Compare Simpson Bay Villa Deals

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

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

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

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

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 a garden and barbecue grills.
BEACHFRONT DESIGN VILLA

BEACHFRONT DESIGN VILLA

This villa offers a water park, an outdoor pool, and a terrace. 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 laundry facilities, local meal delivery service, and barbecue grills.
Villa Impala, 5 bedroom villa beachfront in Simpson Bay, Sint Maarten

Villa Impala, 5 bedroom villa beachfront in Simpson Bay, Sint Maarten

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. Staff members can help with accommodation requests, and provide concierge services.
Luxurious Villa " Sea La Vie" in Pelican Key

Luxurious Villa " Sea La Vie" in Pelican Key

At this villa, guests have access to features like laundry facilities. This smoke-free villa also has barbecue grills.
Pool
Kitchen
Villa Turquoise Heaven

Villa Turquoise Heaven

Sint Maarten
At this vacation home, guests have access to features like laundry facilities.
Pelikaan Sunset: A Villa With Stunning Ocean Views

Pelikaan Sunset: A Villa With Stunning Ocean Views

At this villa, guests enjoy an outdoor pool, a gym, and a hot tub. Other amenities at this family-friendly villa include laundry facilities and barbecue grills.
Il Punto Blu - Beautiful renovated condo, AC, WIFI, walkable restaurants/beach.

Il Punto Blu - Beautiful renovated condo, AC, WIFI, walkable restaurants/beach.

At this villa, guests have access to an outdoor pool, laundry facilities, and barbecue grills. This beach villa also has a garden.
Oceanfront amazing 2 BR Villa - 2 min from the beach

Oceanfront amazing 2 BR Villa - 2 min from the beach

This villa offers a water park, an outdoor pool, and laundry facilities. 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 local meal delivery service, a garden, and barbecue grills.
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

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.
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

    Simpson Bay Resort, Marina & Spa

    Simpson Bay Resort, Marina & Spa

    Billy Folly Road 37, Simpson Bay
    $119 nightly
    The price is $124 total per night from Oct 9 to Oct 10
    $124 total
    Oct 9 - Oct 10
    Total with taxes and fees
    8.8/10 Excellent! (1,366 reviews)
    Hilton Vacation Club Flamingo Beach St. Maarten

    Hilton Vacation Club Flamingo Beach St. Maarten

    Pelican Key, Simpson Bay, 6 Billy Folly, Simpson Bay
    $114 nightly
    The price is $119 total per night from Oct 12 to Oct 13
    $119 total
    Oct 12 - Oct 13
    Total with taxes and fees
    9/10 Wonderful! (1,259 reviews)
    The Morgan Resort Spa Village

    The Morgan Resort Spa Village

    2 Beacon Hill Road, Simpson Bay
    $325 nightly
    The price is $338 total per night from Oct 5 to Oct 6
    $338 total
    Oct 5 - Oct 6
    Total with taxes and fees
    8.8/10 Excellent! (1,848 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
47 Villas
Lowest Price
$119
Highest Price
$338
Popular accommodation
One Hundred Million Dollar Yacht On Land 5 star Villa on the ocean, BEACHFRONT DESIGN VILLA, Villa Impala, 5 bedroom villa beachfront in Simpson Bay, Sint Maarten, Luxurious Villa " Sea La Vie" in Pelican Key, Villa Turquoise Heaven, Pelikaan Sunset: A Villa With Stunning Ocean Views, Il Punto Blu - Beautiful renovated condo, AC, WIFI, walkable restaurants/beach., Oceanfront amazing 2 BR Villa - 2 min from the beach, 4 bedroom Pelican Key Private Luxury Villa, Panoramic View Of The Caribbean Sea