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Our top choices for Winter Park vacation homes
1. Funky Remodeled Otown Bungalow Sleeps 8
Funky Remodeled Otown Bungalow Sleeps 8Fairview Shores
10.0 out of 10, Exceptional, (1 review)
"Easy booking/check-in process, great location"
Julia K.
The price is AED 490
AED 923 total
includes taxes & fees
22 Nov - 23 Nov
2. Cozy home 5min to Park Ave and Downtown Orlando
Cozy home 5min to Park Ave and Downtown OrlandoFairview Shores
10.0 out of 10, Exceptional, (1 review)
"Very cute place. Nice outdoor patio."
tyson s.
The price is AED 570
AED 1,025 total
includes taxes & fees
30 Nov - 1 Dec
3. Charming home @wp. Patio +Gazebo. close to highwys
Charming home @wp. Patio +Gazebo. close to highwysFairview Shores
5.4 out of 10, (3 reviews)
"Very clean and location was great"
Vicki V.
The price is AED 461
AED 920 total
includes taxes & fees
18 Nov - 19 Nov
4. Mills House @WP. Sleeps 11 Renovated. Queen beds
Mills House @WP. Sleeps 11 Renovated. Queen bedsFairview 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. "
Larry S.
The price is AED 601
AED 1,133 total
includes taxes & fees
17 Nov - 18 Nov
5. 3-bedroom house in quaint Winter Park with cool vibes
3-bedroom house in quaint Winter Park with cool vibesHannibal Square
The price is AED 937
AED 1,459 total
includes taxes & fees
7 Dec - 8 Dec
6. Spacious 5-bedroom house in gorgeous Winter Park
Spacious 5-bedroom house in gorgeous Winter ParkWinter Park
10.0 out of 10, Exceptional, (5 reviews)
"Rented this property for a friend's engagement party and it worked super well. Host was super nice and great with communication"
Hannah F.
The price is AED 918
AED 1,106 total
includes taxes & fees
16 Nov - 17 Nov
7. 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/FenceGoldenrod
9.6 out of 10, Exceptional, (5 reviews)
"Nice and roomy!"
Ashley C.
The price is AED 672
AED 1,520 total
includes taxes & fees
18 Nov - 19 Nov
8. Spacious 5-bedroom house in welcoming Winter Park
Spacious 5-bedroom house in welcoming Winter ParkWinter Park
The price is AED 951
AED 1,143 total
includes taxes & fees
16 Nov - 17 Nov
9. Top 1% Modern Japandi Retreat - Jacuzzi No Fee
Top 1% Modern Japandi Retreat - Jacuzzi No FeeWinter Park
10.0 out of 10, Exceptional, (8 reviews)
"Clean house, good location to where we wanted to be!"
Jennifer M.
The price is AED 1,451
AED 2,423 total
includes taxes & fees
22 Nov - 23 Nov
10. Luxury Designer Home • Disney, Universal & Downtown
Luxury Designer Home • Disney, Universal & DowntownCollege Park
10.0 out of 10, Exceptional, (2 reviews)
"Great place"
Christian H.
The price is AED 977
AED 2,294 total
includes taxes & fees
16 Nov - 17 Nov
11. 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...
Nyssa S.
The price is AED 1,028
AED 1,236 total
includes taxes & fees
16 Nov - 17 Nov
12. 2/1 with private backyard in the heart of Ivanhoe
2/1 with private backyard in the heart of IvanhoeIvanhoe Village
8.0 out of 10, Very good, (16 reviews)
"Great location"
Josh H.
The price is AED 380
AED 903 total
includes taxes & fees
16 Nov - 17 Nov
13. Stylish & Cozy King Bed Retreat @ Baldwin Park
Stylish & Cozy King Bed Retreat @ Baldwin ParkOrlando
10.0 out of 10, Exceptional, (22 reviews)
"It was a cute property and in a great location to get anywhere in the area"
Devan S.
14. Sunshine Escape Guesthouse ☀
Sunshine Escape Guesthouse ☀Orlando
8.6 out of 10, Excellent, (21 reviews)
"The location worked perfect for our needs in a quiet and safe area. The host was very pleasant and we had a wonderful experience dealing with him and any concerns were met and promptly taken care of. We would definitely stay there again "
Robin R.
The price is AED 215
AED 596 total
includes taxes & fees
17 Nov - 18 Nov
15. Cozy, Private, Modern 1BD/1BA Apt in College Park Home. Pet Friendly!
Cozy, Private, Modern 1BD/1BA Apt in College Park Home. Pet Friendly!College Park
10.0 out of 10, Exceptional, (4 reviews)
"Quiet location, easy access to many amenities.Host genuinely cares about the clienteles well being and that needs are accommodated for if required."
Kevin G.
The price is AED 247
AED 631 total
includes taxes & fees
16 Nov - 17 Nov
16. CUTE and COZY studio w/ jacuzzi!
CUTE and COZY studio w/ jacuzzi!Azalea Park
8.6 out of 10, Excellent, (10 reviews)
"This cute lil place is perfect for a few nights for one person or a couple. It’s quiet, private and safe, and appointed with everything you need. The bed is comfy and the coffee was great. "
Lindsay W.
The price is AED 232
AED 629 total
includes taxes & fees
18 Nov - 19 Nov
17. Studio in the heart of Orlando
Studio in the heart of OrlandoAzalea Park
9.4 out of 10, Exceptional, (6 reviews)
"Can’t complain. Would re book for sure."
Matthew
The price is AED 176
AED 551 total
includes taxes & fees
1 Dec - 2 Dec
18. Private Luxury Pool / Swim up bar / Smart-home
Private Luxury Pool / Swim up bar / Smart-homeCollege Park
9.6 out of 10, Exceptional, (90 reviews)
"It's a absolute vibe. I enjoyed myself completely lovely setup easy access to everything so many things provided for you and your comfort. I'm sure we'll do it again."
Mayah Y.
The price is AED 988
AED 1,819 total
includes taxes & fees
18 Nov - 19 Nov
19. “The Clementine” Boho Home in Orlando’s Food Scene
“The Clementine” Boho Home in Orlando’s Food ScenePark Lake - Highland
9.6 out of 10, Exceptional, (27 reviews)
"A phenomenal stay!"
Samuel S.
The price is AED 456
AED 843 total
includes taxes & fees
29 Nov - 30 Nov
20. Luxury Ranch 2 Master Kg Bed w/ heated Salted Pool
Luxury Ranch 2 Master Kg Bed w/ heated Salted PoolCollege Park
9.6 out of 10, Exceptional, (15 reviews)
"Property was great, and host extremely responsivewould go back there anytime"
Tom47 D.
The price is AED 1,242
AED 3,281 total
includes taxes & fees
1 Dec - 2 Dec
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.
Learn more about Winter Park
Stroll through the Morse Museum to see the world's largest collection of Tiffany glass, then boat through the Winter Park Chain of Lakes. Charming Park Avenue offers upscale shopping and outdoor cafés where you can people-watch before catching a sunset concert in Central Park.
