Compare Simpson Bay Villa Deals

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Featured Villas in Simpson Bay

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

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

Cole Bay Sint Maarten
Guests of this villa enjoy features like an outdoor pool, a gym, and an arcade/game room. Other amenities at this family-friendly villa include laundry facilities, barbecue grills, and a garden.
Pool
Kitchen
Oceanfront amazing 2 BR Villa - 2 min from the beach

Oceanfront amazing 2 BR Villa - 2 min from the beach

Beacon Hill
Guests staying at this villa enjoy an outdoor pool, laundry facilities, and local meal delivery service. Transportation is made easy with limo/town car service. Friendly staff can provide concierge services, and also offer advice about sightseeing. Other amenities at this beach villa include barbecue grills and a garden.
Pool
Kitchen
3 BR/3 bath. Sint Maarten DIRECT BEACHFRONT & PRIVATE POOL! From 250/nt!!

3 BR/3 bath. Sint Maarten DIRECT BEACHFRONT & PRIVATE POOL! From 250/nt!!

Beacon Hill
Guests staying at this villa have access to laundry facilities, a garden, and barbecue grills.
Pool
Kitchen
Stunning Beach Front Villa With Infinity Pool

Stunning Beach Front Villa With Infinity Pool

Pelican Key, Simpson Bay Sint Maarten
At this villa, guests have access to features like laundry facilities.
Pool
Kitchen
Charming 2-bedroom villa with AC, WiFi, stunning ocean views

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

Koolbaai
Guests staying at this villa have access to laundry facilities, a garden, and barbecue grills.
Pool
Kitchen
BEACHFRONT DESIGN VILLA

BEACHFRONT DESIGN VILLA

Beacon Hill Sint Maarten
Guests staying at this villa enjoy an outdoor pool, a terrace, and laundry facilities. Transportation is made easy with limo/town car service. Helpful staff is there to provide concierge services, as well as offer insight about the area. Other amenities at this beach villa include local meal delivery service, a garden, and barbecue grills.
Pool
Kitchen
One Hundred Million Dollar Yacht On Land 5 star Beachhoiuse on the Ocean

One Hundred Million Dollar Yacht On Land 5 star Beachhoiuse on the Ocean

St Maarten
Guests staying at this villa enjoy an outdoor pool, laundry facilities, and local meal delivery service. Staff members can answer questions about accommodations, and also provide concierge services. Other amenities at this beach villa include barbecue grills and a garden.
Villa Bonjour water front villa next to Maho

Villa Bonjour water front villa next to Maho

Simpson Bay Sint Maarten
Guests staying at this villa enjoy an outdoor pool, laundry facilities, and local meal delivery service. Helpful staff is there to provide concierge services, as well as offer insight about the area. Other amenities at this beach villa include a garden and barbecue grills.
Luxurious Villa " Sea La Vie" in Pelican Key

Luxurious Villa " Sea La Vie" in Pelican Key

Koolbaai Sint Maarten
At this villa, guests have access to an outdoor pool, laundry facilities, and barbecue grills.
Pool
Kitchen
Don't see what you're looking for?
See all available properties in Simpson Bay
View all properties
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.

Hotel Options in Simpson Bay

    The Morgan Resort Spa Village

    The Morgan Resort Spa Village

    2 Beacon Hill Road Simpson Bay
    $308 nightly
    The price is $320 total per night from Jun 17 to Jun 18
    $320 total
    Jun 17 - Jun 18
    Total with taxes and fees
    9/10 Wonderful! (2,221 reviews)
    Simpson Bay Resort, Marina & Spa

    Simpson Bay Resort, Marina & Spa

    Billy Folly Road 37 Simpson Bay
    $235 nightly
    The price is $247 total per night from Jun 15 to Jun 16
    $247 total
    Jun 15 - Jun 16
    Total with taxes and fees
    9/10 Wonderful! (1,780 reviews)
    Hilton Vacation Club Flamingo Beach St. Maarten

    Hilton Vacation Club Flamingo Beach St. Maarten

    Pelican Key, Simpson Bay, 6 Billy Folly Simpson Bay
    $135 nightly
    The price is $142 total per night from Jun 17 to Jun 18
    $142 total
    Jun 17 - Jun 18
    Total with taxes and fees
    9.2/10 Wonderful! (1,605 reviews)

Luxury Villas

Book luxury villas in Simpson Bay
There are plenty of ways to up your vacation game, but one of the best is by staying in a luxury villa in Simpson Bay. Villas, with their thoughtful layout and elegant décor, let you travel in style. They come in a variety of sizes and offer a great experience, whether you’re traveling on your own or with a group of friends. Orbitz has fantastic deals on villas in Simpson Bay, so book one now. You’ll feel like a million bucks before you even check in.

Spacious luxury villas in Simpson Bay
You won’t have a problem finding your own space in Simpson Bay. If you’re traveling in a group, go for a three-bedroom or larger villa; separate bedrooms can make it that much easier to keep the peace, especially when you’re all staying in one house. You can also explore Simpson Bay on your own and use a one-bedroom villa as your home base.

A top-end villa experience in Simpson Bay rivals that of a luxury resort. Float in a swimming pool with an elaborate mosaic bottom, work out in your own gym, and let the daily housekeeping staff clean up after you while a private chef whips up one delicious meal after another. This is the life!

Simpson Bay Villas essential information

Accommodation
42 Villas
Lowest Price
$142
Highest Price
$320
Popular accommodation
4 bedroom Pelican Key Private Luxury Villa, Panoramic View Of The Caribbean Sea, Oceanfront amazing 2 BR Villa - 2 min from the beach, 3 BR/3 bath. Sint Maarten DIRECT BEACHFRONT & PRIVATE POOL! From 250/nt!!, Stunning Beach Front Villa With Infinity Pool , Charming 2-bedroom villa with AC, WiFi, stunning ocean views, BEACHFRONT DESIGN VILLA, One Hundred Million Dollar Yacht On Land 5 star Beachhoiuse on the Ocean, Villa Bonjour water front villa next to Maho, Luxurious Villa " Sea La Vie" in Pelican Key