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Windermere Holiday Rentals

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Our top choices for Windermere holiday rentals

voco Kissimmee Orlando by IHG

voco Kissimmee Orlando by IHG
4.0 star property
Kissimmee
7.4 out of 10, Good, (1001)
"Place was clean, staff great, cozy very nice area swimming pool"
United States
KRYSTLE
The price is S$116
includes taxes & fees
18 Dec - 19 Dec
voco Kissimmee Orlando by IHG

Margaritaville Cottages Orlando by Rentyl

Margaritaville Cottages Orlando by Rentyl
4.0 star property
Kissimmee
8.8 out of 10, Excellent, (1746)
"Great place "
United States
Lauren
The price is S$536
includes taxes & fees
15 Dec - 16 Dec
Margaritaville Cottages Orlando by Rentyl

The Point by Edge

The Point by Edge
4.0 star property
Florida Center
8.4 out of 10, Very good, (829)
"Great accommodations!"
United States
Champayne
The price is S$105
includes taxes & fees
4 Jan - 5 Jan, 2026
The Point by Edge

The View Studio Suites and Event Venue

The View Studio Suites and Event Venue
3.0 star property
Orlando
8.4 out of 10, Very good, (1469)
"Good staff Good location "
Canada
Maryon
The price is S$124
includes taxes & fees
15 Dec - 16 Dec
The View Studio Suites and Event Venue

Orlando Lakefront Tiny House Community

Orlando Lakefront Tiny House Community
3.0 star property
Orlando
9.4 out of 10, Exceptional, (331)
"We enjoyed our stay."
United States
Ardeeh
The price is S$198
includes taxes & fees
15 Dec - 16 Dec
Orlando Lakefront Tiny House Community

Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration
3.0 star property
Kissimmee
8.6 out of 10, Excellent, (3098)
"Great place to stay"
United States
Jose
The price is S$217
includes taxes & fees
4 Jan - 5 Jan, 2026
Vacation Village Orlando, Celebration

Regal Oaks Resort Vacation Townhomes by IDILIQ

Regal Oaks Resort Vacation Townhomes by IDILIQ
4.0 star property
Kissimmee
8.4 out of 10, Very good, (3025)
" Clean room and a great staff"
United States
Victor
The price is S$467
includes taxes & fees
5 Jan - 6 Jan, 2026
Regal Oaks Resort Vacation Townhomes by IDILIQ

Floridays Resort Orlando

Floridays Resort Orlando
3.5 star property
International Drive District
8.6 out of 10, Excellent, (11612)
"Great place to stay"
United States
Ana
The price is S$267
includes taxes & fees
7 Jan - 8 Jan, 2026
Floridays Resort Orlando

Barefoot Suites

Barefoot Suites
3.0 star property
Kissimmee
9.0 out of 10, Wonderful, (1798)
"Barefoot Suites is just an overall an awesome place to stay."
United States
Loretta
Barefoot Suites

Florida Hotel & Conference Center in the Florida Mall

Florida Hotel & Conference Center in the Florida Mall
3.5 star property
Orlando
9.2 out of 10, Wonderful, (2327)
"Great location "
United States
Zandra
Florida Hotel & Conference Center in the Florida Mall

Holiday Inn Club Vacations Orlando Breeze Resort by IHG

Holiday Inn Club Vacations Orlando Breeze Resort by IHG
3.5 star property
Davenport
9.2 out of 10, Wonderful, (500)
"Everything was great "
United States
Bobby
The price is S$177
includes taxes & fees
18 Dec - 19 Dec
Holiday Inn Club Vacations Orlando Breeze Resort by IHG

Champions Gate Resort Home w BBQ Pool

Champions Gate Resort Home w BBQ Pool
2.0 star property
Champions Gate
9.2 out of 10, Wonderful, (7)
"Very relaxing and my property assistant was great over the phone "
United States
Robert
Champions Gate Resort Home w BBQ Pool

Champions Gate condos by UNE

Champions Gate condos by UNE
4.0 star property
Champions Gate
8.8 out of 10, Excellent, (53)
"Home and owners were amazing. We would definitely stay again if need. Great for soccer families as there is a little field right across the street. "
United States
Melissa
The price is S$406
includes taxes & fees
15 Dec - 16 Dec
Champions Gate condos by UNE
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

Frequently asked questions

Can I find holiday rentals in Windermere?

Yes, we have holiday rentals where you'll be only 4.1 mi (6.6 km) from Universal Studios Florida, offering you a more secluded option if you'd like a quiet spot to stay. Windermere is known for its restaurants and shopping. Make sure you have time to check out the beaches and sporting events during your trip.

What are some of the best holiday rentals that Windermere has to offer?

The Berkley, Orlando: This holiday home rental outside of Windermere offers a furnished patio, a terrace and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a microwave and a coffee maker. You can relax into your holiday with an arcade/games room and 1 hot tub.

How many holiday rentals are there in Windermere?

Expedia has 13 holiday rentals for your stay in Windermere.

What’s there to see and do in Windermere?

Lake Butler and Tibet Butler Preserve are a couple of lovely local spots to get outside and enjoy nature. In the wider area, you’ll find popular places such as Universal Studios Florida and Universal Orlando Resort.

What’s a holiday rental in Windermere like?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windermere. Holiday rentals feature amenities such as laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a clean environment, a holiday rental can provide a sense of seclusion away from public hotel lifts and busy concierge desks while still allowing you to travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive option for family gatherings.