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
Filters
0
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
Show map
Search results; Over 1,000 homes in Winter Park
Over 1,000 homes in Winter Park
Superhost
Superhost
Home in Winter Park
Cute bungalow minutes walk from Park Ave.
2 bedrooms
,
·
2 beds
,
·
2 private bathrooms
7–13 Nov
7–13 Nov
$2,591 SGD
Show price breakdown
for 6 nights
$2,591 SGD for 6 nights
,
·
4.96 out of 5 average rating, 26 reviews
4.96 (26)
Guest favourite
Guest favourite
Home in Orlando
Sleeps 6 | Car Rental | Prime DTO Location
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
21–26 Jun
21–26 Jun
$1,575 SGD
Show price breakdown
for 5 nights
$1,575 SGD for 5 nights
Free cancellation
4.99 out of 5 average rating, 75 reviews
4.99 (75)
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
30 Jun – 5 Jul
30 Jun – 5 Jul
$1,584 SGD
$1,331 SGD
Show price breakdown
for 5 nights
Free cancellation
5.0 out of 5 average rating, 21 reviews
5.0 (21)
Top guest favourite
Guest favourite
Home in Orlando
Stylish & Cozy King Bed Retreat @ Baldwin Park
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
2–7 Jul
2–7 Jul
$1,700 SGD
Show price breakdown
for 5 nights
$1,700 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 59 reviews
5.0 (59)
Top guest favourite
Guest favourite
Guest house in Orlando
The Sacred Space Downtown Orlando Milk District
1 bedroom
1 bedroom
,
·
1 queen bed
1 queen bed
19–24 Jun
19–24 Jun
$885 SGD
$784 SGD
Show price breakdown
for 5 nights
Free cancellation
5.0 out of 5 average rating, 261 reviews
5.0 (261)
Top guest favourite
Guest favourite
Villa in Orlando
Modern 3BR Family Home Near Shops & Disney
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
5–10 Jul
5–10 Jul
$2,029 SGD
$1,674 SGD
Show price breakdown
for 5 nights
Free cancellation
5.0 out of 5 average rating, 6 reviews
5.0 (6)
Guest favourite
Guest favourite
Home in Orlando
Harmony | Heated Pool | 10 min Universal & Epic.
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
5–10 Jul
5–10 Jul
$2,733 SGD
$2,206 SGD
Show price breakdown
for 5 nights
Free cancellation
5.0 out of 5 average rating, 94 reviews
5.0 (94)
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
31 Jul – 5 Aug
31 Jul – 5 Aug
$904 SGD
Show price breakdown
for 5 nights
$904 SGD for 5 nights
Free cancellation
4.97 out of 5 average rating, 168 reviews
4.97 (168)
Superhost
Superhost
Home in Orlando
Tropical Oasis|Lounge|Putting Green|Heated Pool
3 bedrooms
3 bedrooms
,
·
6 beds
6 beds
22–27 Jul
22–27 Jul
$3,002 SGD
Show price breakdown
for 5 nights
$3,002 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Guest favourite
Guest favourite
Home in Longwood
The Lakefront Brantley House
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
18–25 Jul
18–25 Jul
$2,683 SGD
Show price breakdown
for 7 nights
$2,683 SGD for 7 nights
Free cancellation
5.0 out of 5 average rating, 21 reviews
5.0 (21)
Guest favourite
Guest favourite
Home in Orlando
Eola Retreat + Private Hot Tub + Grill
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
19–24 Jul
19–24 Jul
$1,308 SGD
$1,140 SGD
Show price breakdown
for 5 nights
5.0 out of 5 average rating, 13 reviews
5.0 (13)
Home in Kissimmee
Orlando Dream Escape
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
2–7 Aug
2–7 Aug
$1,666 SGD
Show price breakdown
for 5 nights
$1,666 SGD for 5 nights
Free cancellation
New place to stay
New
Top guest favourite
Guest favourite
Bungalow in Orlando
Den on Daniels
1 bedroom
1 bedroom
,
·
1 bed
1 bed
28 Jun – 3 Jul
28 Jun – 3 Jul
$1,417 SGD
Show price breakdown
for 5 nights
$1,417 SGD for 5 nights
Free cancellation
4.98 out of 5 average rating, 134 reviews
4.98 (134)
Guest favourite
Guest favourite
Townhouse in Oviedo
3BR Villa in Gated Oviedo Near UCF & Orlando
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
11–16 Jul
11–16 Jul
$1,729 SGD
$1,475 SGD
Show price breakdown
for 5 nights
Free cancellation
5.0 out of 5 average rating, 5 reviews
5.0 (5)
Superhost
Superhost
Apartment in Kissimmee
3121 Modern Condo Near Disney | Storey Lake Resort
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
30 Sept – 5 Oct
30 Sept – 5 Oct
$1,085 SGD
$951 SGD
Show price breakdown
for 5 nights
Free cancellation
5.0 out of 5 average rating, 4 reviews
5.0 (4)
Top guest favourite
Guest favourite
Guest house in Orlando
~ Luxe Modern Suite • Heated Pool • 2BR Gem
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
17–22 Oct
17–22 Oct
$1,226 SGD
$1,071 SGD
Show price breakdown
for 5 nights
Free cancellation
4.97 out of 5 average rating, 37 reviews
4.97 (37)
Top guest favourite
Guest favourite
Guest house in Orlando
The Cottage A Pet Friendly Guesthouse
1 bedroom
1 bedroom
,
·
1 king bed
1 king bed
18–23 Jul
18–23 Jul
$950 SGD
Show price breakdown
for 5 nights
$950 SGD for 5 nights
Free cancellation
4.98 out of 5 average rating, 130 reviews
4.98 (130)
Guest favourite
Guest favourite
Flat in Orlando
Spacious2BR PetFriendly Oasis Sleeps 6, Pool &Gym
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
15–20 Jul
15–20 Jul
$1,370 SGD
$1,112 SGD
Show price breakdown
for 5 nights
Free cancellation
5.0 out of 5 average rating, 5 reviews
5.0 (5)
Top guest favourite
Guest favourite
Home in Ocoee
Lakefront in West Orlando Florida
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
21–26 Jun
21–26 Jun
$2,275 SGD
Show price breakdown
for 5 nights
$2,275 SGD for 5 nights
Free cancellation
4.91 out of 5 average rating, 90 reviews
4.91 (90)
1
2
3
4
…
15