A lakeside community with houses and boats.

Holiday Homes in Windermere

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Windermere holiday homes

Interior

1. Tiny tropical Orlando Univesal-Disney

Tiny tropical Orlando Univesal-Disney
Orlando
6.8 out of 10, (38 reviews)
"Great stay!"
United States
Allison C.
The price is NZ$202
includes taxes & fees
18 Aug - 19 Aug
Tiny tropical Orlando Univesal-Disney
Outdoor pool

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

Private Spacious Room in Home, with Pool-The Oasis Room
Clermont
9.6 out of 10, Exceptional, (36 reviews)
"I enjoyed my stay very much. If I am ever in the area again, I would definitely stay here again. Very nice place."
United States
Matthew H.
The price is NZ$183
includes taxes & fees
18 Aug - 19 Aug
Private Spacious Room in Home, with Pool-The Oasis Room
Smart TV, video games, printers

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

Mid-century Modern Villa w/ Pool Near Universal
Orlando
10.0 out of 10, Exceptional, (31 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 NZ$847
includes taxes & fees
25 Aug - 26 Aug
Mid-century Modern Villa w/ Pool Near Universal
Smart TV

4. 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 NZ$711
includes taxes & fees
24 Aug - 25 Aug
Rose's Lakeview
Interior

5. Magical Stay Near Universal Studios Florida

Magical Stay Near Universal Studios Florida
Oak Ridge
8.4 out of 10, Very good, (18 reviews)
"We had a great stay"
United States
Russell H.
The price is NZ$646
includes taxes & fees
18 Aug - 19 Aug
Magical Stay Near Universal Studios Florida
Pool

6. 3 Bedrooms/ 3.5 Bathrooms/ Vista Cay (4845-148)

3 Bedrooms/ 3.5 Bathrooms/ Vista Cay (4845-148)
Orlando
8.0 out of 10, Very good, (5 reviews)
"We had a wonderful stay at your property! The neighborhood was very nice, house was clean, super easy to access. "
United States
Erika A.
The price is NZ$790
includes taxes & fees
24 Aug - 25 Aug
3 Bedrooms/ 3.5 Bathrooms/ Vista Cay (4845-148)
Exterior

7. Vista Cay Retreat: Stunning 3-Level Townhome/ 3 BD/ 3.5 BA (5076-90 TC)

Vista Cay Retreat: Stunning 3-Level Townhome/ 3 BD/ 3.5 BA (5076-90 TC)
Orlando
The price is NZ$872
includes taxes & fees
18 Aug - 19 Aug
Vista Cay Retreat: Stunning 3-Level Townhome/ 3 BD/ 3.5 BA (5076-90 TC)
Living area

8. 3-bedroom house in nice Orlando with cool AC for relaxing stay

3-bedroom house in nice Orlando with cool AC for relaxing stay
Tangelo Park
The price is NZ$469
includes taxes & fees
19 Aug - 20 Aug
3-bedroom house in nice Orlando with cool AC for relaxing stay
Microwave, oven, stovetop, paper towels

9. 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
10.0 out of 10, Exceptional, (6 reviews)
"Was great! Thank you "
United States
Jade L.
The price is NZ$216
includes taxes & fees
31 Aug - 1 Sept
Charming 1-bedroom mother-in-law suite w/ full kitchen in delightful Apopka
Dining

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

Modern & Homely Entire House Orlando. Key Location!
Tangelo Park
10.0 out of 10, Exceptional, (16 reviews)
"Very easy and gracious hosts, highly recommended for affordable option near the parks!"
United States
Drew E.
The price is NZ$675
includes taxes & fees
31 Aug - 1 Sept
Modern & Homely Entire House Orlando. Key Location!
Pool

11. 5BR house sleeps 14 with pool table in orlando

5BR house sleeps 14 with pool table in orlando
Orlando
8.0 out of 10, Very good, (1 review)
"No wash cloths, no oven mitts (left some there after ordering on Amazon), smoke detector chirping, communication with host was poor. Very slow to respond if at all."
United States
Sarah C.
The price is NZ$865
includes taxes & fees
19 Aug - 20 Aug
5BR house sleeps 14 with pool table in orlando
Pool

12. 3 BD/ 2 BA/ Lucaya Village (22-102)

3 BD/ 2 BA/ Lucaya Village (22-102)
Kissimmee
The price is NZ$608
includes taxes & fees
18 Aug - 19 Aug
3 BD/ 2 BA/ Lucaya Village (22-102)
Desk, WiFi, bed sheets

13. 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
The price is NZ$267
includes taxes & fees
18 Aug - 19 Aug
Studio in the heart of Orlando
Pool

14. WATERFRONTWntrGdnPoolHSE VIEWS Dock Wildl Nr Disn

WATERFRONTWntrGdnPoolHSE VIEWS Dock Wildl Nr Disn
Winter Garden
10.0 out of 10, Exceptional, (34 reviews)
"Great location and a comfortable stay. "
United States
Tim S.
The price is NZ$837
includes taxes & fees
8 Sept - 9 Sept
WATERFRONTWntrGdnPoolHSE VIEWS Dock Wildl Nr Disn
Pool

15. 3 Bedroom 2 Bath Condo Disney area 8601

3 Bedroom 2 Bath Condo Disney area 8601
Orlando
9.6 out of 10, Exceptional, (47 reviews)
"Very close to all the parks we visited. "
United States
Kelly B.
The price is NZ$462
includes taxes & fees
18 Aug - 19 Aug
3 Bedroom 2 Bath Condo Disney area 8601
Outdoor pool, a heated pool

16. Large, beautiful, very comfortable one bedroom on small lake

Large, beautiful, very comfortable one bedroom on small lake
Lake Weldona
9.8 out of 10, Exceptional, (69 reviews)
"Love the location. "
United States
Jolyn W.
The price is NZ$442
includes taxes & fees
18 Aug - 19 Aug
Large, beautiful, very comfortable one bedroom on small lake
Pool

17. 4 BD/ 3 BA/ Lucaya Village (21-101)

4 BD/ 3 BA/ Lucaya Village (21-101)
Kissimmee
9.2 out of 10, Wonderful, (9 reviews)
"Was a nice location close to many attractions"
United States
Tammy W.
The price is NZ$832
includes taxes & fees
23 Aug - 24 Aug
4 BD/ 3 BA/ Lucaya Village (21-101)
Pool

18. 4 BD/ 3 BA/ Lucaya Village (23-108)

4 BD/ 3 BA/ Lucaya Village (23-108)
KISSIMMEE
The price is NZ$815
includes taxes & fees
18 Aug - 19 Aug
4 BD/ 3 BA/ Lucaya Village (23-108)
Indoor pool

19. Lakefront 5BR Retreat | Pool, Hot Tub & Lake Views

Lakefront 5BR Retreat | Pool, Hot Tub & Lake Views
Orlando
9.2 out of 10, Wonderful, (73 reviews)
"Great host and excellent communication."
United States
Derek S.
The price is NZ$997
includes taxes & fees
31 Aug - 1 Sept
Lakefront 5BR Retreat | Pool, Hot Tub & Lake Views
Dining

20. 4 BD/ 3 BA/ Lucaya Village (26-108)

4 BD/ 3 BA/ Lucaya Village (26-108)
Kissimmee
The price is NZ$791
includes taxes & fees
18 Aug - 19 Aug
4 BD/ 3 BA/ Lucaya Village (26-108)
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windermere Hotel Reviews

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent
"All good"
STANISLAV 4-night trip
Posted less than an hour ago
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Find out more about Windermere

Windermere Holiday Homes information

Number of reviews
380
Accommodation
27842 Holiday Homes
Lowest Price
NZ$183
Highest Price
NZ$997