Compare Winter Park Guest House Rentals

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Featured Guest Houses in Winter Park

$109 nightly

$124 total

Jun 12 - Jun 13

Total with taxes and fees

At Enchanted Fantasy, guests have access to an outdoor pool, free WiFi in public areas, and microwave in a common area. If you plan to drive, free offsite parking is available. Additional amenities include a refrigerator in a common area, laundry facilities, and a TV in a common area.

$171 nightly

$190 total

Jun 17 - Jun 18

Total with taxes and fees

At this guesthouse, guests have access to a hot tub, laundry facilities, and local meal delivery service. This smoke-free guesthouse also has a garden.

$328 nightly

$364 total

Jun 14 - Jun 15

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.

SPRING LAKE GETAWAY SUITE (Detached Guest House)

At this guesthouse, guests enjoy features like beach towels.

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

City Guesthouse in beautiful Historic Downtown Sanford

$228 nightly

$252 total

Jun 12 - Jun 13

Total with taxes and fees

This guesthouse is a smoke-free guesthouse.

Enchanted Dreams features an outdoor pool, free WiFi in public areas, and microwave in a common area. A stay here includes free parking. Additional amenities include a refrigerator in a common area, laundry facilities, and a communal living room.

$287 nightly

$319 total

Jun 22 - Jun 23

Total with taxes and fees

Guests of this guesthouse enjoy features like an outdoor pool, a hot tub, and laundry facilities. Additional amenities include a garden and barbecue grills.

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.

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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

$143 nightly

$161 total

Jul 6 - Jul 7

Total with taxes and fees

9.2/10 Wonderful! (5,749 reviews)

DoubleTree by Hilton at the Entrance to Universal Orlando

5780 Major Blvd Orlando FL

$89 nightly

$101 total

Jul 12 - Jul 13

Total with taxes and fees

8.6/10 Excellent! (6,987 reviews)

Universal's Cabana Bay Beach Resort

6550 Adventure Way Orlando FL

$162 nightly

$182 total

Jun 28 - Jun 29

Total with taxes and fees

9/10 Wonderful! (7,006 reviews)

Winter Park Guest Houses essential information

Accommodation	28 Guest Houses
Lowest Price	$101
Highest Price	$364
Popular accommodation	Enchanted Fantasy, Quiet Oasis in Lovely Neighborhood, Mills Cottage by the Little Lake, SPRING LAKE GETAWAY SUITE (Detached Guest House), Adorable 1bed 1 bath guest house, City Guesthouse in beautiful Historic Downtown Sanford, Enchanted Dreams, Historic lakefront guesthouse, Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool and Patio