A lakeside community with houses and boats.

Holiday Homes in Windermere

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Windermere holiday homes

A covered swimming pool with a view of the surrounding garden and trees.

1. Mini golf course, 1 mile to Universal, Pool

Mini golf course, 1 mile to Universal, Pool
Orlando
10.0 out of 10, Exceptional, (36 reviews)
"Family friendly great location to Parks "
United States
Joe R.
Mini golf course, 1 mile to Universal, Pool
A compact kitchen with white cabinets, a microwave, and a stove. There is a dining area with a black table, white plates, and a vase of flowers.

2. Entire guesthouse in Orlando, Florida

Entire guesthouse in Orlando, Florida
Tangelo Park
9.2 out of 10, Wonderful, (10 reviews)
"Property was small a true guest house but definitely priced appropriately"
United States
James V.
The price is €132
includes taxes & fees
20 Oct - 21 Oct
Entire guesthouse in Orlando, Florida
A spacious living room with a sofa, coffee table, and TV.

3. Mid-century Modern Villa w/ Pool Near Universal

Mid-century Modern Villa w/ Pool Near Universal
Orlando
9.8 out of 10, Exceptional, (37 reviews)
"Great location close to Universal! We really enjoyed the neighborhood which was great for walking our dog."
United States
Mike B.
The price is €487
includes taxes & fees
16 Oct - 17 Oct
Mid-century Modern Villa w/ Pool Near Universal
Terrace/patio

4. Orlando Tiny Home retreat Near Downtown with garden, with animals and AC.

Orlando Tiny Home retreat Near Downtown with garden, with animals and AC.
West Lakes District
10.0 out of 10, Exceptional, (4 reviews)
"Tammie is an amazing host! Super comfy and cute tiny home! Definitely booking again!"
United States
chelsea
The price is €142
includes taxes & fees
11 Oct - 12 Oct
Orlando Tiny Home retreat Near Downtown with garden, with animals and AC.
A covered outdoor swimming pool with lounge chairs and a hot tub.

5. Private Spacious Room in Home, with Pool-The Oasis Room

Private Spacious Room in Home, with Pool-The Oasis Room
Clermont
9.4 out of 10, Exceptional, (40 reviews)
"Stayed for one night and looking forward to staying again. Communication was great and place as described"
United States
Juan m.
Private Spacious Room in Home, with Pool-The Oasis Room
A modern living room with a sofa, coffee table, TV, and decorative items.

6. Rose's Lakeview

Rose's Lakeview
Orlando
9.0 out of 10, Wonderful, (22 reviews)
"Comfortable, clean stay - good location for our event. "
United States
Kari B.
The price is €379
includes taxes & fees
10 Oct - 11 Oct
Rose's Lakeview
A spacious living area with a dining table, chairs, a sofa, and a kitchen in the background.

7. House with large deck, walking distance to Historic Downtown Winter Garden

House with large deck, walking distance to Historic Downtown Winter Garden
Winter Garden
9.8 out of 10, Exceptional, (29 reviews)
"If you need a nice place to stay in downtown Winter Garden, please consider this place. It is the perfect size for a party of 4 and it is conveniently located to downtown restaurant’s. We stayed 8 nights and could not have been happier."
United States
Sam M.
House with large deck, walking distance to Historic Downtown Winter Garden
A compact kitchen with a built-in refrigerator, a white door with glass panels, and a potted plant.

8. PROMO NOW: The Secret Garden Games Getaway

PROMO NOW: The Secret Garden Games Getaway
Orlando
9.6 out of 10, Exceptional, (11 reviews)
"Everything was very nice. We had a wonderful stay with all my employees. The hosts were very attentive to us and answered us promptly."
United States
Rick L.
The price is €344
includes taxes & fees
7 Oct - 8 Oct
PROMO NOW: The Secret Garden Games Getaway
A modern living room with a leather sofa, a wooden coffee table, a TV, and a chandelier.

9. Shadow Bay Luxe Home with a Private Screened Pool near Universal Studios.

Shadow Bay Luxe Home with a Private Screened Pool near Universal Studios.
Kirkman South
10.0 out of 10, Exceptional, (28 reviews)
"The house was beautiful and it’s an awesome location! Would definitely stay again."
United States
Tom H.
Shadow Bay Luxe Home with a Private Screened Pool near Universal Studios.
A modern living room with a white brick fireplace, a dining area with a glass table and chairs, and a grey sofa.

10. Magical Stay Near Universal Studios Florida

Magical Stay Near Universal Studios Florida
Oak Ridge
8.6 out of 10, Excellent, (22 reviews)
"Nice place to stay. We were in Orlando for the Southern Baptist Convention. Good location and plenty of room for everyone. I would stay there again."
United States
Billy T.
The price is €355
includes taxes & fees
20 Oct - 21 Oct
Magical Stay Near Universal Studios Florida
A modern kitchen with a built-in island, a dining area with a view, and a large window.

11. Home near Sea world/Universal/Convention center

Home near Sea world/Universal/Convention center
Orlando
9.0 out of 10, Wonderful, (7 reviews)
"Clean place and great location. We will definitely stay here again."
United States
Justin D.
The price is €280
includes taxes & fees
7 Oct - 8 Oct
Home near Sea world/Universal/Convention center
A spacious living room with a wooden dining table, benches, and a large mirror. There is a fireplace, a bookshelf, and a door leading to another room.

12. Modern & Homely Entire House Orlando. Key Location!

Modern & Homely Entire House Orlando. Key Location!
Tangelo Park
9.8 out of 10, Exceptional, (20 reviews)
"Very easy and gracious hosts, highly recommended for affordable option near the parks!"
United States
Drew E.
Modern & Homely Entire House Orlando. Key Location!
Private kitchen

13. Charming 1-bedroom mother-in-law suite w/ full kitchen in delightful Apopka

Charming 1-bedroom mother-in-law suite w/ full kitchen in delightful Apopka
Apopka
9.8 out of 10, Exceptional, (8 reviews)
"Great place to stay. We plan on staying again."
United States
Nancee H.
Charming 1-bedroom mother-in-law suite w/ full kitchen in delightful Apopka
A paved courtyard with palm trees and a pergola structure.

14. THE BEST LOCATION IN ORLANDO LAKEFRONT VILLA

THE BEST LOCATION IN ORLANDO LAKEFRONT VILLA
Orlando
9.2 out of 10, Wonderful, (93 reviews)
"We had a great time, it was a wonderful location/set-up for our needs, and the host was very responsive. Thank you for a lovely stay! "
United States
Lisa B.
The price is €214
includes taxes & fees
12 Oct - 13 Oct
THE BEST LOCATION IN ORLANDO LAKEFRONT VILLA
A decorative stone fountain with a twisted base, surrounded by vibrant red flowers and tropical foliage, set against a backdrop of a pool and palm trees.

15. Maple Leaf Inn & Suites

Maple Leaf Inn & Suites
2.5 star property
Kissimmee
6.8 out of 10, (72 reviews)
"The room was clean and the staff was okay "
United States
Shaneka
The price is €60
includes taxes & fees
7 Oct - 8 Oct
Maple Leaf Inn & Suites
A bed with white bedding and two blue pillows with a coral reef design, a tall green plant beside the bed, and a window with grey curtains in the background.

16. Studio in the heart of Orlando

Studio in the heart of Orlando
Azalea Park
9.4 out of 10, Exceptional, (6 reviews)
"Can’t complain. Would re book for sure."
United States
Matthew
Studio in the heart of Orlando
A modern kitchen with white cabinets, a granite countertop, and a central island with bar stools.

17. Chic Orlando Family Getaway w/ Fenced Yard!

Chic Orlando Family Getaway w/ Fenced Yard!
Rosemont
9.4 out of 10, Exceptional, (30 reviews)
"This is a great location for those traveling with families. It was close enough to the main Orlando attractions and great room for 7 people. Very clean and host is amazing at communicating."
United States
Kassandra H.
Chic Orlando Family Getaway w/ Fenced Yard!
A compact living space with a dining table, chairs, a sofa, a TV, and a refrigerator.

18. LOCATION! LOCATION! LOCATION! Best location in Orlando

LOCATION! LOCATION! LOCATION! Best location in Orlando
Orlando
8.8 out of 10, Excellent, (22 reviews)
"AMAZING!!! I would highly recommend. Close to all Universal parks, as well as close to a variety of eating spots. Very clean, and I appreciate the quietness. Especially when you’ve spent all day at the theme parks and you want to relax and recoup. "
United States
Keisha M.
LOCATION! LOCATION! LOCATION! Best location in Orlando
A modern living room with a sofa, ottoman, and glass dining table. There is a kitchen area with a microwave and cabinets.

19. Enchanting Newly Renovated 1.5miles to Disney and Near Tons of Restaurants 760

Enchanting Newly Renovated 1.5miles to Disney and Near Tons of Restaurants 760
Kissimmee
9.0 out of 10, Wonderful, (59 reviews)
"The property was cozy and comfortable. It was perfect for myself and my husband. The beds were comfortable, shower was a good size, water was hot."
United States
Mari L.
Enchanting Newly Renovated 1.5miles to Disney and Near Tons of Restaurants 760
A compact room with a bed, a small table with plates, a microwave, and a green wall with a neon sign.

20. CUTE and COZY studio w/ jacuzzi!

CUTE and COZY studio w/ jacuzzi!
Azalea Park
8.6 out of 10, Excellent, (10 reviews)
"ABSOLUTE WORST EXPERIENCE I HAVE EVER HAD IN MY 54 YEARS OF LIFE!"
United States
Lettisha E.
CUTE and COZY studio w/ jacuzzi!
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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Top Windermere Hotel Reviews

Marriott's Grande Vista

Marriott's Grande Vista

10/10 Excellent
"The resort was absolutely wonderful with tons to do!"
Sarah Karinne 2-night trip
Posted less than an hour ago
Marriott's Grande Vista

Find out more about Windermere

Windermere Holiday Homes information

Number of reviews
472
Accommodation
28054 Holiday Homes
Lowest Price
€60
Highest Price
€487