Compare Winter Park Guest House Rentals

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Featured Guest Houses in Winter Park

$110 nightly

$124 total

May 31 - Jun 1

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 communal living room.

Pool

Free WiFi

$171 nightly

$190 total

Jun 3 - Jun 4

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.

Pool

Hot Tub

SPRING LAKE GETAWAY SUITE (Detached Guest House)

At this guesthouse, guests enjoy features like beach towels.

Free WiFi

Air conditioning

$130 nightly

$148 total

May 29 - May 30

Total with taxes and fees

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 TV in a common area.

Pool

Parking included

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

Pet friendly

Free WiFi

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

Free WiFi

Air conditioning

City Guesthouse in beautiful Historic Downtown Sanford

$228 nightly

$252 total

May 30 - May 31

Total with taxes and fees

This guesthouse is a smoke-free guesthouse.

Air conditioning

Parking available

Downtown Lake Eola Historic House 1 OR 2 BED

$166 nightly

$184 total

Jun 1 - Jun 2

Total with taxes and fees

This guesthouse is a smoke-free guesthouse.

Free WiFi

Air conditioning

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.

Pool

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.

Hotel Options in Winter Park

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

8800 Vistana Centre Dr Orlando FL

$143 nightly

$161 total

Jun 17 - Jun 18

Total with taxes and fees

9.2/10 Wonderful! (5,594 reviews)

Hyatt Regency Orlando International Airport

9300 Jeff Fuqua Boulevard Orlando FL

$203 nightly

$228 total

Jun 15 - Jun 16

Total with taxes and fees

9.4/10 Exceptional! (4,169 reviews)

Universal's Cabana Bay Beach Resort

6550 Adventure Way Orlando FL

$150 nightly

$169 total

May 31 - Jun 1

Total with taxes and fees

9/10 Wonderful! (6,890 reviews)

Winter Park Guest Houses essential information

Accommodation	28 Guest Houses
Lowest Price	$124
Highest Price	$252
Popular accommodation	Enchanted Fantasy, Quiet Oasis in Lovely Neighborhood, SPRING LAKE GETAWAY SUITE (Detached Guest House), Enchanted Dreams, Adorable 1bed 1 bath guest house, Winter Park Getaway, City Guesthouse in beautiful Historic Downtown Sanford, Downtown Lake Eola Historic House 1 OR 2 BED, Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool and Patio