Compare Winter Park Guest House Rentals

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Featured Guest Houses in Winter Park

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
Quiet Oasis in Lovely Neighborhood

Quiet Oasis in Lovely Neighborhood

Orlando FL
$172 nightly
The price is $191 total per night
$191 total
Sep 16 - Sep 17
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
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
Downtown Lake Eola Historic House 1 OR 2 BED

Downtown Lake Eola Historic House 1 OR 2 BED

Orlando FL
$156 nightly
The price is $173 total per night
$173 total
Sep 10 - Sep 11
Total with taxes and fees
This guesthouse is a smoke-free guesthouse.
Free WiFi
Air conditioning
Mills Cottage by the Little Lake

Mills Cottage by the Little Lake

Orlando FL
$273 nightly
The price is $303 total per night
$303 total
Sep 10 - Sep 11
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
Historic lakefront guesthouse

Historic lakefront guesthouse

Orlando FL
$300 nightly
The price is $333 total per night
$333 total
Sep 14 - Sep 15
Total with taxes and fees
Guests of this guesthouse enjoy features like an outdoor pool, a hot tub, and laundry facilities. Additional amenities include barbecue grills and a garden.
Pool
Hot Tub
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
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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
    $209 nightly
    The price is $235 total per night from Sep 14 to Sep 15
    $235 total
    Sep 14 - Sep 15
    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
    $131 nightly
    The price is $147 total per night from Sep 14 to Sep 15
    $147 total
    Sep 14 - Sep 15
    Total with taxes and fees
    9.2/10 Wonderful! (6,711 reviews)
    Marriott's Grande Vista

    Marriott's Grande Vista

    5925 Avenida Vista Orlando FL
    $95 nightly
    The price is $107 total per night from Sep 30 to Oct 1
    $107 total
    Sep 30 - Oct 1
    Total with taxes and fees

Winter Park Guest Houses essential information

Accommodation
30 Guest Houses
Lowest Price
$107
Highest Price
$333
Popular accommodation
Mystical Dreams, Quiet Oasis in Lovely Neighborhood, Adorable 1bed 1 bath guest house, Downtown Lake Eola Historic House 1 OR 2 BED, Mills Cottage by the Little Lake, Historic lakefront guesthouse, 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

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