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
17 July - 19 July
In two months
28 Aug - 30 Aug
In three months
25 Sept - 27 Sept
In four months
23 Oct - 25 Oct

Our top choices for Windermere holiday homes

Outdoor pool

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

Private Spacious Room in Home, with Pool-The Oasis Room
Clermont
9.8 out of 10, Exceptional, (31 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 AU$152
includes taxes & fees
1 July - 2 July
Private Spacious Room in Home, with Pool-The Oasis Room
Pool

Spacious & Private Guest Pool House Oasis

Spacious & Private Guest Pool House Oasis
Union Park
9.8 out of 10, Exceptional, (25 reviews)
"The pool house looked exactly like the pictures and it was a very comfortable place to stay. My husband and I really enjoyed it and would definitely stay there again in the future."
United States
Dionne T.
The price is AU$391
includes taxes & fees
1 July - 2 July
Spacious & Private Guest Pool House Oasis
Exterior

Mi Casa Es Su Casa!!🏡 4 Bdrm home with pool

Mi Casa Es Su Casa!!🏡 4 Bdrm home with pool
Orlando
8.6 out of 10, Excellent, (114 reviews)
"Easy check, great location. Very quiet neighborhood, no complaints . Host did very well. Really enjoyed our stay"
United States
Matthew J.
The price is AU$664
includes taxes & fees
1 July - 2 July
Mi Casa Es Su Casa!!🏡 4 Bdrm home with pool
Terrace/patio

The Cozy Crash Pad: Tiny House Experience

The Cozy Crash Pad: Tiny House Experience
Orlando
8.8 out of 10, Excellent, (27 reviews)
"Overall a good experience. Quiet location. Ideal for solo travelers. I'd give it a 10-out-of-10 if it had a stove top & oven, but space is tight here. A place to hang close would also be nice."
United States
Joseph M.
The price is AU$215
includes taxes & fees
7 July - 8 July
The Cozy Crash Pad: Tiny House Experience
Smart TV

NEW! Spacious designer 2-Bed/2.5-Bath townhome near Downtown Orlando

NEW! Spacious designer 2-Bed/2.5-Bath townhome near Downtown Orlando
Lancaster Park
10.0 out of 10, Exceptional, (18 reviews)
"Clean, good location, easy check in/check out"
United States
Chris
The price is AU$483
includes taxes & fees
6 July - 7 July
NEW! Spacious designer 2-Bed/2.5-Bath townhome near Downtown Orlando
Fridge, microwave, oven, stovetop

Orlando Vacation homeAway near Universal with hot/tub

Orlando Vacation homeAway near Universal with hot/tub
Oak Ridge
8.8 out of 10, Excellent, (25 reviews)
"Thank you for the wonderful stay!"
United States
Lauren W.
The price is AU$338
includes taxes & fees
1 July - 2 July
Orlando Vacation homeAway near Universal with hot/tub
1 bedroom, desk, WiFi, bed sheets

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 AU$238
includes taxes & fees
27 July - 28 July
Studio in the heart of Orlando
Microwave, oven, stovetop, paper towels

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, (3 reviews)
"Was great! Thank you "
United States
Jade L.
The price is AU$195
includes taxes & fees
1 July - 2 July
Charming 1-bedroom mother-in-law suite w/ full kitchen in delightful Apopka
Exterior

Eastpark. Pet friendly! Lake Nona

Eastpark. Pet friendly! Lake Nona
East Park
9.2 out of 10, Wonderful, (100 reviews)
"Very nice accommodations. Great stay!!"
United States
John G.
The price is AU$410
includes taxes & fees
14 July - 15 July
Eastpark. Pet friendly! Lake Nona
Interior entrance

Family Friendly Davenport Pool Villa

Family Friendly Davenport Pool Villa
4.0 star property
Florida Pines
8.0 out of 10, Very good, (1 review)
"The villa was very clean, it was in a quiet community. The private pool was amazing. It was very relaxing for my family and a baby. Only downside was we had to go out and buy more toilet paper, paper towels, salt/pepper, and a large fan. Some of the rooms would get pretty warm since the AC can’t be set past 74. But, overall it was a nice stay! We would stay there again in the future!"
United States
Joseph
The price is AU$780
includes taxes & fees
13 July - 14 July
Family Friendly Davenport Pool Villa
Fridge, microwave, oven, stovetop

Charming Heated Pool home in Altamonte Springs

Charming Heated Pool home in Altamonte Springs
Altamonte Springs
9.4 out of 10, Exceptional, (28 reviews)
"Everything was awesome "
United States
Kyle T.
The price is AU$566
includes taxes & fees
1 July - 2 July
Charming Heated Pool home in Altamonte Springs
Dining

Private house with pool Kissimmee/Orlando

Private house with pool Kissimmee/Orlando
Buena Ventura Lakes
9.8 out of 10, Exceptional, (58 reviews)
"Great house. Clean and quiet. "
United States
Sara M.
The price is AU$643
includes taxes & fees
5 July - 6 July
Private house with pool Kissimmee/Orlando
Fridge, microwave, stovetop, dishwasher

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!
Fridge, microwave, oven, stovetop

Charming 2-bedroom Florida Getaway! Sleeps 6

Charming 2-bedroom Florida Getaway! Sleeps 6
Kissimmee
9.8 out of 10, Exceptional, (16 reviews)
"House is very cute and perfect if you have kids with the amenities on site! "
United States
Ashley J.
The price is AU$428
includes taxes & fees
6 July - 7 July
Charming 2-bedroom Florida Getaway! Sleeps 6
Smart TV, ping pong

Quiet retreat 15 minutes from downtown Orlando, Orlando Airport International!

Quiet retreat 15 minutes from downtown Orlando, Orlando Airport International!
Azalea Park
9.6 out of 10, Exceptional, (25 reviews)
"Quiet neighborhood, good location."
United States
River
The price is AU$406
includes taxes & fees
1 July - 2 July
Quiet retreat 15 minutes from downtown Orlando, Orlando Airport International!
Fridge, microwave, oven, stovetop

Renovated Peaceful Luxury Walk to Mall Park Publix

Renovated Peaceful Luxury Walk to Mall Park Publix
Altamonte Springs
9.2 out of 10, Wonderful, (19 reviews)
"Host responded quickly to our texts.Location was excellent for our needs."
United States
Angie Y.
The price is AU$293
includes taxes & fees
13 July - 14 July
Renovated Peaceful Luxury Walk to Mall Park Publix
Exterior

Stay @ The Enchanted Escape !

Stay @ The Enchanted Escape !
Vacation Village
10.0 out of 10, Exceptional, (3 reviews)
"This place is perfect for our needs. We enjoy every monitoring. Looking forward to returning in the fall!"
United States
Joanne T.
The price is AU$564
includes taxes & fees
6 July - 7 July
Stay @ The Enchanted Escape !
Exterior detail

Fully renovated 3-bedroom townhome Kissimmee - Close to theme parks and airport

Fully renovated 3-bedroom townhome Kissimmee - Close to theme parks and airport
Buena Ventura Lakes
9.4 out of 10, Exceptional, (6 reviews)
"Great Property!"
United States
Mike R.
Fully renovated 3-bedroom townhome Kissimmee - Close to theme parks and airport
3 bedrooms, desk, iron/ironing board, free WiFi

Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!

Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!
Casselberry
9.8 out of 10, Exceptional, (50 reviews)
"The house was very clean and the owner was very prompt in answering our one question. The A/C worked great. "
United States
Michael
The price is AU$368
includes taxes & fees
7 July - 8 July
Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!
Interior

It’s only 15 minutes drive to Disney World and the amazing outlets in Orlando

It’s only 15 minutes drive to Disney World and the amazing outlets in Orlando
Kissimmee
9.8 out of 10, Exceptional, (35 reviews)
"Great location and condo."
United States
Lonnie M.
The price is AU$498
includes taxes & fees
19 July - 20 July
It’s only 15 minutes drive to Disney World and the amazing outlets in Orlando
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

Holiday Inn & Suites Orlando SW - Celebration Area by IHG

Holiday Inn & Suites Orlando SW - Celebration Area by IHG

10/10 Excellent
"Todo excelente, desde la limpieza, las facilidades y el desayuno todo muy bueno. Un poco más de amabilidad de algunas de las empleadas del bufet y listo"
ELI E RODRIGUEZ 3-night trip
Posted less than an hour ago
Holiday Inn & Suites Orlando SW - Celebration Area by IHG

Find out more about Windermere

Windermere Holiday Homes information

Number of reviews
517
Accommodation
26808 Holiday Homes
Lowest Price
AU$152
Highest Price
AU$780