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Browse Select Simpson Bay Villas

BEACHFRONT DESIGN VILLA
Outdoor pool
BEACHFRONT DESIGN VILLA
9.8 out of 10, Exceptional, (112)
"An excellent property"
BEACHFRONT DESIGN VILLA
3 BR/3 bath. Sint Maarten DIRECT BEACHFRONT WITH POOL! Rates start at $225/nt!!
Pool
3 BR/3 bath. Sint Maarten DIRECT BEACHFRONT WITH POOL! Rates start at $225/nt!!
10.0 out of 10, Exceptional, (85)
"Beautiful "
3 BR/3 bath. Sint Maarten DIRECT BEACHFRONT WITH POOL! Rates start at $225/nt!!
* Holidays Specials* ALMA - DIRECT BEACH ACCESS 4 BR VILLA
Terrace/patio
* 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
Villa Bonjour water front villa next to Maho
Property grounds
Villa Bonjour water front villa next to Maho
10.0 out of 10, Exceptional, (8)
"Beautiful home and a wonderful stay. Gwen was friendly and helpful. Highly recommend and would love to be able to return!"
Villa Bonjour water front villa next to Maho
One Hundred Million Dollar Yacht On Land 5 star Villa Namaste with Generator
Outdoor pool, an infinity pool
One Hundred Million Dollar Yacht On Land 5 star Villa Namaste with 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 Namaste with Generator
Oceanfront amazing 2 BR Villa - 2 min from the beach
Outdoor pool
Oceanfront amazing 2 BR Villa - 2 min from the beach
9.6 out of 10, Exceptional, (91)
"We had a wonderful week in St Maarten at the Cliffside property overlooking Simpson Bay. Perfect for 2 couples with great outdoor spaces and views of the water on 2 sides. We will definitely be back!"
Oceanfront amazing 2 BR Villa - 2 min from the beach
Pelican Key Private Luxury Villa With Panoramic View Of The Caribbean Sea
Beach
Pelican Key Private Luxury Villa With Panoramic View Of The Caribbean Sea
9.6 out of 10, Exceptional, (35)
"I couldn’t post the review here that I wanted because it’s too long. I put it up on Reddit. We had a couple of issues. Michael was very responsive and had them fixed for us. The view was beautiful, and the outside deck was the best."
Pelican Key Private Luxury Villa With Panoramic View Of The Caribbean Sea
BLUE OPAL Private Pool-Generator, Ocean Views Pelican Key - Simpson Bay
5 bedrooms, in-room safe, desk, travel crib
BLUE OPAL Private Pool-Generator, Ocean Views Pelican Key - Simpson Bay
10.0 out of 10, Exceptional, (23)
"The house was amazing and very convenient to the restaurants and beaches. Elysa is a wonderful host and very responsive to any requests. We enjoyed our stay here immensely and would recommend booking with Elysa and the management company if you are looking to travel to Sint Maarten."
BLUE OPAL Private Pool-Generator, Ocean Views Pelican Key - Simpson Bay
Oceanfront Villa With Private Pool
Pool
Oceanfront Villa With Private Pool
10.0 out of 10, Exceptional, (2)
"We stayed here after a wedding to decompress and relax. The house was very nice. The pool was refreshing and the view amazing. Going to bed each night listening to the waves was beyond soothing. Also close to everything you could need!"
Oceanfront Villa With Private Pool
Pelikaan Sunset: A Villa With Stunning Ocean Views
Property grounds
Pelikaan Sunset: A Villa With Stunning Ocean Views
10.0 out of 10, Exceptional, (5)
"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.
Outdoor pool
Il Punto Blu: Newly Renovated 3 Bdrm, Beachfront, Pool, walkable to restaurants.
9.2 out of 10, Wonderful, (5)
"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!
Outdoor pool
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
Beach/ocean view
Luxurious Villa " Sea La Vie" in Pelican Key
10.0 out of 10, Exceptional, (2)
"Our host was very attentive and proactive in addressing some potential concerns we may encounter due to island wide power outages. This was absolutely out of his control yet he went above and beyond to ensure we would be minimally impacted while on vacation. The villa was lovely and well maintained. We had a couple maintenance needs as you would in any house but they were addressed right away and had no impact on our stay. We enjoyed our stay and would highly recommend."
Luxurious Villa " Sea La Vie" in Pelican Key
Cliff House
Outdoor pool
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
Terrace/patio
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
Pool
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 Saint-Tropez Breathtaking Sea Views
Outdoor pool
Villa Saint-Tropez Breathtaking Sea Views
10.0 out of 10, Exceptional, (1)
"This Villa was better than we had imagined. The view is spectacular. The Concierge and her team were fabulous and very responsive to all of our questions and requests. From car rentals to activities etc; The bedrooms are spacious and feel slightly apart from the living area which creates a lovely feeling of privacy. We were there with two of our adult children and their spouses and everyone thoroughly enjoyed the spaciousness and the views. The Concierge aided us in securing a Private Chef...
Villa Saint-Tropez Breathtaking Sea Views
Amazing Ocean Front Villa in Pelican Key - Pool and Private Ocean Access
Pool
Amazing Ocean Front Villa in Pelican Key - Pool and Private Ocean Access
10.0 out of 10, Exceptional, (35)
"this is one of my favorite places I have stayed in Saint Martin. The views were absolutely tremendous. The caretakers were very informative and went through the entire house Upon arrival, the pool was amazing and the ability to jump in the ocean right off the back of the house was even better. Living room opened up to the pool, deck and swimming area. They had plenty of living space outside on the deck and you were able to watch an Unbelievable sunset from the house every day. Thank you so much...
Amazing Ocean Front Villa in Pelican Key - Pool and Private Ocean Access
Anchor House
Luxury Condo, 3 Bedrooms | Water view
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
Property grounds
Pelican Key "shoreline" Villa 3bd+canapé
Pelican Key "shoreline" Villa 3bd+canapé
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See all available properties in 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.
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Other property types in Simpson Bay

Tradewinds at Simpson Bay
Exterior
Tradewinds at Simpson Bay
3.5 star property
8.8 out of 10, Excellent, (11)
"It’s beautiful and all the restaurants are across the way! "
Tradewinds at Simpson Bay
The Horny Toad Guesthouse
Orchid | View from room
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 price is CA $231
CA $299 total
includes taxes & fees
Oct 1 - Oct 2
The Horny Toad Guesthouse
Simpson Bay Suites
Beach nearby, white sand, sun loungers, beach umbrellas
Simpson Bay Suites
3.5 star property
6.8 out of 10, (102)
"They are very accommodating 👍"
The price is CA $145
CA $163 total
includes taxes & fees
Oct 7 - Oct 8
Simpson Bay Suites
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?
Choose from multiple villas in Simpson Bay with a total average guest review rating of 9.7. Villa Amaryllis comes highly recommended by travelers. This 5-star stay has a garden and a swimming pool. Villa Starfish Coral Beach Club By Redawning is another popular option. It has a 5-star rating and amenities including a garden and a swimming pool.
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?
Villa Amaryllis is an excellent 5-star villa in Simpson Bay. Around 3 kilometres from downtown, a swimming pool and concierge services are among the amenities here. Villa Starfish Coral Beach Club By Redawning is another high-end stay around 8 kilometres from the city center. Also rated 5 stars, this property includes a swimming pool and a villa.
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.
What is there to do near my villa in Simpson Bay?
Simpson Bay has enough activities and experiences to keep you amused for weeks, starting with Simpson Bay Beach. Kim Sha Beach, Lay Bay Beach and Hollywood Casino are other renowned attractions. If you’re in town a while, Dunes Casino and Flamingo Beach will cap off your itinerary nicely.