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
$173 nightly
The price is $192 total per night
$192 total
Aug 20 - Aug 21
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
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
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.
Historic lakefront guesthouse

Historic lakefront guesthouse

Orlando FL
$290 nightly
The price is $322 total per night
$322 total
Sep 8 - Sep 9
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
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
Enchanted Fantasy

Enchanted Fantasy

2 out of 5
2622 Calistoga Ave Kissimmee FL
$114 nightly
The price is $129 total per night
$129 total
Aug 10 - Aug 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 TV in a common area.
Pool
Free WiFi
Mills Cottage by the Little Lake

Mills Cottage by the Little Lake

Orlando FL
$299 nightly
The price is $332 total per night
$332 total
Aug 10 - Aug 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
Downtown Lake Eola Historic House 1 OR 2 BED

Downtown Lake Eola Historic House 1 OR 2 BED

Orlando FL
$157 nightly
The price is $174 total per night
$174 total
Aug 10 - Aug 11
Total with taxes and fees
This guesthouse is a smoke-free guesthouse.
Free WiFi
Air conditioning
Enchanted Dreams

Enchanted Dreams

3 out of 5
2624 Calistoga Ave Kissimmee FL
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 communal living room.
Pool
Parking included
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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

    DoubleTree by Hilton at the Entrance to Universal Orlando

    DoubleTree by Hilton at the Entrance to Universal Orlando

    5780 Major Blvd Orlando FL
    $78 nightly
    The price is $88 total per night from Sep 1 to Sep 2
    $88 total
    Sep 1 - Sep 2
    Total with taxes and fees
    8.6/10 Excellent! (7,021 reviews)
    Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

    Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

    8800 Vistana Centre Dr Orlando FL
    $123 nightly
    The price is $139 total per night from Sep 7 to Sep 8
    $139 total
    Sep 7 - Sep 8
    Total with taxes and fees
    9.2/10 Wonderful! (6,405 reviews)
    Rosen Inn Lake Buena Vista

    Rosen Inn Lake Buena Vista

    8442 Palm Parkway Orlando FL
    $66 nightly
    The price is $75 total per night from Aug 13 to Aug 14
    $75 total
    Aug 13 - Aug 14
    Total with taxes and fees
    8.6/10 Excellent! (5,973 reviews)

Winter Park Guest Houses essential information

Accommodation
30 Guest Houses
Lowest Price
$75
Highest Price
$332
Popular accommodation
Quiet Oasis in Lovely Neighborhood, Mystical Dreams, SPRING LAKE GETAWAY SUITE (Detached Guest House), Historic lakefront guesthouse, Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool and Patio, Enchanted Fantasy, Mills Cottage by the Little Lake, Downtown Lake Eola Historic House 1 OR 2 BED, Enchanted Dreams

More to Explore