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Livin the Dream❤️Closest FREE Resort to Disney! AC game rm!

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Sunny Pool Deck w/ Loungers and Dining Table
Master King bedroom Suite
Even better at night!
Free Resort & Waterpark!!
Living Room

Reviews

10 out of 10
Exceptional
6 bedrooms4 bathroomsSleeps 16325.2 sq m

Popular amenities

  • Parking available
  • Pet-friendly
  • Dryer
  • Washer
  • Outdoor space

Explore the area

Map
Kissimmee, FL
  • Mystic Dunes Golf Club
    ‪5 min drive‬
  • ESPN Wide World of Sports Complex
    ‪14 min drive‬
  • Disney's Animal Kingdom® Theme Park
    ‪20 min drive‬
  • Kissimmee, FL (ISM-Kissimmee Gateway)
    ‪22 min drive‬

Rooms & beds

6 bedrooms (sleeps 16)

Master Suite

1 Crib

4 bathrooms

Hall Bath

King Suite

Mainfloor Bath just outside Queen Rm

Master Suite

Spaces

Deck or patio
Kitchen
Separate dining area
Dining Area

About this property

Livin the Dream❤️Closest FREE Resort to Disney! AC game rm!

Come make memories in famous Windsor Hills with all the resort amenities!

* just 2 miles from our gate to Disney
* Private Heated Pool & Spa - Southeast facing - Sun ALL Day!
* FREE Water park
* FREE Baby gear
* AC game room w/ pool table, air hockey, and 2 gaming systems
* FREE Fiber 500MB Wifi
* 9 TVs
* Fully equipped kitchen
* Playgrounds
* Beach Volleyball, Basketball, Tennis & putting green
* Pool tables, Ping Pong & Arcade
* Poolside Marketplace Bar & Grill
* Fitness Center

Whether you have babies, teens, or adults, you'll enjoy Livin' the Dream!

- Pool/spa heat available for $25/day
- Pets considered, but MUST BE PRE-APPROVED PRIOR TO BOOKING
- Weber Grill Rental (3 burner) available onsite $75/week
- This home comes with 14 wristbands for the resort.
- 3 vehicles allowed per reservation
- 3.5% Booking fee is non-refundable if cancelled

Livin' the Dream is a 2-level with:
- 1 Queen bedroom and full bathroom on the main floor
- Two of the 3 King bedrooms upstairs have their own 'en suite bathrooms
- Remaining King and 2 twin rooms share a full hall bathroom, which is set up perfect for sharing with separate doors to access the tub/shower room and stool. The kids rooms have 2 Twins in one and a Twin and bunkbeds with Twin over Full beds (updated since photo)
- Queen pull-out sofa
- All bedrooms have private tv's
- All NEW Hybrid Pillowtop Mattresses 10-2023

Kitchen is fully stocked, including 12 cup regular & Keurig coffee makers, blender, crock pot, griddle, rice cooker, mixer, pots and pans and cooking utensils. This kitchen has all you need to prepare meals, not just a bare minimum of equipment.

All linens, including pool towels provided.

We have baby items for your use at no charge:
* 2 pack and plays w/mattresses & sheets
* 1 Full-size crib w/ sheets
* 1 baby gate for the staircase
* 2 safety bed rails
* 1 baby monitor
* 1 high chair
* 2 umbrella strollers
* 3 step stools - 2 double as booster seats
* Pool safety gate
* Baby bath
* Full size crib

Being a Windsor Hills Resort guest means you will have the free access to the fantastic amenities that Windsor Hills Resort offers.

Windsor Hills resort features a lagoon style pool with water-slides, kid's splash pad/play area, hot tub, air conditioned game room, fitness center, movie theater, poolside marketplace bar & grill, basketball courts, sand volleyball court, playgrounds, dog park, putting green and tennis courts.

There are golf courses to suit all styles and abilities. Come stay at Windsor Hills for your next golf week, Livin' the Dream has many courses within half hour drive. The nearest golf course is Mystic Dunes - rated Orlando's #2 golf course!

We want to customize your kid's rooms! Just let us know after your booking if you would prefer our standard bedspreads or:
- Frozen
- Incredibles
- Star Wars
- Finding Nemo
- Planes
- Mickey faces
- Mickey Mouse clubhouse

Livin' the Dream can be used for families, business trips, or sports teams. It's also suitable for short or long-term stays for insurance, corporate travel, wedding travel, college graduation and military. This home is NOT suited for parties.

Property manager

Laura Jury
Premier Host

Languages

English

Add dates for prices

Amenities

Pool
Hot tub
Kitchen
Washer
Dryer
Pet-friendly

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House Rules

Check in after 4:00 PM
Minimum age to rent: 24
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadlock

We should mention

A car is recommended for transport to and from this property

About the area

Kissimmee

Located in Windsor Hills, a neighbourhood in Kissimmee, this holiday home is near theme parks. Old Town and Flamingo Crossings Town Center are worth checking out if shopping is on the agenda, while those wishing to experience the area's popular attractions can visit Walt Disney World® Resort and Disney's Hollywood Studios®. Travelling with kids? Make time for Disney's Animal Kingdom® Theme Park, or head to an event or a match at ESPN Wide World of Sports Complex. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Map
Kissimmee, FL

What's nearby

  • Mystic Dunes Golf Club - 5 min drive - 3.0 km
  • Island H2O Live! - 6 min drive - 4.5 km
  • Disney's Hollywood Studios® - 13 min drive - 10.1 km
  • ESPN Wide World of Sports Complex - 14 min drive - 9.4 km
  • Disney's Animal Kingdom® Theme Park - 20 min drive - 13.8 km

Getting around

  • Kissimmee Station - 26 min drive
  • Kissimmee, FL (ISM-Kissimmee Gateway) - 22 min drive

Restaurants

  • ‪McDonald's - ‬4 min drive
  • ‪Starbucks - ‬4 min drive
  • ‪Taco Bell - ‬5 min drive
  • ‪IHOP - ‬4 min drive
  • ‪Giordano's - ‬5 min drive

Frequently asked questions

Does Livin the Dream❤️Closest FREE Resort to Disney! AC game rm! have a pool?

Yes, this property has a pool. Pool types include heated pools.

Is Livin the Dream❤️Closest FREE Resort to Disney! AC game rm! pet-friendly?

Yes, pets are allowed at this property.

How much is parking at Livin the Dream❤️Closest FREE Resort to Disney! AC game rm!?

Limited spots are available.

What time is check-in at Livin the Dream❤️Closest FREE Resort to Disney! AC game rm!?

Check-in begins at 4:00 PM.

What time is check-out at Livin the Dream❤️Closest FREE Resort to Disney! AC game rm!?

Checkout is at 10:00 AM.

Where is Livin the Dream❤️Closest FREE Resort to Disney! AC game rm! located?

This family-friendly Kissimmee holiday home is located in Windsor Hills, within 3 mi (5 km) of Mystic Dunes Golf Club and Island H2O Live!. Walt Disney World® Resort and Old Town are also within 6 miles (10 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 85 out of 90 reviews
Rating 8 - Good. 4 out of 90 reviews
Rating 6 - Okay. 0 out of 90 reviews
Rating 4 - Poor. 1 out of 90 reviews
Rating 2 - Terrible. 0 out of 90 reviews

10/10

Cleanliness

10/10

Amenities

10/10

Property conditions & facilities

10/10

Eco-friendliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

James W.

Liked: Cleanliness, communication, location, listing accuracy
Thank you for a great stay!!
Overall our star was terrific. The home was very nice and was everything we were looking for and expecting. I gave only 3 stars for the check in process since we waited at least 40 minutes in traffic to get on site. I understand this is not the responsibility of the host but more help is needed at the entry gate during the busy check in times. I’m certain we weren’t the only guests and residents who were frustrated. It was a mess for all autos trying to enter the property. Those working the gate were polite and did a good job but it was terrible trying to get to the gate. Another employee out front could have suggested and help manage the process to get autos in the correct lanes for much easier entry.
Stayed 6 nights in Mar 2025

10/10 Excellent

Christen F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Best Overall
We had a great time staying at "Livin the Dream." We traveled with 8 adults, an 11 year old, and a 1, 3, and 4 year old. Of all my vacation stays, this was hands down THE BEST stay.The home was clean, cozy, and smart!If you are a parent to toddlers, YOU NEED this home. If you are a parent to pre-teens/teenagers, you NEED this home. We traveled with home cameras and sounds machines for the littles, and I was even impressed by the location of the outlets in each room. The host was kind, helpful, and accommodating.I would 10000% stay here again.
Stayed 4 nights in Mar 2025

10/10 Excellent

Gina H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Winter break
I brought my son and two of his friends to Florida for winter break
Stayed 3 nights in Feb 2025

8/10 Good

christine d.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great house for groups
House was wonderful. Very clean. Plenty of space. Pool was nice. Dryer didn’t work (we were informed on day of check in and even after repaired still did not work). This would have been nice to have but for our short stay was not essential.
Stayed 5 nights in Feb 2025

10/10 Excellent

Timothy C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
So good you don’t want to leave!!!
This is by far the best place we have ever stayed close to Disney!!! You won’t find a more accommodating host, a more secure neighborhood, or a place any closer to shopping, restaurants, or Disney than this!!! We thoroughly enjoyed our stay! The house has more than enough room for our large extended family. The host has thought through anything one may need from infants to the elderly, and it’s all there. Will definitely stay there again!!! Definitely a five star stay!!!
Stayed 4 nights in Jan 2025

10/10 Excellent

Michael C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Family/Disney/New Years Eve
Family of 14 with 7 adults and 7 kids. 4 night stay. Close to Walmart to buy food. Close to Walt Disney World. Place was clean and as advertised. Check in was a breeze. We had a slight issue with staying an extra day for the door code and it was remedied immediately! We left a few swimming masks and that was taken care of without an issue. We would definitely stay again.
Stayed 4 nights in Dec 2024

10/10 Excellent

Reaves M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Family Disney Christmas Vacation
My family truly enjoyed our stay. It was the perfect size for my group of 9. It was clean and had several conveniences. The online photos are accurate. The neighborhood was well kept and quiet. I would come back anytime!
Stayed 6 nights in Dec 2024

10/10 Excellent

Lindsay k.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful, large, and comfortable house close to Disney!
We had a wonderful stay at this house, we had 5 adults and 2 teenagers with us and everyone got a large comfortable room of their own to enjoy. Everything was very clean and the beds were super comfortable (which is very important to me as far as VRBOs go)! We didn’t get to enjoy the pool or hot tub. Actually it wasn’t a hot tub, it’s more of just a sitting pool, it was actually colder than the main pool when we were there even though we paid to heat it. It was a particularly cool day and evening so it was because of that but for some reason I was thinking the listing said hot tub which it definitely is not. Anyway, that was no big deal, we had a wonderful stay, loved the pool table and air hockey table and would absolutely stay again! We recommended this house to our extended family as well for when they go to Disney! Don’t hesitate to rent!
Stayed 1 night in Dec 2024

10/10 Excellent

MQ H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Speechless!
I had to pleasure of staying at this incredible property and I must say it was an awesome experience. We came to enjoy Universal Studios and we did just that. The property only added enjoyment to what we thought would be a long drawn out process. We had every intention of staying at the park from open to close but we managed to sacrifice a day at the park to simply enjoy the property. My family and friends were amazed at how comfortable every aspect of the property was from sleeping to the many amenities. Absolutely NOTHING went wrong regarding the property and I hope future guests are as lucky. Mrs. Laura and her team were ready to accommodate at any given moment had we needed it and that added to the overall experience! What a way to bring in my wife's birthday! I highly recommend this property or the others they offer. You won't regret it. 5* I enjoyed my stay 4* There are many issues to fix 3* Major problems during my stay 2* This home should not be listed 1* It was so terrible, I left early
Stayed 6 nights in Nov 2024

10/10 Excellent

Jeffrey C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing
Overall an amazing place. Plenty of space for us, kids, and grandkids. Plenty to do for the grands, and the pool and spa was used by all. Location, location, location. Close to all parks and Walmart right around the corner (lol). Will definitely recommend to anyone vacatioing in the area. Thank you vey much. Many wonderful memories were made.
Stayed 6 nights in Nov 2024

10/10 Excellent

Judy D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Family Vaca
We enjoyed our second stay at your house. Quiet neighborhood, plenty of room, pool and hot tub were thoroughly enjoyed. Borrowing one of your strollers helped the children on our second day at Disney, thanks. Would definitely stay aging.
Stayed 6 nights in Nov 2024

10/10 Excellent

Judy D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Livin the dream
The house is beautiful and very welcoming. We enjoyed our stay and look forward to staying again!
Stayed 5 nights in Oct 2024

10/10 Excellent

Sharon N.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful home.
Lovely comfortable home close to all the parks. Safe beautiful gated community with waterpark and pool.
Stayed 6 nights in Sep 2024

10/10 Excellent

Lisa S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Family Weekend
Beautiful home! Hosts were incredibly responsive and so informative! Highly recommend!
Stayed 3 nights in Aug 2024

10/10 Excellent

Aisha H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Exactly what I expected
The home was beautiful and Laura was very easy to reach whenever we needed anything. Gave a great hotel vibe with more privacy! Great location, perfect for teenagers, and close to everything we needed.
Stayed 5 nights in Aug 2024

10/10 Excellent

Natalie C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Home away from home
The stay at Living the Dream was absolutely great. It was just as pictured, clean, comfortable and conveniently located to Disney, other attractions as well as places to eat and shop. There were 10 of us and while we are a close knit family, we appreciated having enough space to “spread out” and have not be on top of each other. Laura was an excellent hostess, extremely responsive and very helpful. I would recommend this home to anyone and would gladly stay here the next time we do a family vacation in Orlando.
Stayed 6 nights in Jul 2024

10/10 Excellent

melody h.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfectly perfect
Such a lovely house and perfect for our family get together. It was clean and well kept. Perfect house and perfect location.
Stayed 4 nights in Jul 2024

10/10 Excellent

Patrisha G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Family vacation
We are a large family traveling with dogs also. This home had plenty of room for us all. Everything was perfect. We’ve already agreed that this is where we will stay when visiting Orlando!
Stayed 4 nights in Jul 2024

10/10 Excellent

Monika L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place
We had a wonderful time at this property. Everything was very clean and well organized. Very large house with plenty of beds and rooms. The game room was a pleasant addition that everyone really enjoyed.
Stayed 3 nights in Jun 2024

10/10 Excellent

Vickie P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
College Grad Celebration
A Nana with four 22 yr old college grads enjoyed our stay. Loved the home, great layout. Very comfortable, clean, convenient to Disney Parks, shopping, 192 restaurants. We enjoyed the pool very much, lots of room. A beautiful and quiet neighborhood tucked out of the busy traffic, but close to everything. Our host could not be more responsive. Will definitely stay again. Thank you Laura for making our stay so special.
Stayed 3 nights in Jun 2024

10/10 Excellent

Amanda G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect!
Amazing location to ESPN & Disney. Home was very clean and as described in VRBO. Would definitely stay again. In addition, the host was very quick with any questions we had. A++
Stayed 5 nights in May 2024

10/10 Excellent

Natalie M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent place to stay!
The house is beautifully decorated, clean, and communication with management/owners made the whole process so easy. Highly recommend!
Stayed 4 nights in May 2024

10/10 Excellent

Tom A.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great Memories
This was the first Disney trip for my girls. Our entire family of 7 lived the home. We would absolutely stay here again. Host was excellent at communication with use leading up to our stay.
Stayed 14 nights in Mar 2024

10/10 Excellent

Jacob D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent Stay
We had a wonderful stay at this home. The property and amenities were every bit as described and more. The cleanliness exceeded our expectations. Laura was wonderful to work with and was very accommodating. You could tell she really cared about her tenants having a good stay. The pool and spa heat worked great, much better than some of the other properties we have stayed at in the area. We will definitely try to stay here again in the future.
Stayed 12 nights in Feb 2024

10/10 Excellent

Don E.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Family Disney World Visit - February 2024!
Very pleased with our 10 day stay at "Livin the Dream"! We were 11, ranging from 30 months to 72 years. The house worked great for all. Sleeping arrangements comfortably accommodated all & ready access for all to bathrooms. We found it to be a very well-equipped from kitchen, to pool to bedrooms & bathrooms– everything needed to settle in & enjoy the stay. Special note regarding all the baby/toddler equipment onsite which was clean, in good repair& saved transporting our own or renting. Our 5 grandsons (30 months to 9 years) loved the games room. They were either there or in the pool – they weren’t hard to keep track of! The house is located in a quiet neighborhood away from the busyness of Kissimmee, yet a location easy for getting to Disney parks & close to grocery stores & restaurants. Unfortunately weather& schedule limited time at the clubhouse & community areas but they're nicely equipped& very popular. A special shout-out to Laura the host who was exceptional to deal with & definitely among the best- if not the best- ever encountered. Highly responsive to inquiries we made of her, proactively reached out with information/suggestions/support. When things went awry on our end, was quick to provide solutions & help. I believe the truest test in assessing a property is would I recommend it to family and friends if they were visiting that locale. I have no qualms in recommending this house to anyone looking for a large, comfortable, well-equipped vacation home in Kissimmee
Stayed 12 nights in Feb 2024

About the host

Hosted by Laura Jury

Host profile image
I was born and raised on a farm in south-central Michigan, and am blessed to still live just 3.5 miles from the farm with my high-school sweetheart husband and 2 young boys. Before becoming a full-time mom, I had a successful 9-year career in technology sales.

As a family, we enjoy fishing, camping, hunting, baking, playing games and traveling in our free time.

We love our National Parks for the hiking, wildlife and amazing landscapes and have visited the Great Smokey Mountains in TN, Yellowstone in Wyoming, the Florida Everglades, and Denali in Alaska.

Once we started our family, we began using other's short term vacation rentals for long-weekend anniversary getaways and family vacations in Michigan and have always had a wonderful experience. We appreciate being able to cook our own meals for the most part and to relax and play games in a home instead of a hotel, not to mention we can create a very budget-friendly vacation by not eating out every night.

Why they chose this property

Our favorite warm weather destination is Florida. When winter comes, it's easy for us to take a quick Allegiant Air flight to several destinations throughout Florida. That's why we chose Kissimmee as our first vacation home location. It's ideally located to the most popular attractions and the resort we chose is known as the closest to Disney, but is very private.

We've spent a good amount of time at our place and can make specific recommendations to help you get the most of your stay - see our guidebook. We are happy to share our place with others, so they can create lasting memories just as we have. We feel there is no better way to spend our time and our money, but to create memories with the ones we love.

What makes this property unique

We love Windsor Hills Resort because it's close to everything and has so much to do!

We can go to the east or west side of the state to the beaches in just over an hour and can pick a new park to visit every time too.

Languages:

English

Premier Host

They consistently provide great experiences for their guests
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