Features Bed Details Property Details Rates Availability Location Facilities Guest Reviews Virtual Tour
3 King 1 Queen 4 Twin 1 Double 1 Sofa
Come make memories in famous Windsor Hills with all the resort amenities!
****BE SURE TO WATCH THE VIRTUAL TOUR VIDEO****
* just 2 miles from our gate to Disney
* Private Heated Pool & Spa - Faces Southeast and has sun all day!!
* FREE Water park
* FREE Baby gear
* FREE Fiber 500MB Wifi
* 9 TVs
* 2 gaming system TVs
* Fully equipped kitchen
* Playgrounds
* Beach Volleyball, Basketball, Tennis & putting green
* Pool tables, Ping Pong & Arcade
* Poolside Marketplace Bar & Grill
* Fitness Center
* Bathrooms equipped with hair dryers & plenty of linens
Whether you have babies, teens, or adults, you'll enjoy Livin' the Dream!
- Pool/spa heat available for $25/day (discounts for longer stays)
- Grill Rental $75 Weber 3 burner
- Pets Considered - MUST BE PRE-APPROVED BY OWNER
- Windsor Hills provides 14 resort wristbands with this home
- 3 vehicle MAX and no visitors are allowed due to parking restrictions of the resort
Livin' the Dream is a 2-level with:
- 1 Queen bedroom and full bath on the main floor
- Two of the 3 King rooms 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.
- Twin over Full bunkbed, so smaller adults or 2 children can sleep on the bottom if needed.
- All bedrooms have private tv's with Roku installed to viewing access.
- 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 included.
We have baby items for your use at no charge:
* 2 pack and plays w/ mattresses & sheets
* 1 Full size crib & 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
* Pool safety gate
* Baby bath
* Full size crib
We want to customize your kid's rooms with Disney character bedding! See the pictures for choices and let us know what your preferences are!
We can help you arrange for more than 1 villa, just ask!!
These rates were set in USD.  These rates were last updated 1 month ago.
Rate | Period | Nightly | Min Stay | Change Over | Tax Rate |
---|---|---|---|---|---|
Regular | 05 Jan 2025 - 15 Feb 2025 | $290.00 | US State Taxes 13.50% | ||
Canadian Holiday | 16 Feb 2025 - 20 Feb 2025 | $400.00 | US State Taxes 13.50% | ||
Regular | 21 Feb 2025 - 13 Mar 2025 | $375.00 | US State Taxes 13.50% | ||
Spring Break | 14 Mar 2025 - 20 Mar 2025 | $447.00 | US State Taxes 13.50% | ||
Spring Break | 21 Mar 2025 - 05 Apr 2025 | $575.00 | US State Taxes 13.50% | ||
Spring Break/Passover | 06 Apr 2025 - 20 Apr 2025 | $447.00 | US State Taxes 13.50% | ||
Regular | 21 Apr 2025 - 08 May 2025 | $300.00 | US State Taxes 13.50% | ||
Mother's Day | 09 May 2025 - 10 May 2025 | $350.00 | US State Taxes 13.50% | ||
Regular | 11 May 2025 - 22 May 2025 | $285.00 | US State Taxes 13.50% | ||
Memorial | 23 May 2025 - 25 May 2025 | $400.00 | US State Taxes 13.50% | ||
Regular | 26 May 2025 - 19 Jun 2025 | $320.00 | US State Taxes 13.50% | ||
Summer | 20 Jun 2025 - 02 Jul 2025 | $400.00 | US State Taxes 13.50% | ||
July 4th | 03 Jul 2025 - 05 Jul 2025 | $500.00 | US State Taxes 13.50% | ||
Summer | 06 Jul 2025 - 16 Aug 2025 | $400.00 | US State Taxes 13.50% | ||
Regular | 17 Aug 2025 - 28 Aug 2025 | $280.00 | US State Taxes 13.50% | ||
Labor Day | 29 Aug 2025 - 31 Aug 2025 | $400.00 | US State Taxes 13.50% | ||
Regular | 01 Sep 2025 - 25 Nov 2025 | $280.00 | US State Taxes 13.50% | ||
Thanksgiving | 26 Nov 2025 - 29 Nov 2025 | $550.00 | US State Taxes 13.50% | ||
Regular | 30 Nov 2025 - 18 Dec 2025 | $295.00 | US State Taxes 13.50% | ||
Christmas/New Year | 19 Dec 2025 - 26 Dec 2025 | $675.00 | US State Taxes 13.50% | ||
Christmas/New Year | 27 Dec 2025 - 31 Dec 2025 | $750.00 | US State Taxes 13.50% | ||
Regular | 01 Jan 2026 - 14 Feb 2026 | $320.00 | US State Taxes 13.50% | ||
Canadian Holiday | 15 Feb 2026 - 19 Feb 2026 | $350.00 | US State Taxes 13.50% | ||
Regular | 20 Feb 2026 - 12 Mar 2026 | $340.00 | US State Taxes 13.50% | ||
Spring Break | 13 Mar 2026 - 19 Mar 2026 | $447.00 | US State Taxes 13.50% | ||
Spring Break | 20 Mar 2026 - 04 Apr 2026 | $575.00 | US State Taxes 13.50% | ||
Passover | 05 Apr 2026 - 09 Apr 2026 | $395.00 | US State Taxes 13.50% | ||
Easter | 10 Apr 2026 - 19 Apr 2026 | $425.00 | US State Taxes 13.50% | ||
Regular | 20 Apr 2026 - 07 May 2026 | $275.00 | US State Taxes 13.50% | ||
Mother's Day | 08 May 2026 - 09 May 2026 | $350.00 | US State Taxes 13.50% | ||
Regular | 10 May 2026 - 21 May 2026 | $280.00 | US State Taxes 13.50% | ||
Memorial | 22 May 2026 - 24 May 2026 | $375.00 | US State Taxes 13.50% | ||
Regular | 25 May 2026 - 18 Jun 2026 | $290.00 | US State Taxes 13.50% | ||
Summer | 19 Jun 2026 - 01 Jul 2026 | $415.00 | US State Taxes 13.50% | ||
4th of July | 02 Jul 2026 - 04 Jul 2026 | $500.00 | US State Taxes 13.50% | ||
Summer | 05 Jul 2026 - 01 Aug 2026 | $415.00 | US State Taxes 13.50% | ||
Regular | 02 Aug 2026 - 27 Aug 2026 | $275.00 | US State Taxes 13.50% | ||
Labor Day | 28 Aug 2026 - 30 Aug 2026 | $400.00 | US State Taxes 13.50% | ||
Regular | 31 Aug 2026 - 24 Nov 2026 | $300.00 | US State Taxes 13.50% | ||
Thanksgiving | 25 Nov 2026 - 28 Nov 2026 | $500.00 | US State Taxes 13.50% | ||
Regular | 29 Nov 2026 - 17 Dec 2026 | $265.00 | US State Taxes 13.50% | ||
Christmas/New Year | 18 Dec 2026 - 25 Dec 2026 | $675.00 | US State Taxes 13.50% | ||
Christmas/New Year | 26 Dec 2026 - 31 Dec 2026 | $750.00 | US State Taxes 13.50% |
The following booking options are available for the property:
Cleaning Fee 225.00 Per Booking
Booking (Processing) Fee 4.00 Pct
Livin' the Dream is 3/4 mile walk from the pool/clubhouse and there is always plenty of parking if you prefer to drive.
Windsor Hills is very close to the ESPN Sports Complex, Disney and other area attractions.
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 can also offer service staff for your event - just ask for details!
 Hello Laura, I cannot begin to thank you enough for your amazing home and hospitality! Thank you for making the lodging part of our vacation a seamless and stress-free stay. From our very first communication, you have not disappointed. Everything Chauntae mention about you and your homes was spot on. It has been an absolute pleasure. Our time at Livin' the Dream was nothing short of amazing. From the cleanliness of the home, the amazing decor, the comfortable beds, the great pool, the cool game room, the abundance of items provided to ensure our comfortability, it was all well-received! We thoroughly enjoyed the fantastic amenities at Windsor Hills Resort as well. It is safe to say, you now have another NYC client that will be returning to visit :)  
Tanicia J - 29 Aug 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 
Don Ekstrom - 24 Feb 2024
Last Updated - 15 hours ago