Search Winter Park Villa Rentals from CA $173

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Browse Select Winter Park Villas

Modern Luxury Villa with Everything
Pool

Modern Luxury Villa with Everything

9.8 out of 10, Exceptional, (356)
"Property was as advertised. Very clean and comfortable for our large family! The kids loved the pool and game room. The beds were very comfortable. As others have mentioned there are minor “ lived in” things about the house, this actually made me more comfortable because we all know littles can be hard on stuff. The adults were able to relax. I would 100 recommend!"
Modern Luxury Villa with Everything
Lakeview Luxury Villa with Everything
Pool

Lakeview Luxury Villa with Everything

9.8 out of 10, Exceptional, (306)
"We absolutely love staying in the Luxury homes offered by David (DHV)! This was our second time staying and it is truly a luxury vacation. You will not be disappointed if you stay in one of his homes."
Lakeview Luxury Villa with Everything
Villa in Kissimmee next to Disney!
Pool

Villa in Kissimmee next to Disney!

9.0 out of 10, Wonderful, (13)
"My family of 8 stayed here with our 2 dogs right after Hurricane Milton. I didn't have high expectations as a hurricane just hit, but the home was clean and ready for us. My kids were very excited about the home, especially the large pool and the "smart" refrigerator where they could watch YouTube and have dance parties together in the kitchen. The games in the garage were also a big hit with the kids as they loved playing pool and darts especially. The outside was my favorite part with the...
Villa in Kissimmee next to Disney!
Ultimate Lakeview Villa with Everything!
Pool

Ultimate Lakeview Villa with Everything!

9.4 out of 10, Exceptional, (89)
"Perfect house for large group of people. It had everything that we needed. "
Ultimate Lakeview Villa with Everything!
9 BR/5 BA Resort Villa in Storey Lake Closed to Disney
Outdoor pool

9 BR/5 BA Resort Villa in Storey Lake Closed to Disney

10.0 out of 10, Exceptional, (6)
"The property was exactly as promised "
9 BR/5 BA Resort Villa in Storey Lake Closed to Disney
Ultimate Lakeview Villa with Everything!
Pool

Ultimate Lakeview Villa with Everything!

9.8 out of 10, Exceptional, (325)
"The house is exactly as listed. We stayed in this house to explore the parks and locations in Orlando. We had to leave this home to go to another house for the remainder of our stay in Florida so we were closer to the wedding venue over the weekend. Our kids were so upset to leave this house. I think some of the adults were equally upset, too. Between the heated pool, hottub, the game room (the kids have a newfound love of pool now), and the theatre room, they had zero desire to leave! We had...
Ultimate Lakeview Villa with Everything!
Lakeview Luxury Villa with Everything!
Pool

Lakeview Luxury Villa with Everything!

9.6 out of 10, Exceptional, (79)
"The home was just as advertised. We enjoyed all of it. The home could use some minor tweaks, such as some serving dishes (we had Thanksgiving here!) and the theatre seats and game room accessories were in need of replacement, like the pool table cue sticks and triangle, but this was a clean, beautiful home that was perfect for our large family and we would definitely stay here again!"
Lakeview Luxury Villa with Everything!
Lakeview Luxury Villa in Storey Lake
Pool

Lakeview Luxury Villa in Storey Lake

10.0 out of 10, Exceptional, (10)
"Thank you for the amazing stay! Easy Uber rides to anywhere you want to go. The house great, modern sleek decor and kids rooms are decorated perfectly! The pool and hot tub were amazing at the end of the long day. Use we go shop for delivery of groceries!!!! Kind souls who do a fabulous job of shopping for you and they will stock your kitchen for you! The home is on the end and corner so you have privacy, but also a great view on the lake to watch wildlife and sip morning coffee: Thank you...
Lakeview Luxury Villa in Storey Lake
🌟 Luxury 12 BR/11.5 BA Villa / Sleep 26
Outdoor pool, a heated pool

🌟 Luxury 12 BR/11.5 BA Villa / Sleep 26

🌟 Luxury 12 BR/11.5 BA Villa / Sleep 26
Vistana1-bedroom villa a few minutes Disney
Pool

Vistana1-bedroom villa a few minutes Disney

2.0 star property
Vistana1-bedroom villa a few minutes Disney
Modern Luxury Villa with Everything
Pool

Modern Luxury Villa with Everything

9.6 out of 10, Exceptional, (204)
"I was impressed overall, but it would be helpful to have light switches labeled, as we inadvertently turned off the theater room projector when trying to shut off hall lights. Also It was not clear to me that you had to buy the pool heat before, but it was easily rectified when we arrived. Also you do have to rent a grill, it does not come automatically. Overall a nice experience, and plenty of room and fun for the kids. Nice perk is the community pool, lazy river and water slide access!"
Modern Luxury Villa with Everything
Ask about Early Check in! Master Bedroom on Main Floor. 10 Min Away from Disney
A heated pool

Ask about Early Check in! Master Bedroom on Main Floor. 10 Min Away from Disney

9.6 out of 10, Exceptional, (128)
"Short story: Great stay. Will do so again. Property was very clean. Plenty of room and living areas. Owner is very polite and accommodating. Communication was on point as well. There were no known issues. Thank you very much. "
Ask about Early Check in! Master Bedroom on Main Floor. 10 Min Away from Disney
Unbeatable Location: Your Dream Villa Next to SeaWorld
Microwave, oven, stovetop, dishwasher

Unbeatable Location: Your Dream Villa Next to SeaWorld

9.4 out of 10, Exceptional, (50)
"Check in was easy. The place was as pictured. It had most everything that was needed in the kitchen. The water pressure in the shower/bathtub was low. The beds would be very comfortable to people below 225 pounds. They felt like we were sleeping on a mattress filled with jello jigglers... lol The owner was prompt in answering when needed."
Unbeatable Location: Your Dream Villa Next to SeaWorld
***10% Discount for all 1st responders*** FREE EARLY CGECK IN WHEN AVAILABLE!
Exterior

***10% Discount for all 1st responders*** FREE EARLY CGECK IN WHEN AVAILABLE!

9.8 out of 10, Exceptional, (94)
"Excellent location, the house is full equipted, we made turkey for Thanksgiving even!. Tons of amenites to use, parking space. The host was super responsive, always checking and answering our questions. We had a great time! Thanks!"
***10% Discount for all 1st responders*** FREE EARLY CGECK IN WHEN AVAILABLE!
Lakeview Luxury Villa with Everything
Pool

Lakeview Luxury Villa with Everything

10.0 out of 10, Exceptional, (63)
"Loved the house, very spacious and great location."
Lakeview Luxury Villa with Everything
Arcade/Ping Pong/Private Pool and Spa/Onsite Cafe/Bar/Themed
Pool

Arcade/Ping Pong/Private Pool and Spa/Onsite Cafe/Bar/Themed

10.0 out of 10, Exceptional, (4)
"My family and I loved our stay. The house was super clean and spacious. The layout was great! Easy travel to Disney. One of my favorite VRBO rentals!!"
Arcade/Ping Pong/Private Pool and Spa/Onsite Cafe/Bar/Themed
Walk to Lake: Stunning Central Florida Home!
Outdoor pool

Walk to Lake: Stunning Central Florida Home!

10.0 out of 10, Exceptional, (38)
"The home is super nice and set up for a family to enjoy. Pool, fire pit, games and grill were great. Beds were comfy. And the host was super attentive of our needs. The small downtown city was a 3 minute drive and had a farmers market and cute little shops. And the rolled ice cream shop was a must! "
Walk to Lake: Stunning Central Florida Home!
Disney Area Boho Villa
Fridge, microwave, oven, stovetop

Disney Area Boho Villa

10.0 out of 10, Exceptional, (11)
"The host was very quick to respond. The place was very clean. Had pool floats music. Everything we wanted for a quick Weekend getaway! "
Disney Area Boho Villa
Lakefront Villa at a Prime Location
Beach

Lakefront Villa at a Prime Location

9.2 out of 10, Wonderful, (51)
"the place was excellent for a stay with family. It's clean, safe, and very close to Orlando's famous attractions. I definitely recommend it. "
The price is CA $173
CA $365 total
includes taxes & fees
Jan 19 - Jan 20
Lakefront Villa at a Prime Location
Amazing resort home near disney and other parks
Outdoor pool, a heated pool

Amazing resort home near disney and other parks

10.0 out of 10, Exceptional, (27)
"We absolutely loved our stay. The house was immaculate and fit our family's needs. The location was absolutely PERFECT and less than 15 minutes from all Disney attractions. Our host was very gracious and courteous and very attentive to our needs. I would definitely recommend this houses"
Amazing resort home near disney and other parks
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Winter Park

The View Studio Suites and Event Venue
Property entrance

The View Studio Suites and Event Venue

3.5 star property
8.4 out of 10, Very good, (688)
"Very comfortable property"
The price is CA $98
CA $111 total
includes taxes & fees
Jan 6 - Jan 7
The View Studio Suites and Event Venue
Lake Buena Vista Resort Village & Spa
2 outdoor pools, a heated pool, open 8:00 AM to 10:00 PM, pool umbrellas

Lake Buena Vista Resort Village & Spa

4.0 star property
8.4 out of 10, Very good, (8242)
"The AC stopped working for 2 days before fixed. Musty smell in the hallway. Parking is an issue."
The price is CA $264
CA $340 total
includes taxes & fees
Jan 6 - Jan 7
Lake Buena Vista Resort Village & Spa
Floridays Resort Orlando
2 outdoor pools, a heated pool, open 7:00 AM to 11:00 PM, pool umbrellas

Floridays Resort Orlando

3.5 star property
8.6 out of 10, Excellent, (11142)
"This property is near all the parks. They have a pool and a store for quick food and a restaurant. The staff is very accommodating. "
The price is CA $220
CA $296 total
includes taxes & fees
Jan 16 - Jan 17
Floridays Resort Orlando
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

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How can I find cheap villas in Winter Park?
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What is there to do near my villa in Winter Park?
Whatever your tastes or interests, Winter Park has plenty of things to keep you busy. Albin Polasek Museum and Sculpture Gardens, Morse Museum of American Art and Winter Park History Museum are on many travelers’ schedules. Don’t forget about Hannibal Square Heritage Center, Rollins Museum of Art and Winter Park Playhouse either. With Expedia’s hotel deals in Winter Park, you’ll be able to see even more fantastic attractions like these with the money you save.