Winter Park Holiday House Rentals from AU$206: Search Holiday Homes

A two-story house with a balcony, surrounded by lush greenery and trees.

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Our top choices for Winter Park holiday homes

A modern living room with a ceiling fan, a flat-screen TV, and a dining area with a white table and chairs.

1. The Canopy on Periwinkle- A Home Away From Home

Goldenrod

Breasia J.

includes taxes & fees

27 Sept - 28 Sept

A modern kitchen with stainless steel appliances, a grey sofa, and a dining area with a floral rug.

2. Charming home @wp. Patio +Gazebo. close to highwys

Fairview Shores

Vicki V.

includes taxes & fees

28 Sept - 29 Sept

A modern kitchen with white cabinets, a wooden dining table set with white plates and a knife, and a potted plant.

3. Cozy home 5min to Park Ave and Downtown Orlando

Fairview Shores

includes taxes & fees

28 Sept - 29 Sept

A modern kitchen with a marble countertop, built-in appliances, and a dining area with a green sofa.

4. Funky Remodeled Otown Bungalow Sleeps 8

Fairview Shores

Julia K.

includes taxes & fees

6 Oct - 7 Oct

A modern kitchen with white cabinets, a stainless steel refrigerator, and a glass dining table with chairs.

5. Spacious 5-bedroom house in gorgeous Winter Park

Winter Park

Hannah F.

includes taxes & fees

27 Sept - 28 Sept

A modern kitchen with dark wooden cabinets, a stainless steel refrigerator, a microwave, and an oven.

6. Mills House @WP. Sleeps 11 Renovated. Queen beds

Fairview Shores

Larry S.

includes taxes & fees

28 Sept - 29 Sept

7. Cute 5-bedroom house in peaceful Winter Park

Winter Park

Mary Ellen R.

includes taxes & fees

27 Sept - 28 Sept

A modern kitchen with dark cabinetry, stainless steel appliances, and a tiled backsplash.

8. Luxury Designer Home • Disney, Universal & Downtown

College Park

includes taxes & fees

28 Sept - 29 Sept

9. Spacious 5-bedroom house in welcoming Winter Park

Winter Park

includes taxes & fees

27 Sept - 28 Sept

10. Cute 5-bedroom,6bed house in superb Winter Park.

Winter Park

"We checked in late and were surprised to find half eaten food in the fridge and freezer. Both were very dirty with a noticeable odor. The dishwasher was full of dirty dishes. The oven was full of dirty pans. Most of the dishes in the cupboards had little bits in them as well. There was a fire alarm battery beeping in one of the bedrooms. There was no coffee maker or wine opener or wine glasses or hand soap. There were very few dishes in general, it would have been challenging to cook and serve...

Nyssa S.

includes taxes & fees

27 Sept - 28 Sept

A compact room with a bed, a small table with plates, a microwave, and a green wall with a neon sign.

11. CUTE and COZY studio w/ jacuzzi!

Azalea Park

Jackson K.

includes taxes & fees

7 Oct - 8 Oct

A modern hotel room with a wooden bed, a desk with chairs, a patterned wall, and a window with blinds.

12. Sunshine Escape Guesthouse ☀

Orlando

Robin R.

includes taxes & fees

28 Sept - 29 Sept

A modern living room with a dining area, featuring a wooden floor, a gray sofa, a dining table with chairs, and a wall-mounted plant.

13. 2/1 with private backyard in the heart of Ivanhoe

Ivanhoe Village

Josh H.

includes taxes & fees

7 Oct - 8 Oct

A gray front door with a glass panel, a wreath, and a doormat with the text "so happy you're here."

14. Cozy, Private, Modern 1BD/1BA Apt in College Park Home. Pet Friendly!

College Park

rimma

includes taxes & fees

28 Sept - 29 Sept

A modern kitchen with wooden cabinets, a central island, and a built-in oven. There is a dining area with a blue sofa and a TV on the wall.

15. Charming Heated Pool home in Altamonte Springs

Altamonte Springs

Kyle T.

A single-story house with a covered porch, a brick pathway leading to the entrance, and a fenced backyard.

16. “The Clementine” Boho Home in Orlando’s Food Scene

Park Lake - Highland

Samuel S.

includes taxes & fees

7 Oct - 8 Oct

A bedroom with a bed, a mirror, a wardrobe, and a floral artwork on the wall.

17. Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!

Casselberry

Kevin K.

includes taxes & fees

28 Sept - 29 Sept

A modern kitchen with a black countertop, two stools, a wooden cabinet, and a TV displaying a mountain landscape.

18. “Downtown Orlando Comfy House”

Lawsona - Fern Creek

Courtanie C.

19. Florida Vacation with pool fun for families

Casselberry

Daniel W.

includes taxes & fees

27 Sept - 28 Sept

20. Orlando Tiny Home retreat Near Downtown with garden, with animals and AC.

West Lakes District

chelsea

includes taxes & fees

30 Sept - 1 Oct

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Top Winter Park Hotel Reviews

Coco Key Hotel & Water Park Resort

8/10 Good

"Overall, my stay at the hotel was good. The hotel amenities were good especially the water park. The hotel was near a lot of restaurants and fun activities. I would definitely stay at this hotel again. My only fault with the hotel was the room. My room lack enough mirrors , the only mirror was in the bathroom."

Universal's Endless Summer Resort - Dockside Inn and Suites

10/10 Excellent

"The rooms were of good size but wished they had more soundproofing. We could easily hear noise coming from side and upstairs neighbors. The cafeteria pizza was hard to chew. Didn't try any other food from there but it looked good. Didn't like having to pay for parking. That should be included in the cost of the room. Overall we enjoyed the location and other amenities the resort had. The team members were great and knowledgeable.We would consider staying here again during there slow season."

Rosen Inn Lake Buena Vista

10/10 Excellent

"It’s a nice hotel with a great value, very close to Disney World, $10 per night parking, which was reasonable, and if there are any issues like in our case, we have stayed there many times and one time the shower faucet wasn’t working correctly and they were there within 10 minutes with a brand new one. We were in a state of shock at their speed and response and we continue to go there every time we’re in Orlando!"

Wyndham I-Drive Avanti Resort & Conference Center

8/10 Good

"I had a great stay at Wyndham I-Drive Avanti Resort & Conference Center! The hotel is beautiful, and the staff was wonderful. A special shoutout to Mary at the front desk—she was such a delight and incredibly helpful throughout my stay! The only issue I experienced was with the hotel phone system. I called several times before and during my stay, and the call would disconnect before I could reach anyone. Other than that, I had a great experience and really enjoyed my stay. I would definitely consider staying here again!"

Find out more about Winter Park

Winter Park Holiday Homes information

Number of reviews	168
Accommodation	5516 Holiday Homes
Lowest Price	AU$206
Highest Price	AU$886

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Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Winter Park holiday homes

1. The Canopy on Periwinkle- A Home Away From Home

2. Charming home @wp. Patio +Gazebo. close to highwys

3. Cozy home 5min to Park Ave and Downtown Orlando

4. Funky Remodeled Otown Bungalow Sleeps 8

5. Spacious 5-bedroom house in gorgeous Winter Park

6. Mills House @WP. Sleeps 11 Renovated. Queen beds

7. Cute 5-bedroom house in peaceful Winter Park

8. Luxury Designer Home • Disney, Universal & Downtown

9. Spacious 5-bedroom house in welcoming Winter Park