Compare Winter Garden Guest House Rentals

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Featured Guest Houses in Winter Garden

The Heirloom Inn

The Heirloom Inn

3 out of 5
644 N Donnelly St Mount Dora FL
$166 nightly
The price is $178 total per night
$178 total
Jan 5 - Jan 6
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
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.
Pool
Free WiFi
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
$128 nightly
The price is $142 total per night
$142 total
Jan 6 - Jan 7
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
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
Downtown Lake Eola Historic House 1 OR 2 BED

Downtown Lake Eola Historic House 1 OR 2 BED

Orlando FL
$122 nightly
The price is $135 total per night
$135 total
Jan 5 - Jan 6
Total with taxes and fees
This guesthouse is a smoke-free guesthouse.
Free WiFi
Air conditioning
Winter Park Getaway

Winter Park Getaway

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

Mills Cottage by the Little Lake

Orlando FL
$306 nightly
The price is $339 total per night
$339 total
Jan 5 - Jan 6
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
$274 nightly
The price is $304 total per night
$304 total
Feb 1 - Feb 2
Total with taxes and fees
Guests staying at this guesthouse enjoy access to a water park, an outdoor pool, and a hot tub. Other amenities at this family-friendly guesthouse include laundry facilities, a garden, and barbecue grills.
Pool
Hot Tub
2 Minutes to Universal Studios Theme Parks - Central, Relaxing and Chic 1BR

2 Minutes to Universal Studios Theme Parks - Central, Relaxing and Chic 1BR

Orlando FL
Guests of this guesthouse enjoy access to a water park, local meal delivery service, and a garden.
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 Garden

    The Grove Resort & Water Park Orlando

    The Grove Resort & Water Park Orlando

    14501 Grove Resort Avenue Winter Garden FL
    $214 nightly
    The price is $240 total per night from Jan 14 to Jan 15
    $240 total
    Jan 14 - Jan 15
    Total with taxes and fees
    8/10 Very Good! (8,869 reviews)
    Home2 Suites by Hilton Orlando at Flamingo Crossings

    Home2 Suites by Hilton Orlando at Flamingo Crossings

    341 Flagler Ave Winter Garden FL
    $114 nightly
    The price is $128 total per night from Jan 25 to Jan 26
    $128 total
    Jan 25 - Jan 26
    Total with taxes and fees
    9.2/10 Wonderful! (5,154 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
    $116 nightly
    The price is $130 total per night from Jan 26 to Jan 27
    $130 total
    Jan 26 - Jan 27
    Total with taxes and fees
    9.4/10 Exceptional! (4,403 reviews)

Winter Garden Guest Houses essential information

Accommodation
49 Guest Houses
Lowest Price
$128
Highest Price
$339
Popular accommodation
The Heirloom Inn, Disney Proximity Escape - Comfort in Kissimmee, The Estate at Mount Dora, SPRING LAKE GETAWAY SUITE (Detached Guest House), Downtown Lake Eola Historic House 1 OR 2 BED, Winter Park Getaway, Mills Cottage by the Little Lake, Historic lakefront guesthouse, 2 Minutes to Universal Studios Theme Parks - Central, Relaxing and Chic 1BR