Search Simpson Bay Villa Rentals from CA $1,341

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Apr 17 - Apr 19
In two months
May 29 - May 31
In three months
Jun 26 - Jun 28
In four months
Jul 24 - Jul 26

Our top choices for Simpson Bay villas

A heated pool

Villa Petite Plage 5 | Beach Front - Located in Exquisite Grand Case with Private Pool

Villa Petite Plage 5 | Beach Front - Located in Exquisite Grand Case with Private Pool
Grand-Case
10.0 out of 10, Exceptional, (4 reviews)
"This property is amazing and the staff was phenomenal - organized, personal, and willing to assist with any part of the stay! It would be a dream come true to be able to return to this property!"
United States
Christy P.
The price is CA $14,040
CA $16,810 total
includes taxes & fees
Apr 12 - Apr 13
Villa Petite Plage 5 | Beach Front - Located in Exquisite Grand Case with Private Pool
Terrace/patio

Luxury villa. Sea view. Private swimming pool. Independent bedroom and suite.

Luxury villa. Sea view. Private swimming pool. Independent bedroom and suite.
SAINT MARTIN
10.0 out of 10, Exceptional, (15 reviews)
"Such a cool property and a great location "
United States
April A.
The price is CA $949
CA $1,341 total
includes taxes & fees
Apr 8 - Apr 9
Luxury villa. Sea view. Private swimming pool. Independent bedroom and suite.
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 CA $953
CA $1,914 total
includes taxes & fees
Apr 13 - Apr 14
Luxury 4BR Villa w/ Private Pool & Ocean Views
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
The price is CA $5,266
CA $5,844 total
includes taxes & fees
Apr 2 - Apr 3
Villa de 10 Chambres les Pieds Dans L'eau à Guana Bay
Villa | Living area

Avenue du lagon

Avenue du lagon
Oyster Pond
The price is CA $2,226
CA $2,941 total
includes taxes & fees
Apr 12 - Apr 13
Avenue du lagon
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 CA $790
CA $1,451 total
includes taxes & fees
Apr 22 - Apr 23
Villa Solandra – 3BR Oceanfront Sunset w/ 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Simpson Bay Hotel Reviews

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

6/10 Okay
"This was a decent place to stay. The room was outdated and somewhat cheap but it was comfortable. Beach was great. Staff was ok. "
Christopher 6-night trip
Posted 2 hours ago
Simpson Bay Resort, Marina & Spa

Find out more about Simpson Bay

Simpson Bay Villas information

Number of reviews
20
Accommodation
43 Villas
Lowest Price
CA $1,341
Highest Price
CA $16,810

Frequently asked questions

How much do villas in Simpson Bay cost?
You'll pay between CA $1,341 and CA $16,810 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 10.0. 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 43 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 $1,341 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.