Private Pool !!

Apartment in Simpson Bay

6.0 out of 10, (1)
"The internet should be improve "
United States
Joelys A.
Beach Front 2 Bed Condon C1.1 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.
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Top Simpson Bay Hotel Reviews

Commodore Suites

Commodore Suites

10/10 Excellent
"Room spotless, staff helpful as needed assistance with tv. The location is great with restaurants, bars and shopping a short walk away. Room is large."
Judith 2-night trip
Posted 2 days ago
Commodore Suites

Price trends for vacation rentals in Simpson Bay

Less expensive
More expensive
This month
Next month
November
February
$425
$427
Month
Price
January
$427
February
$447
March
$420
April
$374
May
$278
June
$283
July
$307
August
$245
September
$171
October
$198
November
$170
December
$425
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 $66 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.

Explore a world of travel with Expedia

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?

White Sands Retreat - Beachside at Beacon Hill: Visitors like this Simpson Bay vacation home rental. It is located on the beach and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of games. Other favorite homes for rent in Simpson Bay are Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool and Charming 3BR Villa w Private Pool in Pelican Key.

How many vacation rentals are there in Simpson Bay?

With 36 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.