Simpson Bay Holiday Rentals

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Holiday Rentals in Simpson Bay

Hilton Vacation Club Royal Palm St. Maarten

4.0 star property
Simpson Bay
9.0 out of 10, Wonderful, (1147)
"Clean room , staff and everything was outstanding "
Canada
devina
The price is NZ$250
includes taxes & fees
15 Dec - 16 Dec
Hilton Vacation Club Royal Palm St. Maarten

The Hills Residence

3.0 star property
Simpson Bay
9.0 out of 10, Wonderful, (47)
"Love the view first of all. Property was in a great location. "
United States
Kevin
The Hills Residence

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

Simpson Bay Suites

3.5 star property
Simpson Bay
6.8 out of 10, (124)
"It’s very nice staff and friendly, it is highly recommended…"
United States
ARMANDO
The price is NZ$267
includes taxes & fees
23 Nov - 24 Nov
Simpson Bay Suites

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

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

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

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)
"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

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.
The price is NZ$917
includes taxes & fees
15 Nov - 16 Nov
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)
"Hope u guys keep up the good work loved it"
United States
Larssrisa A.
The price is NZ$953
includes taxes & fees
18 Nov - 19 Nov
Sunny Days at Simpson Bay Yacht Club

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

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

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.
The price is NZ$393
includes taxes & fees
18 Nov - 19 Nov
1 bedroom with pool in Simpson Bay - GENERATOR

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)
"Great place. Will definitely stay here again."
Canada
Karl B.
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)
"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

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.
The price is NZ$443
includes taxes & fees
15 Nov - 16 Nov
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)
"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

Oceanview Escape in Sint Maarten

Pelican Key
The price is NZ$881
includes taxes & fees
15 Nov - 16 Nov
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

Find out more about Simpson Bay

Everything you need to know about Simpson Bay holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Simpson Bay holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Simpson Bay holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Simpson Bay holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Simpson Bay holiday rentals we have selected for you start as low as NZ$250 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Simpson Bay rentals

At Expedia, we put the best Simpson Bay holiday 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 holiday.

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 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?

Caribbean Sea Studio next to The Morgan Resort: This highly rated holiday home rental in Simpson Bay 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 1 hot tub. Other favourite 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 holiday rentals are there in Simpson Bay?

With 40 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?

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 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.