Search Vacation Homes in Winter Park

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Check prices for these dates

Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec
In one month
9 Jan - 11 Jan
In two months
6 Feb - 8 Feb

Our top choices for Winter Park vacation homes

Terrace/patio
Winter Park Gem, 2BR Near Parks, 3MI to Downtown

Vacation Home in College Park

10.0 out of 10, Exceptional, (1)
"We had a wonderful stay — the house was spotless, comfortable, and offered plenty of space. The peaceful neighborhood and convenient location made it easy to explore the area."
United States
Danielle H.
The price is AED 351
AED 1,033 total
includes taxes & fees
11 Dec - 12 Dec
Winter Park Gem, 2BR Near Parks, 3MI to Downtown
Private kitchen
Funky Remodeled Otown Bungalow Sleeps 8

Vacation Home in Fairview Shores

2.0 star property
The price is AED 418
AED 868 total
includes taxes & fees
14 Dec - 15 Dec
Funky Remodeled Otown Bungalow Sleeps 8
Pool
Magic Studio

Vacation Home in Orlando

9.6 out of 10, Exceptional, (4)
"Clean, roomy for two, comfortable bed, Met all our needs. Plan to stay there again."
United States
Nan D.
The price is AED 400
AED 834 total
includes taxes & fees
31 Dec - 1 January 2026
Magic Studio
Interior
Charming home @wp. Patio +Gazebo. close to highwys

Vacation Home in Fairview Shores

Charming home @wp. Patio +Gazebo. close to highwys
Fridge, microwave, oven, stovetop
Sleek, Spacious & Central – Your Ideal Getaway

Vacation Home in Fairview Shores

2.0 star property
The price is AED 364
AED 711 total
includes taxes & fees
26 Dec - 27 Dec
Sleek, Spacious & Central – Your Ideal Getaway
Private kitchen
Cute 5-bedroom,6bed house in superb Winter Park.

Vacation Home in Winter Park

The price is AED 735
AED 1,732 total
includes taxes & fees
9 Jan - 10 January 2026
Cute 5-bedroom,6bed house in superb Winter Park.
Microwave, oven, stovetop, dishwasher
Charming 3-bedroom house with WiFi, AC in welcoming Winter Park

Vacation Home in Winter Park

Charming 3-bedroom house with WiFi, AC in welcoming Winter Park
Property grounds
Studio in the heart of Orlando

Vacation Home in Azalea Park

9.0 out of 10, Wonderful, (4)
"Very nice and clean and comfortable "
United States
Kahari
The price is AED 154
AED 558 total
includes taxes & fees
11 Dec - 12 Dec
Studio in the heart of Orlando
Outdoor pool, a heated pool
Incredible Fantasy World! Newly Renovated Near Disney with Amazing Amenities

Vacation Home in Kissimmee

9.6 out of 10, Exceptional, (71)
"Unit was just right for one adult and two teens."
United States
Amy G.
Incredible Fantasy World! Newly Renovated Near Disney with Amazing Amenities
Exterior
A Tranquil Hideaway in a peaceful, quiet Deltona neighborhood

Vacation Home in Deltona

9.6 out of 10, Exceptional, (10)
"The space was private, comfortable and very clean. Ashlee is an amazing hostess. "
United States
Belinda M.
The price is AED 288
AED 521 total
includes taxes & fees
14 Dec - 15 Dec
A Tranquil Hideaway in a peaceful, quiet Deltona neighborhood
Game room
Spacious 2-Bedroom House 5 Star Near Disney Mill Creek Resort 2748

Vacation Home in Kissimmee

9.8 out of 10, Exceptional, (14)
"The place was in a great community. We felt very safe and right at home. Very well maintained with so many things to do on property. Great communication from the property owner. You can’t go wrong booking a stay here! We will definitely be back!"
United States
Emily D.
The price is AED 294
AED 790 total
includes taxes & fees
11 Dec - 12 Dec
Spacious 2-Bedroom House 5 Star Near Disney Mill Creek Resort 2748
Fridge, microwave, oven, stovetop
3Bdrm Home Near Downtown Orlando and Winter park

Vacation Home in Orlando

10.0 out of 10, Exceptional, (3)
"We had a good stay with a great host."
United States
Robert B.
The price is AED 456
AED 1,262 total
includes taxes & fees
14 Dec - 15 Dec
3Bdrm Home Near Downtown Orlando and Winter park
Interior
Mi Casa Es Su Casa!!🏡 4 Bdrm home with pool

Vacation Home in Orlando

8.8 out of 10, Excellent, (100)
"We had a great time at the house! Close to everything, spacious, clean, and with a good host! "
Norway
Synnøve Sætervik H.
The price is AED 392
AED 1,769 total
includes taxes & fees
14 Dec - 15 Dec
Mi Casa Es Su Casa!!🏡 4 Bdrm home with pool
Pool
Spacious & Private Guest Pool House Oasis

Vacation Home in Union Park

9.8 out of 10, Exceptional, (19)
"Great location , Very enjoy , private space, would book in the future for sure "
United States
Matt B.
The price is AED 404
AED 1,023 total
includes taxes & fees
15 Dec - 16 Dec
Spacious & Private Guest Pool House Oasis
Fridge, microwave, oven, stovetop
Home Sweet Home

Vacation Home in Sanford

9.6 out of 10, Exceptional, (21)
"It was a great location for our trip and everything was true to the listing. The host was very responsive and helpful."
United States
K B.
The price is AED 291
AED 1,198 total
includes taxes & fees
15 Dec - 16 Dec
Home Sweet Home
Pool
4BD/3BA Modern upgraded Townhome-private pool

Vacation Home in Kissimmee

9.6 out of 10, Exceptional, (12)
"Extremely clean and comfortable property. Would definitely stay again."
United States
Michelle C.
The price is AED 478
AED 1,564 total
includes taxes & fees
19 Dec - 20 Dec
4BD/3BA Modern upgraded Townhome-private pool
1 bedroom, iron/ironing board, free WiFi, bed sheets
The Cozy Crash Pad: Tiny House Experience

Vacation Home in Orlando

9.0 out of 10, Wonderful, (22)
"It was incredible! The tiny home feels incredibly cozy and was super easy to find. We had a wonderful visit."
United States
Tristen H.
The price is AED 235
AED 544 total
includes taxes & fees
14 Dec - 15 Dec
The Cozy Crash Pad: Tiny House Experience
Exterior
“The Clementine” Boho Home in Orlando’s Food Scene

Vacation Home in Park Lake - Highland

9.6 out of 10, Exceptional, (18)
"Clean house with nice kitchen amenities. Good shower and good hot water. Good air conditioning and high ceiling. Very convenient location for good food. Nice host. The Vrbo App is hard to use for communicating."
Canada
Ngar
The price is AED 307
AED 667 total
includes taxes & fees
14 Dec - 15 Dec
“The Clementine” Boho Home in Orlando’s Food Scene
Outdoor dining
Sunshine Escape Guesthouse ☀

Vacation Home in Orlando

9.8 out of 10, Exceptional, (11)
"The property was immaculately clean, stylish, roomy and private! It was so convenient to everything yet on the outskirts in a quiet peaceful neighborhood. "
United States
KELLY Z.
The price is AED 215
AED 584 total
includes taxes & fees
21 Dec - 22 Dec
Sunshine Escape Guesthouse ☀
Fridge, microwave, oven, stovetop
Renovated Peaceful Luxury Walk to Mall Park Publix

Vacation Home in Altamonte Springs

9.4 out of 10, Exceptional, (13)
"Centrally located to family. The unit was comfortable for the 2 of us and we had our own space."
United States
Pat D.
The price is AED 314
AED 693 total
includes taxes & fees
11 Dec - 12 Dec
Renovated Peaceful Luxury Walk to Mall Park Publix
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

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent
"Beautiful resort"
Antonese 3-night trip
Posted 9 hours ago
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

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