Search Vacation Homes in Winter Park

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Compare 4451 Vacation Homes in Winter Park with updated reviews, rates, and availability.

Pool
6BR Home, Prime Location
10.0 out of 10, Exceptional, (3)
"The house so Beautiful and clean. We enjoyed the pool at the house and the waterpark on the premises. It is a great house for a gathering of family and friends. I do suggest updating the mattresses. I couldn’t have asked for a better place for our large group. The check in process was easy and all my emails Were answered promptly. Thank you for your hospitality."
6BR Home, Prime Location
Pool | Outdoor pool, a heated pool
Walking to Water Park 9Br5Ba Pool, Theater, Office, themed rooms
10.0 out of 10, Exceptional, (29)
"This property was perfect for our large group kitchen big enough to fit several people in it. Game rooms and playroom. Perfect for the kids spent many hours in the swimming pool very easy drive to Disney would rent this property again."
Walking to Water Park 9Br5Ba Pool, Theater, Office, themed rooms
Private kitchen
House with pool in Kissimmee and Resort
10.0 out of 10, Exceptional, (6)
"Plenty of room, nice location and very clean"
The price is $160
$562 total
includes taxes & fees
May 17 - May 18
House with pool in Kissimmee and Resort
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Pool
7BR| Near Disney| Verandas Resort|BBQ & Game Room
10.0 out of 10, Exceptional, (4)
"It was a great place—very convenient. The description of bedrooms and bathrooms is accurate. The size is not correct, which isn't a huge deal. The size said it was 11,000 sqft. We thought it was a typo anyway. Also, the HVAC system was difficult. First, they didn't want it below 72, and then the system never came out of temporary, so we set the AC, left, and then when we returned that evening, the house was 78, which is too warm for us. The communication was great. We'd stay again."
7BR| Near Disney| Verandas Resort|BBQ & Game Room
View from property
*8bd Themed-Theater-Arcade-Prvt Pool/Spa-Disney!
10.0 out of 10, Exceptional, (20)
"First time had the whole family together in over 2 years. Grandpa, grandma, the parents and grandkids. We were alarger group. But everything went well. The checkin and communication with owners. The wetup, rooms and accommodations were spot on. Grill, pool and all of the clubhouse amenities with kayaks and lazy river etc etc etc I would highly recommend!"
The price is $210
$619 total
includes taxes & fees
May 19 - May 20
*8bd Themed-Theater-Arcade-Prvt Pool/Spa-Disney!
Fridge, microwave, oven, stovetop
Close to Disney! NO Extra Fees! Gated! Clean & Comfy! Family Friendly!
10.0 out of 10, Exceptional, (197)
"This property was extremely awesone from the gate to the bathroom. The gate attendants was very polite and professional. The pool, splash pad, the hot pool, the Tiki Bar, the welcome center was amazing. Tjetemperature"
Close to Disney! NO Extra Fees! Gated! Clean & Comfy! Family Friendly!
A heated pool
Mickey's Enchanted Retreat: Poolside Cinema, Free Resort, Family Haven
10.0 out of 10, Exceptional, (12)
"We visit Disney fairly often and this property was our favourite place we have rented so far. The home is exactly as shown in photos and is situated in a great location for access to theme parks, shopping, and restaurants. We travelled with two young children and enjoyed visiting the water park at the clubhouse during some downtime as opposed to getting water park Disney pass, they enjoyed visiting the “splash park and Mickey Mouse clubhouse” as much as they enjoyed the theme parks! Access to...
Mickey's Enchanted Retreat: Poolside Cinema, Free Resort, Family Haven
Miscellaneous
Stylish Home w/ Private Pool, 10 Min. From Disney!
4.0 star property
10.0 out of 10, Exceptional, (3)
"I loved this stay! It was a great value and the property owner had very good communication throughout the stay!"
Stylish Home w/ Private Pool, 10 Min. From Disney!
Flat-screen TV, foosball
Beautiful 6 Bed in Sonoma! Kid Themed Rooms, Game Room w/Pool Table, Theater Room! All bedrooms have a private bathroom!
10.0 out of 10, Exceptional, (2)
"Talk about space, cleanliness and location. This property has it all. Only 10 to 15 minutes from the parks. This home is huge, able to host a large family. My entire family was very happy with the home specially the fact that each room had its own full bathroom. The theater room is awesome and the garage is full of entertainment. The pool is an added bonus. This property was very clean, easy to access and well equipped. The only issue, is the driveway, it can only fit 2 vehicles. The driveway...
Beautiful 6 Bed in Sonoma! Kid Themed Rooms, Game Room w/Pool Table, Theater Room! All bedrooms have a private bathroom!
Pool
Quiet Oasis in Lovely Neighborhood
9.8 out of 10, Exceptional, (94)
"Nice room nice neighborhood not far from Disney"
The price is $90
$200 total
includes taxes & fees
May 15 - May 16
Quiet Oasis in Lovely Neighborhood
A heated pool
Drive-In Theater, Forest Bedroom, Huge Pirate Ship, Lake Views, Pool Table, Grill: Movie Magic
9.8 out of 10, Exceptional, (12)
"Amazing place , very responsive Host Everything was perfect the place is beautiful!"
Drive-In Theater, Forest Bedroom, Huge Pirate Ship, Lake Views, Pool Table, Grill: Movie Magic
Outdoor pool, a heated pool
Near Universal, Disney & OCC Vista Cay town home
9.8 out of 10, Exceptional, (17)
"Very nice place to stay near the parks."
Near Universal, Disney & OCC Vista Cay town home
A heated pool
Beautiful Townhome in Storey Lake - at Disney's Gates
9.8 out of 10, Exceptional, (40)
"Overall this was a nice property. It fit the needs of my family very well. It was decorated nice and offered plenty of space. Our complaints though, the mattresses have a cover that is so noisy when you move, and the beds were not comfortable at all. They also didn’t leave us enough toilet paper so we had to go buy our own. Not a big deal, just annoying. Having said that, we would stay again."
Beautiful Townhome in Storey Lake - at Disney's Gates
Fridge, microwave, oven, stovetop
Casa Winter Park
9.8 out of 10, Exceptional, (90)
"We stayed at Casa Winter House for the weekend and had a wonderful time. The house is fully equipped to have a very comfortable stay. There is plenty of parking space and the backyard is huge and perfect for entertaining the family. The host provided all necessary information, we didn’t have to call at all. Absolutely recommend!"
Casa Winter Park
Outdoor pool, open 6:00 AM to 11:00 PM, pool umbrellas, sun loungers
Marriott's Sabal Palms
4.0 star property
9.6 out of 10, Exceptional, (171)
"Great spot! Easy to get in and out. Free parking and no resort fees!"
The price is $231
$260 total
includes taxes & fees
Jun 4 - Jun 5
Marriott's Sabal Palms
Outdoor pool, a heated pool
Beautiful Remodeled 4 Bedroom House
9.6 out of 10, Exceptional, (9)
"If you're in Orlando for vacation this house is basically 20-30 minutes or less to everything. Disney, Universal, Seaworld, and all of the other activities. The level of convenience was huge. There is plenty of space and the backyard is great. The pool is wonderful!"
Beautiful Remodeled 4 Bedroom House
A heated pool
Newly remodeled Town Home 7 in 2022, 1200 Sq ft, SeaWorld Fireworks View
9.6 out of 10, Exceptional, (39)
"Christopher was very communicative. Townhouse is well stocked, lots of towels, plenty of toilet tissue, kitchen essentials. Parking in front of townhouse if you get to it first, otherwise I had to park on the grass area which was fine. Checking in was a breeze, and staff was very nice. Overall great experience. I would stay again when in the area. We were there for a Volleyball tournament and location was very close to the Orlando Convention Center. About 11 mins away. Publix grocery store is...
Newly remodeled Town Home 7 in 2022, 1200 Sq ft, SeaWorld Fireworks View
TV, offices
4BR, 3BA corner house overlooking the lake
9.6 out of 10, Exceptional, (36)
"We loved this property. It was a perfect price point for our week long visit. It had everything we needed and more. We made many new family memories here. We had no issues connecting with a live person when we were in need of something or had a question. We loved it! Yahtzee is now a new family favorite and we will remeber playing it together for years to come!!"
4BR, 3BA corner house overlooking the lake
Water park
Splendid 5Bd Close to Disney at Storey Lake 4251
5.0 star property
9.4 out of 10, Exceptional, (3)
"Excellent property . Really clean and lots of space. Really close to Disney and plenty of restaurants a short drive away. My only complaint is the communication for check in. I got message and phone call 30 mins before check in saying if I don't fill out check in form my booking would be cancelled. This really wasn't ideal as I was driving. After I did it I received so many text and emails to help with my stay. I was getting them from several different numbers. Then 3 hrs after checking out. 4...
Splendid 5Bd Close to Disney at Storey Lake 4251
A heated pool
Free waterpark! Fantasy World Resort Minutes from Disney, Universal & Parks!!
9.4 out of 10, Exceptional, (163)
"We enjoyed our stay . The house was very clean. The beds were extremely comfortable. Our favorite thing was how close we were to the swimming area . The resort is perfect for kids . Over all we enjoyed our trip and will definitely book again if we ever decide to go back to Orlando ."
Free waterpark! Fantasy World Resort Minutes from Disney, Universal & Parks!!
Don't see what you're looking for?
See all available properties in Winter Park
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.

Other property types in Winter Park

Meeting facility
Hyatt Regency Orlando International Airport
4.0 star property
9.4 out of 10, Exceptional, (4810)
"Very convenient. We stayed before our Disney Cruise. "
The price is $199
$224 total
includes taxes & fees
May 29 - May 30
Hyatt Regency Orlando International Airport
Exterior
Holiday Inn Resort Orlando - Lake Buena Vista, an IHG Hotel
3.5 star property
8.6 out of 10, Excellent, (3117)
"Excellent receptionist… will come back for sure ..!!!!"
The price is $82
$122 total
includes taxes & fees
Jun 9 - Jun 10
Holiday Inn Resort Orlando - Lake Buena Vista, an IHG Hotel
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, (7178)
"Fabulous place for a family holiday. Would definitely recommend and would love to return here. Apartments spacious and well-equipped. Reception desk very helpful. Good parking. Bus transfer to theme parks. Lovely pool area. Furnishings need a bit of updating but small thing compared with all the positives of this place. Why stay in a hotel room when you can have all the space these apartments provide "
The price is $156
$202 total
includes taxes & fees
May 16 - May 17
Lake Buena Vista Resort Village & Spa
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.

Winter Park Vacation Homes information

Number of reviews
869
Accommodation
4451 Vacation Homes
Lowest Price
$90
Highest Price
$231

Recent reviews of Winter Park hotels
Expedia verified reviews