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

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Simpson Bay villas

An infinity pool with a clear view of the sea, a wooden table with food and drinks, and a lounge area with a view.

1. 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 CA $826
CA $1,809 total
includes taxes & fees
Oct 7 - Oct 8
Luxury 4BR Villa w/ Private Pool & Ocean Views
A beachfront hotel with clear waters, a red-roofed building, and a hillside backdrop.

2. Happy Kayak in Grand Case Beach 2

Happy Kayak in Grand Case Beach 2
Grand Case
The price is CA $80
CA $88 total
includes taxes & fees
Oct 18 - Oct 19
Happy Kayak in Grand Case Beach 2
A covered balcony with wicker furniture and a view of the sea and hills.

3. 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 CA $665
CA $1,347 total
includes taxes & fees
Oct 27 - Oct 28
Villa Solandra – 3BR Oceanfront Sunset w/ Pool
A narrow outdoor corridor with a wooden pergola, white railings, and a tiled floor.

4. To complete

To complete
Grand Case
The price is CA $78
CA $86 total
includes taxes & fees
Oct 18 - Oct 19
To complete
A rooftop terrace with a pool, lounge chairs, and a table with a drink.

5. Avenue du lagon

Avenue du lagon
Oyster Pond
The price is CA $2,066
CA $2,790 total
includes taxes & fees
Oct 14 - Oct 15
Avenue du lagon
A rooftop terrace with a pool, lounge chairs, and a view of the sea.

6. 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 CA $5,280
CA $5,988 total
includes taxes & fees
Oct 7 - Oct 8
Villa de 10 Chambres les Pieds Dans L'eau à Guana Bay
A narrow outdoor corridor with a wooden pergola, white railings, and a tiled floor.

7. Happy House in Grand Case Beach 1

Happy House in Grand Case Beach 1
Grand Case
The price is CA $88
CA $96 total
includes taxes & fees
Oct 29 - Oct 30
Happy House in Grand Case Beach 1
A wooden table with glass jars and a lantern, overlooking a pool and lush greenery.

8. VILLA 47 SXM - ORIENT BAY-BEACH ACCESS 🌸🌴🐚

VILLA 47 SXM - ORIENT BAY-BEACH ACCESS 🌸🌴🐚
Orient Bay
9.8 out of 10, Exceptional, (10 reviews)
"Excellent property - Sarah and Fred are a pleasure to deal with. Highly recommended and amazing location. "
United States
Maximilian
The price is CA $882
CA $1,053 total
includes taxes & fees
Oct 22 - Oct 23
VILLA 47 SXM - ORIENT BAY-BEACH ACCESS 🌸🌴🐚
Pool

9. New Luxurious Villa FLEURS DE LYS, Sea view and swimming pool

New Luxurious Villa FLEURS DE LYS, Sea view and swimming pool
Saint-Martin
9.0 out of 10, Wonderful, (6 reviews)
"We absolutely loved this place!! It was exactly what the pictures showed! The location is great, the house is great, the hosts were great!!! We will be back!!"
United States
Josh A.
The price is CA $1,200
CA $1,624 total
includes taxes & fees
Oct 11 - Oct 12
New Luxurious Villa FLEURS DE LYS, Sea view and swimming pool
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

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

10/10 Excellent
"Good hotel. Water bugs in my room everyday but besides that it was clean and nice"
KHALIA Halima 5-night trip
Posted 1 hour ago
Simpson Bay Resort, Marina & Spa

Find out more about Simpson Bay

Simpson Bay Villas information

Number of reviews
18
Accommodation
39 Villas
Lowest Price
CA $86
Highest Price
CA $5,988

Frequently asked questions

How much do villas in Simpson Bay cost?
You'll pay between CA $86 and CA $5,988 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?
You can pick from multiple villas in Simpson Bay that have a total average guest review rating of 9.7. Villa Bianca is a hit with Expedia guests. This 4.5-star stay offers a swimming pool and an ocean view. Villa Amaryllis is another good option. It has a 4-star rating and conveniences such as a garden and a swimming pool.
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.
What are the best cheap villas in Simpson Bay?
Villas start at CA $86 per night, so your Simpson Bay adventure doesn't need to take a bite out of your budget! La Brise By Redawning is a wallet-friendly option that comes with plenty of amenities, including a barbecue grill and a swimming pool. Summerwinds 3 Bedrooms 3. 5 Bathrooms Villa is another cheap stay in this sought-after destination. Conveniences here include a swimming pool and a barbecue grill. Exploring free attractions in Simpson Bay will stretch your travel budget even further. Maho Beach and Orient Bay Beach are favourites among tourists. With the dollars you save, you can explore some more! 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 family-friendly villas in Simpson Bay?
Vacationing with the kids in Simpson Bay is easy at Villa Bianca. With conveniences like a barbecue grill and WiFi, your crew can rest and relax at this 4.5-star stay. Villa Amaryllis is another family-friendly option that's ideal for spending your downtime with your favourite people. It has a 4-star rating and conveniences including a barbecue grill and WiFi. Once you've checked in and dropped off your things, there's no shortage of family-friendly attractions to explore around Simpson Bay. Maho Beach and Orient Bay Beach are two popular options.
Are there any 5-star villas in Simpson Bay?
Although there aren't any 5-star villas in Simpson Bay, there are 4-star accommodations that will fit your needs. Located around 3 kilometres from downtown, Villa Amaryllis offers amenities like a swimming pool and concierge services. Another stylish retreat is Villa Amaryllis. It's around 3 kilometres from central Simpson Bay and features conveniences such as concierge services and a swimming pool.
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.