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
Mystical Dreams

Mystical Dreams

3 out of 5
2626 Calistoga Ave Kissimmee FL
$114 nightly
The price is $130 total per night
$130 total
Jul 13 - Jul 14
Total with taxes and fees
Guests of Mystical Dreams enjoy features like 2 outdoor pools, 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
SmartStay Homes

SmartStay Homes

3 out of 5
225 Marcello Boulevard Kissimmee FL
$138 nightly
The price is $157 total per night
$157 total
Jul 13 - Jul 14
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 TV in a common area.
Pool
Parking included
Quiet Oasis in Lovely Neighborhood

Quiet Oasis in Lovely Neighborhood

Orlando FL
$178 nightly
The price is $197 total per night
$197 total
Jul 15 - Jul 16
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 $110 total per night
$110 total
Jul 13 - Jul 14
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
Affordable Stays Kissimmee

Affordable Stays Kissimmee

3 out of 5
266 Marcello Blvd Kissimmee FL
$124 nightly
The price is $141 total per night
$141 total
Aug 10 - Aug 11
Total with taxes and fees
Guests of Affordable Stays Kissimmee enjoy an outdoor pool, free WiFi in public areas, and microwave in a common area. Free parking is available if you drive. Additional amenities include a refrigerator in a common area, laundry facilities, and a communal living room.
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
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
Mills Cottage by the Little Lake

Mills Cottage by the Little Lake

Orlando FL
$363 nightly
The price is $403 total per night
$403 total
Jul 13 - Jul 14
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 Windermere

    Hyatt Regency Orlando International Airport

    Hyatt Regency Orlando International Airport

    9300 Jeff Fuqua Boulevard Orlando FL
    $187 nightly
    The price is $210 total per night from Aug 3 to Aug 4
    $210 total
    Aug 3 - Aug 4
    Total with taxes and fees
    9.4/10 Exceptional! (4,331 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 Aug 3 to Aug 4
    $154 total
    Aug 3 - Aug 4
    Total with taxes and fees
    9.2/10 Wonderful! (6,088 reviews)
    The Grove Resort & Water Park Orlando

    The Grove Resort & Water Park Orlando

    14501 Grove Resort Avenue Winter Garden FL
    $224 nightly
    The price is $252 total per night from Aug 11 to Aug 12
    $252 total
    Aug 11 - Aug 12
    Total with taxes and fees
    8/10 Very Good! (10,428 reviews)

Windermere Guest Houses essential information

Accommodation
67 Guest Houses
Lowest Price
$110
Highest Price
$403
Popular accommodation
Disney Proximity Escape - Comfort in Kissimmee, Mystical Dreams, SmartStay Homes, Quiet Oasis in Lovely Neighborhood, Tempo Trek Lodgings, Affordable Stays Kissimmee, 1580 Sandbagger Drive, Blissful Bay, Mills Cottage by the Little Lake

More to Explore