Winter Park Guest Houses

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Guest Houses in Winter Park

Enchanted Fantasy

Enchanted Fantasy

2 out of 5
2622 Calistoga Ave Kissimmee FL
$114 nightly
The price is $129 total per night
$129 total
Jun 16 - Jun 17
Total with taxes and fees
With a stay at Enchanted Fantasy in Kissimmee, you'll be within a 15-minute drive of Orlando Vineland Premium Outlets and Old Town.
Pool
Free WiFi
Mills Cottage by the Little Lake

Mills Cottage by the Little Lake

Orlando FL
$330 nightly
The price is $366 total per night
$366 total
Jun 16 - Jun 17
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
Quiet Oasis in Lovely Neighborhood

Quiet Oasis in Lovely Neighborhood

Orlando FL
$171 nightly
The price is $190 total per night
$190 total
Jun 17 - Jun 18
Total with taxes and fees
Located in Orlando (Southern Oaks), this guesthouse is within a 10-minute drive of Kia Center and Camping World Stadium.
Pool
Hot Tub
SPRING LAKE GETAWAY SUITE (Detached Guest House)

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.
Free WiFi
Air conditioning
Historic lakefront guesthouse

Historic lakefront guesthouse

Orlando FL
$284 nightly
The price is $315 total per night
$315 total
Jun 22 - Jun 23
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
City Guesthouse in beautiful Historic Downtown Sanford

City Guesthouse in beautiful Historic Downtown Sanford

Sanford FL
$227 nightly
The price is $251 total per night
$251 total
Jun 16 - Jun 17
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.
Air conditioning
Parking available
Adorable 1bed 1 bath guest house

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
Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool and Patio

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
Downtown Lake Eola Historic House 1 OR 2 BED

Downtown Lake Eola Historic House 1 OR 2 BED

Orlando FL
$166 nightly
The price is $184 total per night
$184 total
Jun 21 - Jun 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
Enchanted Dreams

Enchanted Dreams

3 out of 5
2624 Calistoga Ave Kissimmee FL
With a stay at Enchanted Dreams in Kissimmee, you'll be within a 15-minute drive of Orlando Vineland Premium Outlets and Old Town.
Pool
Parking included
2 Minutes to Universal Studios Theme Parks - Central, Relaxing and Chic 1BR

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
 Peaceful Two Bedroom Guest House near Wekiva River and State Parks 

 Peaceful Two Bedroom Guest House near Wekiva River and State Parks 

Sorrento FL
With a stay at this guesthouse in Sorrento, you'll be on a river, within a 10-minute drive of Wekiwa Springs State Park and Wekiva River.
Pet friendly
Free WiFi
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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.

Winter Park Guest Houses essential information

Accommodation
30 Guest Houses
Lowest Price
$129
Highest Price
$366
Popular accommodation
Enchanted Fantasy, Mills Cottage by the Little Lake, Quiet Oasis in Lovely Neighborhood, SPRING LAKE GETAWAY SUITE (Detached Guest House), Historic lakefront guesthouse, City Guesthouse in beautiful Historic Downtown Sanford, Adorable 1bed 1 bath guest house, Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool and Patio, Downtown Lake Eola Historic House 1 OR 2 BED, Enchanted Dreams, 2 Minutes to Universal Studios Theme Parks - Central, Relaxing and Chic 1BR,  Peaceful Two Bedroom Guest House near Wekiva River and State Parks 

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