Book Guest Houses in Windermere, FL
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Top Guest Houses in Windermere

Disney Proximity Escape - Comfort in Kissimmee
286 Marcello Blvd Kissimmee FL
An outdoor pool is featured at this guesthouse, along with free WiFi in public areas and express check-out. Luggage storage and a virtual front desk are also provided.
Pool
Free WiFi

Quiet Oasis in Lovely Neighborhood
Orlando FL
$157 nightly
The price is $176 total per night
$176 total
Nov 10 - Nov 11
Total with taxes and fees
A hot tub is featured at this guesthouse, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.
Pool
Hot Tub

Suncrest Residence
1920 Tropical Palms Cir Kissimmee FL
Free Cancellation
Reserve now, pay when you stay
$119 nightly
The price is $135 total per night
$135 total
Nov 8 - Nov 9
Total with taxes and fees
This guesthouse features an outdoor pool, a gym, and a restaurant. Business travelers can take advantage of the free WiFi in public areas. Free self parking, laundry facilities, and a virtual front desk are also on offer.
Pool
Parking included

Downtown Lake Eola Historic House 1 OR 2 BED
Orlando FL
$152 nightly
The price is $170 total per night
$170 total
Nov 9 - Nov 10
Total with taxes and fees
Stay at this guesthouse in Orlando. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Kia Center and Camping World Stadium are located nearby.
Free WiFi
Air conditioning

Mills Cottage by the Little Lake
Orlando FL
$294 nightly
The price is $328 total per night
$328 total
Nov 5 - Nov 6
Total with taxes and fees
This guesthouse features an outdoor pool and a gym. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities. Enjoy the hot tub and conveniences like a garden and barbecue grills.
Pool
Hot Tub

1580 Sandbagger Drive
1580 Sandbagger Dr Four Corners FL
This guesthouse features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the hot tub and perks like free self parking and free WiFi. Laundry facilities are provided for your convenience.
Pool
Hot Tub

Adorable 1bed 1 bath guest house
Orlando FL
This guesthouse features a garden, laundry facilities, and barbecue grills.
Pet friendly
Free WiFi

SmartStay Homes
225 Marcello Boulevard Kissimmee FL
An outdoor pool, free self parking, and laundry facilities are featured at this guesthouse. WiFi in public areas is free. A communal living room and a virtual front desk are also provided.
Pool
Parking included

Blissful Bay
4453 Monado Dr Kissimmee FL
An outdoor pool, free self parking, and laundry facilities are featured at this guesthouse. WiFi in public areas is free. A communal living room is also provided.
Pool
Parking included

Enchanted Fantasy
2622 Calistoga Ave Kissimmee FL
$114 nightly
The price is $129 total per night
$129 total
Nov 5 - Nov 6
Total with taxes and fees
An outdoor pool is featured at this guesthouse, along with free WiFi in public areas and a communal living room. Laundry facilities and a virtual front desk are also provided.
Pool
Free WiFi

SunnyView Residence
6123 Broad Oak Dr Davenport FL
Free Cancellation
Reserve now, pay when you stay
$130 nightly
The price is $146 total per night
$146 total
Nov 5 - Nov 6
Total with taxes and fees
This guesthouse features 2 outdoor pools, a restaurant, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A communal living room, laundry facilities, and a virtual front desk are also on offer.
Pool
Parking included
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.
Top hotels in Windermere

Hyatt Regency Orlando International Airport
9300 Jeff Fuqua Boulevard Orlando FL
$215 nightly
The price is $242 total per night from Nov 25 to Nov 26
$242 total
Nov 25 - Nov 26
Total with taxes and fees
9.4/10 Exceptional! (4,601 reviews)
Windermere Guest Houses essential information
Accommodation | 69 Guest Houses |
|---|---|
Lowest Price | $104 |
Highest Price | $328 |
Popular accommodation | Disney Proximity Escape - Comfort in Kissimmee, Quiet Oasis in Lovely Neighborhood, Suncrest Residence, Downtown Lake Eola Historic House 1 OR 2 BED, Mills Cottage by the Little Lake, 1580 Sandbagger Drive, Adorable 1bed 1 bath guest house, SmartStay Homes, Blissful Bay, Enchanted Fantasy, SunnyView Residence, Mystical Dreams |
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