Details

Property view

Upstay Luxury Home With Pool, Hot Tub, Games Room

$$$$

Cottage in Osceola County, FL

16 guests · 5 bedrooms · 2 baths

Reasons to book

Great for petsBring all your friends and family, even the furry ones

High-end valueWell priced for this area

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

Location

city location on map

Photos

See all properties

Upstay Luxury Home With Pool, Hot Tub, Games Room

Upstay Luxury Home With Pool, Hot Tub, Games Room Cottage in Osceola County

Upstay Luxury Home With Pool, Hot Tub, Games Room Cottage in Osceola County

Upstay Luxury Home With Pool, Hot Tub, Games Room Cottage in Osceola County

Upstay Luxury Home With Pool, Hot Tub, Games Room Cottage in Osceola County

Upstay Luxury Home With Pool, Hot Tub, Games Room Cottage in Osceola County

Don't miss out! Price and availability may change

Cottage in Osceola County, FL

16 guests · 5 bedrooms · 2 baths

Reasons to book

Great for petsBring all your friends and family, even the furry ones

High-end valueWell priced for this area

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

About this cottage rental

Located in Kissimmee, this welcoming cottage brings it all within your reach. Jump into your car and make short work of the 3-minute drive to Reunion Resort Golf Course or the 7-minute drive to ChampionsGate Golf Club (and enjoy the property's convenient onsite parking in the meantime).

Relax by the outdoor pool or sip a drink in the garden of this cottage, which also features a BBQ grill. As for the great indoors, you can come inside and enjoy the free WiFi, TV, and video-game console.

As you settle into this 5-bedroom, 2.5-bathroom rental, you'll find a living room and air conditioning. The kitchen is equipped with an oven, a stovetop, and a dishwasher, as well as a microwave and cookware. And there's a dryer, so you can even pack a bit lighter.

Amenities

Free WiFi/internet

Free Parking

Air conditioning

Pool

Non-smoking

Pets allowed

TV

Heating

Kitchen

WiFi/Internet

Microwave

Dishwasher

Dryer

Kitchenware

Garden

Oven

Stove

Bathtub

Outdoor Cooking

Family friendly

Ironing facilities

Linens

Map of Osceola County, FL

city location on map

$$$$

FAQs

Is parking included with this cottage?

Yes, parking is listed as an amenity at Upstay Luxury Home With Pool, Hot Tub, Games Room. For more information, we encourage you to contact the property about where to park.

Is there a pool at this cottage?

Yes, a swimming pool is available for use at Upstay Luxury Home With Pool, Hot Tub, Games Room. Enjoy the water!

Is Upstay Luxury Home With Pool, Hot Tub, Games Room pet friendly?

Yes! This cottage is pet-friendly. For more information, we recommend contacting the booking provider about animal policies.

What amenities are available at Upstay Luxury Home With Pool, Hot Tub, Games Room?

We found 22 amenities for this rental. This includes free wifi/internet, free parking, air conditioning, pool, and non-smoking.

Explore similar stays in Osceola County

Explore all stays

Upstay Luxury Home With Pool, Hot Tub, Games Room

16 guests · 5 bedrooms · 2 baths

Free WiFi/internet · Air conditioning · Pool

Looking for a memorable stay in Osceola County? Our Cottage might just be what you're looking for. Enjoy amenities including Non-smoking, Air conditioning and Outdoor Cooking, and more during your stay.

You can save with One Key

9.4 / 10

Outstanding(3 Ratings)

Luxury Disney Getaway with Heated Pool & Jacuzzi - 7895

20 guests · 6 bedrooms · 5 baths

WiFi/Internet · Air conditioning · Kitchen

Soak up the beauty of Osceola County in our House, Luxury Disney Getaway with Heated Pool & Jacuzzi - 7895. With a range of amenities such as Air conditioning, Dryer and WiFi/Internet, you'll feel right at home.

8.8 / 10

Excellent(4 Ratings)

Disney World Group Getaway in Reunion Resort!

16 guests · 6 bedrooms · 4 baths

WiFi/Internet · Air conditioning · Pool

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 Air conditioning, Outdoor Cooking and Free Parking, and more.

9.4 / 10

Outstanding(3 Ratings)

Luxury Disney Getaway with Heated Pool & Jacuzzi - 7895

20 guests · 6 bedrooms · 5 baths

WiFi/Internet · Air conditioning · Kitchen

Experience vacation in Osceola County with our House, Luxury Disney Getaway with Heated Pool & Jacuzzi - 7895. Enjoy amenities such as Air conditioning, Dryer and WiFi/Internet, and more.

8.8 / 10

Excellent(4 Ratings)

Disney World Group Getaway in Reunion Resort!

16 guests · 6 bedrooms · 4 baths

WiFi/Internet · Air conditioning · Pool

Soak up the beauty of Osceola County in our House, Disney World Group Getaway in Reunion Resort!. With a range of amenities such as Air conditioning, Outdoor Cooking and Free Parking, you'll feel right at home.

You can save with One Key

6.6 / 10

Average(4 Ratings)

“Spacious 10BR Villa w/ Pool, Theater & Themed Kids’ Rooms – Near Disney”

22 guests · 10 bedrooms · 9 baths

WiFi/Internet · Air conditioning · Pool

Discover the beauty of Osceola County with a stay at “Spacious 10BR Villa w/ Pool, Theater & Themed Kids’ Rooms – Near Disney”, a top rated House with amenities such as Air conditioning, Outdoor Cooking and Dryer, and more.

You can save with One Key

Prime Location Near Disney with Private Theater

16 guests · 8 bedrooms · 7 baths

WiFi/Internet · Air conditioning · Pool

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 $448 per night.

6.6 / 10

Average(4 Ratings)

“Spacious 10BR Villa w/ Pool, Theater & Themed Kids’ Rooms – Near Disney”

22 guests · 10 bedrooms · 9 baths

WiFi/Internet · Air conditioning · Pool

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

Prime Location Near Disney with Private Theater

16 guests · 8 bedrooms · 7 baths

WiFi/Internet · Air conditioning · Pool

House in Osceola County, for $448 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)

You can save with One Key

Near Disney Home with Pool & BBQ, Encore Resort

16 guests · 8 bedrooms · 6 baths

WiFi/Internet · Air conditioning · TV

Discover the beauty of Osceola County with a stay at Near Disney Home with Pool & BBQ, Encore Resort, a top rated House with amenities such as Air conditioning, Balcony/Terrace and Outdoor Cooking, and more.

New to VacationRenter

Near Disney 8BR Pool Home with Marvel Game Room

16 guests · 8 bedrooms · 7 baths

WiFi/Internet · Air conditioning · Pool

Indulge in a peaceful retreat at Near Disney 8BR Pool Home with Marvel Game Room, our elegant House in Osceola County. Enjoy amenities including Air conditioning, Balcony/Terrace and Outdoor Cooking, and more.

Near Disney Home with Pool & BBQ, Encore Resort

16 guests · 8 bedrooms · 6 baths

WiFi/Internet · Air conditioning · TV

Indulge in a peaceful retreat at Near Disney Home with Pool & BBQ, Encore Resort, our elegant House in Osceola County. Enjoy amenities including Air conditioning, Balcony/Terrace and Outdoor Cooking, and more.

New to VacationRenter

Near Disney 8BR Pool Home with Marvel Game Room

16 guests · 8 bedrooms · 7 baths

WiFi/Internet · Air conditioning · Pool

Enjoy the best of Osceola County in our House, Near Disney 8BR Pool Home with Marvel Game Room. A stunning property with amenities including Air conditioning, Balcony/Terrace and Outdoor Cooking, and more.

You can save with One Key

8.6 / 10

Excellent(5 Ratings)

The Golf Course House, pets OK+mini home theater, sleeps 18!

18 guests · 6 bedrooms · 6 baths

Free WiFi/internet · Air conditioning · Pool

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

Encore 10BR Escape with Pool, Spa & Game Room

24 guests · 10 bedrooms · 10 baths

WiFi/Internet · Air conditioning · Pool

Looking to create some memories in Osceola County? Look no further than our House, Encore 10BR Escape with Pool, Spa & Game Room. Enjoy top-rated amenities including Air conditioning, Outdoor Cooking and Dryer, and more.

4 / 10

(4 Ratings)

9BR/8.5BA Encore Resort Kissimmee Home w/ Pool View

22 guests · 9 bedrooms · 8 baths

WiFi/Internet · Air conditioning · Pool

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 $435 per night.

You can save with One Key

Encore 10BR Escape with Pool, Spa & Game Room

24 guests · 10 bedrooms · 10 baths

WiFi/Internet · Air conditioning · Pool

Nestled in Osceola County, this House is perfect for your next vacation. Enjoy Encore 10BR Escape with Pool, Spa & Game Room's top-rated amenities, including Air conditioning, Outdoor Cooking and Dryer, and more.

4 / 10

(4 Ratings)

9BR/8.5BA Encore Resort Kissimmee Home w/ Pool View

22 guests · 9 bedrooms · 8 baths

WiFi/Internet · Air conditioning · Pool

This inviting House in Osceola County can fit your needs for many types of vacations, at $435 per night.

10 / 10

Outstanding(1 Rating)

6BR family retreat w/ heated pool & hot tub

16 guests · 6 bedrooms · 6 baths

WiFi/Internet · Air conditioning · Pool

The best choice in Osceola County for House, for $361 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

7 / 10

Good(7 Ratings)

5 Mi to Disney: Oasis w/ Pool & Patio

16 guests · 8 bedrooms · 8 baths

Free WiFi/internet · Air conditioning · Pool

Looking to create some memories in Osceola County? Look no further than our House, 5 Mi to Disney: Oasis w/ Pool & Patio. Enjoy top-rated amenities including Air conditioning, Dryer and Heating, and more.

10 / 10

Outstanding(1 Rating)

6BR family retreat w/ heated pool & hot tub

16 guests · 6 bedrooms · 6 baths

WiFi/Internet · Air conditioning · Pool

This attractive House in Osceola County, $361 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

8.7 / 10

Excellent(3 Ratings)

Family Escape Home 8Br+ Pool +Game Room Near Disney

18 guests · 8 bedrooms · 7 baths

WiFi/Internet · Air conditioning · Pool

Looking for a memorable stay in Osceola County? Our House might just be what you're looking for. Enjoy amenities including Air conditioning, Balcony/Terrace and Outdoor Cooking, and more during your stay.

9.6 / 10

Outstanding(39 Ratings)

Luxury Renovation-Huge Upgrades! MustSee Pool -LED Games Room! Themed Rooms!

20 guests · 7 bedrooms · 6 baths

WiFi/Internet · Air conditioning · Pool

Indulge in a peaceful retreat at Luxury Renovation-Huge Upgrades! MustSee Pool -LED Games Room! Themed Rooms!, our elegant House in Osceola County. Enjoy amenities including Air conditioning, Dryer and Gym, and more.

8 / 10

Excellent(4 Ratings)

Fantastic vacation with a private pool - FENCED POOL - Pet friendly

20 guests · 8 bedrooms · 7 baths

WiFi/Internet · Air conditioning · Pool

The best choice in Osceola County for Villa, for $480 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

You can save with One Key

9.6 / 10

Outstanding(39 Ratings)

Luxury Renovation-Huge Upgrades! MustSee Pool -LED Games Room! Themed Rooms!

20 guests · 7 bedrooms · 6 baths

WiFi/Internet · Air conditioning · Pool

Nestled in Osceola County, this House is perfect for your next vacation. Enjoy Luxury Renovation-Huge Upgrades! MustSee Pool -LED Games Room! Themed Rooms!'s top-rated amenities, including Air conditioning, Dryer and Gym, and more.

You can save with One Key

8 / 10

Excellent(4 Ratings)

Fantastic vacation with a private pool - FENCED POOL - Pet friendly

20 guests · 8 bedrooms · 7 baths

WiFi/Internet · Air conditioning · Pool

Soak up the beauty of Osceola County in our Villa, Fantastic vacation with a private pool - FENCED POOL - Pet friendly. With a range of amenities such as Air conditioning, Outdoor Cooking and Cribs or cots available, you'll feel right at home.

Luxury 8BR Villa w/ Pool & Spa Near Disney

20 guests · 8 bedrooms · 7 baths

Free WiFi/internet · Air conditioning · Pool

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Osceola County, at $507 per night for your next great vacation.

Luxury 8BR Villa w/ Pool, Game & Theater room

16 guests · 8 bedrooms · 7 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 Luxury 8BR Villa w/ Pool, Game & Theater room's exceptional amenities, such as Air conditioning, Outdoor Cooking and Cribs or cots available.

You can save with One Key

Luxury 8BR Villa w/ Pool & Spa Near Disney

20 guests · 8 bedrooms · 7 baths

Free WiFi/internet · Air conditioning · Pool

The best choice in Osceola County for Villa, for $512 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

Luxury 8BR Villa w/ Pool, Game & Theater room

16 guests · 8 bedrooms · 7 baths

Free WiFi/internet · Air conditioning · Pool

Experience the best of Osceola County with this House available for $489. This property is equipped with amenities including Air conditioning, Outdoor Cooking and Cribs or cots available, and more.

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