Skip to content
We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.
Homes
Homes
Experiences
Experiences
Services
Services
Start your search
Location
Homes in Winter Park
Check in / Check out
Any week
Guests
Add guests
Become a host
Help Centre
Become a host
It’s easy to start hosting and earn extra income.
Refer a host
Find a co-host
Log in or sign up
filters
Filters
Price
Type of place
Show map
Search results; Over 1,000 homes in Winter Park
Over 1,000 homes in Winter Park
Superhost
Superhost
Guest house in Winter Park
Cozy guest house close to Downtown Orlando
1 bedroom
,
·
2 beds
,
·
1 private bathroom
14–19 Sept
14–19 Sept
$787 SGD
$698 SGD
Show price breakdown
for 5 nights
,
·
4.86 out of 5 average rating, 196 reviews
4.86 (196)
Top guest favourite
Guest favourite
Flat in Winter Park
Apt D -Modern Elegance in the Heart of Winter Park
2 bedrooms
2 bedrooms
,
·
2 queen beds
2 queen beds
,
·
2 bathrooms
2 bathrooms
18–23 Sept
18–23 Sept
$930 SGD
Show price breakdown
for 5 nights
$930 SGD for 5 nights
4.96 out of 5 average rating, 235 reviews
4.96 (235)
Top guest favourite
Guest favourite
Home in Orlando
Not just 2 private bedrooms; the entire upstairs!
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
28 Sept – 3 Oct
28 Sept – 3 Oct
$865 SGD
$758 SGD
Show price breakdown
for 5 nights
Free cancellation
5.0 out of 5 average rating, 214 reviews
5.0 (214)
Guest favourite
Guest favourite
Home in Winter Park
Luxury Designer Home • Downtown,Universal & Disney
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
,
·
3.5 bathrooms
3.5 bathrooms
3–8 Oct
3–8 Oct
$2,215 SGD
$1,956 SGD
Show price breakdown
for 5 nights
5.0 out of 5 average rating, 7 reviews
5.0 (7)
Featured hotel
Featured hotel
Hotel in Winter Park
Parlor king
1 bedroom
1 bedroom
,
·
1 king bed
1 king bed
,
·
1 bathroom
1 bathroom
24–29 Sept
24–29 Sept
$2,605 SGD
Show price breakdown
for 5 nights
$2,605 SGD for 5 nights
+$361 SGD Airbnb credit
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Top guest favourite
Guest favourite
Home in Longwood
The Lakefront Brantley House
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2.5 bathrooms
2.5 bathrooms
12–19 Sept
12–19 Sept
$2,628 SGD
Show price breakdown
for 7 nights
$2,628 SGD for 7 nights
5.0 out of 5 average rating, 24 reviews
5.0 (24)
Superhost
Superhost
Home in Winter Park
Cute bungalow minutes walk from Park Ave.
2 bedrooms
2 bedrooms
,
·
2 queen beds
2 queen beds
,
·
2 bathrooms
2 bathrooms
7–13 Nov
7–13 Nov
$2,470 SGD
Show price breakdown
for 6 nights
$2,470 SGD for 6 nights
4.96 out of 5 average rating, 28 reviews
4.96 (28)
Top guest favourite
Guest favourite
Flat in Orlando
Spacious2BR PetFriendly Oasis Sleeps 6, Pool &Gym
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
13–18 Sept
13–18 Sept
$956 SGD
$788 SGD
Show price breakdown
for 5 nights
Extended stay discount
5.0 out of 5 average rating, 18 reviews
5.0 (18)
Top guest favourite
Guest favourite
Home in Orlando
4BR: Lakefront Retreat with Harry Potter Game Loft
4 bedrooms
4 bedrooms
,
·
3 bathrooms
3 bathrooms
12–17 Oct
12–17 Oct
$2,147 SGD
$1,933 SGD
Show price breakdown
for 5 nights
Free cancellation
5.0 out of 5 average rating, 37 reviews
5.0 (37)
Top guest favourite
Guest favourite
Home in Orlando
Stylish & Cozy King Bed Retreat @ Baldwin Park
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
2 bathrooms
2 bathrooms
12–17 Oct
12–17 Oct
$1,163 SGD
Show price breakdown
for 5 nights
$1,163 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 65 reviews
5.0 (65)
Guest house in Winter Park
Cute & Quaint Private Guesthouse with 1 bed/1 bath
1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
1 bathroom
1 bathroom
12–17 Sept
12–17 Sept
$711 SGD
Show price breakdown
for 5 nights
$711 SGD for 5 nights
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Room in Orlando
Orlando Comfort
2 beds
2 beds
,
·
1 bathroom
1 bathroom
26 Sept – 1 Oct
26 Sept – 1 Oct
$644 SGD
Show price breakdown
for 5 nights
$644 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 4 reviews
5.0 (4)
Room in Oviedo
Modern Oviedo Stay | Cozy & Peaceful Nature Suite
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
11–16 Sept
11–16 Sept
$403 SGD
Show price breakdown
for 5 nights
$403 SGD for 5 nights
New place to stay
New
Top guest favourite
Guest favourite
Guest house in Orlando
~ Luxe Modern Suite • Heated Pool • 2BR Gem
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
22–27 Nov
22–27 Nov
$1,179 SGD
Show price breakdown
for 5 nights
$1,179 SGD for 5 nights
Free cancellation
4.98 out of 5 average rating, 54 reviews
4.98 (54)
Room in Winter Park
Quiet, comfortable room in Orlando (Winter Park)
1 bed
1 bed
,
·
1 bathroom
1 bathroom
10–15 Sept
10–15 Sept
$432 SGD
Show price breakdown
for 5 nights
$432 SGD for 5 nights
Top guest favourite
Guest favourite
Guest house in Orlando
Detached suite in Mills 50 food paradise
1 bedroom
1 bedroom
,
·
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
19–24 Sept
19–24 Sept
$696 SGD
$610 SGD
Show price breakdown
for 5 nights
Free cancellation
5.0 out of 5 average rating, 142 reviews
5.0 (142)
Guest favourite
Guest favourite
Home in Orlando
Harmony | Heated Pool | 10 min Universal & Epic.
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
23–28 Sept
23–28 Sept
$2,024 SGD
Show price breakdown
for 5 nights
$2,024 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 106 reviews
5.0 (106)
Room in Winter Park
LBeTwo Queen desk closet
1 bed
1 bed
,
·
1 bathroom
1 bathroom
19–24 Sept
19–24 Sept
$374 SGD
$337 SGD
Show price breakdown
for 5 nights
Free cancellation
New place to stay
New
Guest favourite
Guest favourite
Room in Orlando
Stylish Private bd/bth. 5% wkly/10% mthly discount
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
20–25 Sept
20–25 Sept
$525 SGD
Show price breakdown
for 5 nights
$525 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 13 reviews
5.0 (13)
1
2
3
4
…
15
