Compare Winter Springs Guest House Rentals

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Featured Guest Houses in Winter Springs

The Ann Stevens House

The Ann Stevens House

3 out of 5
201 E Kicklighter Rd Lake Helen FL
Free Cancellation
Reserve now, pay when you stay
$159 nightly
The price is $179 total per night
$179 total
Apr 7 - Apr 8
Total with taxes and fees
A local mainstay since 1895, The Ann Stevens House offers free WiFi in public areas, express check-out, and a terrace. If you drive, take advantage of free parking. Friendly staff can provide tour or ticket assistance, and also offer advice about sightseeing. This guesthouse also has a garden.
Parking included
Free WiFi
Mills Cottage by the Little Lake

Mills Cottage by the Little Lake

Orlando FL
$342 nightly
The price is $380 total per night
$380 total
Apr 6 - Apr 7
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.
Downtown Lake Eola Historic House 1 OR 2 BED

Downtown Lake Eola Historic House 1 OR 2 BED

Orlando FL
$151 nightly
The price is $168 total per night
$168 total
Apr 7 - Apr 8
Total with taxes and fees
This guesthouse is a smoke-free guesthouse.
Free WiFi
Air conditioning
Adorable 1bed 1 bath guest house

Adorable 1bed 1 bath guest house

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

Winter Park Getaway

Winter Park FL
Guests staying at this guesthouse have access to barbecue grills and a garden.
Historic lakefront guesthouse

Historic lakefront guesthouse

Orlando FL
$280 nightly
The price is $312 total per night
$312 total
Apr 15 - Apr 16
Total with taxes and fees
Guests of this guesthouse enjoy features like an outdoor pool, a hot tub, and laundry facilities. Additional amenities include barbecue grills and a garden.
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.
 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.
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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 Springs

    Hyatt Regency Orlando International Airport

    Hyatt Regency Orlando International Airport

    9300 Jeff Fuqua Boulevard Orlando FL
    $199 nightly
    The price is $224 total per night from Apr 8 to Apr 9
    $224 total
    Apr 8 - Apr 9
    Total with taxes and fees
    9.4/10 Exceptional! (4,081 reviews)
    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 May 3 to May 4
    $150 total
    May 3 - May 4
    Total with taxes and fees
    9/10 Wonderful! (6,538 reviews)
    Rosen Inn at Pointe Orlando

    Rosen Inn at Pointe Orlando

    9000 International Drive Orlando FL
    $88 nightly
    The price is $99 total per night from Apr 5 to Apr 6
    $99 total
    Apr 5 - Apr 6
    Total with taxes and fees
    8.6/10 Excellent! (6,181 reviews)

Winter Springs Guest Houses essential information

Accommodation
23 Guest Houses
Lowest Price
$99
Highest Price
$380
Popular accommodation
The Ann Stevens House, 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,  Peaceful Two Bedroom Guest House near Wekiva River and State Parks 

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