Compare Winter Garden Guest House Rentals

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Featured Guest Houses in Winter Garden

The Estate at Mount Dora

The Estate at Mount Dora

3.5 out of 5
1029 E 5th Avenue Mount Dora FL
Free Cancellation
Reserve now, pay when you stay
$108 nightly
The price is $120 total per night
$120 total
Jun 10 - Jun 11
Total with taxes and fees
A local mainstay since 1877, The Estate at Mount Dora offers free WiFi in public areas, express check-in, and express check-out. You can take advantage of free parking if you drive. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include a terrace and a garden.
Pet friendly
Parking included
Disney Proximity Escape - Comfort in Kissimmee

Disney Proximity Escape - Comfort in Kissimmee

3 out of 5
286 Marcello Blvd Kissimmee FL
Guests of Disney Proximity Escape - Comfort in Kissimmee enjoy features like an outdoor pool, free WiFi in public areas, and express check-out. Limited parking is available. Staff members can answer questions about accommodations, and also provide luggage storage.
The Heirloom Inn

The Heirloom Inn

3 out of 5
644 N Donnelly St Mount Dora FL
$139 nightly
The price is $147 total per night
$147 total
Jun 11 - Jun 12
Total with taxes and fees
At The Heirloom Inn, guests have access to free WiFi in public areas, express check-in, and express check-out. Free parking is available if you drive. This guesthouse also has a garden.
Pet friendly
Parking included
Enchanted Fantasy

Enchanted Fantasy

2 out of 5
2622 Calistoga Ave Kissimmee FL
$110 nightly
The price is $124 total per night
$124 total
Jun 8 - Jun 9
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
Quiet Oasis in Lovely Neighborhood

Quiet Oasis in Lovely Neighborhood

Orlando FL
$171 nightly
The price is $190 total per night
$190 total
Jun 17 - Jun 18
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
Mills Cottage by the Little Lake

Mills Cottage by the Little Lake

Orlando FL
$319 nightly
The price is $354 total per night
$354 total
Jun 8 - Jun 9
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
Magical Dreams

Magical Dreams

3 out of 5
231 Marcello Blvd Kissimmee FL
Guests of Magical Dreams enjoy 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
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
SmartStay Homes

SmartStay Homes

3 out of 5
225 Marcello Boulevard Kissimmee FL
$138 nightly
The price is $157 total per night
$157 total
Jul 8 - Jul 9
Total with taxes and fees
Guests of SmartStay Homes enjoy an outdoor pool, free WiFi in public areas, and microwave in a common area. If you drive, take advantage of free parking. Additional amenities include a refrigerator in a common area, laundry facilities, and a TV in a common area.
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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 Garden

    The Grove Resort & Water Park Orlando

    The Grove Resort & Water Park Orlando

    14501 Grove Resort Avenue Winter Garden FL
    $248 nightly
    The price is $279 total per night from Jun 9 to Jun 10
    $279 total
    Jun 9 - Jun 10
    Total with taxes and fees
    8/10 Very Good! (10,115 reviews)
    Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

    Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

    631 FLAGLER AVE Winter Garden FL
    $93 nightly
    The price is $104 total per night from Jun 16 to Jun 17
    $104 total
    Jun 16 - Jun 17
    Total with taxes and fees
    9.4/10 Exceptional! (4,928 reviews)
    Home2 Suites by Hilton Orlando at Flamingo Crossings

    Home2 Suites by Hilton Orlando at Flamingo Crossings

    341 Flagler Ave Winter Garden FL
    $98 nightly
    The price is $110 total per night from Jun 22 to Jun 23
    $110 total
    Jun 22 - Jun 23
    Total with taxes and fees
    9.2/10 Wonderful! (5,604 reviews)

Winter Garden Guest Houses essential information

Accommodation
72 Guest Houses
Lowest Price
$104
Highest Price
$354
Popular accommodation
The Estate at Mount Dora, Disney Proximity Escape - Comfort in Kissimmee, The Heirloom Inn, Enchanted Fantasy, Quiet Oasis in Lovely Neighborhood, Mills Cottage by the Little Lake, Magical Dreams, SPRING LAKE GETAWAY SUITE (Detached Guest House), SmartStay Homes