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
$139 nightly
The price is $156 total per night
$156 total
Oct 16 - Oct 17
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
Quiet Oasis in Lovely Neighborhood

Quiet Oasis in Lovely Neighborhood

Orlando FL
$171 nightly
The price is $190 total per night
$190 total
Oct 7 - Oct 8
Total with taxes and fees
At this guesthouse, guests have access to a hot tub, laundry facilities, and local meal delivery service. Additional amenities include barbecue grills and a garden.
Pool
Hot Tub
Mills Cottage by the Little Lake

Mills Cottage by the Little Lake

Orlando FL
$334 nightly
The price is $371 total per night
$371 total
Oct 7 - Oct 8
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
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
Downtown Lake Eola Historic House 1 OR 2 BED

Downtown Lake Eola Historic House 1 OR 2 BED

Orlando FL
$147 nightly
The price is $163 total per night
$163 total
Oct 7 - Oct 8
Total with taxes and fees
This guesthouse is a smoke-free guesthouse.
Free WiFi
Air conditioning
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
 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
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
Historic lakefront guesthouse

Historic lakefront guesthouse

Orlando FL
$283 nightly
The price is $314 total per night
$314 total
Oct 7 - Oct 8
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.
Pool
Hot Tub
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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
    $220 nightly
    The price is $248 total per night from Nov 2 to Nov 3
    $248 total
    Nov 2 - Nov 3
    Total with taxes and fees
    DoubleTree by Hilton at the Entrance to Universal Orlando

    DoubleTree by Hilton at the Entrance to Universal Orlando

    5780 Major Blvd Orlando FL
    $93 nightly
    The price is $104 total per night from Nov 1 to Nov 2
    $104 total
    Nov 1 - Nov 2
    Total with taxes and fees
    8.6/10 Excellent! (7,077 reviews)
    Universal's Cabana Bay Beach Resort

    Universal's Cabana Bay Beach Resort

    6550 Adventure Way Orlando FL
    $150 nightly
    The price is $169 total per night from Nov 3 to Nov 4
    $169 total
    Nov 3 - Nov 4
    Total with taxes and fees
    9/10 Wonderful! (7,736 reviews)

Winter Springs Guest Houses essential information

Accommodation
23 Guest Houses
Lowest Price
$104
Highest Price
$371
Popular accommodation
The Ann Stevens House, Quiet Oasis in Lovely Neighborhood, Mills Cottage by the Little Lake, Adorable 1bed 1 bath guest house, Downtown Lake Eola Historic House 1 OR 2 BED, SPRING LAKE GETAWAY SUITE (Detached Guest House),  Peaceful Two Bedroom Guest House near Wekiva River and State Parks , Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool and Patio, Historic lakefront guesthouse

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