Compare Winter Springs Guest House Rentals

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Featured Guest Houses in Winter Springs

Quiet Oasis in Lovely Neighborhood

Quiet Oasis in Lovely Neighborhood

Orlando FL
$171 nightly
The price is $190 total per night
$190 total
May 25 - May 26
Total with taxes and fees
At this guesthouse, guests have access to a hot tub, laundry facilities, and local meal delivery service. This smoke-free guesthouse also has a garden.
Pool
Hot Tub
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
Adorable 1bed 1 bath guest house

Adorable 1bed 1 bath guest house

Orlando FL
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

Winter Park FL
Guests staying at this guesthouse have access to a garden and barbecue grills.
Free WiFi
Air conditioning
City Guesthouse in beautiful Historic Downtown Sanford

City Guesthouse in beautiful Historic Downtown Sanford

Sanford FL
$228 nightly
The price is $252 total per night
$252 total
May 24 - May 25
Total with taxes and fees
This guesthouse is a smoke-free guesthouse.
Air conditioning
Parking available
Downtown Lake Eola Historic House 1 OR 2 BED

Downtown Lake Eola Historic House 1 OR 2 BED

Orlando FL
$166 nightly
The price is $184 total per night
$184 total
May 26 - May 27
Total with taxes and fees
This guesthouse is a smoke-free guesthouse.
Free WiFi
Air conditioning
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
May 29 - May 30
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
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
Mills Cottage by the Little Lake

Mills Cottage by the Little Lake

Orlando FL
$326 nightly
The price is $362 total per night
$362 total
May 25 - May 26
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
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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
    $199 nightly
    The price is $224 total per night from May 25 to May 26
    $224 total
    May 25 - May 26
    Total with taxes and fees
    9.4/10 Exceptional! (4,166 reviews)
    Universal's Cabana Bay Beach Resort

    Universal's Cabana Bay Beach Resort

    6550 Adventure Way Orlando FL
    $150 nightly
    The price is $169 total per night from May 25 to May 26
    $169 total
    May 25 - May 26
    Total with taxes and fees
    9/10 Wonderful! (6,824 reviews)
    DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel

    DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel

    7400 Canada Ave Orlando FL
    $83 nightly
    The price is $93 total per night from Jun 1 to Jun 2
    $93 total
    Jun 1 - Jun 2
    Total with taxes and fees
    8.6/10 Excellent! (1,439 reviews)

Winter Springs Guest Houses essential information

Accommodation
23 Guest Houses
Lowest Price
$93
Highest Price
$362
Popular accommodation
Quiet Oasis in Lovely Neighborhood, SPRING LAKE GETAWAY SUITE (Detached Guest House), Adorable 1bed 1 bath guest house, Winter Park Getaway, City Guesthouse in beautiful Historic Downtown Sanford, Downtown Lake Eola Historic House 1 OR 2 BED, The Ann Stevens House, Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool and Patio, Mills Cottage by the Little Lake

More to Explore