Villas in Simpson Bay

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Featured Villas in Simpson Bay

Cliff House

3.5 star property
9.0 out of 10, Wonderful, (2)
"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 The Art of House - 3 bedrooms - Pool

4.0 star property
Villa The Art of House - 3 bedrooms - Pool

Dream be True Stunning 3-bed Villa in Simpson BAY

3.5 star property
Dream be True Stunning 3-bed Villa in Simpson BAY

Beach secrets

3.5 star property
Beach secrets

Villa Blue Lagoon

3.5 star property
Villa Blue Lagoon

Villa Bianca

4.5 star property
Villa Bianca
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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Other property types in Simpson Bay

The Horny Toad Guesthouse

3.0 star property
9.4 out of 10, Exceptional, (51)
"Deb & Doug are accommodating and great to talk to to get ideas of things to do. Perfect place to stay!"
The price is S$299
includes taxes & fees
26 Nov - 27 Nov
The Horny Toad Guesthouse

Simpson Bay Suites

3.5 star property
6.8 out of 10, (104)
"They are very accommodating 👍"
The price is S$204
includes taxes & fees
26 Nov - 27 Nov
Simpson Bay Suites

Tradewinds at Simpson Bay

3.5 star property
8.8 out of 10, Excellent, (11)
"It’s beautiful and all the restaurants are across the way! "
Tradewinds at Simpson 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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

How much do villas in Simpson Bay cost?
Rates for villas in Simpson Bay range between and per night. Whatever your budget, you’ll find something that suits your needs with 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?
A guest favourite is Villa Alabaster At Coral Beach Club By Redawning. Get comfortable at this 4.5-star property which comes with a swimming pool and an oven. Windsong By Redawning is another in-demand option to consider. Spend your break at this 4.5-star stay and take advantage of conveniences like a swimming pool and a garden. You’ll have your pick of multiple villas in Simpson Bay with a total average guest review rating of 8.5.
How many villas are there in Simpson Bay?
Claim your holiday time and choose from 7 villas in Simpson Bay. For a holiday with the family, a romantic break and everything in between, Expedia will help you find the ideal place in a few simple clicks.
Are there any family-friendly villas in Simpson Bay?
A lot of travellers who are looking for a family-friendly villa in Simpson Bay go for Villa Alabaster At Coral Beach Club By Redawning. With a 4.5-star rating and amenities like an oven and a patio, it’ll feel like your home away from home. Windsong By Redawning is a 4.5-star stay that’s also a hit with travelling families. An oven and a barbecue grill help make it a superb base for your Simpson Bay adventure. After checking in and chilling out together in your cosy digs, it’s time to visit some of the local sights. Simpson Bay Beach and Flamingo Beach are top family-friendly attractions in Simpson Bay.
Are there any 5-star villas in Simpson Bay?
If you’re up for a bit of indulgence on your Simpson Bay escape, Villa Amaryllis won’t disappoint. This 5-star villa features concierge services and a swimming pool and is around 3 kilometres from downtown. Another 5-star option that’ll meet your needs is Villa Starfish Coral Beach Club By Redawning. It’s 8 kilometres from the centre of Simpson Bay and has amenities such as a swimming pool and pool sun loungers.
Why book your villa in Simpson Bay with Expedia?
Reserving a villa in Simpson Bay is as easy as clicking on your travel dates and choosing an option that suits your style. Looking for something luxurious or affordable, or a stay that also offers a laundry and kitchen? Use Expedia’s search filters to narrow your results and find the perfect fit.
How can I find cheap villas in Simpson Bay?
The easiest way to get cheap villas in Simpson Bay is with Expedia’s user-friendly filter tool. Narrow down your search by budget, star rating and amenities to grab unbeatable rates in just a few keystrokes.
What is there to do near my villa in Simpson Bay?
Simpson Bay has enough activities and experiences to keep you amused for weeks, starting with Simpson Bay Beach. Kim Sha Beach, Lay Bay Beach and Hollywood Casino are other renowned attractions. If you’re in town a while, Dunes Casino and Flamingo Beach will cap off your itinerary nicely.