Windermere Holiday Rentals

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Check prices for these dates

In two weeks
12 Dec - 14 Dec
In two months
23 Jan - 25 Jan
In three months
20 Feb - 22 Feb
In four months
20 Mar - 22 Mar

Holiday Rentals in Windermere

Interior
Margaritaville Cottages Orlando by Rentyl

Aparthotel in Kissimmee

4.0 star property
8.8 out of 10, Excellent, (1724)
"Amazing accommodations "
Canada
Marina
The price is HK$1,549
HK$3,316 total
includes taxes & fees
25 Nov - 26 Nov
Margaritaville Cottages Orlando by Rentyl
Dock
Barefoot Suites

Aparthotel in Kissimmee

3.0 star property
9.0 out of 10, Wonderful, (1794)
"Barefoot Suites is just an overall an awesome place to stay."
United States
Loretta
Barefoot Suites
Terrace/patio
The Point by Edge

Aparthotel in Florida Center

4.0 star property
8.4 out of 10, Very good, (811)
"Great accommodations!"
United States
Champayne
The price is HK$490
HK$648 total
includes taxes & fees
25 Nov - 26 Nov
The Point by Edge
2 bedrooms, individually decorated, individually furnished
Orlando Lakefront Tiny House Community

Cottage in Orlando

3.0 star property
9.4 out of 10, Exceptional, (331)
"We enjoyed our stay."
United States
Ardeeh
The price is HK$599
HK$1,243 total
includes taxes & fees
7 Dec - 8 Dec
Orlando Lakefront Tiny House Community
2 bars/lounges, poolside bar
Regal Oaks Resort Vacation Townhomes by IDILIQ

Condo resort in Kissimmee

4.0 star property
8.4 out of 10, Very good, (3010)
" Clean room and a great staff"
United States
Victor
Regal Oaks Resort Vacation Townhomes by IDILIQ
2 outdoor pools, a heated pool, open 7:00 AM to 11:00 PM, pool umbrellas
Floridays Resort Orlando

Condo resort in International Drive District

3.5 star property
8.6 out of 10, Excellent, (11585)
"Staff was wonderful "
United States
Dana
Floridays Resort Orlando
Outdoor pool, pool umbrellas, pool loungers
WorldQuest Orlando Resort

Aparthotel in Orlando

4.0 star property
8.4 out of 10, Very good, (4018)
"Very attentive staff and clean rooms. "
United States
Diana-Patricia
WorldQuest Orlando Resort
Outdoor pool, open 7:00 AM to 11:00 PM, pool umbrellas, pool loungers
Marriott's Sabal Palms

Holiday Home in Orlando

4.0 star property
9.6 out of 10, Exceptional, (202)
"Easy check in, pool was awesome "
United States
Lisa
The price is HK$2,327
HK$2,618 total
includes taxes & fees
29 Nov - 30 Nov
Marriott's Sabal Palms
Lobby sitting area
The View Studio Suites and Event Venue

Aparthotel in Orlando

3.0 star property
8.4 out of 10, Very good, (1404)
"Nice breakfast, friendly staff, great location "
United States
Yessica
The price is HK$525
HK$591 total
includes taxes & fees
1 Dec - 2 Dec
The View Studio Suites and Event Venue
Exterior
voco Kissimmee Orlando by IHG

Aparthotel in Kissimmee

4.0 star property
7.4 out of 10, Good, (1011)
"Great stay "
United States
Rocio
The price is HK$479
HK$721 total
includes taxes & fees
30 Nov - 1 Dec
voco Kissimmee Orlando by IHG
Reception
Florida Hotel & Conference Center in the Florida Mall

Aparthotel in Orlando

3.5 star property
9.2 out of 10, Wonderful, (2261)
"Clean fresh smelling room, real friendly staff, great atmosphere. Always love staying here"
United States
Alexander
Florida Hotel & Conference Center in the Florida Mall
Water park
Reunion Resort & Golf Club

Aparthotel in Reunion

5.0 star property
8.8 out of 10, Excellent, (1427)
"Was amazing beautiful and is an special place to go with kids , we love it !! "
United States
Yamila
The price is HK$1,629
HK$2,218 total
includes taxes & fees
9 Dec - 10 Dec
Reunion Resort & Golf Club
Outdoor pool
The Point Hotel & Suites

Aparthotel in Florida Center

3.5 star property
8.0 out of 10, Very good, (3291)
"Great place to stay "
United States
Kevaughn
The price is HK$1,043
HK$1,263 total
includes taxes & fees
1 Dec - 2 Dec
The Point Hotel & Suites
Exterior
Barefoot'n Resort Kissimmee Orlando

Aparthotel in Kissimmee

2.5 star property
9.0 out of 10, Wonderful, (158)
"Enjoyed the closeness of Old Town Kissimmee"
United States
Mary
The price is HK$661
HK$848 total
includes taxes & fees
1 Dec - 2 Dec
Barefoot'n Resort Kissimmee Orlando
Private pool
Formosa Valley Resort by UNE Homes

Holiday Home in Kissimmee

4.0 star property
9.4 out of 10, Exceptional, (191)
"Overall a clean house, one of the best properties I’ve stayed in. "
United States
Cristian
Formosa Valley Resort by UNE Homes
Aerial view
Vacation Village Orlando, Celebration

Condo in Kissimmee

3.0 star property
8.6 out of 10, Excellent, (3059)
"Great place to stay"
United States
Jose
The price is HK$744
HK$1,039 total
includes taxes & fees
7 Dec - 8 Dec
Vacation Village Orlando, Celebration
Pool
Storey Lake Resort 2bd Condo Overlooking Water #840 2 Bedroom Condo

Condo in Kissimmee

3.0 star property
10.0 out of 10, Exceptional, (1)
"we had a great time and enjoyed the condo for the short time we were there."
United States
Sherri Ann
The price is HK$1,000
HK$3,975 total
includes taxes & fees
6 Dec - 7 Dec
Storey Lake Resort 2bd Condo Overlooking Water #840 2 Bedroom Condo
4 outdoor pools, pool umbrellas, pool loungers
Bahama Bay Resort

Condo resort in Bahama Bay

3.5 star property
8.6 out of 10, Excellent, (2090)
"Really enjoyed our stay, the room was comfortable clean and had every thing we needed. Will definitely be back soon"
United Kingdom
Rosalyn
The price is HK$1,982
HK$2,708 total
includes taxes & fees
14 Dec - 15 Dec
Bahama Bay Resort
2 outdoor pools, open 8 AM to 10 PM, pool loungers
Holiday Inn Club Vacations Orlando Breeze Resort by IHG

Aparthotel in Davenport

3.5 star property
9.2 out of 10, Wonderful, (497)
"Everything was excellent! "
United States
Laura
The price is HK$625
HK$818 total
includes taxes & fees
19 Dec - 20 Dec
Holiday Inn Club Vacations Orlando Breeze Resort by IHG
Private kitchen
Century Millenia

Apartment in Florida Center

3.0 star property
9.0 out of 10, Wonderful, (101)
" Kitchen was fully equipped, staff was available and informative, clean, and parking was available. "
United States
Elizabeth
Century Millenia
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

Rosen Inn at Pointe Orlando

Rosen Inn at Pointe Orlando

10/10 Excellent
"Everything was great besides me being unaware that I had to pay to park I did not like that"
Cornelius 3-night trip
Posted 4 hours ago
Rosen Inn at Pointe Orlando

Find out more about Windermere

Search for holiday rentals in Windermere on Expedia! You can easily find your home rentals, villas, holiday apartments in Windermere using one of the methods below:

  • View our selection of featured holiday rentals in Windermere
  • Use the map to find apartments and other holiday homes in the Windermere neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Windermere while they last

Look no further and take a look at our great range of rental properties in Windermere!

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.