Winter Park Holiday Homes from €140: 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

1. Funky Remodeled Otown Bungalow Sleeps 8

Fairview Shores

Julia K.

includes taxes & fees

13 Aug - 14 Aug

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

Fairview Shores

includes taxes & fees

12 Aug - 13 Aug

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

Fairview Shores

Vicki V.

includes taxes & fees

13 Aug - 14 Aug

4. Cute 5-bedroom house in peaceful Winter Park

Winter Park

Mary Ellen R.

includes taxes & fees

7 Aug - 8 Aug

Coffee/tea maker, fridge, microwave, oven

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

Fairview Shores

Larry S.

includes taxes & fees

12 Aug - 13 Aug

6. Spacious 5-bedroom house in gorgeous Winter Park

Winter Park

Hannah F.

includes taxes & fees

6 Sept - 7 Sept

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

Goldenrod

Breasia J.

includes taxes & fees

11 Aug - 12 Aug

8. Luxury Designer Home • Disney, Universal & Downtown

College Park

includes taxes & fees

12 Aug - 13 Aug

9. 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

5 Sept - 6 Sept

10. Private Luxury Pool / Swim up bar / Smart-home

College Park

Dennis P.

includes taxes & fees

9 Aug - 10 Aug

11. Studio in the heart of Orlando

Azalea Park

Matthew

includes taxes & fees

11 Aug - 12 Aug

12. PROMO NOW: 3brdrm home near Downtown Orlando and Winterpark

Orlando

Kadijah J.

includes taxes & fees

12 Aug - 13 Aug

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

Park Lake - Highland

Samuel S.

includes taxes & fees

11 Aug - 12 Aug

3 bedrooms, desk, iron/ironing board, free WiFi

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

Casselberry

Kevin K.

includes taxes & fees

11 Aug - 12 Aug

15. NEW! Spacious designer 2-Bed/2.5-Bath townhome near Downtown Orlando

Lancaster Park

Chris

16. Large, beautiful, very comfortable one bedroom on small lake

Lake Weldona

Jolyn W.

includes taxes & fees

11 Aug - 12 Aug

17. Florida Vacation with pool fun for families

Casselberry

Daniel W.

includes taxes & fees

10 Aug - 11 Aug

18. Travel Themed Property with Backyard Oasis

Maitland

Roy W.

19. Spacious & Private Guest Pool House Oasis

Union Park

Dionne T.

includes taxes & fees

11 Aug - 12 Aug

20. A Home Where Eclectic Luxury Meets Affordability

Altamonte Springs

Sandra F.

includes taxes & fees

13 Aug - 14 Aug

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Top Winter Park Hotel Reviews

Westgate Lakes Resort & Spa Universal Studios Area

10/10 Excellent

"The room was clean and stocked. The facility was top notch as well."

Holiday Inn Resort Orlando Suites - Waterpark by IHG

8/10 Good

"Floors were dusty, no sponge, paper towels, or dish soap provided until we called hate that everything closes early even though online it states a different time I get it. It may not be super busy, but if there is customers, there should still be a way to have access to things like for example if I want water at 11 or 12 in the evening if I came back from Disney and it’s super late, everything is closed Also the rooms do need an upgrade lighting in the rooms was terrible and some of the lamps didn’t even work overall stuff was great and when we ordered stuff, they were very helpful and assisted breakfast was incredible. Brunch desktop was very pleasant. Everyone around had smiles."

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

10/10 Excellent

"If I could give this resort more than 5 stars, I absolutely would! Our stay at Sheraton Vistana Villages Resort Villas was nothing short of incredible. The entire property is beautiful, peaceful, and exceptionally well cared for. The pools were spotless every single day and quickly became one of our favorite places to relax. The villa was spacious, comfortable, and had more than enough room for everyone to spread out and feel at home. Every detail made our stay easy and enjoyable. One feature that really stood out was the informative text messages we received throughout our stay. They kept us updated on activities, amenities, and important resort information, which made everything so convenient. The staff was welcoming, friendly, and made us feel valued from the moment we arrived. You can truly see the pride they take in providing a great guest experience. My only regret is forgetting to take advantage of the special discounted offer to book another stay within a week. I was so disappointed because I would have booked another vacation without hesitation! We loved every minute of our stay and are already talking about coming back. Next time, I want to bring our entire family because this resort is the perfect place to relax, reconnect, and make unforgettable memories. Thank you for such an amazing experience, we can't wait to return!"

Find out more about Winter Park

Winter Park Holiday Homes information

Number of reviews	428
Accommodation	5366 Holiday Homes
Lowest Price	€140
Highest Price	€564

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Winter Park holiday homes

1. Funky Remodeled Otown Bungalow Sleeps 8

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

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

4. Cute 5-bedroom house in peaceful Winter Park

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

6. Spacious 5-bedroom house in gorgeous Winter Park

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

8. Luxury Designer Home • Disney, Universal & Downtown

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

10. Private Luxury Pool / Swim up bar / Smart-home

11. Studio in the heart of Orlando

12. PROMO NOW: 3brdrm home near Downtown Orlando and Winterpark

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

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

15. NEW! Spacious designer 2-Bed/2.5-Bath townhome near Downtown Orlando

16. Large, beautiful, very comfortable one bedroom on small lake

17. Florida Vacation with pool fun for families

18. Travel Themed Property with Backyard Oasis

19. Spacious & Private Guest Pool House Oasis

20. A Home Where Eclectic Luxury Meets Affordability

Find holiday rentals that suit your style

Top Winter Park Hotel Reviews

Westgate Lakes Resort & Spa Universal Studios Area

Holiday Inn Resort Orlando Suites - Waterpark by IHG

Wyndham I-Drive Avanti Resort & Conference Center

Drury Plaza Hotel Orlando - Disney Springs Area

Rosen Inn Lake Buena Vista

Rosen Inn International

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

B&B Hotel Orlando International Drive Near Universal - Newly Renovated!

Find out more about Winter Park

Winter Park Holiday Homes information

Holiday Homes in Winter Park

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Winter Park holiday homes

1. Funky Remodeled Otown Bungalow Sleeps 8

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

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

4. Cute 5-bedroom house in peaceful Winter Park

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

6. Spacious 5-bedroom house in gorgeous Winter Park

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

8. Luxury Designer Home • Disney, Universal & Downtown

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

10. Private Luxury Pool / Swim up bar / Smart-home

11. Studio in the heart of Orlando

12. PROMO NOW: 3brdrm home near Downtown Orlando and Winterpark

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

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

15. NEW! Spacious designer 2-Bed/2.5-Bath townhome near Downtown Orlando

16. Large, beautiful, very comfortable one bedroom on small lake

17. Florida Vacation with pool fun for families

18. *Travel Themed Property with Backyard Oasis*

19. Spacious & Private Guest Pool House Oasis

20. A Home Where Eclectic Luxury Meets Affordability

Find holiday rentals that suit your style

Top Winter Park Hotel Reviews

Westgate Lakes Resort & Spa Universal Studios Area

Find out more about Winter Park

Winter Park Holiday Homes information

18. Travel Themed Property with Backyard Oasis