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Compare 38 Villas in Simpson Bay with updated reviews, rates, and availability.

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

10.0 out of 10, Exceptional, (91)
"We made a last minute decision to take a family trip to St. Maarten over Christmas Break. It was perfect. The property had a cancellation and opened up right when we wanted to visit. The pictures are very accurate. The three bedrooms are on the small side, but it was nice to have a bedroom and bath for each of our boys. The kitchen was adequate for breakfast and snacks. Grocery stores are plentiful. We could have fixed dinner, but there are so many good restaurants to explore. The location is...
3 BR/3 bath. Sint Maarten DIRECT BEACHFRONT WITH POOL! Rates start at $225/nt!!

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

9.8 out of 10, Exceptional, (67)
""We had an incredible stay at Villa Namaste! The property is gorgeous, with every room beautifully appointed. The view from the patio is breathtaking—worth every penny. Sitting in the infinity edge pool, looking out over the bluest Caribbean waters while watching mega yachts sail by, was a highlight of our days. The villa is also conveniently located close to many cool restaurants, some even within walking distance, which was perfect for our evenings out. The staff, particularly Olive and...
One Hundred Million Dollar Yacht On Land 5 star Villa with backup Generator

Stunning Beach Front Villa With Infinity Pool

9.6 out of 10, Exceptional, (7)
"The property has a great location. Near all the local entertainment and stores, yet off the beaten path. When contacting the property manager, Geraldine, she was always Johnny on the spot. The same goes for the property owners, Mitchell and Lisa. They always responded quickly to emails. Very short wait time. The villa was verry clean and well stocked.The only real issue was bedroom 4 nearest to the entrance door at times had a sewer gas smell emitting down the entrance hall and in the bedroom....
Stunning Beach Front Villa With Infinity Pool

BEACHFRONT DESIGN VILLA

9.8 out of 10, Exceptional, (113)
"The house was comfortable and plenty of space for 7 adults. The outside seating areas were perfect for playing games and lounging. The small issues we encountered were consist hot water in the showers. The water was more tepid than hot in all showers but the red bathroom. We had some remotes and safes needing new batteries. It would be helpful to have manuals for the kitchen appliances and a/c remotes. Overall, the stay was pleasant and would recommend to friends."
BEACHFRONT DESIGN VILLA

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

10.0 out of 10, Exceptional, (37)
"We had a lovely trip to Sint Maarten! It started off rocky with flight cancellations and lots of moving pieces. Nadine and Olivier were very accommodating and helpful. The property was lovely and you cannot beat the views, the pool, outdoor gathering g space and access to the ocean. Lots of places to easily walk to from rental and quiet neighborhood. "
Amazing Ocean Front Villa in Pelican Key - Pool and Private Ocean Access

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

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

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

10.0 out of 10, Exceptional, (49)
"We stayed at this property April 21-26 and have nothing but positive things to say. From the moment we walked in the door we knew our holiday would be one to remember. There were 7 adults in our group and more than enough space for everyone. All the bedrooms were spacious with ensuites which was a huge bonus. Beds and linens were great. The kitchen was well stocked with left over spices and oils for us to use. There were two fridges which were perfect for drinks and food. No shortage on space...
* Holidays Specials* ALMA - DIRECT BEACH ACCESS 4 BR VILLA

Cliff House

3.5 star property
9.0 out of 10, Wonderful, (2)
"Amazing location. Views of the bay and the ocean on each side. Walkable to Maho restaurants and grocery. Would stay again"
Cliff House

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, (38)
"Having Peaches to show you the house when you arrive shouldn't be underestimated. She is awesome! Thanks again Peaches. Pool was great, beds were comfortable, kitchen fully stocked, comfortable living room, great covered patio and comfortable chairs, good appliances, technology was easy to use, gated driveway with two remotes, etc. The mosquitos and noseeums (biting insects) were pretty bad, especially around dusk, so put on bug spray or get in the pool. the view is breathtaking and nightly...
Pelican Key Private Luxury Villa With Panoramic View Of The Caribbean Sea

Villa Bonjour water front villa next to Maho

10.0 out of 10, Exceptional, (9)
"Just finished up a 10 day stay over Christmas 2024 with our family! The house is fantastic! Very big, comfortable beds, great a/c and gorgeous views! We spent most meals at the patio table. Our host Gwen was awesome! Always responded very quickly and made sure we had everything we needed! 5 stars!"
Villa Bonjour water front villa next to Maho

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!

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

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.

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

10.0 out of 10, Exceptional, (24)
"Beautiful home, excellent view and location with many restaurants and bars in walking distance. Accommodated an early check in and late check out with no hesitation. Communication with the owner was timely and informative throughout the booking process and leading up to the trip. The on-island concierge was friendly, knowledgeable, responsive and addressed our minimal needs/concerns in a timely manner. Would certainly recommend for a group of friends or family. "
BLUE OPAL Private Pool-Generator, Ocean Views Pelican Key - Simpson Bay

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

10.0 out of 10, Exceptional, (7)
"Absolutely the best place to stay, safe, convenient location and beautiful views from the pool deck. Highly recommend! "
Villa Domila-Luxury 3Bed & 3Bath with private pool-Free airport transfer-Central

Luxurious Villa " Sea La Vie" in Pelican Key

10.0 out of 10, Exceptional, (3)
"Family Christmas. It was a comfortable house with separate bathrooms for each bedroom and a nice size kitchen and living room. Great patio with a dining table as well as sitting area and pool. Good property management. "
Luxurious Villa " Sea La Vie" in Pelican Key

Villa Livity 6 Bed Luxury Sea View boutique villa

Villa Livity 6 Bed Luxury Sea View boutique villa

Villa Francais: 5 BR, 5.5 BA Villa in Pelican Key, Sleeps 10

Villa Francais: 5 BR, 5.5 BA Villa in Pelican Key, Sleeps 10

Villa Zircon in Pelican Key awaits you - GENERATOR

9.4 out of 10, Exceptional, (3)
"We had a fantastic stay at Villa Zircon in Pelican Key The property was clean and had everything we needed. Central location made it easy and quick to be anywhere. Any question we’re replied to immediately ⭐️"
Villa Zircon in Pelican Key awaits you - GENERATOR
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, (8)
"Wow! Such a great experience staying at The Hills residence! Beautiful 2 bedroom really cozy, quiet, beautiful roof top pool. Free parking very close to all the food and shopping "
The Hills Residence

Simpson Bay Suites

3.5 star property
6.8 out of 10, (112)
"The location close to the airport "
The price is AED 621
AED 695 total
includes taxes & fees
2 Feb - 3 Feb
Simpson Bay Suites

Tradewinds at Simpson Bay

3.5 star property
9.2 out of 10, Wonderful, (18)
"Very nice host with incredibly fast responses to questions. I would stay there again. "
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?
Rates for villas in Simpson Bay range between and per night. Whatever your budget, you’ll find something that suits your needs with 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 option with Expedia guests. Visitors staying at this 4.5-star retreat will enjoy access to a barbecue grill and a terrace. Villa Amaryllis is another sought-after stay. This 4-star villa comes with a garden and a barbecue grill, among many other conveniences.
How many villas are there in Simpson Bay?
Claim your vacation time and choose from 38 villas in Simpson Bay. For a vacation with the family, a romantic break and everything in between, Expedia will help you find the ideal place in a few simple clicks.
Are there any 5-star villas in Simpson Bay?
Simpson Bay doesn’t have any 5-star villas — but you can still vacation here in style! Why not book Villa Bianca? Located about 2 kilometers from the downtown area, this 4-star property offers conveniences like a swimming pool and concierge services. Villa Amaryllis is another fabulous choice just 3 kilometers from central Simpson Bay. Also with a 4-star rating, it comes with amenities such as concierge services and a swimming pool.
Why book your villa in Simpson Bay with Expedia?
Reserving a villa in Simpson Bay is as easy as clicking on your travel dates and choosing an option that suits your style. Looking for something luxurious or affordable, or a stay that also offers a laundry and kitchen? Use Expedia’s search filters to narrow your results and find the perfect fit.
How can I find cheap villas in Simpson Bay?
The easiest way to get cheap villas in Simpson Bay is with Expedia’s user-friendly filter tool. Narrow down your search by budget, star rating and amenities to grab unbeatable rates in just a few keystrokes.