Compare Winter Park Guest House Rentals

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Featured Guest Houses in Winter Park

Mills Cottage by the Little Lake

Mills Cottage by the Little Lake

Orlando FL
$343 nightly
The price is $381 total per night
$381 total
Apr 2 - Apr 3
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
$141 nightly
The price is $156 total per night
$156 total
Mar 19 - Mar 20
Total with taxes and fees
This guesthouse is a smoke-free guesthouse.
Free WiFi
Air conditioning
Adorable 1bed 1 bath guest house

Adorable 1bed 1 bath guest house

Orlando FL
Guests staying at this guesthouse have access to laundry facilities, barbecue grills, and a garden.
Pet friendly
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
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
Historic lakefront guesthouse

Historic lakefront guesthouse

Orlando FL
$255 nightly
The price is $285 total per night
$285 total
Apr 6 - Apr 7
Total with taxes and fees
Guests of this guesthouse enjoy features like an outdoor pool, a hot tub, and laundry facilities. Additional amenities include barbecue grills and a garden.
Pool
Hot Tub
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
Cozy 1BR apt-Pool/Tennis/Gym/Near attractions

Cozy 1BR apt-Pool/Tennis/Gym/Near attractions

Kissimmee FL
$186 nightly
The price is $208 total per night
$208 total
Mar 19 - Mar 20
Total with taxes and fees
At this guesthouse, guests enjoy features like an outdoor pool, a gym, and a hot tub. This guesthouse also has laundry facilities.
Pool
Hot Tub
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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
    $147 nightly
    The price is $166 total per night from Apr 10 to Apr 11
    $166 total
    Apr 10 - Apr 11
    Total with taxes and fees
    9.2/10 Wonderful! (4,869 reviews)
    Hyatt Regency Orlando International Airport

    Hyatt Regency Orlando International Airport

    9300 Jeff Fuqua Boulevard Orlando FL
    $229 nightly
    The price is $258 total per night from Mar 16 to Mar 17
    $258 total
    Mar 16 - Mar 17
    Total with taxes and fees
    9.4/10 Exceptional! (4,053 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 Apr 12 to Apr 13
    $150 total
    Apr 12 - Apr 13
    Total with taxes and fees

Winter Park Guest Houses essential information

Accommodation
26 Guest Houses
Lowest Price
$150
Highest Price
$381
Popular accommodation
Mills Cottage by the Little Lake, Downtown Lake Eola Historic House 1 OR 2 BED, Adorable 1bed 1 bath guest house, SPRING LAKE GETAWAY SUITE (Detached Guest House), Winter Park Getaway, Historic lakefront guesthouse, Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool and Patio, 2 Minutes to Universal Studios Theme Parks - Central, Relaxing and Chic 1BR, Cozy 1BR apt-Pool/Tennis/Gym/Near attractions

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