Compare Windermere Guest House Rentals

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Featured Guest Houses in Windermere

Enchanted Fantasy

Enchanted Fantasy

2 out of 5
2622 Calistoga Ave Kissimmee FL
$110 nightly
The price is $124 total per night
$124 total
May 31 - Jun 1
Total with taxes and fees
At Enchanted Fantasy, guests have access to an outdoor pool, free WiFi in public areas, and microwave in a common area. If you plan to drive, free offsite parking is available. Additional amenities include a refrigerator in a common area, laundry facilities, and a communal living room.
Pool
Free WiFi
Disney Proximity Escape - Comfort in Kissimmee

Disney Proximity Escape - Comfort in Kissimmee

3 out of 5
286 Marcello Blvd Kissimmee FL
Guests of Disney Proximity Escape - Comfort in Kissimmee enjoy features like an outdoor pool, free WiFi in public areas, and express check-out. Limited parking is available. Staff members can answer questions about accommodations, and also provide luggage storage.
Pool
Free WiFi
Quiet Oasis in Lovely Neighborhood

Quiet Oasis in Lovely Neighborhood

Orlando FL
$171 nightly
The price is $190 total per night
$190 total
Jun 3 - Jun 4
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
Tempo Trek Lodgings

Tempo Trek Lodgings

3 out of 5
7324 Oakmoss Loop Davenport FL
$99 nightly
The price is $111 total per night
$111 total
May 29 - May 30
Total with taxes and fees
Guests of Tempo Trek Lodgings enjoy features like an outdoor pool, free WiFi in public areas, and laundry facilities. You can put free parking to good use if you drive. Staff members are on hand to provide luggage storage and access to locker space.
Pool
Parking included
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
Magical Dreams

Magical Dreams

3 out of 5
231 Marcello Blvd Kissimmee FL
$123 nightly
The price is $140 total per night
$140 total
May 29 - May 30
Total with taxes and fees
Guests of Magical Dreams enjoy an outdoor pool, free WiFi in public areas, and microwave in a common area. A stay here includes free parking. Additional amenities include a refrigerator in a common area, laundry facilities, and a TV in a common area.
Pool
Parking included
Harmony Haven

Harmony Haven

2 out of 5
282 Marcello Blvd Kissimmee FL
$113 nightly
The price is $129 total per night
$129 total
May 30 - May 31
Total with taxes and fees
Guests staying at Harmony Haven enjoy an outdoor pool, a gym, and free WiFi in public areas. Additional amenities include a microwave in a common area, a refrigerator in a common area, and laundry facilities.
Pool
Free WiFi
Enchanted Dreams

Enchanted Dreams

3 out of 5
2624 Calistoga Ave Kissimmee FL
$130 nightly
The price is $148 total per night
$148 total
May 29 - May 30
Total with taxes and fees
Enchanted Dreams features an outdoor pool, free WiFi in public areas, and microwave in a common area. A stay here includes free parking. Additional amenities include a refrigerator in a common area, laundry facilities, and a TV in a common area.
Pool
Parking included
1580 Sandbagger Drive

1580 Sandbagger Drive

3 out of 5
1580 Sandbagger Dr Four Corners FL
At 1580 Sandbagger Drive, guests have access to an outdoor pool, free WiFi in public areas, and a hot tub. There's free parking if you drive. This golf guesthouse also has laundry facilities.
Pool
Hot Tub
Don't see what you're looking for?
See all available properties in Windermere
View all properties
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 Windermere

    Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

    Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

    8800 Vistana Centre Dr Orlando FL
    $143 nightly
    The price is $161 total per night from Jun 18 to Jun 19
    $161 total
    Jun 18 - Jun 19
    Total with taxes and fees
    9.2/10 Wonderful! (5,595 reviews)
    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 Jun 15 to Jun 16
    $224 total
    Jun 15 - Jun 16
    Total with taxes and fees
    9.4/10 Exceptional! (4,170 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 31 to Jun 1
    $169 total
    May 31 - Jun 1
    Total with taxes and fees
    9/10 Wonderful! (6,893 reviews)

Windermere Guest Houses essential information

Accommodation
46 Guest Houses
Lowest Price
$111
Highest Price
$224
Popular accommodation
Enchanted Fantasy, Disney Proximity Escape - Comfort in Kissimmee, Quiet Oasis in Lovely Neighborhood, Tempo Trek Lodgings, SPRING LAKE GETAWAY SUITE (Detached Guest House), Magical Dreams, Harmony Haven, Enchanted Dreams, 1580 Sandbagger Drive

More to Explore