Winter Park Holiday Homes from €138: Search Top House Rentals

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

24 Sept - 25 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

7 Oct - 8 Oct

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

7 Oct - 8 Oct

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

7 Oct - 8 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

24 Sept - 25 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

7 Oct - 8 Oct

7. Cute 5-bedroom house in peaceful Winter Park

Winter Park

Mary Ellen R.

includes taxes & fees

24 Sept - 25 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

27 Sept - 28 Sept

9. Spacious 5-bedroom house in welcoming Winter Park

Winter Park

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.

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

24 Sept - 25 Sept

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

27 Sept - 28 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

24 Sept - 25 Sept

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

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

28 Sept - 29 Sept

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

24 Sept - 25 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

24 Sept - 25 Sept

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

West Lakes District

chelsea

includes taxes & fees

28 Sept - 29 Sept

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Top Winter Park Hotel Reviews

Hyatt Regency Orlando International Airport

10/10 Excellent

"Great hotel"

Holiday Inn Resort Orlando Suites - Waterpark by IHG

10/10 Excellent

"My family and I had an amazing 10-night stay here, and we honestly didn’t regret it one bit! ❤️ The staff were super nice, there was so much to do, and my family truly enjoyed everything the property had to offer. One of our absolute favorite activities was definitely Family Karaoke Night! 🎤❤️ When I tell you my family LOVED it, I mean it! The poolside activities were also so much fun. Our vacation was absolutely amazing, and an extra, extra special thank you goes to some wonderful staff members: Joshuel at the front, Christian the bellman, Lange & Vlecka from entertainment, and Walger from Security. A very special shout-out to Lange & Vlecka, who made the poolside activities and Family Karaoke so much fun for our entire family. Their energy and entertainment were definitely some of the highlights of our stay! I really hope management recognizes and acknowledges Joshuel, Christian, Lange, Vlecka, and Walger because they absolutely deserve it. Their friendliness, energy, hospitality, and excellent service helped make our family vacation truly memorable. We had a wonderful experience and made some beautiful family memories. Great job, guys, and thank you so much! ❤️👏🎤"

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	5477 Holiday Homes
Lowest Price	€138
Highest Price	€546

Room 1

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