Holiday Homes in Windermere

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Check prices for these dates

In two weeks
13 Feb - 15 Feb
In two months
27 Mar - 29 Mar
In three months
24 Apr - 26 Apr
In four months
22 May - 24 May

Our top choices for Windermere holiday homes

Design House, 6 Bedrooms, Private Pool | Private kitchen

FL- 1844 GOBI DR

FL- 1844 GOBI DR
3.0 star property
Kissimmee
FL- 1844 GOBI DR
Pool

Spacious & Private Guest Pool House Oasis

Spacious & Private Guest Pool House Oasis
Union Park
9.8 out of 10, Exceptional, (20 reviews)
"Great location , Very enjoy , private space, would book in the future for sure "
United States
Matt B.
The price is NZ$457
includes taxes & fees
29 Jan - 30 Jan
Spacious & Private Guest Pool House Oasis
Exterior detail

Tiny Cottage 15 min from Universal Sleeps 6

Tiny Cottage 15 min from Universal Sleeps 6
Orlovista
10.0 out of 10, Exceptional, (2 reviews)
"Wonderful and convenient spot! Definitely would book again!"
United States
Timothy S
The price is NZ$368
includes taxes & fees
29 Jan - 30 Jan
Tiny Cottage 15 min from Universal Sleeps 6
Outdoor pool

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, (24 reviews)
"Great host great property"
United States
Ken K.
The price is NZ$180
includes taxes & fees
29 Jan - 30 Jan
Private Spacious Room in Home, with Pool-The Oasis Room
Exterior

Charming 2-bedroom apartment in house with AC, WiFi included

Charming 2-bedroom apartment in house with AC, WiFi included
Apopka
9.8 out of 10, Exceptional, (16 reviews)
"It was quiet, clean and had snacks and drinks for us."
United States
Lori
The price is NZ$245
includes taxes & fees
2 Feb - 3 Feb
Charming 2-bedroom apartment in house with AC, WiFi included
Indoor pool, pool umbrellas, pool loungers

Pool •Spa •Game Rm •10 min Disney-Fun Disney Oasis

Pool •Spa •Game Rm •10 min Disney-Fun Disney Oasis
5.0 star property
Lindfields
The price is NZ$586
includes taxes & fees
31 Jan - 1 Feb
Pool •Spa •Game Rm •10 min Disney-Fun Disney Oasis
Lobby sitting area

The Berkley, Orlando

The Berkley, Orlando
4.0 star property
Kissimmee
9.6 out of 10, Exceptional, (2,073 reviews)
"Always enjoy our stay here!"
United States
David
The price is NZ$301
includes taxes & fees
1 Feb - 2 Feb
The Berkley, Orlando
House

Super Glam- Designs Game Room Pool

Super Glam- Designs Game Room Pool
2.0 star property
Kissimmee
10.0 out of 10, Exceptional, (2 reviews)
"Todo bien "
Mexico
Teudis
The price is NZ$784
includes taxes & fees
30 Jan - 31 Jan
Super Glam- Designs Game Room Pool
Interior

Lilac Loft- Lake, Pool, Pickle Ball, Disney, FUN!

Lilac Loft- Lake, Pool, Pickle Ball, Disney, FUN!
Vacation Village
10.0 out of 10, Exceptional, (12 reviews)
"Perfect for a short visit to Orlando area. "
United States
Anastasia E.
The price is NZ$614
includes taxes & fees
29 Jan - 30 Jan
Lilac Loft- Lake, Pool, Pickle Ball, Disney, FUN!
Property grounds

Spacious 2-Bedroom House 5 Star Near Disney Mill Creek Resort 2748

Spacious 2-Bedroom House 5 Star Near Disney Mill Creek Resort 2748
Kissimmee
9.8 out of 10, Exceptional, (14 reviews)
"The place was in a great community. We felt very safe and right at home. Very well maintained with so many things to do on property. Great communication from the property owner. You can’t go wrong booking a stay here! We will definitely be back!"
United States
Emily D.
The price is NZ$375
includes taxes & fees
29 Jan - 30 Jan
Spacious 2-Bedroom House 5 Star Near Disney Mill Creek Resort 2748
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, (27 reviews)
"Very nice place to stay!"
United States
Vasiliy D.
The price is NZ$528
includes taxes & fees
9 Feb - 10 Feb
It’s only 15 minutes drive to Disney World and the amazing outlets in Orlando
Exterior

“The Clementine” Boho Home in Orlando’s Food Scene

“The Clementine” Boho Home in Orlando’s Food Scene
Park Lake - Highland
9.6 out of 10, Exceptional, (19 reviews)
"A phenomenal stay!"
United States
Samuel S.
The price is NZ$301
includes taxes & fees
2 Feb - 3 Feb
“The Clementine” Boho Home in Orlando’s Food Scene
Living room

Doppio Westside

Doppio Westside
4.0 star property
Davenport
9.6 out of 10, Exceptional, (32 reviews)
"The house as beautiful and very clean! The staff were very helpful. "
United States
Myrialisse
The price is NZ$750
includes taxes & fees
29 Jan - 30 Jan
Doppio Westside
Fridge, microwave, oven, stovetop

Renovated Peaceful Luxury Walk to Mall Park Publix

Renovated Peaceful Luxury Walk to Mall Park Publix
Altamonte Springs
9.4 out of 10, Exceptional, (13 reviews)
"Everything was beautiful, enjoyed.My stay host is awesome"
United States
David C.
The price is NZ$314
includes taxes & fees
3 Feb - 4 Feb
Renovated Peaceful Luxury Walk to Mall Park Publix
Dining

Private house with pool Kissimmee/Orlando

Private house with pool Kissimmee/Orlando
Buena Ventura Lakes
9.8 out of 10, Exceptional, (52 reviews)
"The house was clean. We loved the overall design and how spacious it was. The pool was perfect for our children. Everything was perfect for our stay."
United States
Queinton C.
The price is NZ$684
includes taxes & fees
29 Jan - 30 Jan
Private house with pool Kissimmee/Orlando
Smart TV

Centrally home near downtown Orlando!

Centrally home near downtown Orlando!
Paramore
9.8 out of 10, Exceptional, (9 reviews)
"Comfy beds, clean house, close to downtown Orlando "
United States
Joshua H.
The price is NZ$519
includes taxes & fees
1 Feb - 2 Feb
Centrally home near downtown Orlando!
Smart TV, stereo

King bd / Charming 2 story cottage w/ Private Yard

King bd / Charming 2 story cottage w/ Private Yard
Colonialtown North
10.0 out of 10, Exceptional, (17 reviews)
"Place was amazing to stay would deff stay again and recommend it to anyone very spacious, very clean a lot of places nearby and host were amazing "
United States
jesus v.
The price is NZ$920
includes taxes & fees
2 Feb - 3 Feb
King bd / Charming 2 story cottage w/ Private Yard
Outdoor dining

Sunshine Escape Guesthouse ☀

Sunshine Escape Guesthouse ☀
Orlando
9.6 out of 10, Exceptional, (12 reviews)
"The property was immaculately clean, stylish, roomy and private! It was so convenient to everything yet on the outskirts in a quiet peaceful neighborhood. "
United States
KELLY Z.
The price is NZ$282
includes taxes & fees
1 Feb - 2 Feb
Sunshine Escape Guesthouse ☀
Outdoor pool, open 7:00 AM to 11:00 PM, pool umbrellas, pool loungers

Marriott's Sabal Palms

Marriott's Sabal Palms
4.0 star property
Orlando
9.6 out of 10, Exceptional, (212 reviews)
"Room was great, staff friendly and grounds are clean. "
United States
DENNIS
The price is NZ$536
includes taxes & fees
23 Feb - 24 Feb
Marriott's Sabal Palms
Terrace/patio

The Cozy Crash Pad: Tiny House Experience

The Cozy Crash Pad: Tiny House Experience
Orlando
9.0 out of 10, Wonderful, (22 reviews)
"It was incredible! The tiny home feels incredibly cozy and was super easy to find. We had a wonderful visit."
United States
Tristen H.
The price is NZ$246
includes taxes & fees
1 Feb - 2 Feb
The Cozy Crash Pad: Tiny House Experience
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

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent
"From check in until check out we were welcomed with big smiles, helpful staff, we never once thought we were a burden. I will definitely stay here again. "
Cynthia 2-night trip
Posted 1 day ago
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Find out more about Windermere

Windermere Holiday Homes information

Number of reviews
2,561
Accommodation
29729 Holiday Homes
Lowest Price
NZ$180
Highest Price
NZ$920