Compare Winter Springs Guest House Rentals
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Featured Guest Houses in Winter Springs

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)
Altamonte Springs FL
At this guesthouse, guests enjoy features like beach towels.
Free WiFi
Air conditioning

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 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
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
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
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
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
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
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
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
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
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 |
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