1. Sint Maarten
  2. Simpson Bay
  3. Winter Rental

Simpson Bay Winter Rentals & Holiday Homes

Discover winter rentals Simpson Bay - We found 174 exact matches

About Simpson Bay Winter Rental on PetFriendly

Need a pet friendly hotel, resort, or rental for your next winter vacation in Simpson Bay? Explore 174 places to stay in Simpson Bay, for all of your winter travels with your family, friends or a solo escape from your daily life buzz.

At PetFriendly, we offer diverse kinds of hotels, resorts, and private villas Simpson Bay perfect for your seasonal escape and family getaways including your pets’. Our listings include vacation homes, cabins, 5-star hotels, condos, villas, all-inclusive resorts, or pet-friendly apartments that you would love. Pet-friendly winter vacation homes have the best amenities, including Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.

Simpson Bay winter accommodation starts at US $595, and the most popular properties in Simpson Bay are vacation homes, bungalows, cabins, and all-inclusive resorts. Experience the cold with our many hotels, ski resorts, private chalets, and cabins available for rent. PetFriendly offer both short term and long-term stays for anyone who wants to make their winter trip memorable.

PetFriendly is the best place for anyone traveling with their pets who is looking to rent a place in Simpson Bay, want these benefits for yourself? Click the PetFriendly filter option, enter your travel date, check the filters to narrow down your property type and amenities, then choose from the long list of winter vacation rentals without hassle. All our winter homes are the best. Our interactive map is also available, to view all places to stay in or around Simpson Bay and unlock even more amazing deals.

Show more
Show less

Frequently Asked Questions About Simpson Bay Winter Rentals

There are a lot of options in Simpson Bay. If you plan on staying in the Simpson Bay area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Simpson Bay:

The average cost for winter rentals in Simpson Bay is $595 per night. PetFriendly has a wide list of great winter places to stay near Simpson Bay that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Yes, here are the top cottage/chalet rentals in Simpson Bay that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Simpson Bay on PetFriendly

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Simpson Bay to find what works for you.
As of 2025, the data from PetFriendly shows that there are over 174 private swimming pools or indoor pools accommodations near Simpson Bay along with other great amenities.

About 174 holiday rentals in Simpson Bay boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:

Yes, there are many luxury places to stay in Simpson Bay for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Simpson Bay with all the best amenities for your next trip.