Compare Winter Garden Guest House Rentals

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

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
$163 nightly
The price is $181 total per night
$181 total
Nov 15 - Nov 16
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.
Pool
Free WiFi
The Heirloom Inn

The Heirloom Inn

3 out of 5
644 N Donnelly St Mount Dora FL
$174 nightly
The price is $187 total per night
$187 total
Dec 1 - Dec 2
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
Quiet Oasis in Lovely Neighborhood

Quiet Oasis in Lovely Neighborhood

Orlando FL
$164 nightly
The price is $183 total per night
$183 total
Nov 17 - Nov 18
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
Suncrest Residence

Suncrest Residence

3 out of 5
1920 Tropical Palms Cir Kissimmee FL
Free Cancellation
Reserve now, pay when you stay
$120 nightly
The price is $136 total per night
$136 total
Nov 22 - Nov 23
Total with taxes and fees
Guests staying at Suncrest Residence enjoy an outdoor pool, a gym, and free WiFi in public areas. If you decide to drive, there's free parking. Additional amenities include a microwave in a common area, a refrigerator in a common area, and laundry facilities.
Pool
Parking included
Sunrise to Sunset on private 900 sq ft dock with BBQ!

Sunrise to Sunset on private 900 sq ft dock with BBQ!

Tavares FL
Guests staying at this guesthouse have access to laundry facilities, a garden, and barbecue grills.
Pet friendly
Free WiFi
Downtown Lake Eola Historic House 1 OR 2 BED

Downtown Lake Eola Historic House 1 OR 2 BED

Orlando FL
$158 nightly
The price is $176 total per night
$176 total
Nov 22 - Nov 23
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
$285 nightly
The price is $318 total per night
$318 total
Nov 16 - Nov 17
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
1580 Sandbagger Drive

1580 Sandbagger Drive

3 out of 5
1580 Sandbagger Dr Four Corners FL
At 1580 Sandbagger Drive, guests have access to an outdoor pool, free WiFi in public areas, and a hot tub. There's free parking if you drive. This golf guesthouse also has laundry facilities.
Pool
Hot Tub
Don't see what you're looking for?
See all available properties in Winter Garden
View all properties
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
    $222 nightly
    The price is $250 total per night from Dec 7 to Dec 8
    $250 total
    Dec 7 - Dec 8
    Total with taxes and fees
    8.2/10 Very Good! (10,960 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
    $79 nightly
    The price is $89 total per night from Dec 15 to Dec 16
    $89 total
    Dec 15 - Dec 16
    Total with taxes and fees
    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 Nov 29 to Nov 30
    $110 total
    Nov 29 - Nov 30
    Total with taxes and fees
    9.4/10 Exceptional! (6,286 reviews)

Winter Garden Guest Houses essential information

Accommodation
72 Guest Houses
Lowest Price
$89
Highest Price
$318
Popular accommodation
The Estate at Mount Dora, Disney Proximity Escape - Comfort in Kissimmee, The Heirloom Inn, Quiet Oasis in Lovely Neighborhood, Suncrest Residence, Sunrise to Sunset on private 900 sq ft dock with BBQ! , Downtown Lake Eola Historic House 1 OR 2 BED, Mills Cottage by the Little Lake, 1580 Sandbagger Drive