Book Guest Houses in Winter Garden, FL

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Top Guest Houses in Winter Garden

The Heirloom Inn

The Heirloom Inn

3 out of 5
644 N Donnelly St Mount Dora FL
$179 nightly
The price is $193 total per night
$193 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden, express check-in, and express check-out are also on offer.
Disney Proximity Escape - Comfort in Kissimmee

Disney Proximity Escape - Comfort in Kissimmee

3 out of 5
286 Marcello Blvd Kissimmee FL
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An outdoor pool is featured at this guesthouse, along with free WiFi in public areas and express check-out. Luggage storage and a virtual front desk are also provided.
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
Dec 11 - Dec 12
Total with taxes and fees
This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. A terrace, a garden, and express check-in are also on offer.
SPRING LAKE GETAWAY SUITE (Detached Guest House)

SPRING LAKE GETAWAY SUITE (Detached Guest House)

Altamonte Springs FL
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Stay at this guesthouse in Altamonte Springs. Enjoy free WiFi, balconies, and cable/satellite TV service. Our guests praise the helpful staff in our reviews. Popular attractions Cranes Roost Park and RDV Sportsplex are located nearby.
Downtown Lake Eola Historic House 1 OR 2 BED

Downtown Lake Eola Historic House 1 OR 2 BED

Orlando FL
$118 nightly
The price is $130 total per night
$130 total
Dec 9 - Dec 10
Total with taxes and fees
Stay at this guesthouse in Orlando. Enjoy patios, an in-room coffeemaker, and air conditioning. Popular attractions Kia Center and Camping World Stadium are located nearby.
Winter Park Getaway

Winter Park Getaway

Winter Park FL
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This guesthouse includes a garden and barbecue grills.
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
Dec 8 - Dec 9
Total with taxes and fees
This guesthouse features an outdoor pool and a gym. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities. Enjoy the hot tub and conveniences like a garden and barbecue grills.
Historic lakefront guesthouse

Historic lakefront guesthouse

Orlando FL
$240 nightly
The price is $266 total per night
$266 total
Dec 16 - Dec 17
Total with taxes and fees
A water park and an outdoor pool are featured at this smoke-free guesthouse. Families will appreciate the playground and onsite laundry facilities. Enjoy the hot tub and conveniences like a garden and barbecue grills.
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
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This guesthouse features a water park and a garden.
Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool and Patio

Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool and Patio

Orlando FL
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An outdoor pool is featured at this guesthouse, along with free WiFi in public areas and a garden. A library is also provided.
 Peaceful Two Bedroom Guest House near Wekiva River and State Parks 

 Peaceful Two Bedroom Guest House near Wekiva River and State Parks 

Sorrento FL
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This guesthouse featured laundry facilities and barbecue grills.
Resort-style 3BR Townhouse Near Disney Park

Resort-style 3BR Townhouse Near Disney Park

Davenport FL
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Stay at this guesthouse in Davenport. Enjoy an in-room coffeemaker. Popular attractions Disney's Animal Kingdom® Theme Park and Mystic Dunes Golf Club are located nearby.
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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.

Top hotels in Winter Garden

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 4 to Jan 5
$130 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
9.4/10 Exceptional! (4,313 reviews)

Winter Garden Guest Houses essential information

Accommodation
52 Guest Houses
Lowest Price
$116
Highest Price
$373
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, Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool and Patio,  Peaceful Two Bedroom Guest House near Wekiva River and State Parks , Resort-style 3BR Townhouse Near Disney Park

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