Skip to content
We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.
Start your search
Location
Winter Park
Check in / Check out
Any week
Guests
Add guests
Stays
Experiences
Online Experiences
Where
Search by region
I’m flexible
I’m flexible
Florida
Florida
Europe
Europe
Italy
Italy
Caribbean
Caribbean
Mexico
Mexico
Check in
Add dates
Check out
Add dates
Who
Add guests
Search
Airbnb your home
Sign up
Log in
Gift cards
Airbnb your home
Help Center
%{visible} of %{smart_count_str} Airbnb Category showing||||%{visible} of %{smart_count_str} Airbnb Categories showing
Your search
Amazing pools
Vineyards
Play
Countryside
Lakefront
Rooms
Amazing views
New
Trending
Chef's kitchens
Design
Beach
Tiny homes
Mansions
Camping
Beachfront
Cabins
Farms
Grand pianos
Bed & breakfasts
Golfing
Surfing
Lake
Filters
0
Display total before taxes
Show map
Search results; Over 1,000 places in Winter Park
Over 1,000 places in Winter Park
Guest favorite
Guest favorite
Home in Winter Park
Cozy Winter Park Home
4 beds
4 beds
Apr 1 – 6
Apr 1 – 6
$187
$157
night
$157 per night, originally $187
5.0 out of 5 average rating, 26 reviews
5.0 (26)
Guesthouse in Winter Park
Cozy guest house close to Downtown Orlando
2 beds
2 beds
May 29 – Jun 3
May 29 – Jun 3
$90
night
$90 per night
4.85 out of 5 average rating, 106 reviews
4.85 (106)
Guest favorite
Guest favorite
Home in Winter Park
Charming Retreat In Winter Park
4 beds
4 beds
Apr 21 – 26
Apr 21 – 26
$205
$167
night
$167 per night, originally $205
4.94 out of 5 average rating, 18 reviews
4.94 (18)
Superhost
Superhost
Home in Winter Park
𝕊𝕝𝕖𝕖𝕡𝕤 𝟠| 𝕎𝕚𝕟𝕥𝕖𝕣 ℙ𝕒𝕣𝕜|ᴏʀʟᴀɴᴅᴏ
4 beds
4 beds
Apr 1 – 6
Apr 1 – 6
$150
night
$150 per night
4.89 out of 5 average rating, 63 reviews
4.89 (63)
Guest favorite
Guest favorite
Home in Winter Park
Guest Suite in Winter Park/Orlando
1 queen bed
1 queen bed
Apr 13 – 18
Apr 13 – 18
$73
$66
night
$66 per night, originally $73
4.9 out of 5 average rating, 122 reviews
4.9 (122)
Guest favorite
Guest favorite
Home in Maitland
The Butterfly Bungalow near Park Ave
2 beds
2 beds
Apr 7 – 12
Apr 7 – 12
$145
$104
night
$104 per night, originally $145
4.96 out of 5 average rating, 112 reviews
4.96 (112)
Superhost
Superhost
Condo in Winter Park
Lovely Winter Park Home close to Hospitals !
2 beds
2 beds
Apr 26 – May 1
Apr 26 – May 1
$100
night
$100 per night
4.8 out of 5 average rating, 55 reviews
4.8 (55)
Superhost
Superhost
Apartment in Maitland
At Mine | King Suite In North Orlando
1 king bed
1 king bed
Apr 1 – 6
Apr 1 – 6
$102
$59
night
$59 per night, originally $102
4.79 out of 5 average rating, 94 reviews
4.79 (94)
Apartment in Winter Park
COZY! Apt in Winter Park - Upper
1 bed
1 bed
Apr 1 – 6
Apr 1 – 6
$109
night
$109 per night
4.66 out of 5 average rating, 29 reviews
4.66 (29)
Villa in Winter Park
Balfour Villa
Apr 22 – 27
Apr 22 – 27
$199
$178
night
$178 per night, originally $199
4.75 out of 5 average rating, 73 reviews
4.75 (73)
Guest favorite
Guest favorite
Apartment in Winter Park
Get a Little Glam in a Retro Palm Beach-Style Boudoir
1 queen bed
1 queen bed
Apr 21 – 26
Apr 21 – 26
$115
night
$115 per night
4.95 out of 5 average rating, 280 reviews
4.95 (280)
Superhost
Superhost
Guest suite in Maitland
Eulalia Quarter by Winter Park
1 bed
1 bed
Apr 1 – 6
Apr 1 – 6
$92
night
$92 per night
New place to stay
New
Guest favorite
Guest favorite
Apartment in Winter Park
The Lake House
2 beds
2 beds
Apr 28 – May 3
Apr 28 – May 3
$78
night
$78 per night
4.89 out of 5 average rating, 28 reviews
4.89 (28)
Guest favorite
Guest favorite
Bungalow in Winter Park
Cozy 2/2 Bungalow - Downtown Winterpark/Orlando
2 queen beds
2 queen beds
Apr 14 – 19
Apr 14 – 19
$130
night
$130 per night
4.98 out of 5 average rating, 224 reviews
4.98 (224)
Superhost
Superhost
Guest suite in Orlando
The Carriage House @ Oasis in Orlando
1 queen bed
1 queen bed
Apr 1 – 6
Apr 1 – 6
$99
night
$99 per night
4.87 out of 5 average rating, 39 reviews
4.87 (39)
Superhost
Superhost
Townhouse in Orlando
Brand new Townhome, House of Peace.
3 beds
3 beds
Apr 20 – 25
Apr 20 – 25
$90
night
$90 per night
4.81 out of 5 average rating, 37 reviews
4.81 (37)
Guest favorite
Guest favorite
Guest suite in Orlando
Private guest suite - Studio Retreat
2 beds
2 beds
Apr 8 – 13
Apr 8 – 13
$84
$70
night
$70 per night, originally $84
4.86 out of 5 average rating, 92 reviews
4.86 (92)
Condo in Winter Park
2 bedr condo close to Winter Park, UCF, Full Sail
4 beds
4 beds
Apr 8 – 13
Apr 8 – 13
$95
night
$95 per night
4.69 out of 5 average rating, 107 reviews
4.69 (107)
1
2
3
4
…
15