Windermere Guest Houses

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

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™.

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.

Downtown Lake Eola Historic House 1 OR 2 BED

Orlando FL

$132 nightly

$146 total

Feb 2 - Feb 3

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.

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.

Mills Cottage by the Little Lake

Orlando FL

$301 nightly

$334 total

Jan 22 - Jan 23

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.

Historic lakefront guesthouse

Orlando FL

$262 nightly

$292 total

Jan 31 - Feb 1

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™.

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.

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

$187 nightly

$209 total

Jan 20 - Jan 21

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 Sanford-Burnham Medical Research Institute.

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.

Don't see what you're looking for?

See all available properties in Windermere

View all properties

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.