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Featured Villas in Simpson Bay

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

9.8 out of 10, Exceptional, (77)
"We spent ten days in june 2025 at this home. Pool was amazing as was the location. Would definitely rent again. Thank you!"
One Hundred Million Dollar Yacht On Land 5 star Villa on the ocean

BEACHFRONT DESIGN VILLA

9.8 out of 10, Exceptional, (119)
"Great stay, house well equipped, would book it again. "
BEACHFRONT DESIGN VILLA

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

Luxurious Villa " Sea La Vie" in Pelican Key

9.6 out of 10, Exceptional, (8)
"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 Turquoise Heaven

Villa Turquoise Heaven

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

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.

Oceanfront amazing 2 BR Villa - 2 min from the beach

9.4 out of 10, Exceptional, (96)
"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

4 bedroom Pelican Key Private Luxury Villa, Panoramic View Of The Caribbean Sea

9.6 out of 10, Exceptional, (48)
"The house and view are as amazing as the pictures show. Kitchen is well equipped. Plenty of bath towels and beach towels. Supplies are well equipped as well (detergent, paper towels, toilet paper, etc.). Peaches and Michael are both very quick to respond. Would stay here again and recommend to friends. Great location, close to many great restaurants and activities. One of the nicest personal rentals we have ever stayed at."
4 bedroom Pelican Key Private Luxury Villa, Panoramic View Of The Caribbean Sea

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

Villa Bonjour water front villa next to Maho

10.0 out of 10, Exceptional, (14)
"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

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

10.0 out of 10, Exceptional, (103)
"Wirh 3 bedrooms and 3 baths, this was perfect for us and our adult children to spend amazing quality time. The pool and view was the cherry on top. "
3 BR/3 bath. Sint Maarten DIRECT BEACHFRONT WITH POOL! Rates start at $225/nt!!

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

9.6 out of 10, Exceptional, (30)
"Location was great. Outside space was fantastic."
Villa Sunshine: Beachfront! 10 min. walk to the famous Maho Beach!

ALMA - DIRECT BEACH ACCESS 4 BR VILLA

10.0 out of 10, Exceptional, (58)
"House is awesome. Host is amazing. Neighborhood is ok but not as great as house. "
ALMA - DIRECT BEACH ACCESS 4 BR VILLA

Stunning Beach Front Villa With Infinity Pool

9.6 out of 10, Exceptional, (14)
"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

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

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 OPAL 🏝️AMAZING OCEAN VIEWS!! Private Pool Pelican Key - Simpson Bay

9.8 out of 10, Exceptional, (27)
"The pictures don’t do the views justice. The house was absolutely stunning and the property managers were very helpful in every aspect during our stay on the island. Would absolutely stay here again!"
BLUE OPAL 🏝️AMAZING OCEAN VIEWS!! Private Pool Pelican Key - Simpson Bay

Villa Livity 6 Bed Luxury Sea View boutique villa

Villa Livity 6 Bed Luxury Sea View boutique villa
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

Find out more about Simpson Bay

Find out more about Simpson Bay

Simpson Bay Villas information

Number of reviews
450
Accommodation
51 Villas
Lowest Price
Highest Price

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 51 villas in Simpson Bay. No matter if you're travelling with the kids or planning a weekend escape with your buddies, Expedia will help you find the perfect space for your squad.
What are the best cheap villas in Simpson Bay?
Villas start at per night, so your Simpson Bay adventure doesn't need to take a bite out of your budget! La Brise By Redawning is a wallet-friendly option that comes with plenty of amenities, including a barbecue grill and a swimming pool. Summerwinds 3 Bedrooms 3. 5 Bathrooms Villa is another cheap stay in this sought-after destination. Conveniences here include a swimming pool and a barbecue grill. Exploring free attractions in Simpson Bay will stretch your travel budget even further. Maho Beach and Orient Bay Beach are favourites among tourists. With the dollars you save, you can explore some more! 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.