1. USA
  2. Florida
  3. Miami
  4. Anchor Shops
  5. Winter Rental

Anchor Shops Winter Rentals & Holiday Homes

Discover winter rentals Anchor Shops - We found 1904 exact matches

About Anchor Shops Winter Rental on PickleTrip

Planning on a winter vacation in Anchor Shops? Discover 1904 places to stay in Anchor Shops, for those traveling with their family, friends, in groups, or for a wedding retreat.

At PickleTrip™, we have a wide range of listings for accommodations in Anchor Shops, FL that are perfect for your winter trip or seasonal escape. Our listings have private vacation homes, cabins, condos, villas, resorts, or pet-friendly apartments that you would love. PickleTrip™ winter vacation homes have top amenities, including Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.

Anchor Shops winter accommodation starts at US $896, and the most popular properties in Anchor Shops are cabins, bungalows, and rental homes by owner. Planning snowboarding on your next winter vacation? We have many snowboard-friendly ski resorts, chalets, and cabins that are available for you to rent. These rentals are available for both short-term stays and long-term stays, whether you are traveling for a weekend, monthly, or a longer stay, PickleTrip will make your winter trip memorable.

PickleTrip™ offers a great deal for travelers planning on renting a place in Anchor Shops, to enjoy these benefits and to book your winter vacation homes, go to PickleTrip™ filter option, enter your travel date, check the filters to narrow down your property type and amenities, then choose from a long list of our winter vacation rentals without hassle. Our interactive map is also available, to view all places to stay in or around Anchor Shops and unlock even more amazing deals.

Show more
Show less

Frequently Asked Questions About Anchor Shops Winter Rentals

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

The average cost for winter rentals in Anchor Shops is $896 per night. PickleTrip has a wide list of great winter places to stay near Anchor Shops 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 Anchor Shops that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Anchor Shops on PickleTrip

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Anchor Shops to find what works for you.
As of 2025, the data from PickleTrip shows that there are over 1904 private swimming pools or indoor pools accommodations near Anchor Shops along with other great amenities.

About 1904 holiday rentals in Anchor Shops 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 Anchor Shops for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Anchor Shops with all the best amenities for your next trip.