Compare Winter Park Guest House Rentals

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Featured Guest Houses in Winter Park

Enchanted Fantasy

Enchanted Fantasy

2 out of 5
2622 Calistoga Ave Kissimmee FL
$104 nightly
The price is $119 total per night
$119 total
May 11 - May 12
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
Quiet Oasis in Lovely Neighborhood

Quiet Oasis in Lovely Neighborhood

Orlando FL
$173 nightly
The price is $192 total per night
$192 total
May 11 - May 12
Total with taxes and fees
At this guesthouse, guests have access to a hot tub, laundry facilities, and local meal delivery service. This smoke-free guesthouse also has 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
Enchanted Dreams

Enchanted Dreams

3 out of 5
2624 Calistoga Ave Kissimmee FL
$120 nightly
The price is $136 total per night
$136 total
May 11 - May 12
Total with taxes and fees
Enchanted Dreams features an outdoor pool, free WiFi in public areas, and microwave in a common area. A stay here includes free parking. Additional amenities include a refrigerator in a common area, laundry facilities, and a TV in a common area.
Pool
Parking included
Historic lakefront guesthouse

Historic lakefront guesthouse

Orlando FL
$280 nightly
The price is $311 total per night
$311 total
May 11 - May 12
Total with taxes and fees
Guests of this guesthouse enjoy features like an outdoor pool, a hot tub, and laundry facilities. Additional amenities include a garden and barbecue grills.
Pool
Hot Tub
Winter Park Getaway

Winter Park Getaway

Winter Park FL
Guests staying at this guesthouse have access to a garden and barbecue grills.
Free WiFi
Air conditioning
Mills Cottage by the Little Lake

Mills Cottage by the Little Lake

Orlando FL
$335 nightly
The price is $373 total per night
$373 total
May 11 - May 12
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
Downtown Lake Eola Historic House 1 OR 2 BED

Downtown Lake Eola Historic House 1 OR 2 BED

Orlando FL
$172 nightly
The price is $190 total per night
$190 total
May 11 - May 12
Total with taxes and fees
This guesthouse is a smoke-free guesthouse.
Free WiFi
Air conditioning
City Guesthouse in beautiful Historic Downtown Sanford

City Guesthouse in beautiful Historic Downtown Sanford

Sanford FL
$228 nightly
The price is $252 total per night
$252 total
May 10 - May 11
Total with taxes and fees
This guesthouse is a smoke-free guesthouse.
Air conditioning
Parking available
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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

    Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

    Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

    8800 Vistana Centre Dr Orlando FL
    $119 nightly
    The price is $134 total per night from Jun 1 to Jun 2
    $134 total
    Jun 1 - Jun 2
    Total with taxes and fees
    9.2/10 Wonderful! (5,388 reviews)
    Universal's Cabana Bay Beach Resort

    Universal's Cabana Bay Beach Resort

    6550 Adventure Way Orlando FL
    $150 nightly
    The price is $169 total per night from May 10 to May 11
    $169 total
    May 10 - May 11
    Total with taxes and fees
    DoubleTree by Hilton at the Entrance to Universal Orlando

    DoubleTree by Hilton at the Entrance to Universal Orlando

    5780 Major Blvd Orlando FL
    $98 nightly
    The price is $110 total per night from May 31 to Jun 1
    $110 total
    May 31 - Jun 1
    Total with taxes and fees
    8.4/10 Very Good! (6,913 reviews)

Winter Park Guest Houses essential information

Accommodation
28 Guest Houses
Lowest Price
$110
Highest Price
$373
Popular accommodation
Enchanted Fantasy, Quiet Oasis in Lovely Neighborhood, SPRING LAKE GETAWAY SUITE (Detached Guest House), Enchanted Dreams, Historic lakefront guesthouse, Winter Park Getaway, Mills Cottage by the Little Lake, Downtown Lake Eola Historic House 1 OR 2 BED, City Guesthouse in beautiful Historic Downtown Sanford

More to Explore