Compare Winter Park Guest House Rentals

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Featured Guest Houses in Winter Park

Enchanted Fantasy

Enchanted Fantasy

2 out of 5
2622 Calistoga Ave Kissimmee FL
$103 nightly
The price is $117 total per night
$117 total
May 7 - May 8
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
May 1 - May 2
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
$286 nightly
The price is $317 total per night
$317 total
May 11 - May 12
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
$320 nightly
The price is $357 total per night
$357 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
May 4 - May 5
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
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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

    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 20 to May 21
    $121 total
    May 20 - May 21
    Total with taxes and fees
    9.2/10 Wonderful! (5,325 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 31 to Jun 1
    $150 total
    May 31 - Jun 1
    Total with taxes and fees
    9/10 Wonderful! (6,727 reviews)
    DoubleTree by Hilton at the Entrance to Universal Orlando

    DoubleTree by Hilton at the Entrance to Universal Orlando

    5780 Major Blvd Orlando FL
    $89 nightly
    The price is $101 total per night from May 25 to May 26
    $101 total
    May 25 - May 26
    Total with taxes and fees
    8.4/10 Very Good! (6,893 reviews)

Winter Park Guest Houses essential information

Accommodation
28 Guest Houses
Lowest Price
$101
Highest Price
$357
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