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Windermere, Florida, United States of America
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Windermere vacation rentals

We found 27,338 vacation rentals — enter your dates for availability

Discover a selection of more than 10,000 vacation rentals in Windermere, FL that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $85 per night, and houses and condos are popular options for a stay in Windermere. Either way, you'll find a rental for everyone's needs.
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Find spaces that suit your style

Houses

View 18,962 Houses

Condos/Apartments

View 5,987 Condos/Apartments

Villas

View 4,472 Villas

Cottages

View 68 Cottages

Townhouses

View 4,361 Townhouses

Resorts

View 1,448 Resorts

Guest houses

View 18 Guest houses

Studios

View 1,339 Studios

Cabins

View 69 Cabins

Bungalows

View 68 Bungalows

Hotels

View 894 Hotels

Find the best place to stay — Windermere

The Home of Sweet Peace

Sleeps 6 · 4 Bedrooms · 3 Bathrooms
$367 avg/night
(54)

COMPLETE PRIVATE POOl BBQ MANSION AT HEART Of ORLANDO

Sleeps 12 · 5 Bedrooms · 5 Bathrooms
$474 avg/night
(1)

🌴PALMS LUXE PALACE🌴

Sleeps 12 · 4 Bedrooms · 4 Bathrooms
$375 avg/night

GREAT PRICE! TOP RESORT! On Disney's Doorstep!

Sleeps 6 · 3 Bedrooms · 2 Bathrooms
$85 avg/night
(215)

4 Bedroom Villa 2 Miles from Disney Entrance Kissimmee Us192

Sleeps 8 · 4 Bedrooms · 3 Bathrooms
$90 avg/night
(154)

Search 27,338 vacation rentals

Top rated rentals — Windermere
Stayed Jun 2022

First time VRBOer

This was our first time using a service like this and it was SOOO much easier than a hotel stay! “Check-in” was like going to a new home. We settled in and the very next day, Thomas checked on us to make sure all was well and he gave us additional in...

Lillian D.
Lillian D.
Stayed Jun 2022

Great location, plenty of space, pool major bonus!!

Check in was easy, Maddie was super attentive to all our needs. Location was perfect, convenient to grocery and close by to all the parks! The pool was a major plus after a long day at the park! Plenty of room for the family to spread out. Loved that...

Dana S.
Dana S.
Stayed Jun 2022

Amazing experience

From day one Anna was quick to respond to our questions and she is so very kind. The property was super clean and for the number of units there surprisingly quiet. We were so very happy with our choice to stay at this property we will definitely book...

Marcia M.
Marcia M.
Stayed Jun 2022

Great house for our family vacation

This is a great house with a great location. Our family visited old kissimmee, universal studios, islands of adventure, and volcano Bay. We also visited icon park. House was clean and supplied with everything needed. All you need is to pack your clot...

BRADLEY J.
BRADLEY J.

Chalmette

Stayed Jun 2022

Quiet, clean, fun place to stay

This house was just what we needed to get away. The pool was awesome and my kids loved it!! I it was close to entertainment but on a quiet cul de sac allowing us some peace. The peace of a house versus a hotel was necessary and allowed my family to b...

Christy P.
Christy P.
Stayed May 2022

Fantastic house!

We had a wonderful stay in this beautiful house. Thanks Troels! Perfect location for theme parks and was easy to drive to other Florida attractions such as the coast for fishing trips, Kennedy Space Centre and Cocoa Beach. Also short trips south to A...

Alison S.
Alison S.
Stayed May 2022

Great family fun

Our first time to the Disney area and our trip could have not gone better. The house is very nice with a great outdoor area to swim, eat and hang out. The location is great, close enough to the parks you are able to come home during the day for break...

Andrew C.
Andrew C.
Stayed May 2022

Emerald Isle Resort

First time VRBO experience, and will definitely do it again. Condo was clean and comfortable, with plenty of space for the entire family. Owners were friendly, very responsive, and an absolute joy to work with. If we head back down to the Orlando ...

Amanda A.
Amanda A.
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How many vacation rentals are available around Windermere, FL?

Our 2022 property listings offer a large selection of 27,338 vacation rentals around Windermere. From 18,962 house rentals to 5,987 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent Houses in Windermere?

Yes, of course. Vrbo has 18,962 Houses in Windermere. Our other popular types of vacation rentals in Windermere include:

  • Condos/Apartments: 5,987 rentals available
  • Villas: 4,472 rentals available
  • Cottages: 68 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Townhouses and more.

Can I find a vacation rental with pool in Windermere?

Yes, you can select your preferred vacation rental with pool among our 25,258 vacation rentals with pool available in Windermere. Please use our search bar to access the selection of vacation rentals available.

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