Windermere holiday rentals

We found 34,673 holiday rentals — enter your dates for availability
Scroll through and select from holiday rentals in Windermere to find one that's perfect for your trip. Whether you’re staying in a holiday home with friends, family or just with your pet, you'll have the best amenities for spending time at your home away from home, including Wi-Fi and parking. Whatever you're looking for, you're sure to find a property to rent that has what everyone needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Windermere

Showing deals for:27 Nov - 4 Dec

Entrance to the luxurious Emerald Island Resort.
The famous Dolphins await you upon your entrance into the Resort.
Brand new marble 10 seat dining table set for the family feast!
The Fully Renovated home awaits you. Enjoy the outdoor and indoor amenities
Exceptional
(145 reviews)

Waterfront-HUGE Pool-2.7 miles to Disney, w/ 4 Masters Suites, Arcades, Theater!

Kissimmee

8% off
AU$6,229
for 7 nights, 1 home
AU$890 per night
includes taxes & fees
Waterfront-HUGE Pool-2.7 miles to Disney, w/ 4 Masters Suites, Arcades, Theater!
Dining
Pool
Exterior
Private kitchen
Very good
(27 reviews)

Emerald Pleasure Villa - Private Pool, Resort Community, Near Disney

Kissimmee

7% off
AU$2,766
for 7 nights, 1 villa
AU$395 per night
includes taxes & fees
Emerald Pleasure Villa - Private Pool, Resort Community, Near Disney
Foosball Table
Exterior
Patio area and backyard
Dining area next to kitchen and patio
Exceptional
(7 reviews)

Orlando 20 Guest Villa Centrally Located with Game Room

Windermere

16% off
AU$3,681
for 7 nights, 1 home
AU$526 per night
includes taxes & fees
Orlando 20 Guest Villa Centrally Located with Game Room
Room
Private kitchen
Dining
Interior
Exceptional
(150 reviews)

JUST REMODELED!! 3BR/2BR Chic Villa Near Disney UNIT A

Kissimmee

7% off
AU$1,551
for 7 nights, 1 villa
AU$222 per night
includes taxes & fees
JUST REMODELED!! 3BR/2BR Chic Villa Near Disney UNIT A
Living area
Living area
Dining
Private kitchen
Excellent
(18 reviews)

Luxury Pool/Spa themed home near Disney World/Universal

Davenport

6% off
AU$2,225
for 7 nights, 1 home
AU$318 per night
includes taxes & fees
Luxury Pool/Spa themed home near Disney World/Universal
Resort aerial
Lazy river, splash zone
Open concept floor
Open concept floor
Exceptional
(17 reviews)

"Escape to Paradise: Luxurious Vacation Home in Davenport, Florida"

Davenport

7% off
AU$3,164
for 7 nights, 1 villa
AU$452 per night
includes taxes & fees
"Escape to Paradise: Luxurious Vacation Home in Davenport, Florida"
Living area
Pool
Interior
Exterior
Exceptional
(87 reviews)

Experience magic! HR Golf Course view 5bd/3b w/pool-spa near all Disney Parks

Davenport

7% off
AU$2,998
for 7 nights, 1 home
AU$428 per night
includes taxes & fees
Experience magic! HR Golf Course view 5bd/3b w/pool-spa near all Disney Parks
Private kitchen
Interior
Exterior
Living area
Very good
(6 reviews)

Big-Bright and Beautiful 6 bedroom home on Emerald Island Resort

Kissimmee

7% off
AU$2,376
for 7 nights, 1 home
AU$339 per night
includes taxes & fees
Big-Bright and Beautiful 6 bedroom home on Emerald Island Resort
Living area
Private kitchen
Terrace/patio
Dining
Very good
(6 reviews)

Modern Orlando Retreat – Minutes to Disney, Universal & All the Magic!”

Orlando

8% off
AU$2,187
for 7 nights, 1 home
AU$312 per night
includes taxes & fees
Modern Orlando Retreat – Minutes to Disney, Universal & All the Magic!”
Living area
Pool
Interior
Room
Wonderful
(24 reviews)

Magical charm couple miles away from Disney

Kissimmee

7% off
AU$2,232
for 7 nights, 1 home
AU$319 per night
includes taxes & fees
Magical charm couple miles away from Disney
Living area
Pool
Dining
Interior
Exceptional
(183 reviews)

Private Home with Pool / 3 Bed 2 Bath / Disney 15 Minutes Away / Free WiFi

Orlando

7% off
AU$2,215
for 7 nights, 1 home
AU$316 per night
includes taxes & fees
Private Home with Pool / 3 Bed 2 Bath / Disney 15 Minutes Away / Free WiFi
Interior
Pool
Private kitchen
Interior
Exceptional
(35 reviews)

Beautiful Home with a South-Facing Heated Pool-Jacuzzi & BBQ Grill included

Davenport

6% off
AU$3,558
for 7 nights, 1 villa
AU$508 per night
includes taxes & fees
Beautiful Home with a South-Facing Heated Pool-Jacuzzi & BBQ Grill included
Dining
Pool
Room
Private kitchen
Exceptional
(32 reviews)

Expansive Luxury home minutes to Disney, close to all parks!

Davenport

7% off
AU$3,823
for 7 nights, 1 room
AU$546 per night
includes taxes & fees
Expansive Luxury home minutes to Disney, close to all parks!
Garage-turned-games-room with air hockey, foosball, game consoles and more!
Luxury Patio with Private Pool and Hot Tub, Games, Smart TVs, BBQ and more.
Large Capacity Living Area with 3 Big Screen TVs
Private Movie Theatre with giant projection screen and cinema style recliners
Excellent
(15 reviews)

Upstay Family Resort Mansion- Pool, Games, Theater

Kissimmee

8% off
AU$13,076
for 7 nights, 1 home
AU$1,868 per night
includes taxes & fees
Upstay Family Resort Mansion- Pool, Games, Theater
Large Capacity Family Dining Table
Private Swimming Pool and Furnished Sundeck Patio
Large Spacious Bedrooms
Private Games Room with Table Tennis and More
Wonderful
(17 reviews)

Family Resort Home w Pool, BBQ & Game Room

Davenport

7% off
AU$1,793
for 7 nights, 1 home
AU$256 per night
includes taxes & fees
Family Resort Home w Pool, BBQ & Game Room
Interior
Pool
Interior
Property grounds
Wonderful
(28 reviews)

SPECIAL! Get UP TO 20% off Weekly Rental with complementary Pool & Spa Heating!

Davenport

7% off
AU$5,559
for 7 nights, 1 villa
AU$794 per night
includes taxes & fees
SPECIAL! Get UP TO 20% off Weekly Rental with complementary Pool & Spa Heating!
Newly Renovated In-Home Arcade Games Room with Large Smart TV
Disney Themed Large Family Movie Theater
Bedroom 1 (King Bed, Ensuite): A serene master suite with a king-size bed, flat-screen TV, and private ensuite — designed for comfort and relaxation.
Open-Concept Lounge: Relax in the stylish main lounge featuring plush sofas, a large smart TV, and a stunning feature wall with modern lighting — perfect for movie nights or family hangouts.
Excellent
(19 reviews)

Upstay Family Retreat w Pool, Theater & Games Room

Kissimmee

7% off
AU$5,399
for 7 nights, 1 home
AU$771 per night
includes taxes & fees
Upstay Family Retreat w Pool, Theater & Games Room
The downstairs living room has lots of sunlight.
The entire resort is included with your rental.
The dining room has seating for eight.
Outside of our beautiful home awaits.
Exceptional
(18 reviews)

The villa where dreams come true!

Davenport

7% off
AU$2,901
for 7 nights, 1 home
AU$414 per night
includes taxes & fees
The villa where dreams come true!
Outdoor swimming pool and jaccuzi hot tub
Living room with smart TV and high speed internet
Games room with billiards table
King bedroom with en-suite bathroom
Exceptional
(6 reviews)

Upstay: Large Resort Home w Private Pool & Hot Tub

Kissimmee

7% off
AU$4,305
for 7 nights, 1 home
AU$615 per night
includes taxes & fees
Upstay: Large Resort Home w Private Pool & Hot Tub
Dining
Exterior
Pool
Private kitchen
Wonderful
(19 reviews)

New Lovely Home in Sonoma Resort at Tapestry

Kissimmee

8% off
AU$5,952
for 7 nights, 1 home
AU$850 per night
includes taxes & fees
New Lovely Home in Sonoma Resort at Tapestry
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Private kitchen
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Exceptional
(84 reviews)

Spacious 4 bed 3 bath Townhome with pool 5 STARS! Paradise Palms Gated Resort

Kissimmee

7% off
AU$2,377
for 7 nights, 1 home
AU$340 per night
includes taxes & fees
Spacious 4 bed 3 bath Townhome with pool 5 STARS! Paradise Palms Gated Resort
Spacious Open Concept Design
Private Swimming Pool
Garage-turned-games-room with Mario Bros theme
In-home Movie Theatre with Disney-themed Decorations
Wonderful
(20 reviews)

Upstay: 15BR Villa w Games Room, Pool & Cinema

Kissimmee

8% off
AU$13,005
for 7 nights, 1 home
AU$1,858 per night
includes taxes & fees
Upstay: 15BR Villa w Games Room, Pool & Cinema
Dining
Pool
Dining
Living area
Exceptional
(24 reviews)

17 mins to Theme Parks, Your All in One Stay with Heated Pool

Kissimmee

7% off
AU$2,085
for 7 nights, 1 home
AU$298 per night
includes taxes & fees
17 mins to Theme Parks, Your All in One Stay with Heated Pool
Dining
Pool
Terrace/patio
Private kitchen
Wonderful
(12 reviews)

Luxe Solara Retreat- Pool+ BBQ + Lazy River+ 8mi Disney + Resort Access

Kissimmee

7% off
AU$3,231
for 7 nights, 1 home
AU$462 per night
includes taxes & fees
Luxe Solara Retreat- Pool+ BBQ + Lazy River+ 8mi Disney + Resort Access

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Travel to charming Windermere

The beaches and other outdoor surroundings create an inviting atmosphere in Windermere. This romantic city is known for its restaurants, shopping and sporting events. Universal Studios Florida and Universal Orlando Resort are just a couple of the must-see attractions in the area. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in and around Windermere

Are you hoping to find things to do in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Windermere a fun spot to go on holiday. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Universal Studios Florida (4.1 mi / 6.6 km)
  • Universal Orlando Resort (4.4 mi / 7 km)
  • Universal’s Volcano Bay (4.4 mi / 7.1 km)
  • Magic Kingdom® Park (6.1 mi / 9.8 km)
  • Walt Disney World® Resort (6.2 mi / 9.9 km)
  • Epcot® (8.6 mi / 13.8 km)

Exploring the natural features in Windermere

Whether you're an adventurous traveller or just want to take in the scenery, Windermere is a great place to get outside. These are a few of the area's most enchanting features, all within 30 miles (48.2 km) of the city centre:

  • Bill Frederick Park (3.6 mi / 5.8 km)
  • Little Lake Bryan (8.3 mi / 13.4 km)
  • Lake Bryan (9.1 mi / 14.7 km)
  • Lake Eola (10.4 mi / 16.7 km)
  • Lake Eola Park (10.5 mi / 16.8 km)
  • Lake Louisa State Park (11.6 mi / 18.7 km)

Travelling to and around Windermere

Fly into Orlando International Airport (MCO), the closest airport, located 14.5 mi (23.3 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could book a flight to Kissimmee, FL (ISM-Kissimmee Gateway), which is 15.2 mi (24.4 km) away.

Frequently asked questions

What is the best area to stay in Windermere when booking a holiday rental?
When considering a holiday rental in Windermere, Florida, the area surrounding the charming neighbourhood of Windermere itself is an excellent choice. This picturesque locale is known for its beautiful lakes and lush landscapes, providing a serene backdrop for a relaxing getaway. The area features a variety of properties, ranging from cozy villas to spacious family homes, suiting different preferences and group sizes.One of the top attractions nearby is the stunning Lake Butler, where visitors can enjoy various water activities such as kayaking and paddleboarding, making it a great spot for those who appreciate the outdoors. Another point of interest is the charming downtown area, which boasts delightful shops and eateries, allowing guests to savour local cuisine and enjoy a leisurely stroll.Additionally, being in close proximity to the larger Orlando area, guests can easily access world-renowned attractions such as theme parks and entertainment hubs, while still enjoying the tranquility of Windermere.
Where are the best areas for renting a beach house in Windermere?
For renting a beach house in Windermere, the areas surrounding Lake Butler and Lake Bessie are particularly appealing. These locations offer serene waterfront properties that provide direct access to the lakes, ideal for swimming, fishing, and boating. Many beach houses in this vicinity come with private docks, outdoor patios, and spacious gardens, great for enjoying the beautiful Florida weather.In addition, the nearby Windermere Village offers a charming atmosphere with local shops and restaurants, making it convenient for holidaymakers. Properties here often feature modern amenities such as fully equipped kitchens, air conditioning, and private pools, allowing for a comfortable and enjoyable stay.Furthermore, the scenic routes around the lakes provide opportunities for leisurely walks and cycling, while the proximity to Orlando means guests can easily take day trips to popular attractions.
What is the most popular type of holiday rental accomodation in Windermere?
In Windermere, holiday houses are the most popular type of holiday rental, with about 56 available throughout the area. These spacious properties often feature multiple bedrooms, private pools, and large outdoor patios, making them ideal for families or groups looking to relax after a day of exploring. Additionally, there are around 24 villas that offer a touch of luxury, typically equipped with high-end amenities such as gourmet kitchens and game rooms. Several cottages and apartments are also available, providing cozier options for those seeking a more intimate stay.
Are there any family house rentals in Windermere?
In Windermere, there are several family-friendly house rentals available, making it an ideal location for those travelling with children. The area is known for its picturesque surroundings and proximity to various attractions, including the popular Walt Disney World® Resort, which is just a short drive away.Many of the homes in this locale offer spacious living areas, fully equipped kitchens, and outdoor patios or gardens where families can relax and enjoy some quality time together. Visitors can often find properties with amenities such as private pools and game rooms, great for entertaining the kids after a day of adventures.Windermere also features charming neighbourhoods with easy access to local parks and recreational activities, ensuring that families have plenty of options for outdoor fun and exploration.
Can I rent a holiday home with a pool or hot tub in Windermere?
In Windermere, there are several holiday homes available for rent that feature pools and hot tubs. This charming area, known for its picturesque lakes and scenic landscapes, offers a variety of options for travellers seeking a relaxing getaway. Many of these properties are located in family-friendly neighbourhoods and often include amenities such as private swimming pools, hot tubs, outdoor patios, and fully equipped kitchens, making them ideal for both relaxation and entertaining. Find your rental in Windermere with a pool or a hot tub.
Are there pet-friendly house rentals in Windermere?
In Windermere, there are several pet-friendly house rentals available, providing a comfortable and welcoming environment for travellers with pets. Many of these homes are well-equipped with modern amenities such as spacious kitchens, private pools, and outdoor patios, allowing for enjoyable stays with furry companions. The area boasts beautiful natural surroundings, and some rentals may even feature enclosed yards, great for pets to roam freely.Windermere is also conveniently located near various parks and outdoor spaces where pet owners can enjoy leisurely walks or playtime with their pets. The nearby Windermere Town Square offers a charming atmosphere with shops and cafes that may welcome pets, making it a delightful spot for a day out.
Are there any remote work holiday rentals in Windermere?
In Windermere, Florida, there are plenty of options for remote work holiday rentals, with around 84 available throughout the area. These properties often come equipped with essential amenities to cater to remote workers, including reliable Wi-Fi in both rooms and public areas, allowing for seamless connectivity. Many accommodations feature dedicated workspaces, making it easy to stay productive while enjoying a getaway.The charming neighbourhoods of Windermere offer a beautiful backdrop, with serene lakes and lush landscapes that provide a relaxing environment after work hours. Nearby attractions include the picturesque Windermere Town Hall and the scenic parks that invite outdoor activities. Properties in the area typically feature modern furnishings, fully equipped kitchens for convenient meal preparation, and comfortable living spaces, ensuring a pleasant stay for those balancing work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Windermere?
In Windermere, popular rental amenities include kitchens, making it convenient for guests to prepare their own meals. Many properties also offer onsite parking, which is particularly useful for those travelling with vehicles. Additionally, pet-friendly options are available, allowing guests to bring their furry companions along, including provisions for service animals. For those who enjoy a warm beverage, many rentals are equipped with coffee and tea makers, adding to the comfort of a home-like stay.
When is the best time to visit Windermere for a holiday rental?
The most popular time to visit Windermere for a holiday rental is September, as the summer crowds begin to thin out while the weather remains warm and inviting. From July to September, you'll find families and adventure seekers enjoying the area's beautiful lakes and outdoor activities, including kayaking, paddleboarding, and scenic walks along the picturesque waterfront.During September, temperatures are typically pleasant, ranging from 20 to 30 degrees Celsius, making it an ideal time for outdoor exploration and relaxation. The lush surroundings come alive, providing a stunning backdrop for sightseeing and nearby attractions, including the charming downtown area filled with boutique shops and local eateries.For those looking for a more budget-friendly option, consider planning your visit in October. This month offers a quieter experience, with fewer tourists and the chance to enjoy the mild climate while still appreciating the beauty of the area. It's a lovely time for leisurely strolls and enjoying the autumn foliage without the hustle and bustle of the peak season.
What are the top attractions in Windermere?
In Windermere, Florida, visitors can enjoy a variety of attractions that highlight the area's natural beauty and recreational opportunities. The serene Lake Windermere is a focal point, offering activities such as boating, fishing, and picnicking along its shores. Nearby, the charming town centre features quaint shops and dining options, providing a lovely atmosphere for leisurely strolls.For those seeking outdoor adventures, the nearby Butler Chain of Lakes presents a network of lakes great for kayaking and paddleboarding, with scenic views and abundant wildlife. The Windermere Recreation Centre is another great spot, equipped with sports facilities and playgrounds for families.
Are all fees included in the Windermere holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Windermere holiday homes with parking?
Stayz offers a wide selection of holiday homes in Windermere with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Windermere holiday homes?
You can find great discounts on holiday homes in Windermere on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Windermere holiday home booking on Stayz?
To find Windermere holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Windermere?
A long-stay holiday home in Windermere is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Windermere holiday home?
Book your Windermere holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Windermere?
Prices for holiday homes in Windermere vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Windermere to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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