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Compare 39 Villas in Simpson Bay with updated reviews, rates, and availability.

One Hundred Million Dollar Yacht On Land 5 star Villa with backup Generator

9.8 out of 10, Exceptional, (70)
"Me and my wife enjoyed our honeymoon stay here to relax and enjoy the island. The home is in a perfect area even pay cash for rental via Tami we will be back soon great speaker of you want a vibe at the property with pool and drinks. "
One Hundred Million Dollar Yacht On Land 5 star Villa with backup Generator

BEACHFRONT DESIGN VILLA

9.8 out of 10, Exceptional, (115)
"We had 6 adults and 2 children 31/2 and 6. The pool was perfect for everyone. Very well maintained as well. The kids also enjoyed exploring the beach and tide pools, but there is no swimming in the ocean from the house. Many beaches available for swimming nearby. The house is perfect for hanging out. The grounds are very nice with lots of sitting areas and places for the kids to play. This was our second stay in the villa with the same group and we all really enjoyed it. We highly recommend this...
BEACHFRONT DESIGN VILLA

Oceanfront amazing 2 BR Villa - 2 min from the beach

9.6 out of 10, Exceptional, (92)
"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

Pelican Key Private Luxury Villa With Panoramic View Of The Caribbean Sea

9.6 out of 10, Exceptional, (40)
"What a wonderful place to enjoy sun, sand and friends. The villa was very nice and the view was stunning. This spacious home was everything we expected. It was sad to see how the hurricane had impacted some of the area homes, but not this spot. We got lots of steps in walking into town and back up the hill (whew) but that helped walk off the delicious food choices we had close by.Thank you for sharing your beautiful home with our group- we loved every minute of our stay!Julie"
Pelican Key Private Luxury Villa With Panoramic View Of The Caribbean Sea

* Holidays Specials* ALMA - DIRECT BEACH ACCESS 4 BR VILLA

10.0 out of 10, Exceptional, (52)
"Most amazing property on the island.Everything is true to listing and the service provided was top notch."
* Holidays Specials* ALMA - DIRECT BEACH ACCESS 4 BR VILLA

BLUE OPAL Private Pool-Generator, Ocean Views Pelican Key - Simpson Bay

10.0 out of 10, Exceptional, (26)
"What a wonderful time visiting SXM and Blue Opal was definitely a part of that! Beautiful home with ample amount of space for our group of 10 (5 adults, 5 kids)!Air conditioning worked great, the house never felt warm!Plenty of pool toys for the kids.My only recommendation would be to get rid of the projector in the upstairs master bedroom- the blue power lights are super bright at night, my understanding is it didn’t work anyways. "
BLUE OPAL Private Pool-Generator, Ocean Views Pelican Key - Simpson Bay

Cliff House

3.5 star property
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!!"
Cliff House

3 BR/3 bath. Sint Maarten DIRECT BEACHFRONT WITH POOL! Rates start at $225/nt!!

10.0 out of 10, Exceptional, (95)
"Bob is one of the best hosts you will come across. The place was fantastic. The deck with the private pool overlooking the ocean was the winner here. A short 5-10 minute walk to Maho. The place reminded me of a cottage. Has a nice rustic feel to it. Bedrooms and bathrooms were clean.kitchen had everything we needed. Plenty of drinking glasses. Beds were comfortable. Bin was a gracious host who met us and checked us in. He was there if we had any questions but was not intrusive. He leaves you...
3 BR/3 bath. Sint Maarten DIRECT BEACHFRONT WITH POOL! Rates start at $225/nt!!

Stunning Beach Front Villa With Infinity Pool

9.4 out of 10, Exceptional, (9)
"Great location and even better views and outdoor space. The beach area is small and not best for swimming but there are some swimmable beach areas just down the beach. We learned all beaches on the island are public so you can use the resort beach areas which also have bars. Small store a short walk down the road with several restaurants. There were some bugs on the back deck area that you couldn’t see until you popped up with bites, so I recommend bringing bug spray. Bugs/mosquitos love me...
Stunning Beach Front Villa With Infinity Pool

Amazing Ocean Front Villa in Pelican Key - Pool and Private Ocean Access

10.0 out of 10, Exceptional, (40)
"Comfortable, good location great view,very nice pool. Would stay there again."
Amazing Ocean Front Villa in Pelican Key - Pool and Private Ocean Access

Villa Sunshine: Beachfront! 10 min. walk to the famous Maho Beach!

9.6 out of 10, Exceptional, (29)
"The villa was amazing and was perfect for our group. The view was incredible. Will definitely recommend."
Villa Sunshine: Beachfront! 10 min. walk to the famous Maho Beach!

Luxurious Villa " Sea La Vie" in Pelican Key

9.8 out of 10, Exceptional, (6)
"Very comfortable and relaxing. We enjoyed hanging out by the pool and the wonderful views of the ocean. We were close to everything as well."
Luxurious Villa " Sea La Vie" in Pelican Key

Villa Domila-Luxury 3Bed & 3Bath with private pool-Free airport transfer-Central

10.0 out of 10, Exceptional, (10)
"This villa is exactly as it looks in the photos. The view and sunset were spectacular! The communication with the host was excellent. The location was very good as well, either for walking or with a rental. Would definitely stay here again. Thank you!"
Villa Domila-Luxury 3Bed & 3Bath with private pool-Free airport transfer-Central

Charming 2-bedroom villa with AC, WiFi, stunning ocean views

10.0 out of 10, Exceptional, (2)
"This property was a fantastic place to relax and enjoy the views! The villa is well taken care of and it was very comfortable to stay in. The property has a great pool and beautiful views no matter what time of the day or night. Looking forward to going back one day."
Charming 2-bedroom villa with AC, WiFi, stunning ocean views

Il Punto Blu: Newly Renovated 3 Bdrm, Beachfront, Pool, walkable to restaurants.

9.0 out of 10, Wonderful, (6)
"This oceanfront villa offers a stunning Caribbean experience with some minor trade-offs. The spacious, well-appointed interior features comfortable king-size beds and tasteful décor throughout. The common areas are generous, and the front patio is a perfect spot to soak in the breathtaking ocean views. The kitchen comes well-equipped for those who enjoy cooking while on vacation.However, potential guests should note a few practical considerations. While the property overlooks the ocean, there's...
Il Punto Blu: Newly Renovated 3 Bdrm, Beachfront, Pool, walkable to restaurants.

Villa Impala, 5 bedroom villa beachfront in Simpson Bay, Sint Maarten

10.0 out of 10, Exceptional, (1)
"The home is simply amazing. The glass sliders opening to a beachfront patio and pool is truly special. The primary bedroom and shower with a panoramic view of the beach is stunning. The home is even better than the pictures show. Better yet, Jade is an amazing person and host that improves the stay. We wouldnt hesitate to stay here again. "
Villa Impala, 5 bedroom villa beachfront in Simpson Bay, Sint Maarten

Villa Bonjour water front villa next to Maho

10.0 out of 10, Exceptional, (11)
"From start to finish, our experience was absolutely seamless. The booking process was effortless, with quick responses and incredible support.Host: Gwen is an absolute gem! She goes above and beyond to make sure every detail is perfect. There wasn’t a single question she couldn’t answer, and she even arranged our taxi service with VJ Taxi, which was a huge help. Professional, kind, and dedicated—she’s a top-notch host!Taxi Service: VJ Taxi was exceptional. Not only did he provide reliable...
Villa Bonjour water front villa next to Maho

Pelikaan Sunset: A Villa With Stunning Ocean Views

9.8 out of 10, Exceptional, (6)
"Perfect place for a big family vacation."
Pelikaan Sunset: A Villa With Stunning Ocean Views

Villa Sea Forever @ Pelican Key - Paradise Awaits!

10.0 out of 10, Exceptional, (1)
"everything you see in listing is accurate, views.... absolutely amazing, from morning rainbows to the evening sunsets. very bright, and most days do not need AC, as there is a normal cooling breeze, just open front door and slider.... ahhh, perfectwas there for three days alone until sisters come down for a week, location was great, bit hard to find for someone who never has been therereally could not have found a better location.thank you for the perfect vacation.Ernie Viens"
Villa Sea Forever @ Pelican Key - Paradise Awaits!

Villa Livity 6 Bed Luxury Sea View boutique villa

Villa Livity 6 Bed Luxury Sea View boutique 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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Other property types in Simpson Bay

The Hills Residence

3.0 star property
9.4 out of 10, Exceptional, (16)
"Great place to stay! "
The Hills Residence

Simpson Bay Suites

3.5 star property
6.8 out of 10, (116)
"Very convenient and comfortable…"
The price is AED 621
AED 695 total
includes taxes & fees
12 Mar - 13 Mar
Simpson Bay Suites

Tradewinds at Simpson Bay

3.5 star property
9.4 out of 10, Exceptional, (22)
"Adrian and the manager were very accommodating and the stay was amazing. Close to everything and can walk to shops and restaurants. We got the 2 bedroom first floor unit and it was very clean and smell good. Definitely recommend to families, couples etc. "
Tradewinds at Simpson Bay
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.

Frequently asked questions

How much do villas in Simpson Bay cost?
You’ll pay between and per night for a villa in Simpson Bay. Whatever your budget, a fantastic getaway is only a click away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best villas in Simpson Bay?
Simpson Bay has multiple villas with a total average guest review rating of 9.6. Villa Bianca is a popular choice with seasoned Expedia guests. Visitors of this 4.5-star retreat will have use of a swimming pool and a barbecue grill. Villa Amaryllis is another highly rated stay. This 4-star villa offers a swimming pool and a barbecue grill, among many other conveniences.
How many villas are there in Simpson Bay?
Choose from 39 villas in Simpson Bay. No matter if you’re traveling with the kids or planning a weekend escape with your buddies, Expedia will help you find the perfect space for your squad.
Are there any 5-star villas in Simpson Bay?
Unfortunately, there are no 5-star villas in Simpson Bay. However, there are some 4-star accommodations here that’ll suit your needs. Check in to Villa Bianca, around 2 kilometers from the downtown area. a swimming pool and a terrace are two of the many amenities here. Villa Amaryllis is another stylish option featuring a swimming pool and concierge services. It’s located around 3 kilometers from central Simpson Bay.
Why book your villa in Simpson Bay with Expedia?
Expedia makes it a breeze to find your dream villa in Simpson Bay. Taking the kids on a break? Take advantage of our filters to look for stays with amenities like a pool. If you have a certain budget, click on how much you’d like to spend and the star rating of the property. We’ll help you find the perfect fit that gels with your taste and style.
How can I find cheap villas in Simpson Bay?
Expedia can help you easily locate cheap villas in Simpson Bay. Simply use our handy filter tool to select amenities, budget and star rating to refine your search and find an awesome place to stay in a few quick keystrokes.