Details

Outdoor pool

5BR Bear's Den Estate Private Pool & Game Room

$$$$

House in Osceola County, FL

14 guests · 5 bedrooms · 5 baths

Reasons to book

Top-tier experienceA high end property in this area

Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

Includes essentialsFree WiFi/internet, Pool and more

Location

city location on map

Photos

House, Multiple Beds, Pool View (BD016E- The Tropical Bear's Den Oasis) | Private kitchen

House, Multiple Beds, Pool View (BD016E- The Tropical Bear's Den Oasis) | Private kitchen

House, Multiple Beds, Pool View (BD016E- The Tropical Bear's Den Oasis) | Living area

House, Multiple Beds, Pool View (BD016E- The Tropical Bear's Den Oasis) | Interior

House, Multiple Beds, Pool View (BD016E- The Tropical Bear's Den Oasis) | Lobby

House, Multiple Beds, Pool View (BD016E- The Tropical Bear's Den Oasis) | Interior

Interior detail

House, Multiple Beds, Pool View (BD016E- The Tropical Bear's Den Oasis) | Interior

House, Multiple Beds, Pool View (BD016E- The Tropical Bear's Den Oasis) | Exterior

See all properties

5BR Bear's Den Estate Private Pool & Game Room

Outdoor pool

House, Multiple Beds, Pool View (BD016E- The Tropical Bear's Den Oasis) | Private kitchen

House, Multiple Beds, Pool View (BD016E- The Tropical Bear's Den Oasis) | Private kitchen

Outdoor dining

House, Multiple Beds, Pool View (BD016E- The Tropical Bear's Den Oasis) | Living area

Don't miss out! Price and availability may change

House in Osceola County, FL

14 guests · 5 bedrooms · 5 baths

Reasons to book

Top-tier experienceA high end property in this area

Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

Includes essentialsFree WiFi/internet, Pool and more

About this house rental

Located in Kissimmee, this 5-bedroom vacation home lets you experience it all. Fans of nature and the outdoors will love being 17 minutes by car from Northeast Regional Park and 16 minutes from Lake Bryan. Thanks to the convenient onsite parking, you can either leave your vehicle behind and enjoy a short 5-minute walk to Jack Nicklaus Course, or easily tackle the quick 5-minute drive to Reunion Resort Golf Course.

While you're here, you can enjoy all the comforts of home and more, including free WiFi and a billiards table, as well as towels and bed sheets.

Amenities

Free WiFi/internet

Pool

Non-smoking

WiFi/Internet

No pets allowed

Bath or shower

Towels

Map of Osceola County, FL

city location on map

$$$$

FAQs

Is parking included with this house?

Parking is not specified as an available amenity at 5BR Bear's Den Estate Private Pool & Game Room. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

Yes, a swimming pool is available for use at 5BR Bear's Den Estate Private Pool & Game Room. Enjoy the water!

Is 5BR Bear's Den Estate Private Pool & Game Room pet friendly?

Unfortunately, this house is not pet-friendly. Try searching again and filter for "Pets Allowed"

What amenities are available at 5BR Bear's Den Estate Private Pool & Game Room?

We found 7 amenities for this rental. This includes free wifi/internet, pool, non-smoking, wifi/internet, and no pets allowed.

Explore similar stays in Osceola County

Explore all stays

New to VacationRenter

5BR Bear's Den Estate Private Pool & Game Room

14 guests · 5 bedrooms · 5 baths

Free WiFi/internet · Pool

Business stays, family stays, couples stay, getaway vacation, and rental in Osceola County at 5BR Bear's Den Estate Private Pool & Game Room for $828 for your next trip.

You can save with One Key

6 / 10

Average(1 Rating)

Citrus Coast | 6 Bedroom Villa w/ Private Saltwater Pool & Games

14 guests · 6 bedrooms · 6 baths

Discover the beauty of Osceola County with a stay at Citrus Coast | 6 Bedroom Villa w/ Private Saltwater Pool & Games, a top rated Villa with amenities such as No pets allowed, Family friendly and Non-smoking, and more.

New to VacationRenter

5BR Bear's Den Estate Arcade, Pool & Game Room

14 guests · 5 bedrooms · 6 baths

Free WiFi/internet · Air conditioning · Pool

Business stays, family stays, couples stay, getaway vacation, and rental in Osceola County at 5BR Bear's Den Estate Arcade, Pool & Game Room for $825 for your next trip.

Reunion Resort villa for 14 with private pool

14 guests · 6 bedrooms · 5 baths

WiFi/Internet · Air conditioning · Pool

Experience the best of Osceola County with this Villa available for $850. This property is equipped with amenities including Accessible bath/shower, Air conditioning and Balcony/Terrace, and more.

6 / 10

Average(1 Rating)

Citrus Coast | 6 Bedroom Villa w/ Private Saltwater Pool & Games

14 guests · 6 bedrooms · 6 baths

Experience the best of Osceola County with this Villa available for $846. This property is equipped with amenities including No pets allowed, Family friendly and Non-smoking, and more.

8.8 / 10

Excellent(4 Ratings)

Luxury Paradise Palace | 6-Bed Villa w/ Private Pool, Golf Course Views, Custom-Built Kids Bedrooms

16 guests · 6 bedrooms · 6 baths

Enjoy the best of Osceola County in our Villa, Luxury Paradise Palace | 6-Bed Villa w/ Private Pool, Golf Course Views, Custom-Built Kids Bedrooms. A stunning property with amenities including No pets allowed, Family friendly and Non-smoking, and more.

New to VacationRenter

5BR Bear's Den Estate Arcade, Pool & Game Room

14 guests · 5 bedrooms · 6 baths

Free WiFi/internet · Air conditioning · Pool

Are you ready to indulge in a relaxing getaway? Our House in Osceola County has everything you need for a rejuvenating stay. Treat yourself to 5BR Bear's Den Estate Arcade, Pool & Game Room's exceptional amenities, such as Non-smoking, Air conditioning and WiFi/Internet.

6 / 10

Average(2 Ratings)

Paradise at Bear's Den | 6-Bed Villa w/ Loft, Games Room, and Private Pool

14 guests · 6 bedrooms · 6 baths

This inviting Villa in Osceola County can fit your needs for many types of vacations, at $794 per night.

8.8 / 10

Excellent(4 Ratings)

Luxury Paradise Palace | 6-Bed Villa w/ Private Pool, Golf Course Views, Custom-Built Kids Bedrooms

16 guests · 6 bedrooms · 6 baths

Looking for the perfect place to call home during your trip to Osceola County? This Villa offers a comfort and style with top-notch amenities, including No pets allowed, Family friendly and Non-smoking, and more.

8.8 / 10

Excellent(3 Ratings)

Relaxation at Bear's Den: Private Pool, Grill, Free Water Park, Golf View, Near Disney

18 guests · 6 bedrooms · 6 baths

Looking for a memorable stay in Osceola County? Our House might just be what you're looking for. Enjoy amenities including No pets allowed, Family friendly and Non-smoking, and more during your stay.

6 / 10

Average(2 Ratings)

Paradise at Bear's Den | 6-Bed Villa w/ Loft, Games Room, and Private Pool

14 guests · 6 bedrooms · 6 baths

Enjoy the best of Osceola County in our Villa, Paradise at Bear's Den | 6-Bed Villa w/ Loft, Games Room, and Private Pool. A stunning property with amenities including No pets allowed, Family friendly and Non-smoking, and more.

10 / 10

Outstanding(3 Ratings)

5BR Bear's Den Estate | Arcade, Pool & Game Room

14 guests · 5 bedrooms · 6 baths

This attractive House in Osceola County, $918 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

8.8 / 10

Excellent(3 Ratings)

Relaxation at Bear's Den: Private Pool, Grill, Free Water Park, Golf View, Near Disney

18 guests · 6 bedrooms · 6 baths

Nestled in Osceola County, this House is perfect for your next vacation. Enjoy Relaxation at Bear's Den: Private Pool, Grill, Free Water Park, Golf View, Near Disney's top-rated amenities, including No pets allowed, Family friendly and Non-smoking, and more.

Themed Games, Theater Room | Themed Kids Bedrooms | Private Pool

14 guests · 6 bedrooms · 6 baths

Looking for the perfect place to call home during your trip to Osceola County? This House offers a comfort and style with top-notch amenities, including No pets allowed, Family friendly and Non-smoking, and more.

New to VacationRenter

5BR Bear's Den Theater, Pool & Spa

14 guests · 5 bedrooms · 5 baths

Free WiFi/internet · Pool

Indulge in a peaceful retreat at 5BR Bear's Den Theater, Pool & Spa, our elegant House in Osceola County. Enjoy amenities including Non-smoking, WiFi/Internet and Pool, and more.

You can save with One Key

5BR Bear's Den Estate | Private Pool & Game Room

14 guests · 5 bedrooms · 5 baths

Soak up the beauty of Osceola County in our House, 5BR Bear's Den Estate | Private Pool & Game Room. With a range of amenities such as No pets allowed, Family friendly and Non-smoking, you'll feel right at home.

10 / 10

Outstanding(3 Ratings)

5BR Bear's Den Estate | Arcade, Pool & Game Room

14 guests · 5 bedrooms · 6 baths

Are you ready to indulge in a relaxing getaway? Our House in Osceola County has everything you need for a rejuvenating stay. Treat yourself to 5BR Bear's Den Estate | Arcade, Pool & Game Room's exceptional amenities, such as No pets allowed, Family friendly and Non-smoking.

New to VacationRenter

5BR Bear's Den Theater, Pool & Spa

14 guests · 5 bedrooms · 5 baths

Free WiFi/internet · Pool

Are you ready to indulge in a relaxing getaway? Our House in Osceola County has everything you need for a rejuvenating stay. Treat yourself to 5BR Bear's Den Theater, Pool & Spa's exceptional amenities, such as Non-smoking, WiFi/Internet and Pool.

You can save with One Key

10 / 10

Outstanding(1 Rating)

The Bear's Den Retreat-TB029

14 guests · 6 bedrooms · 6 baths

This Villa in Osceola County, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

Themed Games, Theater Room | Themed Kids Bedrooms | Private Pool

14 guests · 6 bedrooms · 6 baths

This House in Osceola County, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

Private Paradise | 8 Bed Pool Home located at Reunion Resort

20 guests · 8 bedrooms · 8 baths

Enjoy the best of Osceola County in our Villa, Private Paradise | 8 Bed Pool Home located at Reunion Resort. A stunning property with amenities including No pets allowed, Family friendly and Non-smoking, and more.

5BR Bear's Den Estate | Private Pool & Game Room

14 guests · 5 bedrooms · 5 baths

Indulge in a peaceful retreat at 5BR Bear's Den Estate | Private Pool & Game Room, our elegant House in Osceola County. Enjoy amenities including No pets allowed, Family friendly and Non-smoking, and more.

Wow Themed Kids Bedrooms | Games Room | Private Pool with Summer Kitchen | Water Views

16 guests · 6 bedrooms · 7 baths

Are you ready to indulge in a relaxing getaway? Our House in Osceola County has everything you need for a rejuvenating stay. Treat yourself to Wow Themed Kids Bedrooms | Games Room | Private Pool with Summer Kitchen | Water Views's exceptional amenities, such as No pets allowed, Family friendly and Non-smoking.

10 / 10

Outstanding(1 Rating)

The Bear's Den Retreat-TB029

14 guests · 6 bedrooms · 6 baths

This attractive Villa in Osceola County, $886 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

You can save with One Key

7.8 / 10

Good(12 Ratings)

Legends Estate: Private Pool, Game Loft, Theater, Near Diseny

in Four Corners

14 guests · 7 bedrooms · 6 baths

Soak up the beauty of Osceola County in our House, Legends Estate: Private Pool, Game Loft, Theater, Near Diseny. With a range of amenities such as No pets allowed, Family friendly and Non-smoking, you'll feel right at home.

Wow Themed Kids Bedrooms | Games Room | Private Pool with Summer Kitchen | Water Views

16 guests · 6 bedrooms · 7 baths

Business stays, family stays, couples stay, getaway vacation, and rental in Osceola County at Wow Themed Kids Bedrooms | Games Room | Private Pool with Summer Kitchen | Water Views for $738 for your next trip.

You can save with One Key

Beautiful Villa located on Reunion Resort, Reunion Resort Villa 1014

14 guests · 6 bedrooms · 5 baths

Nestled in Osceola County, this Villa is perfect for your next vacation. Enjoy Beautiful Villa located on Reunion Resort, Reunion Resort Villa 1014's top-rated amenities, including No pets allowed, Family friendly and Non-smoking, and more.

You can save with One Key

7.6 / 10

Good(6 Ratings)

Signature Golden Villa | West-Facing Private Pool, Custom-Built Kids Bedrooms, Luxury Throughout

14 guests · 6 bedrooms · 5 baths

Soak up the beauty of Osceola County in our Villa, Signature Golden Villa | West-Facing Private Pool, Custom-Built Kids Bedrooms, Luxury Throughout. With a range of amenities such as No pets allowed, Family friendly and Non-smoking, you'll feel right at home.

Beautiful Villa located on Reunion Resort, Reunion Resort Villa 1014

14 guests · 6 bedrooms · 5 baths

Looking to create some memories in Osceola County? Look no further than our Villa, Beautiful Villa located on Reunion Resort, Reunion Resort Villa 1014. Enjoy top-rated amenities including No pets allowed, Family friendly and Non-smoking, and more.

7.6 / 10

Good(6 Ratings)

Signature Golden Villa | West-Facing Private Pool, Custom-Built Kids Bedrooms, Luxury Throughout

14 guests · 6 bedrooms · 5 baths

When traveling to Osceola County, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $664 per night.

Osceola County travel inspiration

The Best American Lake Town Awards 2026: Where Shoreline Meets Soul

America’s Best Hidden Beach Towns (2026 Awards)

Best Small Towns for Spring Getaways (2026)

The Ultimate Packing List For Your Vacation (2026)

Where Everyone Knows Your Name: America’s Most Welcoming Small Towns (2026)

35 Road Trip Necessities for the Perfect Journey

How to Pack a Suitcase: 12 Steps to Perfect Packing

Top 25 Packing Tips for 2026 (Smarter, Lighter, Stress-Free Travel)

Keep exploring