Book Guest Houses in Winter Park, FL
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Top Guest Houses in Winter Park
Mills Cottage by the Little Lake
Orlando FL
$311 nightly
The price is $347 total per night
$347 total
Mar 25 - Mar 26
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.
Pool
Hot Tub
Downtown Lake Eola Historic House 1 OR 2 BED
Orlando FL
$151 nightly
The price is $168 total per night
$168 total
Mar 24 - Mar 25
Total with taxes and fees
Stay at this guesthouse in Orlando. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Kia Center and Camping World Stadium are located nearby.
Free WiFi
Air conditioning
Adorable 1bed 1 bath guest house
Orlando FL
This guesthouse features a garden, laundry facilities, and barbecue grills.
Pet friendly
Free WiFi
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
Winter Park Getaway
Winter Park FL
This guesthouse includes a garden and barbecue grills.
Free WiFi
Air conditioning
Historic lakefront guesthouse
Orlando FL
$265 nightly
The price is $296 total per night
$296 total
Apr 20 - Apr 21
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
Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool and Patio
Orlando FL
An outdoor pool is featured at this guesthouse, along with free WiFi in public areas and a garden. A library is also provided.
Pool
Free WiFi
2 Minutes to Universal Studios Theme Parks - Central, Relaxing and Chic 1BR
Orlando FL
A garden is available at this guesthouse.
Cozy 1BR apt-Pool/Tennis/Gym/Near attractions
Kissimmee FL
$189 nightly
The price is $211 total per night
$211 total
Mar 28 - Mar 29
Total with taxes and fees
This guesthouse features an outdoor pool and a gym. A hot tub and laundry facilities are also provided.
 Peaceful Two Bedroom Guest House near Wekiva River and State Parks 
Sorrento FL
This guesthouse featured laundry facilities and barbecue grills.
Private studio; big outdoor space
Orlando FL
An outdoor pool is featured at this guesthouse, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.
Pool
Pet friendly
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 Park
Hyatt Regency Orlando International Airport
9300 Jeff Fuqua Boulevard Orlando FL
$199 nightly
The price is $224 total per night from Mar 23 to Mar 24
$224 total
Mar 23 - Mar 24
Total with taxes and fees
9.4/10 Exceptional! (4,061 reviews)
Winter Park Guest Houses essential information
Accommodation | 26 Guest Houses |
|---|---|
Lowest Price | $98 |
Highest Price | $347 |
Popular accommodation | Mills Cottage by the Little Lake, Downtown Lake Eola Historic House 1 OR 2 BED, Adorable 1bed 1 bath guest house, SPRING LAKE GETAWAY SUITE (Detached Guest House), Winter Park Getaway, Historic lakefront guesthouse, Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool and Patio, 2 Minutes to Universal Studios Theme Parks - Central, Relaxing and Chic 1BR, Cozy 1BR apt-Pool/Tennis/Gym/Near attractions,  Peaceful Two Bedroom Guest House near Wekiva River and State Parks , Private studio; big outdoor space , Private Poolside Guest House In Winter Park/Orlando |
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