Simpson Bay Vacation Rentals

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Vacation Rentals in Simpson Bay

Outdoor pool, sun loungers
Hilton Vacation Club Royal Palm St. Maarten
Hilton Vacation Club Royal Palm St. Maarten
4.0 star property
9.0 out of 10, Wonderful, (1132)
"Amazing hotel and staff. "
$163 nightly
The price is $171
Oct 18 - Oct 19
Total with taxes and fees
Hilton Vacation Club Royal Palm St. Maarten
Amazing Top Floor Apartment | Balcony
The Hills Residence
The Hills Residence
3.0 star property
9.0 out of 10, Wonderful, (46)
"This apartment was nice, clean, modern, walking distance to restaurants and shops. "
The Hills Residence
Beach nearby, white sand, sun loungers, beach umbrellas
Simpson Bay Suites
Simpson Bay Suites
3.5 star property
6.8 out of 10, (124)
"Highly recommended and friendly staff…"
$116 nightly
The price is $121
Oct 15 - Oct 16
Total with taxes and fees
Simpson Bay Suites
Exterior
Tradewinds at Simpson Bay
Tradewinds at Simpson Bay
3.5 star property
9.4 out of 10, Exceptional, (28)
"We enjoyed the stay to the fullest"
Tradewinds at Simpson Bay
On the beach
Beachfront Ultra Luxury - New Modern 2 Bed/2.5 Bath
Beachfront Ultra Luxury - New Modern 2 Bed/2.5 Bath
9.6 out of 10, Exceptional, (14)
"I would stay here again"
Beachfront Ultra Luxury - New Modern 2 Bed/2.5 Bath
Property grounds
Maho Beach House - Spacious 1 Bedroom Suite
Maho Beach House - Spacious 1 Bedroom Suite
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...
Maho Beach House - Spacious 1 Bedroom Suite
Property grounds
Turquoise paradise, directly ON beach, gated w underground parking!
Turquoise paradise, directly ON beach, gated w underground parking!
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! "
$475 nightly
The price is $475
Oct 15 - Oct 16
Total with taxes and fees
Turquoise paradise, directly ON beach, gated w underground parking!
Orchid | View from room
The Horny Toad Guesthouse
The Horny Toad Guesthouse
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!"
The Horny Toad Guesthouse
Outdoor pool
Oceanfront amazing 2 BR Villa - 2 min from the beach
Oceanfront amazing 2 BR Villa - 2 min from the beach
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."
Oceanfront amazing 2 BR Villa - 2 min from the beach
Property grounds
Caribbean Sea Studio next to The Morgan Resort
Caribbean Sea Studio next to The Morgan Resort
8.0 out of 10, Very Good, (1)
Caribbean Sea Studio next to The Morgan Resort
Property grounds
Oceanfront amazing 2 bedrooms Condo
Oceanfront amazing 2 bedrooms Condo
9.6 out of 10, Exceptional, (59)
"Gorgeous property, great pool, and convenient location... walkable to maho beach! Would stay again!"
Oceanfront amazing 2 bedrooms Condo
Pool
Sunny Days at Simpson Bay Yacht Club
Sunny Days at Simpson Bay Yacht Club
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"
$433 nightly
The price is $452
Oct 15 - Oct 16
Total with taxes and fees
Sunny Days at Simpson Bay Yacht Club
On the beach, beach towels
One Hundred Million Dollar Yacht On Land 5 star Villa on the ocean
One Hundred Million Dollar Yacht On Land 5 star Villa on the ocean
9.8 out of 10, Exceptional, (77)
"We spent ten days in june 2025 at this home. Pool was amazing as was the location. Would definitely rent again. Thank you!"
One Hundred Million Dollar Yacht On Land 5 star Villa on the ocean
Outdoor pool
4 bedroom Pelican Key Private Luxury Villa, Panoramic View Of The Caribbean Sea
4 bedroom Pelican Key Private Luxury Villa, Panoramic View Of The Caribbean Sea
9.6 out of 10, Exceptional, (48)
"Amazing property! Amazing experience with Michael and peaches! Would recommend the property to anyone wanting a nice place to stay in Sint Maarten."
4 bedroom Pelican Key Private Luxury Villa, Panoramic View Of The Caribbean Sea
Outdoor dining
Large WATERFRONT 1BR/1Bath Apt in Beautiful St Martin in Simpson Bay
Large WATERFRONT 1BR/1Bath Apt in Beautiful St Martin in Simpson Bay
10.0 out of 10, Exceptional, (11)
"Will stay again. "
Large WATERFRONT 1BR/1Bath Apt in Beautiful St Martin in Simpson Bay
Beach
Pirates Booty - Beach Bar Studio next to The Morgan Resort
Pirates Booty - Beach Bar Studio next to The Morgan Resort
8.6 out of 10, Excellent, (4)
"Welcoming love the area we will be coming back thank you so much "
Pirates Booty - Beach Bar Studio next to The Morgan Resort
Terrace/patio
ALMA - DIRECT BEACH ACCESS 4 BR VILLA
ALMA - DIRECT BEACH ACCESS 4 BR VILLA
10.0 out of 10, Exceptional, (58)
"The house was beautiful and location was perfect. It was a short walk to beaches, shops, restaurants, and a market. Communication with the property team and housekeeping was easy and they were all super friendly. 10/10 would recommend! "
ALMA - DIRECT BEACH ACCESS 4 BR VILLA
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 !!
Beach Front 2 Bed Condon C1.1 with Sea View and Private Pool !!
Pool
1 bedroom with pool in Simpson Bay - GENERATOR
1 bedroom with pool in Simpson Bay - GENERATOR
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."
$217 nightly
The price is $223
Oct 15 - Oct 16
Total with taxes and fees
1 bedroom with pool in Simpson Bay - GENERATOR
Terrace/patio
Anchor House - Direct Oceanfront - Luxury & Modern Style
Anchor House - Direct Oceanfront - Luxury & Modern Style
10.0 out of 10, Exceptional, (146)
"The property itself was beautiful and the view was or if this world! Access to nightlife, beaches, restaurants was perfect. So quiet and peaceful. We were so sad to leave!"
Anchor House - Direct Oceanfront - Luxury & Modern Style
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

10/10 Excellent
"We keep coming back to the Atrium because the rooms are clean and comfortable, it is in a great location with lots of dining options around and the staff is very accommodating. It helps that parking is free and easy too!"
Louis 1-night trip
Posted 21 hours ago
The Atrium Beach Resort and Spa, an Ascend Collection Resort

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 $121 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?

Caribbean Sea Studio next to The Morgan Resort: Visitors like this Simpson Bay vacation home rental. It is located on the beach and has an outdoor pool, a patio, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Kick off your shoes and enjoy yourself with a garden and a hot tub. Other favorite homes for rent in Simpson Bay are Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool and White Sands Retreat - Beachside at Beacon Hill.

How many vacation rentals are there in Simpson Bay?

With 39 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?

Flamingo Beach and Simpson Bay Beach are a couple of lovely local spots to get outside and enjoy nature. Kim Sha Beach and Hollywood Casino are other places to visit while you're in town.

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.