Compare Winter Springs Guest House Rentals

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Featured Guest Houses in Winter Springs

The Ann Stevens House

The Ann Stevens House

3 out of 5
201 E Kicklighter Rd Lake Helen FL
$159 nightly
The price is $179 total per night
$179 total
Jan 5 - Jan 6
Total with taxes and fees
A local mainstay since 1895, The Ann Stevens House offers free WiFi in public areas, express check-out, and a terrace. If you drive, take advantage of free parking. Friendly staff can provide tour or ticket assistance, and also offer advice about sightseeing. This guesthouse also has a garden.
Parking included
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
Downtown Lake Eola Historic House 1 OR 2 BED

Downtown Lake Eola Historic House 1 OR 2 BED

Orlando FL
$114 nightly
The price is $126 total per night
$126 total
Jan 4 - Jan 5
Total with taxes and fees
This guesthouse is a smoke-free guesthouse.
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
Mills Cottage by the Little Lake

Mills Cottage by the Little Lake

Orlando FL
$306 nightly
The price is $339 total per night
$339 total
Jan 5 - Jan 6
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
Historic lakefront guesthouse

Historic lakefront guesthouse

Orlando FL
$274 nightly
The price is $304 total per night
$304 total
Feb 1 - Feb 2
Total with taxes and fees
Guests staying at this guesthouse enjoy access to a water park, an outdoor pool, and a hot tub. Other amenities at this family-friendly guesthouse include laundry facilities, a garden, and barbecue grills.
Pool
Hot Tub
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
Guests of this guesthouse enjoy access to a water park, local meal delivery service, and a garden.
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
 Peaceful Two Bedroom Guest House near Wekiva River and State Parks 

 Peaceful Two Bedroom Guest House near Wekiva River and State Parks 

Sorrento FL
At this guesthouse, guests have access to features like laundry facilities. This guesthouse also has barbecue grills.
Pet friendly
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 Springs

    Wyndham I-Drive Avanti Resort & Conference Center

    Wyndham I-Drive Avanti Resort & Conference Center

    6515 International Drive Orlando FL
    $80 nightly
    The price is $90 total per night from Jan 5 to Jan 6
    $90 total
    Jan 5 - Jan 6
    Total with taxes and fees
    7.2/10 Good! (3,946 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 Jan 6 to Jan 7
    $150 total
    Jan 6 - Jan 7
    Total with taxes and fees
    8.8/10 Excellent! (5,897 reviews)
    Rosen Inn at Pointe Orlando

    Rosen Inn at Pointe Orlando

    9000 International Drive Orlando FL
    $73 nightly
    The price is $83 total per night from Jan 28 to Jan 29
    $83 total
    Jan 28 - Jan 29
    Total with taxes and fees
    8.4/10 Very Good! (5,475 reviews)

Winter Springs Guest Houses essential information

Accommodation
23 Guest Houses
Lowest Price
$83
Highest Price
$339
Popular accommodation
The Ann Stevens House, SPRING LAKE GETAWAY SUITE (Detached Guest House), Downtown Lake Eola Historic House 1 OR 2 BED, Winter Park Getaway, Mills Cottage by the Little Lake, Historic lakefront guesthouse, 2 Minutes to Universal Studios Theme Parks - Central, Relaxing and Chic 1BR, Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool and Patio,  Peaceful Two Bedroom Guest House near Wekiva River and State Parks 

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