Simpson Bay Holiday Rentals

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Check prices for these dates

Tonight
26 Oct - 27 Oct
Tomorrow
27 Oct - 28 Oct
Next weekend
31 Oct - 2 Nov
In two weeks
7 Nov - 9 Nov

Holiday Rentals in Simpson Bay

Outdoor pool, pool 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, (1134)
"Great place, friendly and helpful staff."
United States
Jose
The price is HK$1,157
HK$1,418 total
includes taxes & fees
19 Nov - 20 Nov
Hilton Vacation Club Royal Palm St. Maarten
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. "
United States
Lionel
The Hills Residence
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"
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
6.8 out of 10, (124)
"Highly recommended and friendly staff…"
United States
ARMANDO
The price is HK$839
HK$940 total
includes taxes & fees
27 Oct - 28 Oct
Simpson Bay Suites
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"
United Kingdom
Marisca P.
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...
United States
Ben B.
Maho Beach House - Spacious 1 Bedroom Suite
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."
United States
Nicolas C.
Oceanfront amazing 2 BR Villa - 2 min from the beach
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! "
United States
Rachel S.
The price is HK$3,069
HK$4,033 total
includes taxes & fees
27 Oct - 28 Oct
Turquoise paradise, directly ON beach, gated w underground parking!
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!"
United States
Melanie Pacoli
The Horny Toad Guesthouse
Property grounds
Oceanfront amazing 2 bedrooms Condo
Oceanfront amazing 2 bedrooms Condo
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
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, (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
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
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"
United States
JEROME J.
The price is HK$1,865
HK$3,677 total
includes taxes & fees
27 Oct - 28 Oct
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)
"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 on the ocean
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 !!
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. "
United States
Ruslan
Large WATERFRONT 1BR/1Bath Apt in Beautiful St Martin in Simpson Bay
Terrace/patio
Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool
Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool
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
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 "
United States
Juan D.
Pirates Booty - Beach Bar Studio next to The Morgan Resort
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."
United States
Richard S.
The price is HK$894
HK$1,731 total
includes taxes & fees
27 Oct - 28 Oct
1 bedroom with pool in Simpson Bay - GENERATOR
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! "
United States
Sherri R.
ALMA - DIRECT BEACH ACCESS 4 BR VILLA
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
"Rooms are beautiful and very clean."
Cheryl 5-night trip
Posted 2 days ago
The Villas at Simpson Bay Resort

Find out more about Simpson Bay

Search for holiday rentals in Simpson Bay on Expedia! You can easily find your home rentals, villas, holiday apartments in Simpson Bay using one of the methods below:

  • View our selection of featured holiday rentals in Simpson Bay
  • Use the map to find apartments and other holiday homes in the Simpson Bay neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Simpson Bay while they last

Look no further and take a look at our great range of rental properties in Simpson Bay!

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.