Compare Winter Park Guest House Rentals

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Featured Guest Houses in Winter Park

Enchanted Fantasy

Enchanted Fantasy

2 out of 5
2622 Calistoga Ave Kissimmee FL
$102 nightly
The price is $116 total per night
$116 total
May 16 - May 17
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.
Pool
Free WiFi
SPRING LAKE GETAWAY SUITE (Detached Guest House)

SPRING LAKE GETAWAY SUITE (Detached Guest House)

Altamonte Springs FL
At this guesthouse, guests enjoy features like beach towels.
Free WiFi
Air conditioning
Enchanted Dreams

Enchanted Dreams

3 out of 5
2624 Calistoga Ave Kissimmee FL
$120 nightly
The price is $136 total per night
$136 total
Apr 27 - Apr 28
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
Historic lakefront guesthouse

Historic lakefront guesthouse

Orlando FL
$281 nightly
The price is $312 total per night
$312 total
Apr 27 - Apr 28
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.
Pool
Hot Tub
Winter Park Getaway

Winter Park Getaway

Winter Park FL
Guests staying at this guesthouse have access to barbecue grills and a garden.
Free WiFi
Air conditioning
Mills Cottage by the Little Lake

Mills Cottage by the Little Lake

Orlando FL
$328 nightly
The price is $365 total per night
$365 total
May 24 - May 25
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.
Pool
Hot Tub
Downtown Lake Eola Historic House 1 OR 2 BED

Downtown Lake Eola Historic House 1 OR 2 BED

Orlando FL
$170 nightly
The price is $188 total per night
$188 total
Apr 28 - Apr 29
Total with taxes and fees
This guesthouse is a smoke-free guesthouse.
Free WiFi
Air conditioning
Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool and Patio

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

Orlando FL
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
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
At this guesthouse, guests have access to features like local meal delivery service. This smoke-free guesthouse also has a garden.
Free WiFi
Air conditioning
Don't see what you're looking for?
See all available properties in Winter Park
View all properties
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

    Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

    8800 Vistana Centre Dr Orlando FL
    $107 nightly
    The price is $121 total per night from May 18 to May 19
    $121 total
    May 18 - May 19
    Total with taxes and fees
    9.2/10 Wonderful! (5,286 reviews)
    Universal's Cabana Bay Beach Resort

    Universal's Cabana Bay Beach Resort

    6550 Adventure Way Orlando FL
    $133 nightly
    The price is $150 total per night from May 25 to May 26
    $150 total
    May 25 - May 26
    Total with taxes and fees
    9/10 Wonderful! (6,688 reviews)
    Rosen Inn at Pointe Orlando

    Rosen Inn at Pointe Orlando

    9000 International Drive Orlando FL
    $89 nightly
    The price is $100 total per night from Apr 29 to Apr 30
    $100 total
    Apr 29 - Apr 30
    Total with taxes and fees
    8.6/10 Excellent! (6,390 reviews)

Winter Park Guest Houses essential information

Accommodation
28 Guest Houses
Lowest Price
$100
Highest Price
$365
Popular accommodation
Enchanted Fantasy, SPRING LAKE GETAWAY SUITE (Detached Guest House), Enchanted Dreams, Historic lakefront guesthouse, Winter Park Getaway, Mills Cottage by the Little Lake, Downtown Lake Eola Historic House 1 OR 2 BED, Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool and Patio, 2 Minutes to Universal Studios Theme Parks - Central, Relaxing and Chic 1BR

More to Explore