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Compare 45 Villas in Simpson Bay with updated reviews, rates, and availability.

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

9.8 out of 10, Exceptional, (71)
"Me and my wife enjoyed our honeymoon stay here to relax and enjoy the island. The home is in a perfect area even pay cash for rental via Tami we will be back soon great speaker of you want a vibe at the property with pool and drinks. "
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!!

10.0 out of 10, Exceptional, (99)
"Had a great stay see u soon No complaints here "
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

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)
"This home was beautiful and the perfect place to stay! The home is professionally managed and very nicely appointed. The view and pool are breathtaking. It’s also so rare to find a place where each guest can have their own bedroom and bathroom. I would absolutely stay here again!"
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!

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

10.0 out of 10, Exceptional, (3)
"Great quiet location. Absolutely beautiful views and sunsets on the pool deck. Definitely a nice hidden gem. "
Charming 2-bedroom villa with AC, WiFi, stunning ocean views

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

Villa Bonjour water front villa next to Maho

10.0 out of 10, Exceptional, (13)
"The house is in a great location and is beautiful. Beds were a little hard but other than that I would give it a 5 star review. We spent most days just hanging by the pool. The house has everything you could ask for or need. Great vacation."
Villa Bonjour water front villa next to Maho

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)
"Most amazing property on the island.Everything is true to listing and the service provided was top notch."
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)
"Amazing location. Views of the bay and the ocean on each side. Walkable to Maho restaurants and grocery. Would stay again"
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)
"Perfect place for a big family vacation."
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

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!
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 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.
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.