A lakeside community with houses and boats.

Holiday Homes in Windermere

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Check prices for these dates

In two weeks
17 Jul - 19 Jul
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 €94
includes taxes & fees
1 Jul - 2 Jul
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 €240
includes taxes & fees
1 Jul - 2 Jul
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 €402
includes taxes & fees
1 Jul - 2 Jul
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 €132
includes taxes & fees
14 Jul - 15 Jul
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 €296
includes taxes & fees
6 Jul - 7 Jul
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 €203
includes taxes & fees
1 Jul - 2 Jul
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 €146
includes taxes & fees
27 Jul - 28 Jul
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 €120
includes taxes & fees
1 Jul - 2 Jul
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 €252
includes taxes & fees
14 Jul - 15 Jul
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 €472
includes taxes & fees
13 Jul - 14 Jul
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 €348
includes taxes & fees
1 Jul - 2 Jul
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 €389
includes taxes & fees
5 Jul - 6 Jul
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.
The price is €460
includes taxes & fees
29 Jul - 30 Jul
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 €262
includes taxes & fees
6 Jul - 7 Jul
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 €245
includes taxes & fees
13 Jul - 14 Jul
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 €174
includes taxes & fees
6 Jul - 7 Jul
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 €346
includes taxes & fees
6 Jul - 7 Jul
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.
The price is €310
includes taxes & fees
1 Jul - 2 Jul
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 €221
includes taxes & fees
7 Jul - 8 Jul
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 €301
includes taxes & fees
20 Jul - 21 Jul
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.
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Top Windermere Hotel Reviews

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

10/10 Excellent
"Stayed at the grove 3x already , loved it every time . P"
Milourse 3-night trip
Posted less than an hour ago
The Grove Resort & Water Park Orlando

Find out more about Windermere

Windermere Holiday Homes information

Number of reviews
517
Accommodation
26969 Holiday Homes
Lowest Price
€94
Highest Price
€472