Book Guest Houses in Winter Garden, FL
Seize Your Someday with our amazing deals for the whole family!
Save an extra 10% or more on select hotels with Member Discounts
Access exclusive hotel deals, only with the Travelocity app
Top 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
$118 nightly
The price is $131 total per night
$131 total
Apr 27 - Apr 28
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.
Pet friendly
Parking included
The Heirloom Inn
644 N Donnelly St Mount Dora FL
$138 nightly
The price is $146 total per night
$146 total
May 4 - May 5
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.
Pet friendly
Parking included
Disney Proximity Escape - Comfort in Kissimmee
286 Marcello Blvd Kissimmee FL
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.
Pool
Free WiFi
Enchanted Fantasy
2622 Calistoga Ave Kissimmee FL
$103 nightly
The price is $117 total per night
$117 total
May 10 - May 11
Total with taxes and fees
An outdoor pool is featured at this guesthouse, along with free WiFi in public areas and a communal living room. Laundry facilities and a virtual front desk are also provided.
Pool
Free WiFi
Tempo Trek Lodgings
7324 Oakmoss Loop Davenport FL
$94 nightly
The price is $105 total per night
$105 total
May 1 - May 2
Total with taxes and fees
An outdoor pool, free self parking, and laundry facilities are featured at this guesthouse. WiFi in public areas is free. Luggage storage, locker space, and a virtual front desk are also on offer.
Pool
Parking included
SPRING LAKE GETAWAY SUITE (Detached Guest House)
Altamonte Springs FL
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 Wekiwa Springs State Park and Cranes Roost Park are located nearby.
Free WiFi
Air conditioning
Magical Dreams
231 Marcello Blvd Kissimmee FL
$113 nightly
The price is $128 total per night
$128 total
Apr 26 - Apr 27
Total with taxes and fees
An outdoor pool, free self parking, and laundry facilities are featured at this guesthouse. WiFi in public areas is free. A communal living room and a virtual front desk are also provided.
Pool
Parking included
Enchanted Dreams
2624 Calistoga Ave Kissimmee FL
$120 nightly
The price is $136 total per night
$136 total
Apr 26 - Apr 27
Total with taxes and fees
An outdoor pool, free self parking, and laundry facilities are featured at this guesthouse. WiFi in public areas is free. A communal living room and a virtual front desk are also provided.
Pool
Parking included
Leisure Lounge
6024 Broad Oak Dr Davenport FL
$110 nightly
The price is $123 total per night
$123 total
Apr 27 - Apr 28
Total with taxes and fees
An outdoor pool, free self parking, and laundry facilities are featured at this guesthouse. WiFi in public areas is free. A communal living room is also provided.
Pool
Parking included
Harmony Haven
282 Marcello Blvd Kissimmee FL
$102 nightly
The price is $116 total per night
$116 total
May 7 - May 8
Total with taxes and fees
This guesthouse features an outdoor pool and a gym. WiFi in public areas is free. A communal living room, laundry facilities, and a virtual front desk are also on offer.
Pool
Free WiFi
Historic lakefront guesthouse
Orlando FL
$281 nightly
The price is $312 total per night
$312 total
Apr 27 - Apr 28
Total with taxes and fees
This guesthouse features an outdoor pool and a hot tub. A garden, laundry facilities, and barbecue grills are also on offer.
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 hotels in Winter Garden
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
631 FLAGLER AVE Winter Garden FL
$101 nightly
The price is $114 total per night from May 13 to May 14
$114 total
May 13 - May 14
Total with taxes and fees
9.4/10 Exceptional! (4,676 reviews)
Winter Garden Guest Houses essential information
Accommodation | 62 Guest Houses |
|---|---|
Lowest Price | $105 |
Highest Price | $312 |
Popular accommodation | The Estate at Mount Dora, The Heirloom Inn, Disney Proximity Escape - Comfort in Kissimmee, Enchanted Fantasy, Tempo Trek Lodgings, SPRING LAKE GETAWAY SUITE (Detached Guest House), Magical Dreams, Enchanted Dreams, Leisure Lounge, Harmony Haven, Historic lakefront guesthouse, Winter Park Getaway |
More ways to wander Winter Garden
Flights to Winter Garden
The best fares to get you there
Winter Garden Hotels
Winter Garden Vacation Rentals
Great Deals on Alternative Accommodations
Winter Garden Car Rentals
Affordable cars to get you around town
Winter Garden Vacations
Save more by combining flights, hotels and cars
Things to do in Winter Garden
Explore More Ways to Travel with Travelocity
- Apartments in Parrish
- B&B in Parrish
- Cabins in Parrish
- Condos in Parrish
- Cottages in Parrish
- Extended Stay Hotels in Parrish
- Guest Houses in Parrish
- Motels in Parrish
- Rv Parks in Parrish
- Villas in Parrish
- Hotels near Resurrection Catholic Church
- Orlando Hotels
- Hotels near West Orange Trail
- Hotels near Oakland Nature Preserve
- Hotels near Carter Family Bowl
- Hotels near Walt Disney World® Resort
- Hotels near Winter Garden Art Association
- Hotels near Winter Garden Heritage Museum
- Farmstay in Ocoee
- B&B in Ocoee
- Cabins in Ocoee
- Condo Resorts in Ocoee
- Condos in Ocoee
- Extended Stay Hotels in Ocoee
- Guest Houses in Ocoee
- Hostels in Ocoee
- Casino Resorts & in Ocoee
- Cheap Hotels in Ocoee
- Convention Center Hotels in Ocoee
- Kid Friendly Hotels in Ocoee
- Golf Resorts & in Ocoee
- Historic Hotels in Ocoee
- Hotels with Hot Tubs in Ocoee
- La Quinta Inn & Suites Hotels in Ocoee
- Luxury Hotels in Ocoee
- Pet Friendly Hotels in Ocoee
- Red Roof Inn Hotels in Ocoee
- Spa Resorts & in Ocoee
- Winery Hotels in Ocoee
- Wyndham Hotels in Ocoee
- Ocoee Hotels
- Houseboats in Ocoee
- Motels in Ocoee
- Vacation Homes in Ocoee
- Rv Parks in Ocoee
- Resorts in Ocoee
- Town Houses in Ocoee
- Villas in Ocoee
- Cottages in Black Jack Island
- Rv Parks in Black Jack Island
- Hotels near Central Florida Railroad Museum
- Apartments in Windermere
- B&B in Windermere
- Cottages in Windermere
- Extended Stay Hotels in Windermere
- Motels in Windermere
- Rv Parks in Windermere
- Resorts in Windermere
- Town Houses in Windermere
- B&B in Polk City
- Cabins in Polk City
- Extended Stay Hotels in Polk City
- Vacation Homes in Polk City
- Marriott Hotels & Resorts in Killarney
- Killarney Hotels
- Farmstay in Gotha
- Cabins in Gotha
- Condos in Gotha
- Cottages in Gotha
- Motels in Gotha
- Town Houses in Gotha
- Villas in Gotha
- Apartments in Pinellas Park
- Holiday Park Resorts in Pinellas Park
- Hostels in Pinellas Park
- Inns in Pinellas Park
- Motels in Pinellas Park
- Vacation Homes in Pinellas Park
- Resorts in Pinellas Park
- Villas in Pinellas Park
- Hotels in Ocoee
- Car rentals at Orlando Airport (MCO)
- Flights to Orlando
- Flights to Florida
- Car rentals in Ocoee
- Hotels near Universal Studios Florida
- Visit Walt Disney World® Resort
- Flights to Ocoee
- Car rentals in Orlando
- Hotels near Walt Disney World® Resort
- Orlando vacations
- Hotels in Orlando
- Resorts in Orlando