Compare Windermere Guest House Rentals

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Featured Guest Houses in Windermere

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
$172 nightly
The price is $191 total per night
$191 total
Oct 1 - Oct 2
Total with taxes and fees
At this guesthouse, guests have access to a hot tub, laundry facilities, and local meal delivery service. Additional amenities include barbecue grills and a garden.
Pool
Hot Tub
Enchanted Fantasy

Enchanted Fantasy

2 out of 5
2622 Calistoga Ave Kissimmee FL
$103 nightly
The price is $116 total per night
$116 total
Oct 2 - Oct 3
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
Mills Cottage by the Little Lake

Mills Cottage by the Little Lake

Orlando FL
$334 nightly
The price is $371 total per night
$371 total
Oct 4 - Oct 5
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
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
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
SmartStay Homes

SmartStay Homes

3 out of 5
225 Marcello Boulevard Kissimmee FL
$135 nightly
The price is $153 total per night
$153 total
Oct 1 - Oct 2
Total with taxes and fees
Guests of SmartStay Homes enjoy an outdoor pool, free WiFi in public areas, and microwave in a common area. If you drive, take advantage of free parking. Additional amenities include a refrigerator in a common area, laundry facilities, and a communal living room.
Pool
Parking included
Blissful Bay

Blissful Bay

3 out of 5
4453 Monado Dr Kissimmee FL
At Blissful Bay, guests have access to an outdoor pool, free WiFi in public areas, and microwave in a common area. There's free parking if you drive. Additional amenities include a refrigerator in a common area, laundry facilities, and a TV in a common area.
Pool
Parking included
Tempo Trek Lodgings

Tempo Trek Lodgings

3 out of 5
7324 Oakmoss Loop Davenport FL
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
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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 Windermere

    Hyatt Regency Orlando International Airport

    Hyatt Regency Orlando International Airport

    9300 Jeff Fuqua Boulevard Orlando FL
    $222 nightly
    The price is $250 total per night from Oct 26 to Oct 27
    $250 total
    Oct 26 - Oct 27
    Total with taxes and fees
    9.4/10 Exceptional! (4,495 reviews)
    Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

    Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

    8800 Vistana Centre Dr Orlando FL
    $137 nightly
    The price is $154 total per night from Oct 27 to Oct 28
    $154 total
    Oct 27 - Oct 28
    Total with taxes and fees
    9.2/10 Wonderful! (6,893 reviews)
    Marriott's Grande Vista

    Marriott's Grande Vista

    5925 Avenida Vista Orlando FL
    $96 nightly
    The price is $108 total per night from Oct 27 to Oct 28
    $108 total
    Oct 27 - Oct 28
    Total with taxes and fees
    9/10 Wonderful! (5,073 reviews)

Windermere Guest Houses essential information

Accommodation
65 Guest Houses
Lowest Price
$108
Highest Price
$371
Popular accommodation
Disney Proximity Escape - Comfort in Kissimmee, Quiet Oasis in Lovely Neighborhood, Enchanted Fantasy, Mills Cottage by the Little Lake, 1580 Sandbagger Drive, Adorable 1bed 1 bath guest house, SmartStay Homes, Blissful Bay, Tempo Trek Lodgings

More to Explore