Skip to content
We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.
Homes
Homes
NEW
NEW
Experiences
Experiences, new
NEW
NEW
Services
Services, new
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
Top guest favourite
Guest favourite
Cottage in Winter Park
Winter Park Pearl 6 min drive to historic Park Ave
3 bedrooms
,
·
3 beds
,
·
1.5 private bathrooms
1–6 Aug
1–6 Aug
$1,597 SGD
$1,375 SGD
Show price breakdown
for 5 nights
,
·
4.95 out of 5 average rating, 463 reviews
4.95 (463)
Guest favourite
Guest favourite
Flat in Winter Park
The Grove
1 bedroom
1 bedroom
,
·
1 queen bed
1 queen bed
24–29 Aug
24–29 Aug
$557 SGD
Show price breakdown
for 5 nights
$557 SGD for 5 nights
5.0 out of 5 average rating, 6 reviews
5.0 (6)
Top guest favourite
Guest favourite
Guest suite in Orlando
A SUITE RETREAT with a Garden View in the City
1 bedroom
1 bedroom
,
·
1 queen bed
1 queen bed
2–7 Aug
2–7 Aug
$569 SGD
$495 SGD
Show price breakdown
for 5 nights
4.97 out of 5 average rating, 474 reviews
4.97 (474)
Top guest favourite
Guest favourite
Guest house in Orlando
Modern 1950s Studio • Near Downtown & Theme Parks
1 bedroom
1 bedroom
,
·
1 queen bed
1 queen bed
1–6 Aug
1–6 Aug
$796 SGD
$670 SGD
Show price breakdown
for 5 nights
4.97 out of 5 average rating, 175 reviews
4.97 (175)
Top guest favourite
Guest favourite
Home in Winter Park
Modern 2BR Near Park Ave Perfect for Groups
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
3–8 Aug
3–8 Aug
$1,123 SGD
Show price breakdown
for 5 nights
$1,123 SGD for 5 nights
5.0 out of 5 average rating, 26 reviews
5.0 (26)
Top guest favourite
Guest favourite
Home in Orlando
The Palm | Stylish Stay Close to Downtown Orlando
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
16–21 Aug
16–21 Aug
$918 SGD
$841 SGD
Show price breakdown
for 5 nights
5.0 out of 5 average rating, 9 reviews
5.0 (9)
Top guest favourite
Guest favourite
Home in Orlando
Sleeps 6 | Car Rental | Prime DTO Location
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
11–16 Aug
11–16 Aug
$1,784 SGD
$1,394 SGD
Show price breakdown
for 5 nights
Free cancellation
4.99 out of 5 average rating, 80 reviews
4.99 (80)
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
1–6 Aug
1–6 Aug
$640 SGD
Show price breakdown
for 5 nights
$640 SGD for 5 nights
5.0 out of 5 average rating, 134 reviews
5.0 (134)
Top guest favourite
Guest favourite
Guest house in Orlando
1924 Spanish Carriage House Lower
1 bedroom
1 bedroom
,
·
2 beds
2 beds
1–6 Aug
1–6 Aug
$1,210 SGD
Show price breakdown
for 5 nights
$1,210 SGD for 5 nights
4.98 out of 5 average rating, 144 reviews
4.98 (144)
Guest house in Winter Park
Cute & Quaint Private Guesthouse with 1 bed/1 bath
1 bedroom
1 bedroom
,
·
1 bed
1 bed
1–6 Aug
1–6 Aug
$760 SGD
Show price breakdown
for 5 nights
$760 SGD for 5 nights
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Superhost
Superhost
Flat in Orlando
Luxury 1BR & Resort Amenities + 6min to Epic-Unive
1 bedroom
1 bedroom
,
·
2 beds
2 beds
2–7 Aug
2–7 Aug
$944 SGD
$773 SGD
Show price breakdown
for 5 nights
Extended stay discount
New place to stay
New
Guest favourite
Guest favourite
Townhouse in Oviedo
3BR Villa in Gated Oviedo Near UCF & Orlando
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
5–10 Sept
5–10 Sept
$1,327 SGD
Show price breakdown
for 5 nights
$1,327 SGD for 5 nights
5.0 out of 5 average rating, 7 reviews
5.0 (7)
Top guest favourite
Guest favourite
Guest house in Orlando
Cozy Modern Retreat | Patio | Self Check-In
1 queen bed
1 queen bed
5–10 Aug
5–10 Aug
$618 SGD
Show price breakdown
for 5 nights
$618 SGD for 5 nights
5.0 out of 5 average rating, 7 reviews
5.0 (7)
Guest favourite
Guest favourite
Home in Orlando
2 King Beds • Minutes to AdventHealth + Downtown
2 bedrooms
2 bedrooms
,
·
2 king beds
2 king beds
1–6 Aug
1–6 Aug
$1,299 SGD
$1,069 SGD
Show price breakdown
for 5 nights
5.0 out of 5 average rating, 5 reviews
5.0 (5)
Top guest favourite
Guest favourite
Home in Orlando
Not just 2 private bedrooms; the entire upstairs!
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
3–8 Aug
3–8 Aug
$930 SGD
$775 SGD
Show price breakdown
for 5 nights
Free cancellation
5.0 out of 5 average rating, 212 reviews
5.0 (212)
Top guest favourite
Guest favourite
20
Reviews
5.0
Stars
Rating
9
Years hosting
Place to stay in Orlando
Handicap Accessible Master room
1 bedroom
1 bedroom
,
·
1 king bed
1 king bed
27 Jan – 1 Feb
27 Jan – 1 Feb
$272 SGD
Show price breakdown
for 5 nights
$272 SGD for 5 nights
5.0 out of 5 average rating, 20 reviews
5.0 (20)
Guest favourite
Guest favourite
Home in Orlando
New SunRise Cozy & StylishHome sleep5/2bath
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
16–21 Aug
16–21 Aug
$838 SGD
Show price breakdown
for 5 nights
$838 SGD for 5 nights
5.0 out of 5 average rating, 8 reviews
5.0 (8)
Top guest favourite
Guest favourite
Home in Orlando
Sunny Oasis: Downtown Orlando with Suburban feel
2 bedrooms
2 bedrooms
,
·
2 double beds
2 double beds
4–9 Aug
4–9 Aug
$965 SGD
Show price breakdown
for 5 nights
$965 SGD for 5 nights
5.0 out of 5 average rating, 13 reviews
5.0 (13)
Guest favourite
Guest favourite
Loft in Orlando
studio apartment located in quiet neighborhood
1 bedroom
1 bedroom
,
·
2 beds
2 beds
1–6 Aug
1–6 Aug
$549 SGD
Show price breakdown
for 5 nights
$549 SGD for 5 nights
4.93 out of 5 average rating, 28 reviews
4.93 (28)
1
2
3
4
…
15