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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, (99)
"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!!

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

9.8 out of 10, Exceptional, (71)
"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

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

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

Stunning Beach Front Villa With Infinity Pool

9.4 out of 10, Exceptional, (13)
"My group sailed in the 45th Heinekens Regatta and 7 of us stayed in this Villa . We had a great time and will consider coming back . The maid comes every day except Sunday . She keeps this property very clean and it was a pleasure to stay here "
Stunning Beach Front Villa With Infinity 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

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!

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

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

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

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

ALMA - DIRECT BEACH ACCESS 4 BR VILLA

10.0 out of 10, Exceptional, (56)
"Beautiful location and interior. Some of the furniture is a bit low making the up and down process a bit of a strain for seniors."
ALMA - DIRECT BEACH ACCESS 4 BR VILLA

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.

Villa Livity 6 Bed Luxury Sea View boutique villa

Villa Livity 6 Bed Luxury Sea View boutique villa

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

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

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

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

Villa Zircon in Pelican Key awaits you - GENERATOR

9.4 out of 10, Exceptional, (3)
"We were a family of 8 adults staying and the villa was perfect for us. Clean, quality sheets, towells, and very comfortable beds. The pool and views were wonderful."
Villa Zircon in Pelican Key awaits you - GENERATOR

Newly renovated 7 bedroom villa in the Dutch side of St. Maarten

Newly renovated 7 bedroom villa in the Dutch side of St. Maarten
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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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.
How many villas are there in Simpson Bay?
Choose from 42 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.
Are there any 5-star villas in Simpson Bay?
Unfortunately, there are no 5-star villas in Simpson Bay. However, there are some terrific 4-star stays here that’ll suit your needs. Check out Villa Amaryllis, approximately 3 kilometers from the downtown area. Concierge services and a swimming pool are a couple of the many conveniences here. Villa Amaryllis is another upmarket option including concierge services and a swimming pool. This property is located about 3 kilometers from central Simpson Bay.