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
Free Cancellation
Reserve now, pay when you stay
$139 nightly
The price is $156 total per night
$156 total
Feb 20 - Feb 21
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
$132 nightly
The price is $146 total per night
$146 total
Feb 26 - Feb 27
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
$318 nightly
The price is $353 total per night
$353 total
Feb 23 - Feb 24
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
$260 nightly
The price is $290 total per night
$290 total
Feb 24 - Feb 25
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
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
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

    DoubleTree by Hilton at the Entrance to Universal Orlando

    DoubleTree by Hilton at the Entrance to Universal Orlando

    5780 Major Blvd Orlando FL
    $106 nightly
    The price is $119 total per night from Mar 9 to Mar 10
    $119 total
    Mar 9 - Mar 10
    Total with taxes and fees
    8.4/10 Very Good! (6,887 reviews)
    Universal's Cabana Bay Beach Resort

    Universal's Cabana Bay Beach Resort

    6550 Adventure Way Orlando FL
    $157 nightly
    The price is $177 total per night from Mar 4 to Mar 5
    $177 total
    Mar 4 - Mar 5
    Total with taxes and fees
    9/10 Wonderful! (6,343 reviews)
    Sonesta Essential Orlando Airport

    Sonesta Essential Orlando Airport

    8101 Aircenter Ct Orlando FL
    $101 nightly
    The price is $114 total per night from Feb 24 to Feb 25
    $114 total
    Feb 24 - Feb 25
    Total with taxes and fees
    8/10 Very Good! (582 reviews)

Winter Springs Guest Houses essential information

Accommodation
23 Guest Houses
Lowest Price
$114
Highest Price
$353
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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