A wooden pier extending into calm waters with sailboats anchored nearby.

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Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sept - 27 Sept
In four months
23 Oct - 25 Oct

Our top choices for Simpson Bay villas

Terrace/patio

Villa de 10 Chambres les Pieds Dans L'eau à Guana Bay

Villa de 10 Chambres les Pieds Dans L'eau à Guana Bay
Sint Maarten
10.0 out of 10, Exceptional, (2 reviews)
The price is £3,250
includes taxes & fees
30 Jun - 1 Jul
Villa de 10 Chambres les Pieds Dans L'eau à Guana Bay
Property grounds

Villa Esperanza Ocean View Villa |Private Pool | Gated Community | Walk to Beach

Villa Esperanza Ocean View Villa |Private Pool | Gated Community | Walk to Beach
Dawn Beach Estates
The price is £876
includes taxes & fees
23 Jul - 24 Jul
Villa Esperanza Ocean View Villa |Private Pool | Gated Community | Walk to Beach
Pool

Luxury 4BR Villa w/ Private Pool & Ocean Views

Luxury 4BR Villa w/ Private Pool & Ocean Views
Indigo Bay
10.0 out of 10, Exceptional, (1 review)
"This property has a breathtaking view and is in the perfect location—close to stores and just minutes from the beaches.Fritz, the host, was amazing! The island had just gone through a major storm the day before we arrived, and despite the circumstances, Fritz was always available and ready to help with anything we needed. He even offered us an extra day to make up for any inconvenience, which was so thoughtful and appreciated.I would absolutely stay here again and would highly recommend this...
United States
Ms Light T.
The price is £1,084
includes taxes & fees
1 Jul - 2 Jul
Luxury 4BR Villa w/ Private Pool & Ocean Views
Property grounds

Villa Solandra – 3BR Oceanfront Sunset w/ Pool

Villa Solandra – 3BR Oceanfront Sunset w/ Pool
Indigo Bay
10.0 out of 10, Exceptional, (1 review)
"Our stay at Villa Solandra was nothing short of amazing. The check in process was seamless, the communication with the host was always smooth and timely, the villa itself was beautiful. It was clean, great location, and the view is insane. This place was part of the reason we had such a memorable time in St. Maarten. "
United States
Olivia G.
The price is £672
includes taxes & fees
30 Jun - 1 Jul
Villa Solandra – 3BR Oceanfront Sunset w/ Pool
Villa | Living area

Avenue du lagon

Avenue du lagon
Oyster Pond
The price is £1,483
includes taxes & fees
1 Jul - 2 Jul
Avenue du lagon
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

Hilton Vacation Club Flamingo Beach St. Maarten

Hilton Vacation Club Flamingo Beach St. Maarten

10/10 Excellent
"I had a wonderful stay at the Hilton Flamingo Beach Resort and would absolutely return. The room and resort facilities were clean, well-maintained, and made for a very comfortable stay. The front desk staff were consistently friendly and incredibly helpful, especially when assisting me with booking taxis throughout my trip. One of the biggest highlights was the location—right on the beach and within walking distance of so many great bars and restaurants, making it easy to explore the area without needing a car. Overall, it was a relaxing, convenient, and enjoyable experience. I look forward to staying here again on my next visit!"
Sherilyn 4-night trip
Posted less than an hour ago
Hilton Vacation Club Flamingo Beach St. Maarten

Find out more about Simpson Bay

Simpson Bay Villas information

Number of reviews
2
Accommodation
40 Villas
Lowest Price
£672
Highest Price
£3,250

Frequently asked questions

How much do villas in Simpson Bay cost?
You'll pay between £672 and £3,250 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?
Select from multiple villas in Simpson Bay that have a total average guest review rating of 10.0. Villa Bianca is a hit with Expedia guests. This 4.5-star stay has a swimming pool and an ocean view. Villa Amaryllis is another great option. It has a 4-star rating and amenities including a barbecue grill and a swimming pool.
How many villas are there in Simpson Bay?
Choose from 40 villas in Simpson Bay. No matter if you're travelling with the kids or planning a weekend escape with your buddies, Expedia will help you find the perfect space for your squad.
What are the best cheap villas in Simpson Bay?
La Brise By Redawning is one of the most affordable villas in Simpson Bay and includes a swimming pool and a barbecue grill. Another popular choice that's easy on the hip pocket is Summerwinds 3 Bedrooms 3. 5 Bathrooms Villa. Conveniences here include a swimming pool and a barbecue grill. Rates for villas start from £672 per night. Taking advantage of free attractions in Simpson Bay will stretch your travel dollars even further. Maho Beach and Orient Bay Beach are tourist favourites. With the cash you save, you can keep on sightseeing! This price was 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.
Are there any 5-star villas in Simpson Bay?
Unfortunately, there are no 5-star villas in Simpson Bay. However, there are some terrific 4-star stays here that'll suit your needs. Check out Villa Amaryllis, approximately 3 kms (2 miles) from the downtown area. Concierge services and a swimming pool are a couple of the many conveniences here. Villa Amaryllis is another upmarket option including concierge services and a swimming pool. This property is located about 3 kms (2 miles) 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.
What is there to do near my villa in Simpson Bay?
Simpson Bay has enough activities and sights to keep you amused for weeks (or months!), beginning with Simpson Bay Beach. Flamingo Beach, Kim Sha Beach and Hollywood Casino are other renowned attractions. If you're lingering longer, Dunes Casino and Lay Bay Beach are great additions to your itinerary.