Search Villas in Simpson Bay

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
11 Rab. II - 13 Rab. II
In two weeks
18 Rab. II - 20 Rab. II
In one month
2 Jum. I - 4 Jum. I
In two months
30 Jum. I - 1 Jum. II

Compare 46 Villas in Simpson Bay with updated reviews, rates, and availability.

* 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, (52)
"Most amazing property on the island.Everything is true to listing and the service provided was top notch."
* Holidays Specials* ALMA - DIRECT BEACH ACCESS 4 BR VILLA
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, (41)
"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
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, (95)
"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 with backup Generator
On the beach, beach towels

One Hundred Million Dollar Yacht On Land 5 star Villa with backup Generator

9.8 out of 10, Exceptional, (70)
"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 with backup Generator
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, (26)
"What a wonderful time visiting SXM and Blue Opal was definitely a part of that! Beautiful home with ample amount of space for our group of 10 (5 adults, 5 kids)!Air conditioning worked great, the house never felt warm!Plenty of pool toys for the kids.My only recommendation would be to get rid of the projector in the upstairs master bedroom- the blue power lights are super bright at night, my understanding is it didn’t work anyways. "
BLUE OPAL Private Pool-Generator, Ocean Views Pelican Key - Simpson Bay
Cliff House
Outdoor pool

Cliff House

3.5 star property
8.8 out of 10, Excellent, (3)
"Muna, housekeeper, was lovely. Warm and friendly. Stacey, the manager, also warm and friendly and very responsive. The owner, John, was just the same too. Property could use some sprucing, mainly water pressure and pool pump, however we learned it was an area outage. Overall, we loved the privacy and all the birds and iguanas and the setting is BEYOND beautiful!!"
Cliff House
Stunning Beach Front Villa With Infinity Pool
Pool

Stunning Beach Front Villa With Infinity Pool

9.4 out of 10, Exceptional, (10)
"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
Outdoor pool

BEACHFRONT DESIGN VILLA

9.8 out of 10, Exceptional, (116)
"This house provided a wonderful location for our two families, totaling 7 people (3 older teenagers) to spend Spring Break. The house had beautiful outdoor spaces that provided shaded areas throughout the day. There were nice places for everyone; spots to read, have morning coffee, yoga, relax in the pool. The beach was beautiful to look at and listen to but not a good spot for children or casual swimming. The location was easily walkable to Maho beach for pictures but traffic could be a little...
BEACHFRONT DESIGN VILLA
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, (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
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, (40)
"Comfortable, good location great view,very nice pool. Would stay there again."
Amazing Ocean Front Villa in Pelican Key - Pool and Private Ocean Access
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, (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!
Luxurious Villa " Sea La Vie" in Pelican Key
Beach/ocean view

Luxurious Villa " Sea La Vie" in Pelican Key

9.8 out of 10, Exceptional, (6)
"My wife and I and our 2 adult kids stayed for a week. This was the perfect location for us!! Loved the house, the view, the private pool and a garage for our rental car. Would definitely stay here again. Michael, the owner is very responsive, as well as the property care taker who is available for any needs. Highly recommend Sea La Vie if you’re looking for an awesome location for SXM. "
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, (2)
"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
Il Punto Blu: Newly Renovated 3 Bdrm, Beachfront, Pool, walkable to restaurants.
Interior

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.
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
Villa Domila-Luxury 3Bed & 3Bath with private pool-Free airport transfer-Central
Beach nearby, sun loungers, beach towels

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

10.0 out of 10, Exceptional, (10)
"This villa is exactly as it looks in the photos. The view and sunset were spectacular! The communication with the host was excellent. The location was very good as well, either for walking or with a rental. Would definitely stay here again. Thank you!"
Villa Domila-Luxury 3Bed & 3Bath with private pool-Free airport transfer-Central
Pelikaan Sunset: A Villa With Stunning Ocean Views
Terrace/patio

Pelikaan Sunset: A Villa With Stunning Ocean Views

9.8 out of 10, Exceptional, (6)
"A wonderful villa, especially for larger groups. VERY professionally run. An exceptionally positive experience for stay in Sint Maarten."
Pelikaan Sunset: A Villa With Stunning Ocean Views
Villa Bonjour water front villa next to Maho
Property grounds

Villa Bonjour water front villa next to Maho

10.0 out of 10, Exceptional, (12)
"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 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
Villa Sea Forever @ Pelican Key - Paradise Awaits!
Beach nearby, beach towels

Villa Sea Forever @ Pelican Key - Paradise Awaits!

10.0 out of 10, Exceptional, (1)
"everything you see in listing is accurate, views.... absolutely amazing, from morning rainbows to the evening sunsets. very bright, and most days do not need AC, as there is a normal cooling breeze, just open front door and slider.... ahhh, perfectwas there for three days alone until sisters come down for a week, location was great, bit hard to find for someone who never has been therereally could not have found a better location.thank you for the perfect vacation.Ernie Viens"
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.
Don't see what you're looking for?
See all available properties in Simpson Bay
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Simpson Bay

Hilton Vacation Club Royal Palm St. Maarten
Outdoor pool, sun loungers

Hilton Vacation Club Royal Palm St. Maarten

4.0 star property
9.0 out of 10, Wonderful, (1069)
"The staff was outstanding. ALL of them, but I really appreciated Ms. Diana’s special attention in the restaurant. She was always right on top of things for us. "
The price is SAR 942
SAR 1,088 total
includes taxes & fees
1 May - 2 May
Hilton Vacation Club Royal Palm St. Maarten
The Hills Residence
Amazing Top Floor Apartment | Balcony

The Hills Residence

3.0 star property
9.4 out of 10, Exceptional, (20)
"I loved staying at The Hills because it was very centric, easy to move around. The property has an amazing view with a pool, beautiful decor comfortable bed. I love it all. I will recommend it. I am staying here again. "
The Hills Residence
Simpson Bay Suites
Beach nearby, white sand, sun loungers, beach umbrellas

Simpson Bay Suites

3.5 star property
6.8 out of 10, (118)
"Highly recommended and friendly staff…"
The price is SAR 506
SAR 567 total
includes taxes & fees
16 Apr - 17 Apr
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?
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?
Simpson Bay has multiple villas with a total average guest review rating of 9.7. Villa Bianca is a popular choice with seasoned Expedia guests. Visitors of this 4.5-star retreat will have use of a swimming pool and a barbecue grill. Villa Amaryllis is another highly rated stay. This 4-star villa offers a swimming pool and a barbecue grill, among many other conveniences.
How many villas are there in Simpson Bay?
Choose from 46 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 4-star accommodations here that’ll suit your needs. Check in to Villa Bianca, around 2 kilometers from the downtown area. a swimming pool and a terrace are two of the many amenities here. Villa Amaryllis is another stylish option featuring a swimming pool and concierge services. It’s located around 3 kilometers from central Simpson Bay.
Why book your villa in Simpson Bay with Expedia?
Expedia makes it a breeze to find your dream villa in Simpson Bay. Taking the kids on a break? Take advantage of our filters to look for stays with amenities like a pool. If you have a certain budget, click on how much you’d like to spend and the star rating of the property. We’ll help you find the perfect fit that gels with your taste and style.
How can I find cheap villas in Simpson Bay?
Expedia can help you easily locate cheap villas in Simpson Bay. Simply use our handy filter tool to select amenities, budget and star rating to refine your search and find an awesome place to stay in a few quick keystrokes.