
Villa vacation rentals in Winter Garden
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Top-rated villa rentals in Winter Garden
Guests agree: these villas are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Winter Garden villa rentals
Private villa rentals

Luxury Wellness Villa - Private Spa & Pool
We had such a lovely stay! The place was just as pictured. Plenty of space for the 9 of us to lounge around the house and hangout by the pool. We will definitely be back!

Graystone Villa, 3 bedrooms with private pool
Can’t say enough about Nicola and her property. Our vacation started out rocky at a not so stellar condo. Thankfully we found her property and she was able to accommodate my family the very next day. The house is just as described, very spacious and clean! The location was perfect and close to many restaurants and shopping. Nicola was quick to respond to any of our needs. I will definitely be booking here if we are ever in the area. THANK YOU for being amazing!!

Luxury 9Beds Villas With Pool Spa In Solara
This was our second time staying at Chuck’s place. The resort amenities are great and our family utilized the splash pad, pool, gym, basketball courts and restaurant. The house is great and accommodates our family of 14 perfectly. We had a great stay!

Private Villa with Pool near Disney
It was a great place to stay. We would not hesitate to stay here again if we are in the area.

33 Disney Villa ★ GameRoom ★ Movie Theater ★ Pool
Had a great stay with our family. Lots to do in/around the area. Kids enjoyed the themed rooms as well as the pool. Cal was quick to get us setup with everything we needed after a last minute booking. Publix/target/walmart were all within a few min drive of the house. There was a bit of noise from one of the neighbouring houses one night but it wasn’t loud enough to disturb the children who were sleeping. Would definitely stay again!

Seasons Retreat, 5 Bed, 4 Bath, Private Pool Villa
Great home and very comfortable! We enjoyed our stay! Mr. George is a great host and very accommodating.

Wonderful Villa at Storey lake Resort 5 Rooms Pool
Adanel host my family of 15 and I , and one 5 pound potty trained Yokie. The living space and kitchen was what we needed. The kids enjoyed the games. He allowed early check in which was a plus. When we first walked in, it smelled very refreshing. The only downside was the people next door played music all night,but other than that we had a great time! I will stay again. communication was a great.

7BR Villa • Spa&Pool • 9 miles to WDW • Waterpark
We had a great stay with our two young kids. My son is non-verbal with ASD. We appreciated the kid’s plates/bowls that kept food from touching (iykyk!) The pool safety fence and locks on the doors were great. The bathroom door that leads to the pool didn’t have a higher up lock, but we just made sure an adult slept in that bedroom. Plenty of pool towels. They loved the treehouse bunk and toys to play with. The blackout curtains kept light out of the bedrooms so they didn’t wake too early. The hosts were great and always responsive. We had a fun stay!
Luxury villa rentals

Prestige 5: Lux Windsor West, S Fc Pool, Lake View
We’ve just returned from a large family holiday! With family flying in from Boston and Las Vegas, Orlando was a central location for us to kick back & enjoy each other’s company. Plenty of space for our 13 person group! The pool and hot tub were perfect, large kitchen where we cooked big meals & fun game space on the 2nd floor! We enjoyed a day at the club house & pool - a quick walk from the home we stayed in. Loved having a lake behind us, making it feel peaceful and private. Communication before, during & after was easy and prompt.

Blue Paradise-15 Bdrms, Sleeps 32-Theater, GameRm
We were a group of 16 golfers playing 5 courses nearby. The size of the house with enough bedrooms to give everyone a private room was the initial attraction. It was soon evident that Parmi was a great communicator with very fast feedback and accurate info. The house was clean and very functional with our highlight being the steak dinner on the last night. We bought 16 one pound steaks and grilled them in the outdoor grill - our chef did a perfect job. With two large dining tables, the meals were very comfortable. These tables later handled a two table poker tournament. The hot and bubbly spa soothed our aching bones after golf. All in all, a PERFECT house for our needs. Thanx !!!!

Close to Parks, 9Bd, Karaoke, Pool, Spa, Theater
Absolutely loved our stay in this peaceful oasis! Close to grocery shopping and theme parks but the real treasures are all the activities to do within the house. Endless fun in the karaoke room and movie theater room!

*Private Resort Oasis: Golf-Front, Pool/Spa/Cinema
Really enjoyed our time at this lovely home. We were spoiled with a few pleasant surprises to welcome us and make our children feel at home too which was really nice. Great games room and cinema area, direct sunlight (if you want it) from lots of different outdoor areas within the boundary, very spacious throughout. Fantastically equipped kitchen! Bedrooms were very suitable for our needs and decorated beautifully. Beds clean and comfy. Very peaceful at night time. I can’t really fault it in any way. Would certainly recommend staying in this place.

New Luxury 9-BR Villa w. Pool/SPA and Amazing View
George was a great host! We loved the place! It was very clean and comfortable. There were great entertainment amenities. It was a fantastic spot for our family vacation!

Luxury Themed Villa 9 BR | Close to Disney
I really enjoyed my stay at Jennifer's place. She was an amazing host and the house was just as pictured. Check in was easy and everything was nice and clean. It was the perfect place for my family of 10+ and our kids enjoyed every minute of our stay. She has everything you need for children; high chairs, crib, playpens, life vests, toys, etc. Check out was just as easy as check in! I have no complaints. Thank you so much Jennifer!

Jas Vacation Home 314
Beautiful home ! Stunning neighborhood! Everything was just as pictured. Communication with the owner was easy and he was very quick to respond.

7BR Villa SouthFacing on StarLake, 2 MLs to Disney
Beautiful for big families
Villa rentals with a pool

5bedroom,pool,18min to Disney, Kissimmee davenport
Very beautiful home and Miguel is very accommodating and responsive. Would definitely stay at his home again.

Nr Disney Villa with private pool and cinema room
We had very few issues at Paula”s but when we did, it was very comforting to have a local maintenance contact we could call who were always responsive and helpful with local activities suggestions. If the opportunity comes again, we would stay at Paula”s.

4 Bedroom Villa - with Pool - Near Disney & More
This house is very comfortable! We have 5 kids and they all enjoyed using the pool and pool table. I recommend highly paying for the pool heat; more so for the evening swim. We still used the pool daily, but I will definitely ask to have it heated before we come next time. We felt very safe in this location. Clean, family-friendly surroundings. Easily accessible to all Disney activities! We also spent time in Clearwater and on the Atlantic coast. About 1.5 hours to Gulf or Ocean from her place. We will definitely be back!!❤️

Luxury Villa Pool/Spa 2 Masters, Highlands Reserve
10/10 would recommend this vacation home! Beautiful, spacious home with an awesome outdoor living area. We thoroughly enjoyed the pool and spa as well as the outdoor dining/fire table area that comfortably seated our entire family. The kids really liked the game room. The beds and pillows throughout the home were very comfortable. Dawn was a great host and she has fully stocked the house with all the supplies you could ever need. Plenty of extra towels, blankets, pillows, kitchen items, etc. She even keeps it stocked with a few convenient snacks as well as essentials like spices, coffee, tea, dishwasher tabs, dish liquid, cleaning supplies, etc. There are even little baskets in the bathrooms filled with things you may have forgotten such as toothbrushes, toothpaste, Q-tips, etc. Since we were there around Christmas time, there was a cute little Christmas tree, stockings and a couple of other decorations around the house. She really has thought of everything!

4-bed villa w/ beautiful pool 15 mins from Disney!
It felt right at home from the moment we arrived to the minute we left. Every thing was clean, comfortable and overall a wonderful experience. We would definitely stay there again. Thank you for your hospitality in letting our family stay in your beautiful home. Brittni

Home in Davenport FL, near Disney
The house was spacious in a convenient location and exactly what we were looking for.

Sharedale Lakeside Villa
Spacious house within 25 minutes of the Disney Parks. Liliana was very responsive to all emails and was a pleasure to deal with.

4 Bedroom Villa with Private Pool Near Disney!
We really enjoyed our stay with our daughter and grandchildren. The house had everything we needed for the week. We had no complaints. Location was really close to all parks we visited as well as restaurants. We also felt comfortable to take a nice long evening walk with the babies, the neighborhood was very friendly.
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- Universal Studios Florida
- Orange County Convention Center
- Universal's Volcano Bay
- Old Town Kissimmee
- Reunion Resort Golf Courses - Palmer & Watson
- Discovery Cove
- Disney's Animal Kingdom Theme Park
- Disney Springs
- SeaWorld Orlando
- ESPN Wide World of Sports
- Universal Orlando Resort
- Reunion West
- Amway Center
- Kissimmee Lakefront Park
- ChampionsGate Golf Club
- Epcot
- Disney's Hollywood Studios
- Universal's Islands of Adventure
- Blue Spring State Park
- Magic Kingdom Park
- Aquatica
- ICON Park
- Island H2O Water Park
- Harry Potter and the Escape from Gringotts™
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