Winter Park Guest Houses

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Guest Houses in Winter Park

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

$142 total

Jan 4 - Jan 5, 2026

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

$308 nightly

$342 total

Dec 18 - Dec 19

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

$238 nightly

$264 total

Dec 18 - Dec 19

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

Cozy 1BR apt-Pool/Tennis/Gym/Near attractions

Kissimmee FL

$188 nightly

$210 total

Dec 18 - Dec 19

Total with taxes and fees

With a stay at this guesthouse in Kissimmee (Buena Ventura Lakes), you'll be within a 10-minute drive of Austin-Tindall Regional Park and Nemours Children's Hospital.

Pool

Hot Tub

City Guesthouse in beautiful Historic Downtown Sanford

Sanford FL

With a stay at this guesthouse in Sanford, you'll be within a 10-minute drive of Central Florida Zoo & Botanical Gardens and Historic Downtown Sanford.

Air conditioning

Parking available

Private studio; big outdoor space

Orlando FL

Located in Wedgefield, this guesthouse is in a rural location, within a 15-minute drive of Econlockhatchee River and Wedgefield Golf Club.

Pool

Pet friendly

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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.