Book Guest Houses in Winter Garden
Wander Wisely with exceptional service, 24/7 support
Save an extra 10% or more on select hotels with Member Discounts
Access exclusive hotel deals, only with the Travelocity app
Featured Guest Houses in Winter Garden
The Estate at Mount Dora
1029 E 5th Avenue Mount Dora FL
Free cancellation
Reserve now, pay when you stay
The price is CA $118 per night
CA $118
CA $191 total
Jul 28 - Jul 29
includes taxes & fees
Stay at this guesthouse in Mount Dora. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Mount Dora Community Building and Mount Dora History Museum are located nearby.
Pet-friendly
Parking included
Disney Proximity Escape - Comfort in Kissimmee
286 Marcello Blvd Kissimmee FL
Stay at this guesthouse in Kissimmee. Enjoy free WiFi, breakfast (surcharge), and premium bedding. Popular attractions Old Town and Give Kids the World Village are located nearby.
Mystical Dreams
2626 Calistoga Ave Kissimmee FL
The price is CA $74 per night
CA $74
CA $180 total
Jul 20 - Jul 21
includes taxes & fees
Stay at this guesthouse in Kissimmee. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Old Town and Orlando Vineland Premium Outlets are located nearby.
The Heirloom Inn
644 N Donnelly St Mount Dora FL
The price is CA $123 per night
CA $123
CA $220 total
Jul 20 - Jul 21
includes taxes & fees
Stay at this guesthouse in Mount Dora. Enjoy free parking, a garden, and cable TV channels. Popular attractions Donnelly Park and The Donnelly House are located nearby.
SmartStay Homes
225 Marcello Boulevard Kissimmee FL
The price is CA $85 per night
CA $85
CA $208 total
Jul 20 - Jul 21
includes taxes & fees
Stay at this guesthouse in Kissimmee. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Old Town and Give Kids the World Village are located nearby.
Quiet Oasis in Lovely Neighborhood
Orlando FL
The price is CA $114 per night
CA $114
CA $266 total
Jul 27 - Jul 28
includes taxes & fees
Stay at this guesthouse in Orlando. Enjoy free WiFi, private pools, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions Kia Center and Camping World Stadium are located nearby.
Disney-Area 3BR Home | Pool, Arcade and Tiki Bar
Davenport FL
Stay at this guesthouse in Davenport. Enjoy an in-room coffeemaker. Popular attractions Disney's Animal Kingdom® Theme Park and ChampionsGate Golf Club are located nearby.
Pet-friendly
Affordable Stays Kissimmee
266 Marcello Blvd Kissimmee FL
The price is CA $68 per night
CA $68
CA $189 total
Aug 17 - Aug 18
includes taxes & fees
Stay at this guesthouse in Kissimmee. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Old Town and Give Kids the World Village are located nearby.
Tempo Trek Lodgings
7324 Oakmoss Loop Davenport FL
The price is CA $47 per night
CA $47
CA $147 total
Jul 27 - Jul 28
includes taxes & fees
Stay at this guesthouse in Davenport. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Reunion Resort Golf Course and ChampionsGate Golf Club are located nearby.
Historic lakefront guesthouse
Orlando FL
The price is CA $135 per night
CA $135
CA $436 total
Jul 21 - Jul 22
includes taxes & fees
Stay at this guesthouse in Orlando. Enjoy free WiFi, private pools, and a garden. Popular attractions Kia Center and Camping World Stadium are located nearby.
1580 Sandbagger Drive
1580 Sandbagger Dr Four Corners FL
Book a stay at this golf guesthouse in Four Corners. Enjoy free WiFi, free parking, and in-room massages. Popular attractions ChampionsGate Golf Club and Reunion Resort Golf Course are located nearby.
Pool
Hot tub
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 trending hotels in Winter Garden
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
631 FLAGLER AVE Winter Garden FL
The price is CA $111 per night from Aug 3 to Aug 4
CA $111
CA $125 total
Aug 3 - Aug 4
includes taxes & fees
9.4/10 Exceptional! (5,226 reviews)
Winter Garden Guest Houses essential information
Accommodation | 70 Guest Houses |
|---|---|
Lowest Price | CA $125 |
Highest Price | CA $436 |
Popular accommodation | The Estate at Mount Dora, Disney Proximity Escape - Comfort in Kissimmee, Mystical Dreams, The Heirloom Inn, SmartStay Homes, Quiet Oasis in Lovely Neighborhood, Disney-Area 3BR Home | Pool, Arcade and Tiki Bar, Affordable Stays Kissimmee, Tempo Trek Lodgings, Historic lakefront guesthouse, 1580 Sandbagger Drive, Blissful Bay |