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Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sept - 28 Sept

Featured Guest Houses in Windermere

Disney Proximity Escape - Comfort in Kissimmee
Outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas, pool loungers

Disney Proximity Escape - Comfort in Kissimmee

3.0 star property
8.2 out of 10, Very good, (27)
"It was very nice 😊 "
Disney Proximity Escape - Comfort in Kissimmee
Winter Park Getaway
Enjoy al fresco dining in this serene outdoor patio area with a table, chairs, and a decorative centerpiece.

Winter Park Getaway

10.0 out of 10, Exceptional, (3)
"The host was very helpful and welcoming without being overbearing as some can be. The space was clean, cute, and well stocked."
Winter Park Getaway
Regal Palms Resort Townhouse - Pool, Waterslide and More!
Relax by the tranquil pool surrounded by lush greenery and palm trees, with lounge chairs and a lifeguard stand for a safe and serene experience.

Regal Palms Resort Townhouse - Pool, Waterslide and More!

2.0 out of 10, (1)
"My family has been coming to Regal Palms for over 14 years, we always made it around someone's birthday and the office always gave us extra wrist bands for family to come for the day to celebrate by pool.The office offered to give me 5 extra wristbands but the property owners would not allow it.It was my granddaughters 9th birthday ( no one was coming back to residence, just pool and play).They also hit me up for 150 dog fee just and hour or so before check in. ( I let them know I was bringing...
Regal Palms Resort Townhouse - Pool, Waterslide and More!
Mills Cottage by the Little Lake
Relax by the serene pool surrounded by lush gardens and shaded lounge chairs.

Mills Cottage by the Little Lake

10.0 out of 10, Exceptional, (45)
"Awesome property, kind host, great location… 1mile to food and drinks, 15 minutes to universal studios."
The price is AU$573
includes taxes & fees
7 Aug - 8 Aug
Mills Cottage by the Little Lake
Historic lakefront guesthouse
Outdoor pool, a heated pool

Historic lakefront guesthouse

10.0 out of 10, Exceptional, (5)
"Great location - property seas very clean and comfortable!"
The price is AU$361
includes taxes & fees
30 July - 31 July
Historic lakefront guesthouse
SPRING LAKE GETAWAY SUITE (Detached Guest House)
Enjoy meals around the central dining table surrounded by four chairs in this well-appointed kitchen.

SPRING LAKE GETAWAY SUITE (Detached Guest House)

10.0 out of 10, Exceptional, (71)
"Perfect house, perfect location, and the host is very pleasant and easy to get in contact with. A great stay."
SPRING LAKE GETAWAY SUITE (Detached Guest House)
Downtown Lake Eola Historic House 1 OR 2 BED
Relax in this inviting living space with a comfortable sofa, coffee table, and side table, surrounded by a potted plant.

Downtown Lake Eola Historic House 1 OR 2 BED

8.8 out of 10, Excellent, (30)
"This was a great option for my friend and I who were traveling. It had two separate bedrooms, a decent kitchen, and a nice seating area. It’s pretty much in downtown, we walked very easily to the Orlando magic stadium and there’s plenty of restaurants within walking distance around the home. would definitely stay here again, and I really appreciated the communication from the property management company. "
The price is AU$265
includes taxes & fees
30 July - 31 July
Downtown Lake Eola Historic House 1 OR 2 BED
2 Minutes to Universal Studios Theme Parks - Central, Relaxing and Chic 1BR
Enjoy outdoor dining or relaxation in the backyard, surrounded by lush greenery and a welcoming atmosphere.

2 Minutes to Universal Studios Theme Parks - Central, Relaxing and Chic 1BR

8.8 out of 10, Excellent, (17)
"One bedroom with comfortable foldout futon in small living room. Small fridge, microwave, kettle were ideal for my stay. "
2 Minutes to Universal Studios Theme Parks - Central, Relaxing and Chic 1BR
Adorable 1bed 1 bath guest house
Relax in a stylish living space with a tufted sofa, matching ottoman, and a side table.

Adorable 1bed 1 bath guest house

10.0 out of 10, Exceptional, (25)
"Our stay was perfect. The accommodations and hosts were excellent. Will definitely consider it again if/when coming to orlando. "
Adorable 1bed 1 bath guest house
Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool and Patio
Enjoy cooking in this well-equipped kitchen with a gas range, refrigerator, and microwave.

Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool and Patio

9.6 out of 10, Exceptional, (15)
"Had a lovely visit in Orlando! Easy to find, host is very nice, communicative and helpful! Would definitely stay again"
Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool and Patio
Cozy 1BR apt-Pool/Tennis/Gym/Near attractions
Relax by the pool surrounded by a shaded area with lounge chairs and a table.

Cozy 1BR apt-Pool/Tennis/Gym/Near attractions

The price is AU$320
includes taxes & fees
29 July - 30 July
Cozy 1BR apt-Pool/Tennis/Gym/Near attractions
Peaceful 2BR Stay • Orlando Comfort • Pets OK
Modern kitchen with oven, microwave, and seating area.

Peaceful 2BR Stay • Orlando Comfort • Pets OK

2.0 star property
Peaceful 2BR Stay • Orlando Comfort • Pets OK
Private Poolside Guest House In Winter Park/Orlando
Relax in a serene backyard oasis surrounded by lush greenery and a pool.

Private Poolside Guest House In Winter Park/Orlando

8.0 out of 10, Very good, (2)
"The property, the location and host are all top notch."
Private Poolside Guest House In Winter Park/Orlando
Magic Oasis Villa at Paradise Palms
Relax in a hot tub surrounded by a paved walkway and stone pillars.

Magic Oasis Villa at Paradise Palms

3.0 star property
10.0 out of 10, Exceptional, (1)
"Outstanding customer service from the host. Beautiful home and surrounding area. "
Magic Oasis Villa at Paradise Palms
Blissful Guest House
Enjoy meals in the compact kitchen with a granite countertop, wooden cabinets, and a stainless steel refrigerator. A dining area with a chair and table is nearby.

Blissful Guest House

3.0 star property
2.0 out of 10, (1)
Blissful Guest House
Kissimmee Lively Room with 2 DBL Beds & Pool
Iron/ironing board, WiFi, bed sheets, wheelchair access

Kissimmee Lively Room with 2 DBL Beds & Pool

2.0 out of 10, (1)
"To start I didn’t stay at the hotel because they wrote to me that if I did not provide payment and a photo I’d to run a background check to know if I was a registered sex ofender or criminal they will not confirm my stay , when I did they told me that in 5 minutes they will notify me if I could stay at their property, they never notified me that it was ok for me and my 4 Hildemaro and wife to stay at their property , well besides I thought Expedia did that for me pay the hotel and my Id because...
Kissimmee Lively Room with 2 DBL Beds & Pool
Family-friendly Room with 2 DBL Beds & Pool in Kissimmee
Iron/ironing board, WiFi, bed sheets, wheelchair access

Family-friendly Room with 2 DBL Beds & Pool in Kissimmee

8.6 out of 10, Excellent, (4)
"The room was clean, the property is well maintained. The staff is very friendly and polite. My only complaint would be the amount of towels. We had 2 towels in the room. The first night we did hear everything around... the room next to us made noise and we could hear clearly everything."
Family-friendly Room with 2 DBL Beds & Pool in Kissimmee
Palatial Palms Villa Pool BBQ Resort
Outdoor spa tub

Palatial Palms Villa Pool BBQ Resort

3.0 star property
10.0 out of 10, Exceptional, (1)
"Amazing property. Comfortable beds, plenty of linen, beautiful pool, & great amenities. I loved the pool side bar area. We ate great food & relaxed in the pool. It has a waterfall & slide, which the kids loved. We did not have time to enjoy all of the amenities but they have a movie theater on site, there is an option for a private rental or you can watchvwhat is playing. They post the movie & viewing times. Basketball, playground & more. My host was very nice & responded quickly to all...
Palatial Palms Villa Pool BBQ Resort
Cozy Wonderfull Clubhouse Close Disney
Classic hotel room with two single beds, a nightstand, and a bedside lamp, featuring Mickey Mouse-themed decorations.

Cozy Wonderfull Clubhouse Close Disney

2.0 star property
Cozy Wonderfull Clubhouse Close Disney
Kissimmee Ideal Room with 2 DBL Beds & Fitness Center
Iron/ironing board, WiFi, bed sheets, wheelchair access

Kissimmee Ideal Room with 2 DBL Beds & Fitness Center

Kissimmee Ideal Room with 2 DBL Beds & Fitness Center
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.
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