Compare Simpson Bay Vacation Rentals

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Simpson Bay Rentals

Hilton Vacation Club Royal Palm St. Maarten

Hilton Vacation Club Royal Palm St. Maarten

4 out of 5
115 Welfare Road, Simpson Bay
Free Cancellation
Reserve now, pay when you stay
0.23 mi from city center
$226 nightly
The price is $237 total per night
$237 total
Aug 26 - Aug 27
Total includes taxes and fees
Guests of Hilton Vacation Club Royal Palm St. Maarten enjoy a full-service spa, an outdoor pool, and a gym. If you drive, put free parking to good use. The front desk has multilingual staff standing by 24 hours a day to assist with dry cleaning/laundry and concierge services. Other amenities at this beach aparthotel include free WiFi in public areas, a business center, and laundry facilities.
Pool
Kitchen
The Hills Residence

The Hills Residence

3 out of 5
69 Welfare Rd, Simpson Bay, Sint Maarten
0.77 mi from city center
$259 nightly
The price is $271 total per night
$271 total
Sep 1 - Sep 2
Total includes taxes and fees
Guests staying at The Hills Residence enjoy 4 outdoor pools, free WiFi in public areas, and laundry facilities. There's free parking if you drive. Front-desk staff can assist with luggage storage and securing valuables. This aparthotel also has local meal delivery service.
Pool
Kitchen
Simpson Bay Suites

Simpson Bay Suites

3.5 out of 5
Elmanar Plaza 3D Billy Folly Road, Cole Bay, Simpson Bay
Free Cancellation
0.51 mi from city center
$116 nightly
The price is $121 total per night
$121 total
Aug 21 - Aug 22
Total includes taxes and fees
A full-service spa, a sauna, and free WiFi in public areas are featured at Simpson Bay Suites. Free parking is included with your stay. The front desk has multilingual staff on hand 24/7 to help with dry cleaning/laundry, securing valuables, and luggage storage. Other amenities at this spa aparthotel include express check-out, a terrace, and laundry facilities.
Kitchen
Parking included
Tradewinds at Simpson Bay

Tradewinds at Simpson Bay

3.5 out of 5
23 Simpson Bay Road, Simpson Bay, Sint Maarten
0.07 mi from city center
An outdoor pool and free WiFi in public areas are features at Tradewinds at Simpson Bay.
Pool
Kitchen
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

0.76 mi from city center
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.
Pool
Kitchen
Beachfront Ultra Luxury - New Modern 2 Bed/2.5 Bath

Beachfront Ultra Luxury - New Modern 2 Bed/2.5 Bath

1.17 mi from city center
Guests of this condo enjoy features like an outdoor pool, a gym, and laundry facilities.
Pool
Kitchen
The Horny Toad Guesthouse

The Horny Toad Guesthouse

3 out of 5
2 Vlaun Drive, Simpson Bay
0.34 mi from city center
Guests of The Horny Toad Guesthouse enjoy features like a gym, free WiFi in public areas, and a computer station. If you drive, put free parking to good use. Front-desk staff can assist with tours/tickets and luggage storage. Other amenities at this beach apartment building include free newspapers, a terrace, and laundry facilities.
Kitchen
Parking included
Maho Beach House - Spacious 1 Bedroom Suite

Maho Beach House - Spacious 1 Bedroom Suite

1.52 mi from city center
At this condo, guests enjoy an outdoor pool, a gym, and free WiFi in public areas. Dry cleaning/laundry services make packing light an option. Other amenities at this beach condo building include a hot tub, express check-in, and express check-out.
Pool
Hot Tub
Oceanfront amazing 2 bedrooms Condo

Oceanfront amazing 2 bedrooms Condo

1.18 mi from city center
Guests staying at this condo 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 condo building include barbecue grills and a garden.
Pool
Kitchen
Turquoise paradise, directly ON beach, gated w underground parking!

Turquoise paradise, directly ON beach, gated w underground parking!

0.06 mi from city center
$440 nightly
The price is $440 total per night
$440 total
Aug 21 - Aug 22
Total includes taxes and fees
At this apartment, guests have access to features like a terrace and laundry facilities.
Kitchen
Washer
A curated two bedroom suite near Maho beach.

A curated two bedroom suite near Maho beach.

1.25 mi from city center
At this apartment, guests have access to features like laundry facilities. This smoke-free apartment building also has a garden.
Kitchen
Washer
Pelican Key Private Luxury Villa With Panoramic View Of The Caribbean Sea

Pelican Key Private Luxury Villa With Panoramic View Of The Caribbean Sea

1.01 mi from city center
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, a garden, and barbecue grills.
Pool
Kitchen
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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.

Simpson Bay Large Group Rentals

How to Book Vacation Rentals in Simpson Bay



🏠 What is the best price for Simpson Bay vacation rentals?

Simpson Bay vacation rentals range in price, starting at $121 per night.


🏠 What types of vacation rentals in Simpson Bay can I rent?

Orbitz offers a wide range of Simpson Bay rentals so you can plan the perfect vacation. Whether you're on a budget or looking for luxury, our rentals include spots for families, couples, activities, leisure, summer, winter, and more. Explore unique property types available such as cabins, cottages, private vacation homes, and Simpson Bay condo rentals.


🏠 Is it free to cancel my Simpson Bay vacation rental with Orbitz?

Most vacation rentals are free to cancel when you do so before the cancellation deadline. However, cancellation policies vary by property. Non-refundable bookings will not receive a refund. We recommend booking with free cancellation in case your plans change.


🏠 How do I find the best deals to rent a Simpson Bay vacation rental with Orbitz?

There are many different options for finding the best deal to suit your needs. Choose exclusive offers on rentals in various locations in Simpson Bay. You can filter by price range, guest rating, property type, neighborhood, and more to customize your search and view the best deals for you.


🏠 How can I cancel my vacation rental booking through Orbitz?

Change of plans? We get it. You can cancel most vacation rentals bookings by getting in touch with the property manager. Sign in to your account and navigate to ‘My Trips’. Choose ‘Itinerary’ to view the property’s contact details. For questions and concerns, you can always visit our customer service portal.


🏠 What are the advantages of booking a vacation rental in Simpson Bay?

Vacation rentals are your home away from home, offering a different kind of experience than traditional hotels. They’re often the best option if you're looking for more space, more privacy, and a place to make your own. Find homes for all kinds of stays with Orbitz. Plan group vacations with short-term rentals or choose from our Simpson Bay apartments and enjoy an extended stay.


🏠 Why should I book my vacation rental with Orbitz in Simpson Bay?

Orbitz offers incredible deals and offers on a large selection of vacation rentals as your one-stop-shop for travel. You’ll get rewards back with every booking, and when you book your stay along with a rental car, flight, or activity, our Simpson Bay package deals will get you even more savings.

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