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

Holiday Homes in Winter Park

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Winter Park holiday homes

Interior

1. Funky Remodeled Otown Bungalow Sleeps 8

Funky Remodeled Otown Bungalow Sleeps 8
Fairview Shores
10.0 out of 10, Exceptional, (1 review)
"Easy booking/check-in process, great location"
United States
Julia K.
The price is AU$358
includes taxes & fees
24 Aug - 25 Aug
Funky Remodeled Otown Bungalow Sleeps 8
Interior

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

Charming home @wp. Patio +Gazebo. close to highwys
Fairview Shores
5.4 out of 10, (3 reviews)
"Very clean and location was great"
United States
Vicki V.
The price is AU$329
includes taxes & fees
11 Aug - 12 Aug
Charming home @wp. Patio +Gazebo. close to highwys
Interior

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

Cozy home 5min to Park Ave and Downtown Orlando
Fairview Shores
The price is AU$340
includes taxes & fees
24 Aug - 25 Aug
Cozy home 5min to Park Ave and Downtown Orlando
Coffee/tea maker, fridge, microwave, oven

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

Mills House @WP. Sleeps 11 Renovated. Queen beds
Fairview Shores
8.0 out of 10, Very good, (2 reviews)
"Comfortable beds and plentiful TV screens. Nice central location to shopping and dining. Lights are bright without dimming options, and some fixtures not working. "
United States
Larry S.
The price is AU$468
includes taxes & fees
24 Aug - 25 Aug
Mills House @WP. Sleeps 11 Renovated. Queen beds
Private kitchen

5. Cute 5-bedroom house in peaceful Winter Park

Cute 5-bedroom house in peaceful Winter Park
Winter Park
10.0 out of 10, Exceptional, (2 reviews)
"This property is perfect for a family get together. Very clean and close to so many restaurants and entertainment. The communication the host was great. I would definely stay there again."
United States
Mary Ellen R.
The price is AU$443
includes taxes & fees
11 Aug - 12 Aug
Cute 5-bedroom house in peaceful Winter Park
Smart TV, fireplace, stereo

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

The Canopy on Periwinkle- A Home Away From Home
Goldenrod
10.0 out of 10, Exceptional, (3 reviews)
"The home is beautiful!! The place was clean, comfortable, and exactly as described. The host was friendly, responsive, and made everything easy. I would definitely stay here again and recommend it to others."
United States
Breasia J.
The price is AU$696
includes taxes & fees
11 Aug - 12 Aug
The Canopy on Periwinkle- A Home Away From Home
Private kitchen

7. Spacious 5-bedroom house in gorgeous Winter Park

Spacious 5-bedroom house in gorgeous Winter Park
Winter Park
10.0 out of 10, Exceptional, (3 reviews)
"Rented this property for a friend's engagement party and it worked super well. Host was super nice and great with communication"
United States
Hannah F.
The price is AU$483
includes taxes & fees
10 Sept - 11 Sept
Spacious 5-bedroom house in gorgeous Winter Park
Smart TV

8. Winter Park Charmer - Heated Pool Home - Close to everything

Winter Park Charmer - Heated Pool Home - Close to everything
Winter Park
8.2 out of 10, Very good, (19 reviews)
"Fabulous place with incredible value "
United States
Kyle C.
The price is AU$585
includes taxes & fees
15 Aug - 16 Aug
Winter Park Charmer - Heated Pool Home - Close to everything
Smart TV

9. Luxury Designer Home • Disney, Universal & Downtown

Luxury Designer Home • Disney, Universal & Downtown
College Park
The price is AU$883
includes taxes & fees
22 Aug - 23 Aug
Luxury Designer Home • Disney, Universal & Downtown
Private kitchen

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

Cute 5-bedroom,6bed house in superb Winter Park.
Winter Park
4.0 out of 10, (1 review)
"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...
United States
Nyssa S.
The price is AU$527
includes taxes & fees
11 Aug - 12 Aug
Cute 5-bedroom,6bed house in superb Winter Park.
Desk, WiFi, bed sheets

11. Studio in the heart of Orlando

Studio in the heart of Orlando
Azalea Park
9.4 out of 10, Exceptional, (6 reviews)
"Can’t complain. Would re book for sure."
United States
Matthew
The price is AU$226
includes taxes & fees
11 Aug - 12 Aug
Studio in the heart of Orlando
Exterior

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

“The Clementine” Boho Home in Orlando’s Food Scene
Park Lake - Highland
9.6 out of 10, Exceptional, (25 reviews)
"A phenomenal stay!"
United States
Samuel S.
The price is AU$278
includes taxes & fees
11 Aug - 12 Aug
“The Clementine” Boho Home in Orlando’s Food Scene
3 bedrooms, desk, iron/ironing board, free WiFi

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

Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!
Casselberry
9.8 out of 10, Exceptional, (54 reviews)
"The residence met all of our needs for an entertaining/relaxing stay."
United States
Kevin K.
The price is AU$355
includes taxes & fees
12 Aug - 13 Aug
Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!
Dining

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

PROMO NOW: 3brdrm home near Downtown Orlando and Winterpark
Orlando
10.0 out of 10, Exceptional, (4 reviews)
"Nice place , will book again "
United States
Kadijah J.
The price is AU$598
includes taxes & fees
11 Aug - 12 Aug
PROMO NOW: 3brdrm home near Downtown Orlando and Winterpark
Coffee/tea maker, fridge, microwave, oven

15. Florida Vacation with pool fun for families

Florida Vacation with pool fun for families
Casselberry
9.4 out of 10, Exceptional, (44 reviews)
"Awesome location, nice home, and great pool"
United States
Daniel W.
The price is AU$473
includes taxes & fees
20 Aug - 21 Aug
Florida Vacation with pool fun for families
Outdoor pool, a heated pool

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

Large, beautiful, very comfortable one bedroom on small lake
Lake Weldona
9.8 out of 10, Exceptional, (69 reviews)
"Love the location. "
United States
Jolyn W.
The price is AU$381
includes taxes & fees
11 Aug - 12 Aug
Large, beautiful, very comfortable one bedroom on small lake
Terrace/patio

17. The Cozy Crash Pad: Tiny House Experience

The Cozy Crash Pad: Tiny House Experience
Orlando
8.8 out of 10, Excellent, (28 reviews)
"Overall a good experience. Quiet location. Ideal for solo travelers. I'd give it a 10-out-of-10 if it had a stove top & oven, but space is tight here. A place to hang close would also be nice."
United States
Joseph M.
The price is AU$209
includes taxes & fees
11 Aug - 12 Aug
The Cozy Crash Pad: Tiny House Experience
Smart TV

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

NEW! Spacious designer 2-Bed/2.5-Bath townhome near Downtown Orlando
Lancaster Park
10.0 out of 10, Exceptional, (19 reviews)
"Clean, good location, easy check in/check out"
United States
Chris
The price is AU$442
includes taxes & fees
11 Aug - 12 Aug
NEW! Spacious designer 2-Bed/2.5-Bath townhome near Downtown Orlando
Pool

19. Spacious & Private Guest Pool House Oasis

Spacious & Private Guest Pool House Oasis
Union Park
9.8 out of 10, Exceptional, (27 reviews)
"The pool house looked exactly like the pictures and it was a very comfortable place to stay. My husband and I really enjoyed it and would definitely stay there again in the future."
United States
Dionne T.
The price is AU$385
includes taxes & fees
11 Aug - 12 Aug
Spacious & Private Guest Pool House Oasis
Smart TV, ping pong

20. Quiet retreat 15 minutes from downtown Orlando, Orlando Airport International!

Quiet retreat 15 minutes from downtown Orlando, Orlando Airport International!
Azalea Park
9.6 out of 10, Exceptional, (25 reviews)
"Quiet neighborhood, good location."
United States
River
The price is AU$398
includes taxes & fees
18 Aug - 19 Aug
Quiet retreat 15 minutes from downtown Orlando, Orlando Airport International!
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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Top Winter Park Hotel Reviews

Drury Plaza Hotel Orlando - Disney Springs Area

Drury Plaza Hotel Orlando - Disney Springs Area

10/10 Excellent
"Always a fantastic stay, the staff are top notch and are like family to us"
Brent 8-night trip
Posted 1 hour ago
Drury Plaza Hotel Orlando - Disney Springs Area

Find out more about Winter Park

Winter Park Holiday Homes information

Number of reviews
4
Accommodation
5617 Holiday Homes
Lowest Price
AU$538
Highest Price
AU$982