Compare Winter Park Guest House Rentals

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Featured Guest Houses in Winter Park

SPRING LAKE GETAWAY SUITE (Detached Guest House)

At this guesthouse, guests enjoy features like beach towels.

Downtown Lake Eola Historic House 1 OR 2 BED

$132 nightly

$146 total

Feb 2 - Feb 3

Total with taxes and fees

This guesthouse is a smoke-free guesthouse.

Guests staying at this guesthouse have access to barbecue grills and a garden.

$299 nightly

$332 total

Jan 27 - Jan 28

Total with taxes and fees

Guests staying at this guesthouse enjoy an outdoor pool, a gym, and a sauna. Other amenities at this family-friendly guesthouse include a hot tub, an arcade/game room, and laundry facilities.

$262 nightly

$292 total

Jan 31 - Feb 1

Total with taxes and fees

Guests staying at this guesthouse enjoy access to a water park, an outdoor pool, and a hot tub. Other amenities at this family-friendly guesthouse include laundry facilities, a garden, and barbecue grills.

2 Minutes to Universal Studios Theme Parks - Central, Relaxing and Chic 1BR

Guests of this guesthouse enjoy access to a water park, local meal delivery service, and a garden.

Free WiFi

Air conditioning

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

Guests of this guesthouse enjoy features like an outdoor pool, free WiFi in public areas, and a library. If you drive, take advantage of free offsite parking. This smoke-free guesthouse also has a garden.

Peaceful Two Bedroom Guest House near Wekiva River and State Parks

At this guesthouse, guests have access to features like laundry facilities. This guesthouse also has barbecue grills.

Guests staying at this guesthouse have access to laundry facilities, a garden, and barbecue grills.

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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.

Hotel Options in Winter Park

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

8800 Vistana Centre Dr Orlando FL

$115 nightly

$130 total

Feb 22 - Feb 23

Total with taxes and fees

9.2/10 Wonderful! (4,345 reviews)

DoubleTree by Hilton at the Entrance to Universal Orlando

5780 Major Blvd Orlando FL

$112 nightly

$126 total

Jan 27 - Jan 28

Total with taxes and fees

8.4/10 Very Good! (6,932 reviews)

Rosen Inn at Pointe Orlando

9000 International Drive Orlando FL

$75 nightly

$85 total

Feb 8 - Feb 9

Total with taxes and fees

8.4/10 Very Good! (5,554 reviews)

Winter Park Guest Houses essential information

Accommodation	26 Guest Houses
Lowest Price	$85
Highest Price	$332
Popular accommodation	SPRING LAKE GETAWAY SUITE (Detached Guest House), Downtown Lake Eola Historic House 1 OR 2 BED, Winter Park Getaway, Mills Cottage by the Little Lake, Historic lakefront guesthouse, 2 Minutes to Universal Studios Theme Parks - Central, Relaxing and Chic 1BR, Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool and Patio, Peaceful Two Bedroom Guest House near Wekiva River and State Parks , Adorable 1bed 1 bath guest house