Winter Springs Guest Houses
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Guest Houses in Winter Springs
The Ann Stevens House
201 E Kicklighter Rd Lake Helen FL
$159 nightly
The price is $179 total per night
$179 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
Located in Lake Helen, The Ann Stevens House is in a rural location, within a 15-minute drive of Stetson University and Blue Spring State Park.
Parking included
Free WiFi
SPRING LAKE GETAWAY SUITE (Detached Guest House)
Altamonte Springs FL
Located in Altamonte Springs, this guesthouse is within a 15-minute drive of Kia Center and Camping World Stadium.
Free WiFi
Air conditioning
Downtown Lake Eola Historic House 1 OR 2 BED
Orlando FL
$129 nightly
The price is $142 total per night
$142 total
Dec 21 - Dec 22
Total with taxes and fees
With a stay at this guesthouse in Orlando (Downtown Orlando), you'll be within a 5-minute drive of Kia Center and Camping World Stadium.
Free WiFi
Air conditioning
Winter Park Getaway
Winter Park FL
Located in Winter Park, this guesthouse is within a 15-minute drive of Kia Center and University of Central Florida.
Free WiFi
Air conditioning
Mills Cottage by the Little Lake
Orlando FL
$330 nightly
The price is $367 total per night
$367 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
With a stay at this guesthouse in Orlando (Lake Weldona), you'll be a 4-minute drive from Kia Center and 6 minutes from Camping World Stadium.
Pool
Hot Tub
Historic lakefront guesthouse
Orlando FL
$265 nightly
The price is $295 total per night
$295 total
Dec 19 - Dec 20
Total with taxes and fees
When you stay at this guesthouse in Orlando, you'll be on a lake, within a 10-minute drive of Kia Center and Camping World Stadium.
Pool
Hot Tub
2 Minutes to Universal Studios Theme Parks - Central, Relaxing and Chic 1BR
Orlando FL
With a stay at this guesthouse in Orlando, you'll be within a 5-minute drive of Universal Orlando Resort and The Wizarding World of Harry Potter™.
Free WiFi
Air conditioning
Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool and Patio
Orlando FL
With a stay at this guesthouse, you'll be centrally located in Orlando, within a 5-minute drive of Kia Center and Camping World Stadium.
Pool
Free WiFi
 Peaceful Two Bedroom Guest House near Wekiva River and State Parks 
Sorrento FL
Located in Sorrento, this guesthouse is on a river, a 2-minute drive from Wekiva River and 6 minutes from Bear Pond Trailhead.
Pet friendly
Free WiFi
Adorable 1bed 1 bath guest house
Orlando FL
With a stay at this guesthouse in Orlando (Union Park), you'll be within a 15-minute drive of University of Central Florida and Kia Center.
Pet friendly
Free WiFi
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.
Winter Springs Guest Houses essential information
Accommodation | 23 Guest Houses |
|---|---|
Lowest Price | $142 |
Highest Price | $367 |
Popular accommodation | The Ann Stevens House, 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, City Guesthouse in beautiful Historic Downtown Sanford, Private studio; big outdoor space |