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Livin' the Dream❤️Closest FREE Resort to Disney!

Windsor Hills Resort

From $200 / night

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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 * 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.

Amenities

Communal Pool
Communal Pool
Private Pool
Private Pool
Spa
Spa
Games Room
Games Room
Communal Gym
Communal Gym
WiFi
WiFi
Internet
Internet
Pets Allowed
Pets Allowed
High Chair
High Chair
Air Con
Air Con
Pack n Play
Pack n Play
South Facing Pool
South Facing Pool
BBQ
BBQ
Air Hockey Table
Air Hockey Table
Big Screen TV
Big Screen TV
DVD Player
DVD Player
Foosball Table
Foosball Table
Grill
Grill
Hair Dryer
Hair Dryer
TV in Every Bedroom
TV in Every Bedroom
Outdoor Hot-tub
Outdoor Hot-tub
Paved Parking
Paved Parking
Pool Access
Pool Access
Pool Table
Pool Table
Video Games
Video Games
Sofa Bed
Sofa Bed
Club House
Club House
Full Kitchen
Full Kitchen
Laundry In Unit
Laundry In Unit
Laundry On Site
Laundry On Site
Microwave
Microwave
Resort Amenities
Resort Amenities
Table Tennis
Table Tennis
Tennis Courts
Tennis Courts
Dishwasher
Dishwasher

Video

Availability

Location

Closest resort to Disney. This home is toward the back of the resort, so it's nice and quiet with almost no traffic. There is no home across from the front, so you have a beautiful, elevated view and can see fireworks all over on special events like 4th of July and New Year's and sometimes for no reason.

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Guest Reviews

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Reviewer Name: Vickie Penick

Review Date: Jun 07, 2024
Star Rating:
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.
Reviewer Name: Amanda Gleason

Review Date: May 22, 2024
Star Rating:
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++
Reviewer Name: Don Ekstrom

Review Date: Feb 24, 2024
Star Rating:
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
Reviewer Name: Rob Ciurla

Review Date: Feb 08, 2024
Star Rating:
Laura was absolutely wonderful! Her communication is unmatched. We always had updates and she even checked in to report about a change in the weather for our stay. You can’t beat that level of attention! We have rented many houses before in the area but this one we will 100% be coming back to. The beds were very comfortable and there was plenty of seating for our party of 10. Everything was fresh, clean and tastefully decorated (something hard to find in most of rental homes) We stayed at Windsor palms resort across the road last year and it was nice but Windsor hills has a lot more to offer while also being family friendly and quiet. Thank you Laura & Fred for such an amazing experience you are super hosts for sure!
Reviewer Name: Treby Hoak

Review Date: Sep 08, 2023
Star Rating:
Wonderful vacation home! The property manager/owner was wonderful! Communication far exceeded any and all expectations, and Laura was very prompt with her responses! Anything we inquired about was answered almost instantly! The check in process was easy and detailed instructions were sent ahead of time. A nice welcome basket was available for us when we arrived, as well all the immediate staples, which made life so much easier. The home itself was well kept and beautifully decorated. The beds were comfortable and everyone in our party slept really well. Plenty of room for our party of 7 and we never felt cramped or packed. We loved the neighborhood and location of the home. It was very quiet and peaceful. We really enjoyed the pool and hot tub area. It was wonderful after a long day at Disney. The location is super convenient and close to the Disney Parks as well as grocery stores. 5 Stars hands down. We will be back to vacation with this host again!
Reviewer Name: Mikel Resnick

Review Date: Jul 03, 2023
Star Rating:
Laura was a fantastic host!!! She was responsive to all our questions and the directions to occupy and leave the house we’re clear and generous. In the 15-years I’ve stayed at VRBO this has been the best experience I’ve had.
Reviewer Name: Melanie J Schmidt

Review Date: Feb 09, 2022
Star Rating:
If I could give over 5 stars I sure would. Laura was amazing and the home was jaw dropping beautiful. The grandkids loved having all the space and sharing rooms that were styled in the theme of their choice. Laura even helped me out of a pickle with Instacart groceries, we were delayed in getting to the house so Laura had her handyman bring groceries in and place items in the refrigerator and freeze. So very personalized service. Absolutely loved this home and we will be back. Thank-you for helping us make a dream come true. The Schmidt's
Reviewer Name: Jessi Burr

Review Date: Nov 28, 2021
Star Rating:
This was an amazing home to stay in! Our family visited Disney World the week of Thanksgiving and this home provided us with everything we needed to complete our trip. The amenities in the resort were amazing and out hosts ensured we had everything we needed to feel at home. We traveled with 3 little ones and this home had all we needed for our little ones to be comfortable and had all the necessary items children require for travel. Our hosts were spot on when it came to communicating with us and we’re available whenever we had any questions. We plan to stay with them again for any future vacations our family plans! My little ones especially enjoyed the bedding we got to choose for them. I highly recommend this home for anyones vacations. Thank you Laura and Fred for helping to make this vacation more magical for our family!
Reviewer Name: Jennifer

Review Date: Oct 08, 2021
Star Rating:
What a dream home! The perfect location. First time ever booking a home to stay at for a Disney/SeaWorld vacation. Very clean! House was very welcoming nice and updated decor. It was nice to not live out of luggage while on vacation. So much space! Game room and pool was perfect for nights after the parks. Laura was a wonderful host, and very responsive! I would definitely recommend and will stay again when in the area. Beats hotel stay by far! Thanks for everything!
Reviewer Name: April

Review Date: Apr 08, 2020
Star Rating:
OMG... OMG.. I can’t say how AMAZING this place is! It’s better than the pictures! You have every dish/utensils you can want for.. including a pizza cutter ?? Enough dishes for a small army. Rooms are clean and have TVs. Pool and hot tub are WELL taken care of and have pool toys as well. If you are reading this review.. PUSH THE BUTTON AND BOOK THIS PLACE! I promise you will not be disappointed! Check in process was seamless and we even had a snack basket waiting. My family will be booking again!
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