Book Guest Houses in Windermere, FL
Seize Your Someday with our amazing deals for the whole family!
Save an extra 10% or more on select hotels with Member Discounts
Access exclusive hotel deals, only with the Travelocity app
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
Tempo Trek Lodgings
7324 Oakmoss Loop Davenport FL
$103 nightly
The price is $116 total per night
$116 total
Sep 30 - Oct 1
Total with taxes and fees
An outdoor pool, free self parking, and laundry facilities are featured at this guesthouse. WiFi in public areas is free. Luggage storage, locker space, and a virtual front desk are also on offer.
Pool
Parking included
Serenity Dreams
6120 Broad Oak Dr Davenport FL
$122 nightly
The price is $137 total per night
$137 total
Oct 20 - Oct 21
Total with taxes and fees
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
Mystical Dreams
2626 Calistoga Ave Kissimmee FL
This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A communal living room, laundry facilities, and a virtual front desk are also on offer.
Pool
Parking included
Quiet Oasis in Lovely Neighborhood
Orlando FL
$171 nightly
The price is $190 total per night
$190 total
Sep 28 - Sep 29
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
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
$137 nightly
The price is $156 total per night
$156 total
Sep 27 - Sep 28
Total with taxes and fees
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
Downtown Lake Eola Historic House 1 OR 2 BED
Orlando FL
$147 nightly
The price is $163 total per night
$163 total
Sep 20 - Sep 21
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
$302 nightly
The price is $335 total per night
$335 total
Sep 20 - Sep 21
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
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
Universal's Endless Summer Resort - Dockside Inn and Suites
7125 Universal Boulevard Orlando FL
$141 nightly
The price is $159 total per night from Sep 28 to Sep 29
$159 total
Sep 28 - Sep 29
Total with taxes and fees
9.2/10 Wonderful! (5,711 reviews)
Windermere Guest Houses essential information
Accommodation | 65 Guest Houses |
|---|---|
Lowest Price | $108 |
Highest Price | $341 |
Popular accommodation | Disney Proximity Escape - Comfort in Kissimmee, Tempo Trek Lodgings, Serenity Dreams, Mystical Dreams, Quiet Oasis in Lovely Neighborhood, 1580 Sandbagger Drive, Adorable 1bed 1 bath guest house, SmartStay Homes, Blissful Bay, Downtown Lake Eola Historic House 1 OR 2 BED, Mills Cottage by the Little Lake, Historic lakefront guesthouse |
More ways to wander Windermere
Explore More Ways to Travel with Travelocity
- Motels in Winter Garden
- Aparthotels in Winter Garden
- Caravanparks in Windermere
- Resorts in Windermere
- Motels in Windermere
- Hostels in Windermere
- Aparthotels in Windermere
- Cottages in Windermere
- Bedandbreakfast in Windermere
- Apartments in Windermere
- Agritourism in Windermere
- Hotels near Walt Disney World Resort
- Hotels near Universal s Volcano Bay
- Hotels near Universal Studios Florida
- Hotels near Universal Orlando Resort
- Hotels near Universal CityWalk
- Villas in Orlando
- Townhouses in Orlando
- Hotels near Orlando FL
- Resorts in Orlando
- Residences in Orlando
- Privatevacationhomes in Orlando
- Motels in Orlando
- Hotels near Orlando FL
- Inns in Orlando
- Hotels in Orlando
- Westgate Vacation Villas Resort
- Waterpark in Orlando
- Walt Disney World Swan
- Walt Disney World Swan Reserve
- Walt Disney World Dolphin
- The Grove Resort & Water Park Orlando
- Apartments in Altamonte Springs
- Cottages in Altamonte Springs
- Guesthouses in Altamonte Springs
- Villas in Altamonte Springs
- Cottages in Casselberry
- Agritourism in Celebration
- Condominiumresort in Celebration
- Hotels near Disney Springs
- Hotels near Disney's Animal Kingdom Theme Park
- Resorts in Disney's Boardwalk
- Hotels near Disney's Hollywood Studios
- Hotels near Florida Mall
- Residences in Florida
- Hotels near Kia Center
- Aparthotels in Kissimmee
- Hotels in Kissimmee
- Motels in Kissimmee
- Resorts in Kissimmee
- Condos in Lake Buena Vista
- Resorts in Lake Buena Vista
- Hotels near Magic Kingdom Park
- Cabins in Maitland
- Condos in Maitland
- Cottages in Maitland
- Caravanparks in Maitland
- Aparthotels in Ocoee
- Motels in Ocoee
- Agritourism in Orange County
- Hotels near Orange County Convention Center
- Bedandbreakfast in Orlando
- Condos in Orlando
- Cottages in Orlando
- Aparthotels in Orlando
- Hostels in Orlando
- Adults Only in Orlando
- All-Inclusive in Orlando
- Drury Plaza Hotel Orlando - Disney Springs Area
- Gaylord Palms Resort & Convention Center
- Free Airport Transportation in Orlando
- Hot Tub in Orlando
- Hilton Vacation Club Aqua Sol Orlando West
- Margaritaville Cottages Orlando by Vstays with H2O Waterpark
- Margaritaville Resort Orlando with H2O Waterpark
- Caravanparks in Winter Park
- Houseboats in Winter Park
- Cottages in Winter Park
- Condos in Winter Park
- Agritourism in Winter Park
- Resorts in Winter Garden
- Flights to Orlando
- Flights to Florida
- JetBlue Airways Boston (BOS) to Orlando (MCO) flights
- Flights from Windsor Locks (BDL) to Orlando (MCO)
- Flights from Baltimore (BWI) to Orlando (MCO)
- Flights from Dallas (DFW) to Orlando (MCO)
- Flights from Newark (EWR) to Orlando (MCO)
- Flights from Jamaica (JFK) to Orlando (MCO)
- Flights from Los Angeles (LAX) to Orlando (MCO)
- Flights from Chicago (ORD) to Orlando (MCO)
- Flights from Philadelphia (PHL) to Orlando (MCO)
- Visit Walt Disney World® Resort
- Cheap Hotels in Orlando
- Hotels near Orange County Convention Center
- Hotels near Universal Studios Florida
- Car rentals at Orlando Airport (MCO)
- Flights to Orlando
- Hotels near Walt Disney World® Resort
- Hotels near Universal CityWalk
- Resorts in Orlando
- Hotels near Universal’s Islands of Adventure
- Hotels in International Drive
- Flights to Florida
- Visit Universal Orlando Resort
- Car rentals in Orlando
- Visit Universal Studios Florida
- Hotels near Universal Orlando Resort
- Visit The Wizarding World of Harry Potter™
- Orlando vacations
- Hotels in Orlando
- Hotels near Universal’s Volcano Bay