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

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Check prices for these dates

In two weeks
7 Aug - 9 Aug
In two months
18 Sept - 20 Sept
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Winter Park holiday homes

Interior

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 £193
includes taxes & fees
9 Aug - 10 Aug
Funky Remodeled Otown Bungalow Sleeps 8
Smart TV, video games

Serene Mid-Century 3/2 w/Bonus Room and Huge Shaded Yard w/Fence

Serene Mid-Century 3/2 w/Bonus Room and Huge Shaded Yard w/Fence
Goldenrod
10.0 out of 10, Exceptional, (4 reviews)
"Nice and roomy!"
United States
Ashley C.
The price is £300
includes taxes & fees
28 Jul - 29 Jul
Serene Mid-Century 3/2 w/Bonus Room and Huge Shaded Yard w/Fence
Interior

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 £170
includes taxes & fees
17 Aug - 18 Aug
Charming home @wp. Patio +Gazebo. close to highwys
Interior

Cozy home 5min to Park Ave and Downtown Orlando

Cozy home 5min to Park Ave and Downtown Orlando
Fairview Shores
The price is £207
includes taxes & fees
9 Aug - 10 Aug
Cozy home 5min to Park Ave and Downtown Orlando
Coffee/tea maker, fridge, microwave, oven

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 £253
includes taxes & fees
3 Aug - 4 Aug
Mills House @WP. Sleeps 11 Renovated. Queen beds
Private kitchen

Spacious 5-bedroom house in gorgeous Winter Park

Spacious 5-bedroom house in gorgeous Winter Park
Winter Park
10.0 out of 10, Exceptional, (2 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 £224
includes taxes & fees
5 Aug - 6 Aug
Spacious 5-bedroom house in gorgeous Winter Park
Private kitchen

Cute 5-bedroom house in peaceful Winter Park

Cute 5-bedroom house in peaceful Winter Park
Winter Park
10.0 out of 10, Exceptional, (1 review)
"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 £234
includes taxes & fees
21 Jul - 22 Jul
Cute 5-bedroom house in peaceful Winter Park
Smart TV, fireplace, stereo

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 £337
includes taxes & fees
2 Aug - 3 Aug
The Canopy on Periwinkle- A Home Away From Home
Smart TV

Luxury Designer Home • Disney, Universal & Downtown

Luxury Designer Home • Disney, Universal & Downtown
College Park
The price is £480
includes taxes & fees
21 Jul - 22 Jul
Luxury Designer Home • Disney, Universal & Downtown
Private kitchen

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 £281
includes taxes & fees
21 Jul - 22 Jul
Cute 5-bedroom,6bed house in superb Winter Park.
Fridge, microwave, oven, stovetop

Stylish & Cozy King Bed Retreat @ Baldwin Park

Stylish & Cozy King Bed Retreat @ Baldwin Park
Orlando
10.0 out of 10, Exceptional, (14 reviews)
"The house was beautiful and the host was very responsive! "
United States
Dawn H.
The price is £239
includes taxes & fees
21 Jul - 22 Jul
Stylish & Cozy King Bed Retreat @ Baldwin Park
1 bedroom, desk, WiFi, bed sheets

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 £120
includes taxes & fees
21 Jul - 22 Jul
Studio in the heart of Orlando
Exterior

“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 £147
includes taxes & fees
21 Jul - 22 Jul
“The Clementine” Boho Home in Orlando’s Food Scene
Pool

Private Luxury Pool / Swim up bar / Smart-home

Private Luxury Pool / Swim up bar / Smart-home
College Park
9.6 out of 10, Exceptional, (82 reviews)
"Host was very responsive to our needs"
United States
Thomas S.
The price is £301
includes taxes & fees
23 Jul - 24 Jul
Private Luxury Pool / Swim up bar / Smart-home
3 bedrooms, desk, iron/ironing board, free WiFi

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, (50 reviews)
"The residence met all of our needs for an entertaining/relaxing stay."
United States
Kevin K.
The price is £189
includes taxes & fees
21 Jul - 22 Jul
Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!
Dining

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 £336
includes taxes & fees
21 Jul - 22 Jul
PROMO NOW: 3brdrm home near Downtown Orlando and Winterpark
Coffee/tea maker, fridge, microwave, oven

Florida Vacation with pool fun for families

Florida Vacation with pool fun for families
Casselberry
9.4 out of 10, Exceptional, (43 reviews)
"Awesome location, nice home, and great pool"
United States
Daniel W.
The price is £252
includes taxes & fees
26 Jul - 27 Jul
Florida Vacation with pool fun for families
Outdoor pool, a heated pool

Large, beautiful, very comfortable one bedroom on small lake

Large, beautiful, very comfortable one bedroom on small lake
Lake Weldona
10.0 out of 10, Exceptional, (67 reviews)
"Love the location. "
United States
Jolyn W.
The price is £208
includes taxes & fees
21 Jul - 22 Jul
Large, beautiful, very comfortable one bedroom on small lake
Smart TV

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 £245
includes taxes & fees
23 Jul - 24 Jul
NEW! Spacious designer 2-Bed/2.5-Bath townhome near Downtown Orlando
Smart TV, ping pong

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 £209
includes taxes & fees
21 Jul - 22 Jul
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

Rosen Inn Lake Buena Vista

Rosen Inn Lake Buena Vista

10/10 Excellent
"Everything about this place was amazing, will be returning next summer"
Sonya 1-night trip
Posted 3 hours ago
Rosen Inn Lake Buena Vista

Find out more about Winter Park

Winter Park Holiday Homes information

Number of reviews
327
Accommodation
5331 Holiday Homes
Lowest Price
£120
Highest Price
£480