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
SPRING LAKE GETAWAY SUITE (Detached Guest House)
Altamonte Springs FL
Stay at this guesthouse in Altamonte Springs. Enjoy free WiFi, balconies, and cable/satellite TV service. Our guests praise the helpful staff in our reviews. Popular attractions Cranes Roost Park and RDV Sportsplex are located nearby.
Free WiFi
Air conditioning
Downtown Lake Eola Historic House 1 OR 2 BED
Orlando FL
$129 nightly
The price is $142 total per night
$142 total
Jan 27 - Jan 28
Total with taxes and fees
Stay at this guesthouse in Orlando. Enjoy patios, an in-room coffeemaker, and air conditioning. Popular attractions Kia Center and Camping World Stadium are located nearby.
Free WiFi
Air conditioning
Winter Park Getaway
Winter Park FL
This guesthouse includes a garden and barbecue grills.
Free WiFi
Air conditioning
Mills Cottage by the Little Lake
Orlando FL
$308 nightly
The price is $341 total per night
$341 total
Jan 12 - Jan 13
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
Historic lakefront guesthouse
Orlando FL
$270 nightly
The price is $300 total per night
$300 total
Feb 1 - Feb 2
Total with taxes and fees
A water park and an outdoor pool are featured at this smoke-free guesthouse. Families will appreciate the playground and onsite laundry facilities. Enjoy the hot tub and conveniences like a garden and barbecue grills.
Pool
Hot Tub
2 Minutes to Universal Studios Theme Parks - Central, Relaxing and Chic 1BR
Orlando FL
This guesthouse features a water park and a garden.
Free WiFi
Air conditioning
Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool and Patio
Orlando FL
An outdoor pool is featured at this guesthouse, along with free WiFi in public areas and a garden. A library is also provided.
Pool
Free WiFi
Adorable 1bed 1 bath guest house
Orlando FL
This guesthouse features a garden, laundry facilities, and barbecue grills.
Pet friendly
Free WiFi
Resort-style 3BR Townhouse Near Disney Park
Davenport FL
Stay at this guesthouse in Davenport. Enjoy an in-room coffeemaker. Popular attractions Disney's Animal Kingdom® Theme Park and Mystic Dunes Golf Club are located nearby.
Pet friendly
Cozy 1BR apt-Pool/Tennis/Gym/Near attractions
Kissimmee FL
$189 nightly
The price is $211 total per night
$211 total
Jan 9 - Jan 10
Total with taxes and fees
This guesthouse features an outdoor pool and a gym. A hot tub and laundry facilities are also provided.
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
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
8800 Vistana Centre Dr Orlando FL
$111 nightly
The price is $125 total per night from Jan 29 to Jan 30
$125 total
Jan 29 - Jan 30
Total with taxes and fees
9.2/10 Wonderful! (4,239 reviews)
Windermere Guest Houses essential information
Accommodation | 46 Guest Houses |
|---|---|
Lowest Price | $84 |
Highest Price | $341 |
Popular accommodation | Disney Proximity Escape - Comfort in Kissimmee, SPRING LAKE GETAWAY SUITE (Detached Guest House), Downtown Lake Eola Historic House 1 OR 2 BED, Winter Park Getaway, Mills Cottage by the Little Lake, Historic lakefront guesthouse, 2 Minutes to Universal Studios Theme Parks - Central, Relaxing and Chic 1BR, Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool and Patio, Adorable 1bed 1 bath guest house, Resort-style 3BR Townhouse Near Disney Park, Cozy 1BR apt-Pool/Tennis/Gym/Near attractions, Family-Friendly 2BR • Wi-Fi + Pets • Near Disney |
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