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Check prices for these dates

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1 Aug - 3 Aug
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22 Aug - 24 Aug
In two months
19 Sep - 21 Sep

Villas in Simpson Bay

Stunning Beach Front Villa With Infinity Pool
Pool

Stunning Beach Front Villa With Infinity Pool

9.4 out of 10, Exceptional, (13)
"Loved the property. Location was fantastic. Views from the house and description of property really didn’t do it justice. Would definitely recommend to anyone visiting the island. "
Stunning Beach Front Villa With Infinity Pool
Villa Bonjour water front villa next to Maho
Property grounds

Villa Bonjour water front villa next to Maho

10.0 out of 10, Exceptional, (13)
"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
One Hundred Million Dollar Yacht On Land 5 star Villa on the ocean
On the beach, beach towels

One Hundred Million Dollar Yacht On Land 5 star Villa on the ocean

9.8 out of 10, Exceptional, (72)
"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 on the ocean
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, (101)
"Super great time. Best location for all activities. Would stay again."
3 BR/3 bath. Sint Maarten DIRECT BEACHFRONT WITH POOL! Rates start at $225/nt!!
Oceanfront amazing 2 BR Villa - 2 min from the beach
Outdoor pool

Oceanfront amazing 2 BR Villa - 2 min from the beach

9.4 out of 10, Exceptional, (95)
"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
Pelikaan Sunset: A Villa With Stunning Ocean Views
Terrace/patio

Pelikaan Sunset: A Villa With Stunning Ocean Views

9.8 out of 10, Exceptional, (7)
"Incredible property for the family. Clean, private and walkable community. Highly recommended"
Pelikaan Sunset: A Villa With Stunning Ocean Views
ALMA - DIRECT BEACH ACCESS 4 BR VILLA
Terrace/patio

ALMA - DIRECT BEACH ACCESS 4 BR VILLA

10.0 out of 10, Exceptional, (58)
"We loved our stay here. The views are gorgeous and the house was clean and exactly as described. Plenty of room for parking if you have a rental and easy enough to walk to the beach bars by Maho if you don’t feel like driving. Communication with the owner was easy and reliable. Only recommendation I’d have would be to replace/upgrade the pillows as they were all flat and not the most comfortable. Everything else was great! "
ALMA - DIRECT BEACH ACCESS 4 BR VILLA
BEACHFRONT DESIGN VILLA
Outdoor pool

BEACHFRONT DESIGN VILLA

9.8 out of 10, Exceptional, (119)
"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
Cliff House
Outdoor pool

Cliff House

3.5 star property
8.8 out of 10, Excellent, (3)
"Great stay at the Cliff house. Very private accommodations and plenty of room for a couple or a family experience. Easy parking, but only a short 7 minute walk into town. "
Cliff House
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, (48)
"Had a great time with friends great house very nice pool nice sun set views"
Pelican Key Private Luxury Villa With Panoramic View Of The Caribbean Sea
Villa Impala, 5 bedroom villa beachfront in Simpson Bay, Sint Maarten
Outdoor dining

Villa Impala, 5 bedroom villa beachfront in Simpson Bay, Sint Maarten

10.0 out of 10, Exceptional, (1)
"The home is simply amazing. The glass sliders opening to a beachfront patio and pool is truly special. The primary bedroom and shower with a panoramic view of the beach is stunning. The home is even better than the pictures show. Better yet, Jade is an amazing person and host that improves the stay. We wouldnt hesitate to stay here again. "
Villa Impala, 5 bedroom villa beachfront in Simpson Bay, Sint Maarten
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, (44)
"Comfortable, good location great view,very nice pool. Would stay there again."
Amazing Ocean Front Villa in Pelican Key - Pool and Private Ocean Access
Blue Pelican Luxury Villa - Featured on HGTV!
Outdoor pool

Blue Pelican Luxury Villa - Featured on HGTV!

10.0 out of 10, Exceptional, (3)
"There aren’t enough good things I can say about this place, incredible location and amazing house. Bill was very easily accessible and really helped make my stay amazing! Looking forward to staying there again."
Blue Pelican Luxury Villa - Featured on HGTV!
Villa Sunshine: Beachfront! 10 min. walk to the famous Maho Beach!
Outdoor pool

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

9.6 out of 10, Exceptional, (30)
"Rikki was waiting at the rental car company for us. He was warm & so helpful. The villa was absolutely spotless & in the best location. The 10 of us girls had an absolutely wonderful time. Can't wait to return to wonderful St Martin."
Villa Sunshine: Beachfront! 10 min. walk to the famous Maho Beach!
Luxurious Villa " Sea La Vie" in Pelican Key
Property grounds

Luxurious Villa " Sea La Vie" in Pelican Key

9.8 out of 10, Exceptional, (7)
"Very comfortable and relaxing. We enjoyed hanging out by the pool and the wonderful views of the ocean. We were close to everything as well."
Luxurious Villa " Sea La Vie" in Pelican Key
Charming 2-bedroom villa with AC, WiFi, stunning ocean views
Terrace/patio

Charming 2-bedroom villa with AC, WiFi, stunning ocean views

10.0 out of 10, Exceptional, (3)
"This property was a fantastic place to relax and enjoy the views! The villa is well taken care of and it was very comfortable to stay in. The property has a great pool and beautiful views no matter what time of the day or night. Looking forward to going back one day."
Charming 2-bedroom villa with AC, WiFi, stunning ocean views
Il Punto Blu - Beautiful renovated condo, AC, WIFI, walkable restaurants/beach.
Interior

Il Punto Blu - Beautiful renovated condo, AC, WIFI, walkable restaurants/beach.

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 - Beautiful renovated condo, AC, WIFI, walkable restaurants/beach.
Villa Sea Forever @ Pelican Key - Paradise Awaits!
Beach nearby, beach towels

Villa Sea Forever @ Pelican Key - Paradise Awaits!

10.0 out of 10, Exceptional, (2)
"Excellent choice for couples or families. "
Villa Sea Forever @ Pelican Key - Paradise Awaits!
Villa Livity 6 Bed Luxury Sea View boutique villa
Outdoor dining

Villa Livity 6 Bed Luxury Sea View boutique villa

Villa Livity 6 Bed Luxury Sea View boutique villa
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

9.8 out of 10, Exceptional, (27)
"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
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

Baker's Suites

Baker's Suites

10/10 Excellent
"Great place"
Jeselle 4-night trip
Posted 2 days ago
Baker's Suites

Frequently asked questions

How much do villas in Simpson Bay cost?
You'll pay between and 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 9.6. 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 45 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.