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

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
The price is CA $153 per night
CA $153
CA $232 total
Oct 8 - Oct 9
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

Disney Proximity Escape - Comfort in Kissimmee

3 out of 5
286 Marcello Blvd Kissimmee FL
Get rates
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.
Pool
Free WiFi
The Heirloom Inn

The Heirloom Inn

3 out of 5
644 N Donnelly St Mount Dora FL
Get rates
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.
Pet-friendly
Parking included
Quiet Oasis in Lovely Neighborhood

Quiet Oasis in Lovely Neighborhood

Orlando FL
The price is CA $115 per night
CA $115
CA $270 total
Oct 5 - Oct 6
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.
Pool
Hot tub
Enchanted Fantasy

Enchanted Fantasy

2 out of 5
2622 Calistoga Ave Kissimmee FL
The price is CA $61 per night
CA $61
CA $167 total
Oct 3 - Oct 4
includes taxes & fees
Stay at this guesthouse in Kissimmee. Enjoy free WiFi, laundry facilities, and air conditioning. Popular attractions Old Town and Orlando Vineland Premium Outlets are located nearby.
Pool
Free WiFi
Mills Cottage by the Little Lake

Mills Cottage by the Little Lake

Orlando FL
The price is CA $236 per night
CA $236
CA $528 total
Oct 4 - Oct 5
includes taxes & fees
Book a stay at this family-friendly guesthouse in Orlando. Enjoy free breakfast, free WiFi, and a fitness center. Popular attractions Kia Center and Camping World Stadium are located nearby.
Pool
Hot tub
1580 Sandbagger Drive

1580 Sandbagger Drive

3 out of 5
1580 Sandbagger Dr Four Corners FL
Get rates
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
SmartStay Homes

SmartStay Homes

3 out of 5
225 Marcello Boulevard Kissimmee FL
The price is CA $74 per night
CA $74
CA $198 total
Oct 10 - Oct 11
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.
Pool
Parking included
Blissful Bay

Blissful Bay

3 out of 5
4453 Monado Dr Kissimmee FL
Get rates
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.
Pool
Parking included
Suncrest Residence

Suncrest Residence

3 out of 5
1920 Tropical Palms Cir Kissimmee FL
Free cancellation
Reserve now, pay when you stay
The price is CA $69 per night
CA $69
CA $192 total
Oct 3 - Oct 4
includes taxes & fees
Book a stay at this business-friendly guesthouse in Kissimmee. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Disney's Animal Kingdom® Theme Park and ESPN Wide World of Sports Complex are located nearby.
Pool
Parking included
Tempo Trek Lodgings

Tempo Trek Lodgings

3 out of 5
7324 Oakmoss Loop Davenport FL
The price is CA $43 per night
CA $43
CA $144 total
Oct 15 - Oct 16
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.
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
Get rates
Stay at this guesthouse in Tavares. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Eustis Mini Mall and Eustis Square are located nearby.
Pet-friendly
Free WiFi
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.

Top trending hotels in Winter Garden

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

2111 FLAGLER AVE Winter Garden FL
The price is CA $156 per night from Oct 26 to Oct 27
CA $156
CA $176 total
Oct 26 - Oct 27
includes taxes & fees
9.6/10 Exceptional! (2,250 reviews)

Winter Garden Guest Houses essential information

Accommodation
69 Guest Houses
Lowest Price
CA $142
Highest Price
CA $528
Popular accommodation
The Estate at Mount Dora, Disney Proximity Escape - Comfort in Kissimmee, The Heirloom Inn, Quiet Oasis in Lovely Neighborhood, Enchanted Fantasy, Mills Cottage by the Little Lake, 1580 Sandbagger Drive, SmartStay Homes, Blissful Bay, Suncrest Residence, Tempo Trek Lodgings, Sunrise to Sunset on private 900 sq ft dock with BBQ!