Search Guest Houses in Winter Springs

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Next weekend
Dec 19 - Dec 21
In two weeks
Dec 26 - Dec 28
In one month
Jan 9 - Jan 11
In two months
Feb 6 - Feb 8

Our top choices for Winter Springs guest houses

Fridge, microwave, coffee/tea maker, cookware/dishes/utensils
Downtown Lake Eola Historic House 1 OR 2 BED

Downtown Lake Eola Historic House 1 OR 2 BED

Downtown Orlando
9.0 out of 10, Wonderful, (34)
"We had a fantastic stay! It is very close to local eateries and entertainment. And the hosts were lovely. "
United States
Alexandra
$129 nightly
The price is $142
Dec 15 - Dec 16
Total with taxes and fees
Downtown Lake Eola Historic House 1 OR 2 BED
Desk, iron/ironing board, WiFi
Love Nest Studio nearby highways and Airport

Love Nest Studio nearby highways and Airport

Orlando
$127 nightly
The price is $127
Jan 5 - Jan 6, 2026
Total with taxes and fees
Love Nest Studio nearby highways and Airport
Outdoor pool, a heated pool
Mills Cottage by the Little Lake

Mills Cottage by the Little Lake

Lake Weldona
10.0 out of 10, Exceptional, (49)
"Super charming "
United States
Lucas
$289 nightly
The price is $321
Dec 11 - Dec 12
Total with taxes and fees
Mills Cottage by the Little Lake
Outdoor pool, a heated pool
Historic lakefront guesthouse

Historic lakefront guesthouse

Orlando
10.0 out of 10, Exceptional, (9)
"Had ana amazing time! The owner is very responsive and the place was a total vibe "
United States
Jonathan O.
$240 nightly
The price is $266
Dec 16 - Dec 17
Total with taxes and fees
Historic lakefront guesthouse
Exterior
The Ann Stevens House

The Ann Stevens House

3.0 star property
Lake Helen
9.4 out of 10, Exceptional, (162)
"This house is wonderful and the management makes the stay memorable. "
United States
Glenda
$139 nightly
The price is $156
Dec 12 - Dec 13
Total with taxes and fees
The Ann Stevens House
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.
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Top Winter Springs Hotel Reviews

Wyndham Garden Orlando Airport

Wyndham Garden Orlando Airport

10/10 Excellent
"All good!"
Eileen 1-night trip
Posted 1 day ago
Wyndham Garden Orlando Airport

Find out more about Winter Springs

Winter Springs Guest Houses information

Number of reviews
252
Accommodation
24 Guest Houses
Lowest Price
$127
Highest Price
$321

Frequently asked questions

What is the nightly rate for a guest house in Winter Springs?
Rates for Winter Springs guest houses vary, but travelers can find great-value prices from $127 with Expedia. A range of factors can affect nightly rates, such as the location, the breakfast offering, and the range of amenities. Travelers looking for a good deal should consider looking for a midweek stay, as weekend rates at Winter Springs guest houses tend to be higher. Remember to also use our filters to sort prices from low to high.
What's the difference between a Winter Springs guest house and a B&B?
A guest house in Winter Springs is typically a larger establishment with more rooms, offering a more hotel-like experience, and may provide additional amenities including luxury bedding. In contrast, a B&B is usually a smaller property that focuses primarily on providing a room and breakfast. A B&B is often more personal, and breakfast is typically included as part of the stay, but other services might be more limited compared to a guest house.

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