Windermere Holiday Rentals

  • 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
12 Jun - 14 Jun
In two months
24 Jul - 26 Jul
In three months
21 Aug - 23 Aug
In four months
18 Sept - 20 Sept

Our top choices for Windermere holiday rentals

Interior

The Farm House - Great Location + Pet Friendly!

The Farm House - Great Location + Pet Friendly!
3.0 star property
Windermere
The price is HK$1,269
HK$4,457 total
includes taxes & fees
28 May - 29 May
The Farm House - Great Location + Pet Friendly!
Property grounds

Shore Steps Cottage - Walking Distance To The Town Of Windermere

Shore Steps Cottage - Walking Distance To The Town Of Windermere
Windermere
The price is HK$1,051
HK$2,786 total
includes taxes & fees
29 May - 30 May
Shore Steps Cottage - Walking Distance To The Town Of Windermere
Interior

Rustic Hideaway - Great Location + Pet Friendly!

Rustic Hideaway - Great Location + Pet Friendly!
3.0 star property
Windermere
The price is HK$1,269
HK$4,783 total
includes taxes & fees
1 Jun - 2 Jun
Rustic Hideaway - Great Location + Pet Friendly!
Exterior

Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration
3.0 star property
Kissimmee
8.6 out of 10, Excellent, (4,223 reviews)
"Great place, great price. Would definitely stay again."
United States
Ebony
The price is HK$508
HK$772 total
includes taxes & fees
2 Jun - 3 Jun
Vacation Village Orlando, Celebration
1 bedroom, iron/ironing board, free WiFi, bed sheets

Cozy Apartment in S Orlando, approx. 20 minutes away from Disney and Universal.

Cozy Apartment in S Orlando, approx. 20 minutes away from Disney and Universal.
Southchase
9.8 out of 10, Exceptional, (28 reviews)
"Everything was amazing described how it was owners were super sweet and loving we were happy to find this place to stay "
United States
Pamela Y.
The price is HK$564
HK$1,056 total
includes taxes & fees
4 Jun - 5 Jun
Cozy Apartment in S Orlando, approx. 20 minutes away from Disney and Universal.
Exterior

Eastpark. Pet friendly! Lake Nona

Eastpark. Pet friendly! Lake Nona
East Park
9.2 out of 10, Wonderful, (99 reviews)
"Very nice accommodations. Great stay!!"
United States
John G.
The price is HK$776
HK$2,202 total
includes taxes & fees
4 Jun - 5 Jun
Eastpark. Pet friendly! Lake Nona
Room

Solara Apartments Spacious 2BR Apartment Sleeps 6 Pet-Friendly

Solara Apartments Spacious 2BR Apartment Sleeps 6 Pet-Friendly
4.0 star property
Kirkman North
The price is HK$746
HK$3,337 total
includes taxes & fees
2 Jun - 3 Jun
Solara Apartments Spacious 2BR Apartment Sleeps 6 Pet-Friendly
Property grounds

Incredible Private Lakefront Cottage Retreat

Incredible Private Lakefront Cottage Retreat
Altamonte Springs
10.0 out of 10, Exceptional, (36 reviews)
"The host was easy to contact and the cottage was very cozy with all necessary amenities. The lakeside location was both beautiful and peaceful, especially considering it is so close to 436 and I4. We definitely plan to return. "
United States
Carol G.
The price is HK$1,128
HK$2,877 total
includes taxes & fees
30 May - 31 May
Incredible Private Lakefront Cottage Retreat
Fridge, microwave, oven, stovetop

Clermont Tiny Home: Main Floor Queen, Lofts & No Pet Fees

Clermont Tiny Home: Main Floor Queen, Lofts & No Pet Fees
Clermont
10.0 out of 10, Exceptional, (18 reviews)
"Very clean and has everything you need."
United States
Kathleen S.
The price is HK$854
HK$2,099 total
includes taxes & fees
4 Jun - 5 Jun
Clermont Tiny Home: Main Floor Queen, Lofts & No Pet Fees
Microwave, oven, stovetop, dishwasher

Think Pink in Kissimmee - Gorgeous 2BD with free WIFI, free parking and more!!

Think Pink in Kissimmee - Gorgeous 2BD with free WIFI, free parking and more!!
Kissimmee
9.6 out of 10, Exceptional, (11 reviews)
"beautiful decor and comfy vibe loved it!"
United States
Janny T.
The price is HK$910
HK$1,864 total
includes taxes & fees
1 Jun - 2 Jun
Think Pink in Kissimmee - Gorgeous 2BD with free WIFI, free parking and more!!
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 HK$1,450
HK$3,469 total
includes taxes & fees
7 Jun - 8 Jun
Private house with pool Kissimmee/Orlando
1 bedroom, iron/ironing board, free WiFi, bed sheets

Beautiful Studio near Int. Drive, Disney & Airport.

Beautiful Studio near Int. Drive, Disney & Airport.
Conway
9.4 out of 10, Exceptional, (23 reviews)
"A very clean property and close to the Hilton where my conference was 10 out of 10 recommend because those other attendees that stayed at the Hilton had a very horrible experience and I was blessed to be staying at this clean private suite."
United States
Diana
The price is HK$423
HK$1,118 total
includes taxes & fees
29 May - 30 May
Beautiful Studio near Int. Drive, Disney & Airport.
1 bedroom, desk, iron/ironing board, free WiFi

Private guest studio in the heart of orlando.

Private guest studio in the heart of orlando.
Orlando
9.8 out of 10, Exceptional, (58 reviews)
"Super clean and updated, loved the location, and quiet neighborhood. Definitely will stay here again!"
United States
Gianna N.
The price is HK$551
HK$1,085 total
includes taxes & fees
9 Jun - 10 Jun
Private guest studio in the heart of orlando.
Interior

Cozy Lake Front Cottage

Cozy Lake Front Cottage
Clermont
10.0 out of 10, Exceptional, (22 reviews)
"Host was very accommodating and the cottage was perfect"
United States
Ashley P.
The price is HK$1,051
HK$2,271 total
includes taxes & fees
29 May - 30 May
Cozy Lake Front Cottage
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, (15 reviews)
"Perfect! Place was clean. Parking was easy. ( Business travel)"
United States
Matt S.
The price is HK$682
HK$2,350 total
includes taxes & fees
31 May - 1 Jun
Charming 2-bedroom Florida Getaway! Sleeps 6
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, (30 reviews)
"Very nice neighborhood and great accommodations. "
United States
Kevin S.
The price is HK$776
HK$1,162 total
includes taxes & fees
28 May - 29 May
Charming 2-bedroom apartment in house with AC, WiFi included
Interior

Cozy studio in fabulous Orlando close to everything

Cozy studio in fabulous Orlando close to everything
Orlando
9.8 out of 10, Exceptional, (19 reviews)
"The host is wonderful and the place was exactly what I needed. The bed was extremely comfortable and the neighborhood really quiet. I will definitely be back and stay here again."
United States
Robin L.
The price is HK$783
HK$1,302 total
includes taxes & fees
4 Jun - 5 Jun
Cozy studio in fabulous Orlando close to everything
2 bedrooms, iron/ironing board, WiFi, bed sheets

Charming 2-bedroom apartment with WiFi, AC in lovely Orlando

Charming 2-bedroom apartment with WiFi, AC in lovely Orlando
Orlando
9.8 out of 10, Exceptional, (12 reviews)
"Very clean and hospitable. Recommend staying here for sure!"
United States
Kyle Y.
The price is HK$823
HK$2,019 total
includes taxes & fees
31 May - 1 Jun
Charming 2-bedroom apartment with WiFi, AC in lovely Orlando
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, (49 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 HK$1,022
HK$1,963 total
includes taxes & fees
8 Jun - 9 Jun
Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!
Fridge, microwave, oven, stovetop

Stylish Boutique Guest house in Winter Park

Stylish Boutique Guest house in Winter Park
Winter Park
10.0 out of 10, Exceptional, (109 reviews)
"Excellent location, peaceful setting "
United States
Christy M.
Stylish Boutique Guest house in Winter Park
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

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

2/10 Terrible
"Staff was extremely rude while checking in, was NOT informed there was an additional $300 hold on a major credit card, women at front desk refused to use a debit card while talking badly in Spanish not realizing I speak fluent Spanish. Extremely unprofessional. We arrived Saturday- house keeping didn’t clean/replace towels, until Monday night when we left Tuesday morning. My watch and money was missing from the room which we locked one of the bedroom doors prior to heading down to the pool. Food was horrible, I ordered chips and salsa and 2 drinks. Total amounted to $74 AFTER tip when I did not tip on my card, we left $5 cash. 0/10 recommend- room was not even clean when we arrived, AFTER speaking with front desk yet again, was told hotel is completely full so we cannot change rooms but there was still reservations thru Expedia & on the grove website. Never again, very disappointed!!!"
Kaylaann 3-night trip
Posted 1 hour ago
The Grove Resort & Water Park 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. Another good choice for your trip to Windermere is Grand Luxury Lakes 3BR Townhouse near Disney.

How many holiday rentals are there in Windermere?

Expedia has 3 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.