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Featured Villas in Simpson Bay

3 BR/3 bath. Sint Maarten DIRECT BEACHFRONT WITH POOL! Rates start at $225/nt!!

10.0 out of 10, Exceptional, (94)
"Bob is one of the best hosts you will come across. The place was fantastic. The deck with the private pool overlooking the ocean was the winner here. A short 5-10 minute walk to Maho. The place reminded me of a cottage. Has a nice rustic feel to it. Bedrooms and bathrooms were clean.kitchen had everything we needed. Plenty of drinking glasses. Beds were comfortable. Bin was a gracious host who met us and checked us in. He was there if we had any questions but was not intrusive. He leaves you...
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, (68)
"We loved this house with the sound of the waves and the ocean front view. Pool was great and was a wonderful place to hang out. The house is Close to many things but still feels very private. House was clean and had everything we needed to cook most our meals. "
One Hundred Million Dollar Yacht On Land 5 star Villa with backup Generator

Stunning Beach Front Villa With Infinity Pool

9.4 out of 10, Exceptional, (8)
"The unit was very much as advertised. Geraldine took excellent care of us. The neighborhood felt safe and was very walkable. Great restaurant close by called Juliette’s. Cabs were easy to get for anyplace you wanted to go. "
Stunning Beach Front Villa With Infinity Pool

BEACHFRONT DESIGN VILLA

9.8 out of 10, Exceptional, (114)
"Great house and fantastic location. The view is amazing, you can see the ocean from most rooms. Happy vibes and the service was awesome!!"
BEACHFRONT DESIGN VILLA

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

10.0 out of 10, Exceptional, (38)
"The view is worth it all! The villa is dated and worn, but the view! We spent most of our time at the villa outside around the table or in the pool looking at the ocean. The crashing waves below are a great sound that even at night with all the windows shut you still hear them! location is prime with quick access and a convenience store is in with walking distance. Owner was great and answered all my questions. Be prepared for the mosquitos that come out at night. Fortunately a collection of bug...
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

* Holidays Specials* ALMA - DIRECT BEACH ACCESS 4 BR VILLA

10.0 out of 10, Exceptional, (50)
"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

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

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, (39)
"Loved the 270 degree views of Sea. Nice house and quiet"
Pelican Key Private Luxury Villa With Panoramic View Of The Caribbean Sea

Villa Bonjour water front villa next to Maho

10.0 out of 10, Exceptional, (10)
"We had a wonderful time celebrating a 50th birthday. Location was perfect. It was close to the airport, airport beach and restaurants. The house was perfect for four couples. The sun came out on the pool deck by 9:00am so plenty of time for swimming and tanning. The house manager was attentive and always available. We highly reccomend staying at Villa BonJour. "
Villa Bonjour water front villa next to Maho

Villa Sunshine: Beachfront! 10 min. walk to the famous Maho Beach!

9.6 out of 10, Exceptional, (29)
"The villa was amazing and was perfect for our group. The view was incredible. Will definitely recommend."
Villa Sunshine: Beachfront! 10 min. walk to the famous Maho Beach!

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

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

9.0 out of 10, Wonderful, (6)
"This oceanfront villa offers a stunning Caribbean experience with some minor trade-offs. The spacious, well-appointed interior features comfortable king-size beds and tasteful décor throughout. The common areas are generous, and the front patio is a perfect spot to soak in the breathtaking ocean views. The kitchen comes well-equipped for those who enjoy cooking while on vacation.However, potential guests should note a few practical considerations. While the property overlooks the ocean, there's...
Il Punto Blu: Newly Renovated 3 Bdrm, Beachfront, Pool, walkable to restaurants.

BLUE OPAL Private Pool-Generator, Ocean Views Pelican Key - Simpson Bay

10.0 out of 10, Exceptional, (25)
"We loved everything about this house and the property management was absolutely superb. Wonderful view, very clean, well stocked and very spacious. "
BLUE OPAL Private Pool-Generator, Ocean Views Pelican Key - Simpson Bay

Villa Domila-Luxury 3Bed & 3Bath with private pool-Free airport transfer-Central

10.0 out of 10, Exceptional, (8)
"Our stay at Villa Domila was a great break from the cold at home. The house is very well located, quiet and out of the heavy traffic areas. But access to all areas of both the Dutch and French sides of the island was quick and easy. The pool was fabulous, very well maintained and the pool chairs very comfy. Beds were comfortable and bathrooms clean. The sofa was low and could use updating but if you are there with a family it made perfect sense. The couple of times we reached out to the owner...
Villa Domila-Luxury 3Bed & 3Bath with private pool-Free airport transfer-Central

Luxurious Villa " Sea La Vie" in Pelican Key

10.0 out of 10, Exceptional, (4)
"House is in a calm neighborhood. Not far from restaurants and grocery shops. There is a garage connected to the house from the behind, which is very nice. Nice pool and terrace on the view side of the house. Good experience all together."
Luxurious Villa " Sea La Vie" in Pelican Key

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

Villa Zircon in Pelican Key awaits you - GENERATOR

9.4 out of 10, Exceptional, (3)
"We had a fantastic stay at Villa Zircon in Pelican Key The property was clean and had everything we needed. Central location made it easy and quick to be anywhere. Any question we’re replied to immediately ⭐️"
Villa Zircon in Pelican Key awaits you - GENERATOR
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

The Hills Residence

3.0 star property
9.4 out of 10, Exceptional, (13)
"My husband and I were pleasantly surprised by this property. Our initial intent was to stay at an all-inclusive in St. Martin, but we found l this property on Expedia and our experience here exceeded our expectations. The unit was essentially brand new, brand new plates, cutlery furniture, towels, beach towels included. The images are a true representation of the suite. There were local restaurants, bars, grocery, convenience stores near by and the kitchen was equipped with all necessary...
The Hills Residence

Simpson Bay Suites

3.5 star property
6.8 out of 10, (112)
"The location close to the airport "
The price is AU$298
includes taxes & fees
18 Feb - 19 Feb
Simpson Bay Suites

Tradewinds at Simpson Bay

3.5 star property
9.2 out of 10, Wonderful, (19)
"Wonderful view, decent location and great host! "
Tradewinds at 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.

Frequently asked questions

How much do villas in Simpson Bay cost?
Villas in Simpson Bay range between and per night. These stays give you the privacy to enjoy your own space at a price that fits your budget. 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.
How many villas are there in Simpson Bay?
Lock in your holiday dates and then choose from 39 villas in Simpson Bay. For a family adventure, a getaway with your besties or anything in between, Expedia will help you find the ideal space in just a click or two.
What is there to do near my villa in Simpson Bay?
Whatever you’re interested in, Simpson Bay has lots of things to keep you busy. Maho Beach, Mullet Bay Beach and Grand Case Beach are on most travellers’ trip plans. Don’t leave without exploring Anse Marcel Beach, Simpson Bay Beach and Cupecoy Beach either. With Expedia’s Simpson Bay hotel deals, you can discover even more popular attractions like these with the cash you save.