Book Guest Houses in Winter Park, FL
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Top Guest Houses in Winter Park
Quiet Oasis in Lovely Neighborhood
Orlando FL
$171 nightly
The price is $190 total per night
$190 total
Aug 31 - Sep 1
Total with taxes and fees
A hot tub is featured at this guesthouse, along with a garden and laundry facilities.
Pool
Hot Tub
Mystical Dreams
2626 Calistoga Ave Kissimmee FL
This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A communal living room, laundry facilities, 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
Historic lakefront guesthouse
Orlando FL
$285 nightly
The price is $316 total per night
$316 total
Sep 8 - Sep 9
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.
Enchanted Fantasy
2622 Calistoga Ave Kissimmee FL
$114 nightly
The price is $129 total per night
$129 total
Aug 28 - Aug 29
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
Downtown Lake Eola Historic House 1 OR 2 BED
Orlando FL
$160 nightly
The price is $178 total per night
$178 total
Aug 30 - Aug 31
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.
Mills Cottage by the Little Lake
Orlando FL
$315 nightly
The price is $350 total per night
$350 total
Aug 30 - Aug 31
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
Enchanted Dreams
2624 Calistoga Ave Kissimmee FL
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
2 Minutes to Universal Studios Theme Parks - Central, Relaxing and Chic 1BR
Orlando FL
A garden is available at this guesthouse.
Free WiFi
Air conditioning
Adorable 1bed 1 bath guest house
Orlando FL
This guesthouse features a garden, laundry facilities, and barbecue grills.
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
Universal's Endless Summer Resort - Dockside Inn and Suites
7125 Universal Boulevard Orlando FL
$126 nightly
The price is $142 total per night from Sep 10 to Sep 11
$142 total
Sep 10 - Sep 11
Total with taxes and fees
9.2/10 Wonderful! (5,630 reviews)
Winter Park Guest Houses essential information
Accommodation | 30 Guest Houses |
|---|---|
Lowest Price | $68 |
Highest Price | $350 |
Popular accommodation | Quiet Oasis in Lovely Neighborhood, Mystical Dreams, SPRING LAKE GETAWAY SUITE (Detached Guest House), Historic lakefront guesthouse, Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool and Patio, Enchanted Fantasy, Downtown Lake Eola Historic House 1 OR 2 BED, Mills Cottage by the Little Lake, Enchanted Dreams, 2 Minutes to Universal Studios Theme Parks - Central, Relaxing and Chic 1BR, Adorable 1bed 1 bath guest house,  Peaceful Two Bedroom Guest House near Wekiva River and State Parks  |
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