Winter Park Guest Houses

Name: City Guesthouse in beautiful Historic Downtown Sanford
Price range: $246 total

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Guest Houses in Winter Park

Enchanted Fantasy

2622 Calistoga Ave Kissimmee FL

$105 nightly

$119 total

May 1 - May 2

Total with taxes and fees

With a stay at Enchanted Fantasy in Kissimmee, you'll be within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets.

Enchanted Dreams

2624 Calistoga Ave Kissimmee FL

$120 nightly

$136 total

Apr 22 - Apr 23

Total with taxes and fees

With a stay at Enchanted Dreams in Kissimmee, you'll be within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets.

Mills Cottage by the Little Lake

Orlando FL

$350 nightly

$388 total

Apr 27 - Apr 28

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.

Downtown Lake Eola Historic House 1 OR 2 BED

Orlando FL

$170 nightly

$188 total

Apr 27 - Apr 28

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.

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.

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 Wekiwa Springs State Park.

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.

Historic lakefront guesthouse

Orlando FL

$285 nightly

$316 total

May 4 - May 5

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.

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.

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™.

Private Poolside Guest House In Winter Park/Orlando

Winter Park FL

With a stay at this guesthouse in Winter Park, you'll be within a 10-minute drive of Kia Center and Camping World Stadium.

City Guesthouse in beautiful Historic Downtown Sanford

Sanford FL

$222 nightly

$246 total

Apr 22 - Apr 23

Total with taxes and fees

With a stay at this guesthouse in Sanford, you'll be a 4-minute walk from Historic Downtown Sanford and 6 minutes by foot from Art Affair Gallery.

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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.