Windermere Guest Houses

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Guest Houses in Windermere

Disney Proximity Escape - Comfort in Kissimmee

286 Marcello Blvd Kissimmee FL

With a stay at Disney Proximity Escape - Comfort in Kissimmee in Kissimmee, you'll be within a 15-minute drive of Old Town and Disney Springs™.

Pool

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

$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.

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

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

Resort-style 3BR Townhouse Near Disney Park

Davenport FL

With a stay at this guesthouse in Davenport (Regal Palms), you'll be within a 15-minute drive of Flamingo Crossings Town Center and Highland Reserve Golf Club.

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.

Family-Friendly 2BR • Wi-Fi + Pets • Near Disney

Orlando FL

With a stay at this guesthouse, you'll be centrally located in Orlando, a 4-minute drive from Kia Center and 9 minutes from Universal Orlando Resort.

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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.