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Charming Dog Friendly Villa w/Pool, Gated Resort, Gameroom, Free wifi, Kid Themed Rooms, Contactless Check-in, Free wifi!

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Reviews

7.4 out of 10
Good
5 bedrooms4 bathroomsSleeps 12

Popular amenities

  • Private pool
  • Onsite parking available
  • Pet-friendly
  • Kitchen
  • Washer/dryer
  • Air-conditioning

Explore the area

View in a map
kissimmee, FL
  • Place, Northeast Regional Park
    ‪3 min drive‬
  • Place, Walt Disney World® Resort
    ‪11 min drive‬
  • Place, Magic Kingdom® Park
    ‪21 min drive‬
  • Airport, Orlando, FL (MCO-Orlando Intl.)
    ‪40 min drive‬

Rooms & beds

5 bedrooms (sleeps 12)

4 bathrooms

Bathroom 1

Bathroom 2

Bathroom 3

Bathroom 4

Spaces

Deck or patio
Porch or lanai
Kitchen
Dining area

About this property

Charming Dog Friendly Villa w/Pool, Gated Resort, Gameroom, Free wifi, Kid Themed Rooms, Contactless Check-in, Free wifi!

?? Spacious 5BR Townhome Near Disney w/ Private Pool – Dog Friendly! ??
Located in the sought-after Windsor at Westside Resort, this beautiful 5-bedroom, 4.5-bath townhome is the perfect place for your next Orlando getaway! Just minutes from Disney, shopping, and dining, you’ll have everything you need for fun and relaxation.

?? Enjoy a private screened splash pool with a covered lanai, two spacious living areas, and a fully equipped kitchen with stainless steel appliances and granite counters. Stay connected with free WiFi and unwind with flat-screen TVs in every bedroom.

?? Sleeps up to 12 guests with 2 master suites, 2 queen bedrooms, 1 twin room, and a fun bunk room with a trundle bed.
?? Washer, dryer, linens, towels, hairdryers, and ironing essentials are all provided for your convenience.

?? Dog friendly! Up to 2 dogs are welcome with a $150 + tax non-refundable pet fee per dog (added after booking). All dogs must be registered and approved. No cats or other animals allowed.

?? Resort Amenities Include:

10,000 sq.ft. clubhouse

Resort-style pool + lazy river + kids splash zone

Tiki bar, lounge, market & deli

Fitness center, game room, sports courts & playground

?? Important Info:

Pool heat available: $25/day (3-night min)

Self-catering home: starter kit provided (TP, paper towels, hand soap, trash bag)

No smoking. No parties or events.

Whether you're visiting the parks or enjoying a relaxing retreat, this stylish, family-friendly home has it all. Book your magical stay today and start making memories!

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House Rules

Check in after 4:00 PM
Minimum age to rent: 21
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

Property # 7649276
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 not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadlock

About the area

Kissimmee

Kissimmee is home to this holiday home. ChampionsGate Golf Club and Mystic Dunes Golf Club are worth checking out if an activity is on the agenda, while those wishing to experience the area's popular attractions can visit Walt Disney World® Resort and Disney's Animal Kingdom® Theme Park. Check out an event or a game at ESPN Wide World of Sports Complex, and consider making time for Old Town, a top attraction not to be missed. Jet skiing, waterskiing and power boating offer great chances to get out on the surrounding water, or you can seek out an adventure with horse riding nearby.
View more Holiday homes in OrlandoOpens in a new window
Map
kissimmee, FL

What's nearby

  • Northeast Regional Park - 3 min drive - 3.4 km
  • Walt Disney World® Resort - 11 min drive - 12.1 km
  • Disney's Animal Kingdom® Theme Park - 16 min drive - 15.1 km
  • Disney Springs™ - 20 min drive - 26.0 km
  • Magic Kingdom® Park - 21 min drive - 25.5 km

Getting around

  • Kissimmee Station - 34 min drive
  • Kissimmee, FL (ISM-Kissimmee Gateway) - 31 min drive

Restaurants

  • ‪Wawa - ‬6 min drive
  • ‪McDonald's - ‬5 min drive
  • ‪7-Eleven - ‬10 min walk
  • ‪Circle K - ‬7 min drive
  • ‪Twistee Treat Berry Town - ‬5 min drive

Frequently asked questions

Is Charming Dog Friendly Villa w/Pool, Gated Resort, Gameroom, Free wifi, Kid Themed Rooms, Contactless Check-in, Free wifi! pet-friendly?

Yes, pets are allowed at this property.

How much does it cost to stay at Charming Dog Friendly Villa w/Pool, Gated Resort, Gameroom, Free wifi, Kid Themed Rooms, Contactless Check-in, Free wifi!?

As of 25 May, 2026, prices found for a 1-night stay for 2 adults at Charming Dog Friendly Villa w/Pool, Gated Resort, Gameroom, Free wifi, Kid Themed Rooms, Contactless Check-in, Free wifi! on 24 Sept, 2026 start from S$343, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Charming Dog Friendly Villa w/Pool, Gated Resort, Gameroom, Free wifi, Kid Themed Rooms, Contactless Check-in, Free wifi!?

On-site parking is available at the property.

What time is check-in at Charming Dog Friendly Villa w/Pool, Gated Resort, Gameroom, Free wifi, Kid Themed Rooms, Contactless Check-in, Free wifi!?

Check-in begins at 4:00 PM.

What time is check-out at Charming Dog Friendly Villa w/Pool, Gated Resort, Gameroom, Free wifi, Kid Themed Rooms, Contactless Check-in, Free wifi!?

Checkout is at 10:00 AM.

Where is Charming Dog Friendly Villa w/Pool, Gated Resort, Gameroom, Free wifi, Kid Themed Rooms, Contactless Check-in, Free wifi! located?

Situated in Kissimmee, this holiday home is 2 mi (3.2 km) from Lake Davenport and 2.6 mi (4.2 km) from Four Corners FC. Northeast Regional Park and Surfari Water Park are also within 6 miles (10 km).

Reviews

7.4

Good

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. 9 out of 25 reviews
Rating 8 - Good. 5 out of 25 reviews
Rating 6 - Okay. 6 out of 25 reviews
Rating 4 - Poor. 3 out of 25 reviews
Rating 2 - Terrible. 2 out of 25 reviews

7.0/10

Cleanliness

8.8/10

Check-in

8.8/10

Communication

9.0/10

Location

8.0/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Mermaid mom

Liked: Cleanliness, check-in, communication, location, listing accuracy
The location at Windsor Westside was fabulous. Had plenty of room for everyone in the family. Everyone has something to do and yet we had our privacy very close to Disney World and other locations. The on-site waterpark was fabulous as well.
Stayed 4 nights in Mar 2026
Verified

10/10 Excellent

Ryan D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great family vacation!

The house was very nice and close to Disney/universal. We also loved the convenience of the resort pool/lazy river & restaurant. We will definitely consider booking this property again!
Stayed 6 nights in Oct 2023
Verified

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family vacation

Very nice place, clean, nice public pool & bar. House is big for a family of 12.
Stayed 5 nights in Aug 2023
Verified

8/10 Good

Matthew K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Stay

Clean and good location.
Stayed 3 nights in Nov 2023
Verified

10/10 Excellent

Heather G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Worked great for us

Worked great with 5 kids and 3 Adults we all got our own space but plenty of space to hang out together i loved the house.
Stayed 7 nights in Jun 2023
Verified

10/10 Excellent

Danielle W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Gret place!!

Overall it was a great place to stay. The only thing i didnt like is the pool gym and basketball court closes at 8:30p. Could at least stay open till 10 like most places. But the community was nice. And the place was clean an accurate on the pictures posted.
Stayed 7 nights in Jul 2023
Verified

2/10 Terrible

dana r.

Disliked: Cleanliness, check-in, communication, listing accuracy

Dirty unkept property. Beautiful location

The house was not cleaned, from the rugs to the glass table, the walls were filthy and the pool was oily with particles floating in it. Management tried to make excuses for the dirt (ie easter break) but this was a buildup of dirt. The kitchen was well maintained but limited utensils. Great location however our checkout was Monday morning and our access keys to the front gate were deactivatef on Sunday.
Stayed 6 nights in Apr 2025
Response from VrboOwner on 12 May, 2025
Thank you for sharing your feedback. We sincerely apologize that your experience did not meet expectations. Cleanliness is something we take very seriously, and we regret that we fell short during your stay. Please know that we are addressing these concerns with our team to ensure this does not happen again. We're glad to hear you enjoyed the location and found the kitchen in good condition, but we also apologize for the inconvenience with the gate access. We appreciate your comments, as they help us improve, and we hope to have the opportunity to provide you with a better experience in the future.
Verified

2/10 Terrible

Misty S.

Disliked: Cleanliness, communication, location, listing accuracy

Very Dirty House

Carpets were so nasty we were afraid to walk around without shoes on inside the house. Large stains on all the carpets. Walls were all scrapped up & had spill/splatter stains on them. Heavy dust on all baseboards. Broken stair railings. Missing blind slats. Heavy ammonia urine smell in one bedroom. Some carpets were not even vacuumed. Loose change, earrings from previous renters. I could go on & on. Do not rent this house!!!
Stayed 5 nights in Apr 2025
Verified

6/10 Okay

Amy H.

Liked: Check-in, communication, location
Disliked: Cleanliness, listing accuracy

Honest Review

I stayed here with my family of 12 for 10 days. Pros- great area, close to everything, resprt facilites were great. Bathrooms were nice but there was only 1 tub. Kitchen was nice and fully stocked. Private pool and dailybtrash service was also a plus. Those are the only nice things i have to say. Cons- I had to call the property at 4:15 after we still had not received the access codes to get in. Carpets were disgusting, look like they had never been cleaned and smelled musty. Every piece of furniture in the house was run down or broken. Beds were all uncomfortable with filthy matresses. The entire house needs to be redone all furniture needs to be replaced along with new carpets, bedding and a complete paint job. The walls were gross and most covered in stains and dirt. Would not recommend staying here if you like to be in a clean environment. We did like having a washer and dryer but The dryer took 3 or 4 cycles for anything to dry. Would definitely not recommend unless it was renovated.
Stayed 10 nights in Jul 2023
Verified

6/10 Okay

Chanie Z.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Overall the house was okay but it's dated and a lot of the furniture was on its last legs. Carpets were very dirty and needed major deep clean.
Stayed 11 nights in Mar 2026
Verified

6/10 Okay

Marina V.

Liked: Location, listing accuracy
Disliked: Check-in

Read all the emails a couple times.

Confusing check in process
Stayed 5 nights in May 2022
Verified

10/10 Excellent

Dedra A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Famcay 2022

Clean, room and great communication with host.
Stayed 6 nights in Jun 2022
Verified

4/10 Poor

Kathleen A.

Liked: Check-in, communication, location
Disliked: Cleanliness

I would not book this home again. Stayed May 11-18, 2022

The couch, chairs and carpet all need replaced. The interior of home needs painted. I had read several reviews. I had messaged prior to booking about the reviews left by others. The bad reviews others left are accurate. I was told the items had been addressed. When I got to the home and messaged about it PMC told me these are just cosmetic items and they can only do what owner approves. The PMC was responsive to messages and sent maintenance over. One of the beds had no comforter PMC said they notified housekeeping and would bring one. Over the week no comforter was brought. Kitchen is not well stocked. Beds are getting old but not the worst we have stayed in. The floor plan of the townhouse is a great one! I would book this area just not this home again.
Stayed 7 nights in May 2022
Verified

6/10 Okay

Rachael A.

Liked: Check-in

Cheer/Disney Trip

This property was centrally located to the parks. The carpet needs updating as does the beds and furniture. It was well used. Patio table and lounge chairs were great to have. Has a good selection of kitchen utensils. It did it’s job but could use upgrades
Stayed 6 nights in Apr 2022
Verified

8/10 Good

Jessica G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Nice condo

Condo is very close to the pool. Plenary of space for our party of 7.
Stayed 4 nights in Mar 2022
Verified

6/10 Okay

Iva N.

Liked: Communication, location

Beautiful NEGLECTED Property

Let Me First Say That The Community/Property Itself Is BEAUTIFUL. The Resort Is AMAZING, Has Everything You Need Conveniently Located Just Over 30 Minutes Away From Theme Parks. The Inground Pool Was A Absolute Pleasure. The Home Was Nicely Decorated, 5 Bedrooms Were Comfortable And Spacious, The 4.5 Bathrooms A True Luxury........No One Had To Wait For A Bathroom EVER And There Was 9 Of Us!!!! The 2nd Floor Family Room Was A Bonus. AGAIN A Very Nice Unit. I However Believe That This Unit Has Been NEGLECTED By Its Properties Management (May Be Due To The 8 Months COVID Had Us All Shut Down......Maybe Not. IDK). The Upholstered Furniture And Carpets Need A GOOD DEEP CLEANING. The CookWare Needs To Be Upgraded, The Remotes To All Of The Television's Need BATTERIES And Designated ROOM TITLE'S On Them. There Needs To Be ADDITIONAL BEDDING Such As Extra Blankets, Pillows And Sheets. And The WIFI Either Needs To Be STRONGER Or They Need To Add Internet Service, We Lost Service As Soon As We Reached The Property, And It Was Very Choppy/Unstable While Inside The Unit. They Do Have A LOCAL LANDLINE PHONE Which Was A Good Idea Being The WiFi Is So Weak. I Would Truly Book This Unit Again, As Well As Recommend To Other Families Visiting The Orlando/Kissimmee Area. I Would However CONTACT PROPERTY MANAGEMENT IN ADVANCE AND MAKE MY PREFERENCES/REQUEST KNOWN. Hope This Review Is Helpful Iva 🤷🏾‍♀️
Stayed 4 nights in Aug 2021
Verified

10/10 Excellent

edward c.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Very nice seamless check in

Felt like home away from home looking forward to renting soon
Stayed 6 nights in Aug 2021
Verified

4/10 Poor

Alix F.

Liked: Check-in, location
Disliked: Cleanliness, listing accuracy

Would not stay again.

The location was ok and the clubhouse and pool was very nice. We came with our family and was not aware there was only designated parking for one car. There is side road parking by it is a first come, first serve. We were there during a busy time so parking was scarce. The listing describe the home correctly, but what they forgot to mention was that all the furniture was worn down, dirty and broken. The place was past due for a deep clean. I mean the baseboards had dust an inch thick on them. They could not have been touch in months. Aside from the disappointment of how unkept and unclean the home was we were also disappointed to see the bed linens were lacking to say the least. I would not recommend the property to anyone until they conducted a DEEP clean and replaced 80% of the furniture.
Stayed 7 nights in Jul 2021
Verified

4/10 Poor

Fluvia M.

Liked: Check-in, communication
Disliked: Cleanliness

A Dirty and Broken Disappointment

This property was dirty and outdated and it really was a big disappointment. We were so excited to finally get to the house after a long day of travel but as soon as we walked in we could tell this was not going to be a good place. The home was disgustingly dirty throughout. The kitchen counters had frosting on them, they were sticky and dirty. The utensils were dirty and had dried up food on them. The floors looked like someone had quickly swept and did not bother to mop. The carpet and couches needed a desperate cleaning (they were turning black in some spots). The vents throughout the house were covered in dust, like they had never been cleaned. The shower curtain upstairs had stains on it and was moldy/smelly. The sheets in one of the main bedrooms upstairs had a blood stain on it!! Then we noticed that a lot of the things in the house were broken/missing. To begin with, the couches/chairs in the living room were ripped up and the cushions were so worn out it felt like you were sliding off of them.One of the knives was broken and the other ones were not sharp at all (could barely cut through fruit and veggies). The ice maker was empty and not working. The dining room chairs all had wobbly legs -- we sat on one on the first day and some screws came out of the leg. Upstairs, one of the bathroom sinks was clogged and a member of our family actually had to unclog it themselves. The trundle in the minion room is not put together, the pieces of wood are under the bed but it looks like no one took the time to actually build it. The downstairs bedroom was missing the comforter in the picture, one of the upstairs masters was missing some pillows and the fitted sheets (we had to go buy pillows). The pool in the back was the only good part that we actually enjoyed. The resort itself was nice, but the community pool is a bit small for the amount of people that were there. And most of the amenities were closed like the hot tub, gym, kids indoor area/arcade. We did not bother calling management because we were so tired and just wanted to get on with our vacations. The pictures in this listing are deceiving -- im sure it was a beautiful home way back then but it shows that they have not taken good care of it. I do NOT recommend this property. We took lots of pictures as well for our own records.
Stayed 7 nights in Jun 2021
Verified

8/10 Good

angel A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Was great for our family vacation

Everything was as stated. The house was clean, pool was clean. The community pool, lazy river area was crowded the entire stay. We just enjoyed our private pool. Would definitely book again.
Stayed 7 nights in Jun 2021
Verified

8/10 Good

Amellia S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Awesome stay

Over all it was very nice and I will rent again
Stayed 5 nights in May 2021
Verified

8/10 Good

chaya r.

Liked: Check-in, communication, location, listing accuracy

Nice vacation

Place was nice,needed some better cleaning called them up and the came quickly,.
Stayed 12 nights in Mar 2021
Verified

10/10 Excellent

Kaitlyn C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

AMAZING EXPERIENCE! VERY NICE AND SUPER CLEAN!

Everything was wonderful. Beautiful home, spacious, and very clean. The pool was nice and we enjoyed it. The pictures doesn't do the house any justice. Check in was a breeze, they send you step by step instructions. Plenty of room for a family. Plenty of appliances and utensils, and they are top notch. We really love it, we expect come again next year. Thanks for this amazing experience!
Stayed 1 night in Sep 2020
Response from VrboOwner on 6 Sept, 2023
Hi Kaitlyn, Thank you so much for staying with us and your feedback on our home. We try to make our vacation homes magical for our guests. We hope that you will stay with us again!
Verified

6/10 Okay

Whitley R.

Liked: Check-in, communication, location, listing accuracy

Nice holiday stay

The property was well managed and a nice stay for the holidays. The only problem we encountered was the toilet in one of the bedrooms not being able to flush and the carpet throughout the apartment needed to be shampooed. Overall th stay was a good one.
Stayed 5 nights in Dec 2019
Verified

10/10 Excellent

Cheryl S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 8 nights in Apr 2024
Response from VrboOwner on 12 May, 2025
Thank you so much for your wonderful 5-star review! It was a pleasure hosting you, and we hope to welcome you back again soon for another fantastic stay!

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