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Compare 37 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, (89)
"Pool was clean, as was the house. Kitchen was very well equipped. The location was perfect, close to a couple restaurants and grocery stores, we were able to easily walk to both. Would stay there again. "
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

BEACHFRONT DESIGN VILLA

9.8 out of 10, Exceptional, (112)
"An excellent property"
BEACHFRONT DESIGN VILLA

* 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

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

10.0 out of 10, Exceptional, (36)
"Our family of 4 thoroughly enjoyed this properly for a week. The properly was perfectly set up for relaxing, sleeping well, and enjoying the incredible natural beauty of the blue waters right outside. We really enjoyed the huge pool and access to the water where we enjoyed snorkeling. The beds were comfortable and the kitchen was well equipped. We enjoyed the added security of a gate. This property is incredible and we highly recommend it for anyone that wants to escape to paradise. The hosts...
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

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

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

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 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

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

9.0 out of 10, Wonderful, (6)
"Don't underestimate the beauty of this condo. The photos do not do it justice. There is plenty of room for three couples or more. The kitchen is spectacular. The balcony is large and enclosed with a beautiful sea view. We were more than happy with our selection."
Il Punto Blu: Newly Renovated 3 Bdrm, Beachfront, Pool, walkable to restaurants.

Blue Pelican Luxury Villa - Featured on HGTV!

10.0 out of 10, Exceptional, (3)
"This is our 4th time to this property and we consider it perfect for pur needs. Its close walk to the ocean or restaurants and a grocery store. Its quiet and clean and safe. The owners are very responsive and the manager a real gem"
Blue Pelican Luxury Villa - Featured on HGTV!

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

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

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

Anchor House

3.5 star property
8.0 out of 10, Very Good, (1)
"Location - Location - Location. What a great location and property. Easy walking distance to Maho Beach and shopping district. If you rent a car - any easy drive to Philipsburg, Mullet Bay Beach etc. Never made it to the french side - but Mullet Beach was excellent with chair/umbrella rentals and a couple of beach bars for your beer/daqueri needs. Anchor House was as pictured. Deck with pool was awesome. Unfortunately to warm to leave doors open and enjoy the crashing waves. Bedroom AC...
Anchor House

Pelican Key "shoreline" Villa 3bd+canapé

Pelican Key "shoreline" Villa 3bd+canapé

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!
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

Simpson Bay Suites

3.5 star property
6.8 out of 10, (111)
"The location close to the airport "
The price is SAR 634
SAR 710 total
includes taxes & fees
20 Jan - 21 Jan
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

The Horny Toad Guesthouse

3.0 star property
9.4 out of 10, Exceptional, (51)
"Deb & Doug are accommodating and great to talk to to get ideas of things to do. Perfect place to stay!"
The Horny Toad Guesthouse
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?
A guest favorite is Villa Alabaster At Coral Beach Club By Redawning. Get comfortable at this 4.5-star property which comes with a swimming pool and an oven. Windsong By Redawning is another in-demand option to consider. Spend your break at this 4.5-star stay and take advantage of conveniences like a swimming pool and a garden. You’ll have your pick of multiple villas in Simpson Bay with a total average guest review rating of 9.5.
How many villas are there in Simpson Bay?
Claim your vacation time and choose from 37 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?
If you’re up for a bit of indulgence on your Simpson Bay escape, Villa Amaryllis won’t disappoint. This 5-star villa features concierge services and a swimming pool and is around 3 kilometers from downtown. Another 5-star option that’ll meet your needs is Villa Starfish Coral Beach Club By Redawning. It’s 8 kilometers from the center of Simpson Bay and has amenities such as a swimming pool and pool sun loungers.
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.