How to Plan an Unforgettable Girls’ Getaway at Bear’s Den Orlando – Galentine’s Idea!

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Kissimmee is known as the vacation home capital of the world with more than 30,000 homes to choose from. While these houses are great for family vacations, they also make the perfect spot for an all-out Galentines getaway. After a great weekend away for an early Galentine's Getaway, I am sharing with you the must-do tips for a great stay at Bear's Den in Kissimmee, Florida. 

We'll have more Galentine's Day ideas soon, for now keep reading to plan a Galentine's getaway, or head to these FREE Things to Do on Valentine's Day for other inspiration.

Unforgettable Girls' Getaway at Bear's Den Orlando

Bear's Den – The Basics

Grab your girlfriends and pick the vacation home that fits your group best. Whether that be a two-bedroom cozy cottage or a 9-bedroom mansion.

Bear’s Den located in Reunion Resort, a massive property in Kissimmee, Florida that offers plenty of amenities. And it's just about 15 – 20 minutes from Walt Disney World. There are three golf courses, 7 restaurants and bars, a 5-acres water park, 7 pools, a fitness center, and tennis and pickleball courts on site.

What's Inside the Homes?

These houses are so amazing your girl group would be comfortable staying in pajamas all weekend, enjoying the luxuries of your accommodations. Most of the bedrooms in these homes have private bathrooms in them. Every grown woman gets her own space to prep and primp in privacy.

  • Individual bedrooms
  • Private bathrooms
  • Large entertaining and living areas
  • Full-size kitchens
  • Additional features like game rooms, movie theaters, and more

These homes are made for entertaining, which means large chef kitchens, beautiful outdoor areas with private swimming pools, and spacious great rooms, sometimes upstairs and downstairs.

You can get homes with bowling alleys, full-on gyms, golf simulators, game rooms, and movie theaters. These homes are a great excuse to get your girls together, relax, laugh, eat and celebrate the friendships you all have formed.

sun setting over a Pool at Vacation Home at Bear's Den Kissimmee - Michelle Spitzer
Bear's Den Orlando Pool at Vacation Home – Michelle Spitzer

Expert Tips for a Great Stay at Bear's Den

  • Hire a private chef
  • Use meal deliveries
  • Book an in-home massage

Private Chefs

While the kitchens are impressive, they also make a great space to bring in a private chef to really make good use of the high-end appliances. Take some time off from cooking and let someone else do the cooking for you and your gal pals.

Photo is taken from a second story, Bear's Den Vacation Home Living Room and Dining Area - Michelle Spitzer
Bear's Den Vacation Home Living Room and Dining Area – Michelle Spitzer

Take A Chef

Scroll through a directory of more than 125 private chefs who will come to your vacation spot and do all the work. From setup, cooking and cleanup, these professionals will handle everything. All you have to do is select which chef you want. You can pick based on what dishes they specialize in, what parts of town they work in and how long they’ve been working.  

Chef Tony Tone

This is a popular pick for locals wanting to pass the cooking duties off to a professional. Chef Anthony Blakey, better known as Chef Tony Tone, is a former Disney chef specializes in brunch and soul food.

 Luxury Pop Up Picnic Company

Your gals can enjoy the outdoor scenery while enjoying a fancy picnic by the pool. Luxury Pop Up Picnic Company will come to your resort home and set up a beautiful display including table, decorations and of course the food and drinks.

If relaxing is top on the agenda for your Galentine’s getaway, you can pick a house with a hot tub, or sauna, or even an area dedicated for massages. To up the relaxation efforts, consider hiring a masseuse or nail technician to come to your home for some pampering.

Two Chef Mission

Husband and wife duo, Tony and Melissa, spent many years in the culinary business, including at Walt Disney World. Besides offering in-home chef services, they can also put together meals and snacks delivered straight to your vacation home.

Their most popular items include breakfast boxes, which can include Mickey-shaped waffles and beignets. Dietary needs can be accommodated, just ask!

Massage Servies

Sol Wellness

This mobile masseuse brings relaxation right to you. Your girls can pick from a 60-minute massage, 90-minute massage, or even a pink Himalayan salt stone massage.

Denise Porter has decades of experience as a licensed massage therapist and will provide soothing and relaxing massages that will be the highlight of your Galentine's getaway in Orlando.

Launch Massage

Here’s another option that will allow you to relax without going anywhere. Launch Massage will come to your vacation home in Bear's Den in Kissimmee with services ranging from chair massages, prenatal massages, and cupping massages.

Golf and Wellness

Many of the homes come equipped with impressive gyms filled with all kinds of equipment to burn some calories. There’s also plenty of room to spread out and do some yoga or Pilates.

The resort grounds also are so nice that your group would enjoy taking a stroll around the property admiring the gorgeous vacation homes and planning which one your group will book for the next getaway.

Bear's Den Vacation Home resort, looking over the Golf Course and Lobby Building - Michelle Spitzer
Bear's Den Golf Course and Lobby Building – Michelle Spitzer

You can also get your sweat on while visiting the property's prestigious golf courses designed by PGA legends Arnold Palmer, Tom Watson, and Jack Nicklaus.

If those big golf courses are intimating, you’re in luck. There’s a miniature golf course on the property.

Pack your tennis skirt for the girls’ getaway and book your group a lesson with one of the resort pros on staff who also teach pickleball. There’s also a state-of-the-art fitness center where you all can do your own workouts.

From packing your schedule with plenty of activities to never leaving your vacation home and bringing the party to you, there are endless options. Enjoy a Galentine’s Day getaway at Bear's Den, or one of the many vacation homes around Kissimmee.

Featured image credit @evablancophotos

Orlando Date Night Guide is a free guide to the best of Orlando! We're supported by our advertisers when they buy digital ads, listings, content, and through affiliate links, so some things you read might be paid for or if you buy something thru a link on our site we might get a commission.

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