Compare Winter Park Guest House Rentals

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Featured Guest Houses in Winter Park

SPRING LAKE GETAWAY SUITE (Detached Guest House)

SPRING LAKE GETAWAY SUITE (Detached Guest House)

Altamonte Springs FL
At this guesthouse, guests enjoy features like beach towels.
Free WiFi
Air conditioning
Downtown Lake Eola Historic House 1 OR 2 BED

Downtown Lake Eola Historic House 1 OR 2 BED

Orlando FL
$129 nightly
The price is $142 total per night
$142 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
This guesthouse is a smoke-free guesthouse.
Free WiFi
Air conditioning
Winter Park Getaway

Winter Park Getaway

Winter Park FL
Guests staying at this guesthouse have access to a garden and barbecue grills.
Free WiFi
Air conditioning
Mills Cottage by the Little Lake

Mills Cottage by the Little Lake

Orlando FL
$312 nightly
The price is $346 total per night
$346 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
Guests staying at this guesthouse enjoy an outdoor pool, a gym, and a sauna. Other amenities at this family-friendly guesthouse include a hot tub, an arcade/game room, and laundry facilities.
Pool
Hot Tub
Historic lakefront guesthouse

Historic lakefront guesthouse

Orlando FL
$257 nightly
The price is $287 total per night
$287 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Guests staying at this guesthouse enjoy access to a water park, an outdoor pool, and a hot tub. Other amenities at this family-friendly guesthouse include laundry facilities, barbecue grills, and a garden.
Pool
Hot Tub
2 Minutes to Universal Studios Theme Parks - Central, Relaxing and Chic 1BR

2 Minutes to Universal Studios Theme Parks - Central, Relaxing and Chic 1BR

Orlando FL
Guests of this guesthouse enjoy access to a water park, local meal delivery service, and a garden.
Free WiFi
Air conditioning
Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool and Patio

Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool and Patio

Orlando FL
Guests of this guesthouse enjoy features like an outdoor pool, free WiFi in public areas, and a library. If you drive, take advantage of free offsite parking. This smoke-free guesthouse also has a garden.
Pool
Free WiFi
 Peaceful Two Bedroom Guest House near Wekiva River and State Parks 

 Peaceful Two Bedroom Guest House near Wekiva River and State Parks 

Sorrento FL
At this guesthouse, guests have access to features like laundry facilities. This guesthouse also has barbecue grills.
Pet friendly
Free WiFi
Adorable 1bed 1 bath guest house

Adorable 1bed 1 bath guest house

Orlando FL
Guests staying at this guesthouse have access to laundry facilities, a garden, and barbecue grills.
Pet friendly
Free WiFi
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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.

Hotel Options in Winter Park

    Universal's Cabana Bay Beach Resort

    Universal's Cabana Bay Beach Resort

    6550 Adventure Way Orlando FL
    $133 nightly
    The price is $150 total per night from Jan 6 to Jan 7
    $150 total
    Jan 6 - Jan 7, 2026
    Total with taxes and fees
    8.8/10 Excellent! (5,803 reviews)
    Wyndham I-Drive Avanti Resort & Conference Center

    Wyndham I-Drive Avanti Resort & Conference Center

    6515 International Drive Orlando FL
    $80 nightly
    The price is $90 total per night from Jan 4 to Jan 5
    $90 total
    Jan 4 - Jan 5, 2026
    Total with taxes and fees
    7.2/10 Good! (3,933 reviews)
    Rosen Inn at Pointe Orlando

    Rosen Inn at Pointe Orlando

    9000 International Drive Orlando FL
    $84 nightly
    The price is $95 total per night from Jan 14 to Jan 15
    $95 total
    Jan 14 - Jan 15, 2026
    Total with taxes and fees
    8.4/10 Very Good! (5,404 reviews)

Winter Park Guest Houses essential information

Accommodation
26 Guest Houses
Lowest Price
$90
Highest Price
$346
Popular accommodation
SPRING LAKE GETAWAY SUITE (Detached Guest House), Downtown Lake Eola Historic House 1 OR 2 BED, Winter Park Getaway, Mills Cottage by the Little Lake, Historic lakefront guesthouse, 2 Minutes to Universal Studios Theme Parks - Central, Relaxing and Chic 1BR, Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool and Patio,  Peaceful Two Bedroom Guest House near Wekiva River and State Parks , Adorable 1bed 1 bath guest house

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