Compare Winter Park Guest House Rentals

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Featured Guest Houses in Winter Park

Quiet Oasis in Lovely Neighborhood

Quiet Oasis in Lovely Neighborhood

Orlando FL
$169 nightly
The price is $188 total per night
$188 total
Oct 15 - Oct 16
Total with taxes and fees
At this guesthouse, guests have access to a hot tub, laundry facilities, and local meal delivery service. Additional amenities include barbecue grills and a garden.
Pool
Hot Tub
Enchanted Fantasy

Enchanted Fantasy

2 out of 5
2622 Calistoga Ave Kissimmee FL
$114 nightly
The price is $129 total per night
$129 total
Oct 10 - Oct 11
Total with taxes and fees
At Enchanted Fantasy, guests have access to an outdoor pool, free WiFi in public areas, and microwave in a common area. If you plan to drive, free offsite parking is available. Additional amenities include a refrigerator in a common area, laundry facilities, and a communal living room.
Pool
Free WiFi
Mills Cottage by the Little Lake

Mills Cottage by the Little Lake

Orlando FL
$368 nightly
The price is $408 total per night
$408 total
Oct 12 - Oct 13
Total with taxes and fees
Guests staying at this guesthouse enjoy an outdoor pool, a gym, and a sauna. Other amenities at this family-friendly guesthouse include a hot tub, an arcade/game room, and laundry facilities.
Pool
Hot Tub
Adorable 1bed 1 bath guest house

Adorable 1bed 1 bath guest house

Orlando FL
Guests staying at this guesthouse have access to laundry facilities, a garden, and barbecue grills.
Pet friendly
Free WiFi
Mystical Dreams

Mystical Dreams

3 out of 5
2626 Calistoga Ave Kissimmee FL
Guests of Mystical Dreams enjoy features like 2 outdoor pools, free WiFi in public areas, and microwave in a common area. There's free parking if you drive. Additional amenities include a refrigerator in a common area, laundry facilities, and a communal living room.
Pool
Parking included
Downtown Lake Eola Historic House 1 OR 2 BED

Downtown Lake Eola Historic House 1 OR 2 BED

Orlando FL
$155 nightly
The price is $172 total per night
$172 total
Oct 12 - Oct 13
Total with taxes and fees
This guesthouse is a smoke-free guesthouse.
Free WiFi
Air conditioning
SPRING LAKE GETAWAY SUITE (Detached Guest House)

SPRING LAKE GETAWAY SUITE (Detached Guest House)

Altamonte Springs FL
At this guesthouse, guests enjoy features like beach towels.
Free WiFi
Air conditioning
� Peaceful Two Bedroom Guest House near Wekiva River and State Parks 

 Peaceful Two Bedroom Guest House near Wekiva River and State Parks 

Sorrento FL
At this guesthouse, guests have access to features like laundry facilities. This guesthouse also has barbecue grills.
Pet friendly
Free WiFi
Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool and Patio

Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool and Patio

Orlando FL
Guests of this guesthouse enjoy features like an outdoor pool, free WiFi in public areas, and a library. If you drive, take advantage of free offsite parking. This smoke-free guesthouse also has a garden.
Pool
Free WiFi
Don't see what you're looking for?
See all available properties in Winter Park
View all properties
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.

Hotel Options in Winter Park

    Hyatt Regency Orlando International Airport

    Hyatt Regency Orlando International Airport

    9300 Jeff Fuqua Boulevard Orlando FL
    $219 nightly
    The price is $246 total per night from Nov 2 to Nov 3
    $246 total
    Nov 2 - Nov 3
    Total with taxes and fees
    Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

    Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

    8800 Vistana Centre Dr Orlando FL
    $137 nightly
    The price is $154 total per night from Oct 29 to Oct 30
    $154 total
    Oct 29 - Oct 30
    Total with taxes and fees
    Marriott's Grande Vista

    Marriott's Grande Vista

    5925 Avenida Vista Orlando FL
    $96 nightly
    The price is $108 total per night from Oct 29 to Oct 30
    $108 total
    Oct 29 - Oct 30
    Total with taxes and fees
    9/10 Wonderful! (5,142 reviews)

Winter Park Guest Houses essential information

Accommodation
30 Guest Houses
Lowest Price
$108
Highest Price
$408
Popular accommodation
Quiet Oasis in Lovely Neighborhood, Enchanted Fantasy, Mills Cottage by the Little Lake, Adorable 1bed 1 bath guest house, Mystical Dreams, Downtown Lake Eola Historic House 1 OR 2 BED, SPRING LAKE GETAWAY SUITE (Detached Guest House),  Peaceful Two Bedroom Guest House near Wekiva River and State Parks , Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool and Patio

More to Explore