Livin the Dream, Closest FREE Resort to Disney! 3 Kings

Kissimmee, Florida
$683 avg/night
Minimum Stay 1 Nights
Bed 6

Bed

Bath 4

Bath

Home Private Vacation Home

Property Type

Sleep 16

Max Sleeps

Night 1 nights

Min Stay

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!
* New 65 Poolside TV
* 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

***Self-managed = better customer service w/ 0% cancellations. 5 Star Stay Properties is our company name & we work hard to live up to it!

- Pool/spa heat available for $25/day
- Pets considered, but MUST BE PRE-APPROVED PRIOR TO BOOKING
- 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
- Blackout Curtains in Bedrooms

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
* 4 step stools - 2 double as booster seats
* 2 carseats and one car booster
* 1 baby walker/activity
* 1 potty seat
* 1 backpack child carrier
* Pool safety gate

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. *We can sleep 16 guests, but NOT 16 adults. Adults may not sleep on the top bunk and to fit 16, 2 people must sleep in the bottom bunk and 2 on the pull-out couch. Groups with 12 or more adults, must be approved by the host.

Read More Expand
  • Feature Features
  • Map Map
  • School District Availability
  • Review Review

Feature Features

  • PETS

    Pet Friendly Service Animals Exempt From Fees
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Deadbolt Lock Fire Extinguisher Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    6 Bedrooms Bed Sheets Provided
  • GENERAL

    Unit Size: 3500 Sq Ft (325 Sq M) Uses Some LED Lighting
  • KITCHEN

    Dishwasher Microwave Mixer Oven Refrigerator Rice Cooker Spices Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Near Laundromat Washing Machine And Dryer
  • PARKING

    Car Recommended Limited Onsite Parking Onsite Parking
  • INTERNET

    Free WiFi
  • OUTDOORS

    Barbecue Grill Patio
  • POOL/SPA

    Heated Pool Hot Tub Private Pool Shared/communal Pool
  • BATHROOMS

    4 Bathrooms Bathtub Or Shower Hair Dryer Towels Provided
  • LANGS SPOKEN

    English
  • THINGS TO DO

    2 Outdoor Pickleball Courts Basketball Nearby Birdwatching Nearby Fitness Center Fitness Facilities Nearby Golf Nearby Golfing On Site Swimming Nearby Tennis On Site Water Park Wildlife And Game Walks Nearby
  • ENTERTAINMENT

    Air Hockey Arcade/game Room Books Games Table Tennis Video Library TV
  • LIVING SPACES

    Dining Room Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Highchair
  • LOCATION HIGHLIGHTS

    Near A Health Or Beauty Spa Near A Hospital Near A Zoo Near Outlet Shopping
  • SERVICES AND CONVENIENCES

    Iron/ironing Board Limited Housekeeping
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 16

Map Map

School District Availability

Review Review

  • Melissa

    Submitted Nov 12, 2023

    Stayed Nov 5, 2023

    The house was beautiful and in a very relaxing area. Disney was not a far drive at all to get too. Laura was amazing to work with from the day we booked our vacation. My family plans to use 5 Star on our next vacation.

  • Todd A.

    Submitted Jun 14, 2026

    Stayed Jun 8, 2026

    Everything about this listing was accurate. We had an amazing time. Pool was very nice.

  • Leah D.

    Submitted Jun 7, 2026

    Stayed May 6, 2026

    We had great time! Laura was very responsive and

  • Kimberly S.

    Submitted May 9, 2026

    Stayed Apr 30, 2026

    The host explained everything clearly. House was clean and welcoming. My son loved the games and of course watching tv from the hot tub!

  • Lauren H.

    Submitted Apr 11, 2026

    Stayed Apr 7, 2026

    This was a beautiful home and very large where we did not feel crowded or cramped. The resort area is clean and nice. The host kept me informed on the check in and check out process and it was very easy. Lots of towels and wash cloths. I would highly recommend this home and would stay again.

  • Melanie G.

    Submitted Mar 12, 2026

    Stayed Mar 5, 2026

    Although our days were spent away from the property; we were pleased with location and the home met our families needs. Service and communication from the property host was excellent!

  • Christy C.

    Submitted Mar 6, 2026

    Stayed Mar 4, 2026

    Amazing

  • Summer C.

    Submitted Feb 9, 2026

    Stayed Feb 4, 2026

    House was clean, well stocked, comfortable beds.

  • Stephanie H.

    Submitted Feb 3, 2026

    Stayed Jan 26, 2026

    We enjoyed our stay here. House was comfortable, conveniently located, and had everything we needed. Host communicated well and promptly. Would definitely stay again!!

  • Carlon O.

    Submitted Jan 24, 2026

    Stayed Jan 18, 2026

    Fantastic home and host! Thanks again!

  • Dianna H.

    Submitted Jan 2, 2026

    Stayed Dec 20, 2025

    We honestly can’t think of a single thing to complain about from our stay at Windsor Hills. Laura’s communication leading up to our visit was excellent and incredibly helpful. With her assistance, we arranged a grocery delivery for our arrival, and for a very reasonable fee her staff received the order and put everything away for us. We arrived late, so having snacks and food ready for the morning was a huge help—especially with kids.The house was spotless and exceptionally well stocked. The kitchen had everything we needed, and we ended up cooking about 90% of our meals there, just like at home.Our kids absolutely loved the game room, and the younger ones were thrilled with the themed bedsheets. For families with young children, the house is extremely well equipped with strollers, booster seats, playpens, bed rails, and more.We stayed over New Year’s and loved being able to walk to the nearby grassy area to watch the Orlando sky light up with fireworks in every direction.The resort facilities were much enjoyed by our children. The house is about a 10 minute, and very easy, walk to the resort pools and clubhouse and about 5 minutes tk the childrens playground.We also opted to have the pool heated and definitely got our money’s worth—everyone enjoyed it so much. We would happily stay here again and highly recommend this property to other families.

  • Courtney L.

    Submitted Nov 16, 2025

    Stayed Nov 13, 2025

    Great location. Gated community. Clean property and plenty of space!

  • Deborah F.

    Submitted Aug 16, 2025

    Stayed Aug 10, 2025

    Fantastic home.. we will definitely rebook

  • Ashley P.

    Submitted Jul 24, 2025

    Stayed Jul 17, 2025

    The living area seating was limited, with more seating in the front room than in the living room with the TV. The AC couldn’t go lower than 70 degrees, and the thermostats routinely shut off causing the house to heat up to 78 degrees. The TV’s were small in main living areas, and we had difficulty getting the TV in the game room to work. The kitchen is not adequately equipped for travelers to cook in the house, thankfully we brought our own cookware, and there were only two dish towels. Paper products including paper towels and toilet paper are not included. We were required to wash towels and all dishes before leaving, meaning you have to trust the previous vacationer washed the dishes before putting them away because the cleaning staff does not wash the dishes, and you need to allot time before you leave to wash towels even though you’re paying a cleaning fee. The house is a far distance from the ‘resort’ to where it is not walkable, and the resort is very small and does not provide towels despite what they say online.

  • Submitted Jul 7, 2025

    Stayed Jun 21, 2025

    The house was well priced for as big as it is and was clean and easy to get in and out of. The property manager was very responsive with any questions and giving any information needed for staying in the home and neighborhood.

  • Amber L.

    Submitted Jul 5, 2025

    Stayed Jun 18, 2025

    This is the cleanest rental property we’ve ever stayed in. It was perfect for our multi-generational trip, with plenty of room for everyone to comfortably gather and, conversely, also enjoy private time. The community pool and waterslides were enjoyed by all, although I would say the fitness room is incredibly small for the size of the development. The location cannot be beat for convenience to groceries, restaurants (you MUST try Cowboy Chicken!), shopping, and Disney. I also appreciated how accessible the host was for any questions, and all directions and instructions for the property were clear and easy to follow. You will not find a better option, so stop searching and book this property ASAP!

  • Rachel E.

    Submitted Jun 11, 2025

    Stayed Jun 7, 2025

    House was beautiful, clean, and had so much space for our family of 8. We loved the area. It was close to Disney and other attractions. Neighborhood was quiet and safe. Love the amenities at the resort! Would 100% recommend!

  • Brian C.

    Submitted Jun 10, 2025

    Stayed Jun 1, 2025

    Kids enjoyed the pool. The property is Conveniently located to Disney properties. It was clean and as described. Property manager (Laura) was accessible if needed.

  • Sandra H.

    Submitted May 16, 2025

    Stayed May 2, 2025

    Our stay was wonderful! Laura was very quick and thorough with answering our questions. Check-in easy, home was well-appointed, with thoughtful details. Pool area accommodated 5 young kids and 6 adults, easily. Resort area and playgrounds were wonderful. Close to alot of activities on 192. Privacy from neighbors was great, beds very comfortable. Definitely would visit again! Thank you for a much needed good time!

  • James W.

    Submitted Mar 31, 2025

    Stayed Mar 22, 2025

    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.

  • Christen F.

    Submitted Mar 16, 2025

    Stayed Mar 3, 2025

    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.

  • Gina H.

    Submitted Feb 20, 2025

    Stayed Feb 17, 2025

    I brought my son and two of his friends to Florida for winter break

  • christine d.

    Submitted Feb 17, 2025

    Stayed Feb 12, 2025

    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.

  • Timothy C.

    Submitted Jan 16, 2025

    Stayed Jan 8, 2025

    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!!!

  • Michael C.

    Submitted Jan 1, 2025

    Stayed Dec 28, 2024

    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.

  • Reaves M.

    Submitted Dec 28, 2024

    Stayed Dec 22, 2024

    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!

  • Lindsay k.

    Submitted Dec 24, 2024

    Stayed Dec 11, 2024

    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!

  • MQ H.

    Submitted Dec 7, 2024

    Stayed Nov 23, 2024

    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

  • Jeffrey C.

    Submitted Nov 24, 2024

    Stayed Nov 17, 2024

    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.

  • Judy D.

    Submitted Nov 16, 2024

    Stayed Nov 9, 2024

    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.

  • Judy D.

    Submitted Oct 18, 2024

    Stayed Oct 6, 2024

    The house is beautiful and very welcoming. We enjoyed our stay and look forward to staying again!

  • Sharon N.

    Submitted Oct 6, 2024

    Stayed Sep 30, 2024

    Lovely comfortable home close to all the parks. Safe beautiful gated community with waterpark and pool.

You might like these similar properties

Your dates are Available!

Total

Includes taxes and fees
$561+
View details