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
Oct 10 - Oct 11
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)

At this guesthouse, guests enjoy features like beach towels.
Free WiFi
Air conditioning
Adorable 1bed 1 bath guest house

Adorable 1bed 1 bath guest house

Guests staying at this guesthouse have access to laundry facilities, a garden, and barbecue grills.
Pet friendly
Free WiFi
Winter Park Getaway

Winter Park Getaway

Guests staying at this guesthouse have access to a garden and barbecue grills.
Free WiFi
Air conditioning
Downtown Orlando Throne Historic Thornton Park

Downtown Orlando Throne Historic Thornton Park

$200 nightly
The price is $222 total per night
$222 total
Oct 6 - Oct 7
Total with taxes and fees
At this guesthouse, guests have access to features like laundry facilities.
Air conditioning
Parking available
 Peaceful Two Bedroom Guest House near Wekiva River and State Parks 

 Peaceful Two Bedroom Guest House near Wekiva River and State Parks 

At this guesthouse, guests have access to features like laundry facilities. This guesthouse also has barbecue grills.
Pet friendly
Free WiFi
Mills Cottage by the Little Lake

Mills Cottage by the Little Lake

$300 nightly
The price is $333 total per night
$333 total
Oct 6 - Oct 7
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

$260 nightly
The price is $289 total per night
$289 total
Oct 8 - Oct 9
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, barbecue grills, and a garden.
Pool
Hot Tub
Downtown Lake Eola Historic House 1 OR 2 BED

Downtown Lake Eola Historic House 1 OR 2 BED

$147 nightly
The price is $162 total per night
$162 total
Oct 5 - Oct 6
Total with taxes and fees
This guesthouse is a smoke-free guesthouse.
Air conditioning
Parking available
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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

    Hyatt Regency Orlando International Airport

    Hyatt Regency Orlando International Airport

    9300 Jeff Fuqua Boulevard, Orlando, FL
    $179 nightly
    The price is $201 total per night from Oct 6 to Oct 7
    $201 total
    Oct 6 - Oct 7
    Total with taxes and fees
    9.4/10 Exceptional! (3,642 reviews)
    Universal's Cabana Bay Beach Resort

    Universal's Cabana Bay Beach Resort

    6550 Adventure Way, Orlando, FL
    $138 nightly
    The price is $155 total per night from Nov 4 to Nov 5
    $155 total
    Nov 4 - Nov 5
    Total with taxes and fees
    8.8/10 Excellent! (5,343 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 $100 total per night from Nov 2 to Nov 3
    $100 total
    Nov 2 - Nov 3
    Total with taxes and fees
    8.4/10 Very Good! (6,687 reviews)

Winter Springs Guest Houses essential information

Accommodation
24 Guest Houses
Lowest Price
$100
Highest Price
$333
Popular accommodation
The Ann Stevens House, SPRING LAKE GETAWAY SUITE (Detached Guest House), Adorable 1bed 1 bath guest house, Winter Park Getaway, Downtown Orlando Throne Historic Thornton Park,  Peaceful Two Bedroom Guest House near Wekiva River and State Parks , Mills Cottage by the Little Lake, Historic lakefront guesthouse, Downtown Lake Eola Historic House 1 OR 2 BED

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