Search Villas in Simpson Bay

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec
In one month
9 Jan - 11 Jan
In two months
6 Feb - 8 Feb

Our top choices for Simpson Bay villas

Fridge, microwave, oven, stovetop
Large 2BR Condo - STEPS FROM BEACH!

Large 2BR Condo - STEPS FROM BEACH!

Large 2BR Condo - STEPS FROM BEACH!
Maho
10.0 out of 10, Exceptional, (1)
"What a perfect unit! She thought of every extra detail down to laundry detergent. The condo was clean, beautifully decorated, and perfect for our stay. The added amenities made it a joy. It was so close to the beach and the beach chairs and towels made it all so easy. Jean was available to answer every questions and to help us with our pre-trip planning. There are many grocery stores close and one of the most beautiful beaches on the island is a short walk away. Thank you for a beautiful...
United States
Cylinda N.
The price is AED 666
AED 1,145 total
includes taxes & fees
31 Dec - 1 January 2026
Large 2BR Condo - STEPS FROM BEACH!
Property grounds
Diamond Retreat Master Chambre

Diamond Retreat Master Chambre

Diamond Retreat Master Chambre
Koolbai
The price is AED 881
AED 1,263 total
includes taxes & fees
11 Jan - 12 January 2026
Diamond Retreat Master Chambre
Outdoor pool, a heated pool
SEA TRUE VILLA ,NEW EDIFICE 2021, LAVISH !

SEA TRUE VILLA ,NEW EDIFICE 2021, LAVISH !

SEA TRUE VILLA ,NEW EDIFICE 2021, LAVISH !
Sint Maarten
9.0 out of 10, Wonderful, (7)
"Everything about this property is perfect, the villa is beautiful in a great location. "
United States
Troy N.
The price is AED 1,377
AED 1,691 total
includes taxes & fees
21 Dec - 22 Dec
SEA TRUE VILLA ,NEW EDIFICE 2021, LAVISH !
Pool
Luxury 4BR Villa w/ Private Pool & Ocean Views

Luxury 4BR Villa w/ Private Pool & Ocean Views

Luxury 4BR Villa w/ Private Pool & Ocean Views
Indigo Bay
10.0 out of 10, Exceptional, (1)
"This property has a breathtaking view and is in the perfect location—close to stores and just minutes from the beaches.Fritz, the host, was amazing! The island had just gone through a major storm the day before we arrived, and despite the circumstances, Fritz was always available and ready to help with anything we needed. He even offered us an extra day to make up for any inconvenience, which was so thoughtful and appreciated.I would absolutely stay here again and would highly recommend this...
United States
Ms Light T.
The price is AED 2,287
AED 4,922 total
includes taxes & fees
15 Dec - 16 Dec
Luxury 4BR Villa w/ Private Pool & Ocean Views
Property grounds
Villa Norman: Unique 3 bedroom, 3 En-Suite Bathroom on 35 Acre Green Farmland

Villa Norman: Unique 3 bedroom, 3 En-Suite Bathroom on 35 Acre Green Farmland

Villa Norman: Unique 3 bedroom, 3 En-Suite Bathroom on 35 Acre Green Farmland
Saint Martin
10.0 out of 10, Exceptional, (3)
"We had an amazing stay and enjoyed the villa very much! The host Romario is very kind, friendly ,and was available any time. We truly enjoyed our stay and looking forward to coming back!"
United States
Roman A.
The price is AED 2,149
AED 3,026 total
includes taxes & fees
12 Dec - 13 Dec
Villa Norman: Unique 3 bedroom, 3 En-Suite Bathroom on 35 Acre Green Farmland
Outdoor dining
Villa Solandra – 3BR Oceanfront Sunset w/ Pool

Villa Solandra – 3BR Oceanfront Sunset w/ Pool

Villa Solandra – 3BR Oceanfront Sunset w/ Pool
Indigo Bay
The price is AED 1,896
AED 3,693 total
includes taxes & fees
15 Dec - 16 Dec
Villa Solandra – 3BR Oceanfront Sunset w/ Pool
Villa | Living area
Avenue du lagon

Avenue du lagon

Avenue du lagon
Oyster Pond
The price is AED 5,325
AED 7,191 total
includes taxes & fees
12 Dec - 13 Dec
Avenue du lagon
Outdoor dining
BO'TJE - Beautiful 4-bedroom villa with AC, WiFi in lovely Tamarind Hill Estate

BO'TJE - Beautiful 4-bedroom villa with AC, WiFi in lovely Tamarind Hill Estate

BO'TJE - Beautiful 4-bedroom villa with AC, WiFi in lovely Tamarind Hill Estate
Tamarind Hill Estates
The price is AED 3,122
AED 3,847 total
includes taxes & fees
16 Dec - 17 Dec
BO'TJE - Beautiful 4-bedroom villa with AC, WiFi in lovely Tamarind Hill Estate
Pool
Villa Sophia: Oceanfront w/ Generator & Pool

Villa Sophia: Oceanfront w/ Generator & Pool

Villa Sophia: Oceanfront w/ Generator & Pool
Tamarind Hill Estates
Villa Sophia: Oceanfront w/ Generator & Pool
Pool
Villa de 10 Chambres les Pieds Dans L'eau à Guana Bay

Villa de 10 Chambres les Pieds Dans L'eau à Guana Bay

Villa de 10 Chambres les Pieds Dans L'eau à Guana Bay
Sint Maarten
The price is AED 14,093
AED 15,882 total
includes taxes & fees
11 Jan - 12 January 2026
Villa de 10 Chambres les Pieds Dans L'eau à Guana 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Simpson Bay Hotel Reviews

Hilton Vacation Club Flamingo Beach St. Maarten

Hilton Vacation Club Flamingo Beach St. Maarten

10/10 Excellent
"I wish the staff were more friendly"
John 3-night trip
Posted 1 day ago
Hilton Vacation Club Flamingo Beach St. Maarten

Frequently asked questions

How much do villas in Simpson Bay cost?
You'll pay between AED 1,145 and AED 15,882 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 9.4. 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 43 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?
Although there aren't any 5-star villas in Simpson Bay, there are 4-star accommodations that will fit your needs. Located around 3 kilometers from downtown, Villa Amaryllis offers amenities like a swimming pool and concierge services. Another stylish retreat is Villa Amaryllis. It's around 3 kilometers from central Simpson Bay and features conveniences such as concierge services and a swimming pool.
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.

Explore a world of travel with Expedia