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
Simpson Bay
9.0 out of 10, Wonderful, (1149)
"Beautiful vacation "
Canada
alonzo
$135 nightly
The price is $141
Dec 15 - Dec 16
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
Simpson Bay
9.0 out of 10, Wonderful, (49)
"Love the view first of all. Property was in a great location. "
United States
Kevin
$259 nightly
The price is $271
Dec 15 - Dec 16
Total with taxes and fees
The Hills Residence
Exterior
Tradewinds at Simpson Bay

Tradewinds at Simpson Bay

3.5 star property
Simpson Bay
9.4 out of 10, Exceptional, (29)
"We enjoyed the stay to the fullest"
United States
Andreas
Tradewinds at Simpson Bay
Beach nearby, white sand, sun loungers, beach umbrellas
Simpson Bay Suites

Simpson Bay Suites

3.5 star property
Simpson Bay
6.8 out of 10, (125)
"It’s very nice staff and friendly, it is highly recommended…"
United States
ARMANDO
$144 nightly
The price is $151
Nov 17 - Nov 18
Total with taxes and fees
Simpson Bay Suites
Outdoor pool
Oceanfront amazing 2 BR Villa - 2 min from the beach

Oceanfront amazing 2 BR Villa - 2 min from the beach

Beacon Hill
9.4 out of 10, Exceptional, (96)
"Loved the Cliff house. The view and easy access to the Dutch side and French side. Will definitely stay here again!!!!"
United States
james t.
Oceanfront amazing 2 BR Villa - 2 min from the beach
Property grounds
Maho Beach House - Spacious 1 Bedroom Suite

Maho Beach House - Spacious 1 Bedroom Suite

Maho, Sint Maarten
10.0 out of 10, Exceptional, (3)
"I recently had the pleasure of staying at a rental in Sint Maarten, and it was an unforgettable experience. The property was stunning, offering breathtaking views and a peaceful atmosphere that made me feel completely at home. The location was ideal—close to beautiful beaches, great restaurants, and all the attractions I wanted to explore on the island.What truly made my trip exceptional, however, was the outstanding help I received from Kaya. As a solo traveler, I really appreciated how...
United States
Toralei H.
Maho Beach House - Spacious 1 Bedroom Suite
On the beach
Beachfront Ultra Luxury - New Modern 2 Bed/2.5 Bath

Beachfront Ultra Luxury - New Modern 2 Bed/2.5 Bath

Simpson Bay
9.6 out of 10, Exceptional, (14)
"Bery nice facility and kitchen and kitchen accessories arebGreat..Check-in was a good process"
United States
Valencia F.
Beachfront Ultra Luxury - New Modern 2 Bed/2.5 Bath
Orchid | View from room
The Horny Toad Guesthouse

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
Property grounds
Oceanfront amazing 2 bedrooms Condo

Oceanfront amazing 2 bedrooms Condo

Beacon Hill
9.6 out of 10, Exceptional, (60)
"the condo is fantastic. It was clean had everything you need. Large outdoor patio over looking the ocean, roof top infinity pool was a fantastic place to go and relax. The location is walking distance to restaurants and bars. over all it is a great place to stay. The only con is the beds are very hard. I would definitely go back."
Canada
Richard I.
Oceanfront amazing 2 bedrooms Condo
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, (20)
"Its was absolutely perfert for our family needs. The owner easyr eTe erweeu easy to work with. So cute !lwwaudlrsrlf"
United States
Debra C.
$519 nightly
The price is $519
Nov 17 - Nov 18
Total with taxes and fees
Turquoise paradise, directly ON beach, gated w underground parking!
Pool
Sunny Days at Simpson Bay Yacht Club

Sunny Days at Simpson Bay Yacht Club

Simpson Bay
10.0 out of 10, Exceptional, (2)
"Hope u guys keep up the good work loved it"
United States
Larssrisa A.
$477 nightly
The price is $498
Nov 17 - Nov 18
Total with taxes and fees
Sunny Days at Simpson Bay Yacht Club
Terrace/patio
Anchor House - Direct Oceanfront - Luxury & Modern Style

Anchor House - Direct Oceanfront - Luxury & Modern Style

Cupecoy
10.0 out of 10, Exceptional, (146)
"Such a beautiful home and it looks exactly like the pictures! The neighborhood is quiet, safe, and just a short walk to the beach & restaurants! We loved our stay here!"
United States
Amber M.
Anchor House - Direct Oceanfront - Luxury & Modern Style
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

Pelican Key
9.6 out of 10, Exceptional, (49)
"Location of property is great close to restaurants and shopping. Great sunsets and ocean views of ships and islands. We had a great time with two other couples."
United States
Murray M.
4 bedroom Pelican Key Private Luxury Villa, Panoramic View Of The Caribbean Sea
Pool
1 bedroom with pool in Simpson Bay - GENERATOR

1 bedroom with pool in Simpson Bay - GENERATOR

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 18 - Nov 19
Total with taxes and fees
1 bedroom with pool in Simpson Bay - GENERATOR
Terrace/patio
Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool

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
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

Simpson Bay
10.0 out of 10, Exceptional, (11)
"Great place. Will definitely stay here again."
Canada
Karl B.
Large WATERFRONT 1BR/1Bath Apt in Beautiful St Martin in Simpson Bay
On the beach, beach towels
One Hundred Million Dollar Yacht On Land 5 star Villa Namaste on the Ocean

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

Pelican Key
9.8 out of 10, Exceptional, (77)
"Over all the stay was wonderful Great location great place. We had a few small issues but was handled very quickly and professionally Thank you for every thing we would definitely book again. "
Canada
Brandon C.
One Hundred Million Dollar Yacht On Land 5 star Villa Namaste on the Ocean
Beach
Pirates Booty - Beach Bar Studio next to The Morgan Resort

Pirates Booty - Beach Bar Studio next to The Morgan Resort

Simpson Bay
8.6 out of 10, Excellent, (4)
"This property is old and musty smelling. Some outlets were halfway falling out, no hot water in shower, bugs crawling around, old hodge podge of items for use. Front door is difficult to shut...otherwise a great location."
United States
Janet T.
$245 nightly
The price is $245
Nov 17 - Nov 18
Total with taxes and fees
Pirates Booty - Beach Bar Studio next to The Morgan Resort
Outdoor pool
Cliff House

Cliff House

3.5 star property
Simpson Bay
8.8 out of 10, Excellent, (3)
"Muna, housekeeper, was lovely. Warm and friendly. Stacey, the manager, also warm and friendly and very responsive. The owner, John, was just the same too. Property could use some sprucing, mainly water pressure and pool pump, however we learned it was an area outage. Overall, we loved the privacy and all the birds and iguanas and the setting is BEYOND beautiful!!"
United States
Shawn
Cliff House
Exterior
Oceanview Escape in Sint Maarten

Oceanview Escape in Sint Maarten

Pelican Key
$470 nightly
The price is $491
Nov 17 - Nov 18
Total with taxes and fees
Oceanview Escape in Sint Maarten
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 Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

10/10 Excellent
"The room and the whole resort was very clean! All the staff were very friendly and helpful. "
BARBARA 4-night trip
Posted 1 day ago
The Villas at Simpson Bay 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 $141 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?

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.