Compare Winter Park Guest House Rentals

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Featured Guest Houses in Winter Park

Quiet Oasis in Lovely Neighborhood

Quiet Oasis in Lovely Neighborhood

Orlando FL
$172 nightly
The price is $191 total per night
$191 total
Oct 26 - Oct 27
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
Downtown Lake Eola Historic House 1 OR 2 BED

Downtown Lake Eola Historic House 1 OR 2 BED

Orlando FL
$147 nightly
The price is $163 total per night
$163 total
Oct 26 - Oct 27
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
$289 nightly
The price is $320 total per night
$320 total
Oct 26 - Oct 27
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, barbecue grills, and a garden.
Pet friendly
Free WiFi
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 26 - Oct 27
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
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 TV in a common area.
Pool
Parking included
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
City Guesthouse in beautiful Historic Downtown Sanford

City Guesthouse in beautiful Historic Downtown Sanford

Sanford FL
This guesthouse is a smoke-free guesthouse.
Air conditioning
Parking available
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
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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
    $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
    $111 nightly
    The price is $125 total per night from Nov 16 to Nov 17
    $125 total
    Nov 16 - Nov 17
    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 Nov 15 to Nov 16
    $108 total
    Nov 15 - Nov 16
    Total with taxes and fees

Winter Park Guest Houses essential information

Accommodation
32 Guest Houses
Lowest Price
$108
Highest Price
$320
Popular accommodation
Quiet Oasis in Lovely Neighborhood, Downtown Lake Eola Historic House 1 OR 2 BED, Mills Cottage by the Little Lake, Adorable 1bed 1 bath guest house, Enchanted Fantasy, Mystical Dreams, Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool and Patio, City Guesthouse in beautiful Historic Downtown Sanford, SPRING LAKE GETAWAY SUITE (Detached Guest House)

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