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
Leisure Lounge
6024 Broad Oak Dr Davenport FL
$110 nightly
The price is $123 total per night
$123 total
Apr 16 - Apr 17
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 is also provided.
Pool
Kitchen
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
Enchanted Fantasy
2622 Calistoga Ave Kissimmee FL
$101 nightly
The price is $115 total per night
$115 total
May 1 - May 2
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
Kitchen
Jade Manor
6122 Broad Oak Dr Davenport FL
$111 nightly
The price is $124 total per night
$124 total
Apr 16 - Apr 17
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
Kitchen
Oasis Private Ensuite Room Shared Home
227 Marcello Blvd Kissimmee FL
$122 nightly
The price is $139 total per night
$139 total
May 16 - May 17
Total with taxes and fees
This guesthouse features 2 outdoor pools, free WiFi in public areas, and a communal living room. Laundry facilities and a virtual front desk are also provided.
Pool
Kitchen
Enchanted Dreams
2624 Calistoga Ave Kissimmee FL
$120 nightly
The price is $136 total per night
$136 total
Apr 16 - Apr 17
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
Kitchen
Harmony Haven
282 Marcello Blvd Kissimmee FL
$104 nightly
The price is $117 total per night
$117 total
Apr 20 - Apr 21
Total with taxes and fees
This guesthouse features an outdoor pool and a gym. WiFi in public areas is free. A communal living room, laundry facilities, and a virtual front desk are also on offer.
Pool
Kitchen
Mills Cottage by the Little Lake
Orlando FL
$337 nightly
The price is $374 total per night
$374 total
Apr 16 - Apr 17
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
Magical Dreams
231 Marcello Blvd Kissimmee FL
$111 nightly
The price is $126 total per night
$126 total
May 1 - May 2
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
Kitchen
Tempo Trek Lodgings
7324 Oakmoss Loop Davenport FL
$94 nightly
The price is $105 total per night
$105 total
Apr 30 - May 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
Kitchen
Downtown Lake Eola Historic House 1 OR 2 BED
Orlando FL
$175 nightly
The price is $195 total per night
$195 total
Apr 20 - Apr 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
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
$249 nightly
The price is $280 total per night from Apr 26 to Apr 27
$280 total
Apr 26 - Apr 27
Total with taxes and fees
9.4/10 Exceptional! (4,123 reviews)
Windermere Guest Houses essential information
Accommodation | 58 Guest Houses |
|---|---|
Lowest Price | $105 |
Highest Price | $374 |
Popular accommodation | Leisure Lounge, Disney Proximity Escape - Comfort in Kissimmee, Enchanted Fantasy, Jade Manor, Oasis Private Ensuite Room Shared Home, Enchanted Dreams, Harmony Haven, Mills Cottage by the Little Lake, Magical Dreams, Tempo Trek Lodgings, Downtown Lake Eola Historic House 1 OR 2 BED, Adorable 1bed 1 bath guest house |
More ways to wander Windermere
Explore More Ways to Travel with Travelocity
- All Inclusive Resorts & in Bay Hill
- Golf Resorts & in Bay Hill
- Bay Hill Hotels
- Hotels near Bill Frederick Park
- B&B in Polk City
- Cabins in Polk City
- Extended Stay Hotels in Polk City
- Vacation Homes in Polk City
- Hotels near Arnold Palmer's Bay Hill Golf Club
- Apartments in Winter Garden
- Hotels near Orlando Intl.
- Hotels near MetroWest Golf Club
- Farmstay in Ocoee
- B&B in Ocoee
- Cabins in Ocoee
- Condo Resorts in Ocoee
- Condos in Ocoee
- Extended Stay Hotels in Ocoee
- Guest Houses in Ocoee
- Hostels in Ocoee
- Houseboats in Ocoee
- Motels in Ocoee
- Vacation Homes in Ocoee
- Rv Parks in Ocoee
- Resorts in Ocoee
- Town Houses in Ocoee
- Villas in Ocoee
- Apartments in Parrish
- B&B in Parrish
- Cabins in Parrish
- Condos in Parrish
- Cottages in Parrish
- Extended Stay Hotels in Parrish
- Guest Houses in Parrish
- Motels in Parrish
- Rv Parks in Parrish
- Villas in Parrish
- Hotels near Orange Tree Golf Club
- Cottages in Black Jack Island
- Rv Parks in Black Jack Island
- Hotels near Universal’s Islands of Adventure
- Condos in Orlando
- Extended Stay Hotels in Orlando
- All Inclusive Resorts & in Orlando
- Hotels with Free Airport Shuttle in Orlando
- Orlando Hotels
- Hotels near Universal’s Volcano Bay
- Hotels near Universal Studios Florida
- Hotels near Walt Disney World® Resort
- Downtown Orlando Hotels
- 5 Star Hotels in Gotha
- Farmstay in Gotha
- Cabins in Gotha
- Condos in Gotha
- Cottages in Gotha
- Hilton Hotels in Gotha
- Gotha Hotels
- Motels in Gotha
- Town Houses in Gotha
- Villas in Gotha
- Apartments in Pinellas Park
- Holiday Park Resorts in Pinellas Park
- Hostels in Pinellas Park
- Inns in Pinellas Park
- Motels in Pinellas Park
- Vacation Homes in Pinellas Park
- Resorts in Pinellas Park
- Villas in Pinellas Park
- Farmstay in Southwest Orlando
- Apartments in Southwest Orlando
- Extended Stay Hotels in Southwest Orlando
- Guest Houses in Southwest Orlando
- Motels in Southwest Orlando
- Hotels near Isleworth Golf and Country Club
- Hotels near Lake Butler
- Jetblue Airways Boston (BOS) to Orlando (MCO) flights
- Flights from Atlanta (ATL) to Orlando (MCO)
- Flights from Dallas (DFW) to Orlando (MCO)
- Flights from Detroit (DTW) to Orlando (MCO)
- Flights from Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
- Flights from New York (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)
- Flights to Florida
- Flights to Orlando
- Flights to Gotha
- 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