Windermere holiday rentals

We found 33,378 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:8 Jan - 15 Jan

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
(146 reviews)

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

Kissimmee

8% off
AU$5,414
for 7 nights, 1 home
AU$773 per night
includes taxes & fees
Waterfront-HUGE Pool-2.7 miles to Disney, w/ 4 Masters Suites, Arcades, Theater!
Room
Pool
Room
Room
Very good
(19 reviews)

5BR Enchanted Oasis: Pool, Close to Disney - Sleeps 12

Davenport

10% off
AU$1,650
for 7 nights, 1 home
AU$236 per night
includes taxes & fees
5BR Enchanted Oasis: Pool, Close to Disney - Sleeps 12
Welcome center
Solterra has some of the finest resort amenities in Florida. All of them are included free of charge with your rental including the lazy river!
The south facing pool feature your own private cabaña.
The SHIELD Safe House has a beautiful pond view.
Exceptional
(95 reviews)

Marvel Villa - 20 minutes to Disney

Davenport

7% off
AU$2,886
for 7 nights, 1 villa
AU$412 per night
includes taxes & fees
Marvel Villa - 20 minutes to Disney
Large Chef's Kitchen with 2 Refrigerator/Freezers & 2 Dishwashers
Our 12BR 11BA Vacation Home is located in the beautiful Solterra Resort
Kitchen & Great Room Area
Entry Way from Front Door
Exceptional
(45 reviews)

Huge Resort Villa Near Disney-Pool-Spa-Game Rm-Sleeps 24+-"Better than Photos"

Davenport

7% off
AU$6,339
for 7 nights, 1 home
AU$906 per night
includes taxes & fees
Huge Resort Villa Near Disney-Pool-Spa-Game Rm-Sleeps 24+-"Better than Photos"
Pool
Interior
Private kitchen
Dining
Exceptional
(63 reviews)

Super Fun House with Amazing Views

Kissimmee

8% off
AU$23,161
for 7 nights, 1 home
AU$3,309 per night
includes taxes & fees
Super Fun House with Amazing Views
Lobby
Living area
living area
Amazing Clubhouse Pool!
Exceptional
(26 reviews)

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

Davenport

7% off
AU$4,526
for 7 nights, 1 villa
AU$647 per night
includes taxes & fees
SPECIAL OFFER! Get UP TO 20% off Weekly Rental with complementary Pool Heating!
Terrace/patio
Property grounds
Pool
Living area
Exceptional
(48 reviews)

Luxury villa with south facing pool/spa, only 15 mins from Disney!

Davenport

8% off
AU$2,161
for 7 nights, 1 villa
AU$309 per night
includes taxes & fees
Luxury villa with south facing pool/spa, only 15 mins from Disney!
Dining
Pool
Exterior
Pool
Exceptional
(87 reviews)

9BR Resort Villa / Private Pool & Spa / Sleeps 22 / Near Disney

Kissimmee

7% off
AU$4,039
for 7 nights, 1 villa
AU$577 per night
includes taxes & fees
9BR Resort Villa / Private Pool & Spa / Sleeps 22 / Near Disney
Exterior
Pool
Room
Living area
Exceptional
(197 reviews)

Magical Vacation Home with Kid-Themed Rooms 3 Miles from Disney

Kissimmee

7% off
AU$3,138
for 7 nights, 1 home
AU$448 per night
includes taxes & fees
Magical Vacation Home with Kid-Themed Rooms 3 Miles from Disney
The Emerald Island Resort fountain at our entrance
Clubhouse and Pool
Sparkling pool with all day full sun
Dining
Exceptional
(124 reviews)

SUNSHINE 🌞 and SMILES😎 - 5 mi to Disney, 4 bdrm / 3 bath, Private Pool

Kissimmee

7% off
AU$2,409
for 7 nights, 1 home
AU$344 per night
includes taxes & fees
SUNSHINE 🌞 and SMILES😎 - 5 mi to Disney, 4 bdrm / 3 bath, Private Pool
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$3,130
for 7 nights, 1 home
AU$447 per night
includes taxes & fees
Upstay: Large Resort Home w Private Pool & Hot Tub
Bronson Gym open to guest 9a to 9pm
Bronson Clubhouse lazy river, community pool, and children's pirate playscape
Fully equipped kitchen
Bronson Clubhouse Bar & Grill
Exceptional
(53 reviews)

NEW 9Bdrm Themed w Arcade near Disney & Universal

Kissimmee

7% off
AU$5,844
for 7 nights, 1 home
AU$835 per night
includes taxes & fees
NEW 9Bdrm Themed w Arcade near Disney & Universal
Look at those spectacular paintings, Mickey's room.
Another view of the dining room
Vacation Flash Deals/Clearance Escapes Book now !
Master bedroom with a comfortable king bed
Wonderful
(20 reviews)

Book Now Black Friday Is Here/5th Night On Us!

Davenport

5% off
AU$2,021
for 7 nights, 1 home
AU$289 per night
includes taxes & fees
Book Now Black Friday Is Here/5th Night On Us!
Garage-turned-games-room with, 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

7% off
AU$8,596
for 7 nights, 1 home
AU$1,228 per night
includes taxes & fees
Upstay Family Resort Mansion- Pool, Games, Theater
Terrace/patio
Pool
Dining
Lobby
Very good
(13 reviews)

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

Kissimmee

7% off
AU$2,729
for 7 nights, 1 home
AU$390 per night
includes taxes & fees
Luxe Solara Retreat- Pool+ BBQ + Lazy River+ 8mi Disney + Resort Access
Dining
Pool
Living area
Interior
Exceptional
(27 reviews)

Really Fun House with tons of room, huge pool plenty to do and a terrific view

Kissimmee

8% off
AU$23,161
for 7 nights, 1 villa
AU$3,309 per night
includes taxes & fees
Really Fun House with tons of room, huge pool plenty to do and a terrific view
Expansive Living Room with Smart TV and High Speed WiFi
Large Swimming Pool, Hot Tub and Private Garden Facing Sundeck
In House Movie Theatre
Fun Games Room with Foosball, Table Tennis and Pool
Excellent
(19 reviews)

Upstay—Vibrant Home w Themed Rooms, Pool & Games

Kissimmee

7% off
AU$3,167
for 7 nights, 1 home
AU$452 per night
includes taxes & fees
Upstay—Vibrant Home w Themed Rooms, Pool & Games
Adult Area With Pool Table And 75" TV
Incredible Game Room
Welcome To The Southern Isles! Full of Fun & Relaxation w/an Outdoor Oasis that is South-Facing And Private.
The Game Room Is "Guarded" By A Full Size Storm Trooper
Exceptional
(12 reviews)

EPIC! Themed-Arcade-Theatre-Pool Table-Pool&Spa-3mi>Disney

Kissimmee

11% off
AU$4,221
for 7 nights, 1 home
AU$603 per night
includes taxes & fees
EPIC! Themed-Arcade-Theatre-Pool Table-Pool&Spa-3mi>Disney
Private kitchen
Exterior
Living area
Dining
Wonderful
(19 reviews)

New Lovely Home in Sonoma Resort at Tapestry

Kissimmee

7% off
AU$3,567
for 7 nights, 1 home
AU$510 per night
includes taxes & fees
New Lovely Home in Sonoma Resort at Tapestry
The living room accent wall is of a galaxy far, far away.
The living room has direct access to the pool.
Access to the community pool and waterslide are included free of charge with your rental. The community pool is a 5 minute walk from the house and has free onsite parking.
Front of house.
Exceptional
(124 reviews)

Star Wars Villa - 10 Mins to Disney

Kissimmee

7% off
AU$3,400
for 7 nights, 1 villa
AU$486 per night
includes taxes & fees
Star Wars Villa - 10 Mins to Disney
Dining
Private kitchen
Pool
Can fit two air mattresses
Very good
(7 reviews)

Potter/Jedi vacation villa- Disney Parks 5 miles

Kissimmee

7% off
AU$1,217
for 7 nights, 1 apartment
AU$174 per night
includes taxes & fees
Potter/Jedi vacation villa- Disney Parks 5 miles
Private kitchen
Pool
Property grounds
Outdoor dining
Exceptional
(84 reviews)

4 Masters, wifi, private pool, Ultimate gameroom, resort community, 3mi to WDW

Kissimmee

7% off
AU$2,846
for 7 nights, 1 home
AU$407 per night
includes taxes & fees
4 Masters, wifi, private pool, Ultimate gameroom, resort community, 3mi to WDW
Living Room at Villa Ichabod
Storey Lake Resort Overview
TRON Game Room at Villa Ichabod
Upstairs Master Bedroom at Villa Ichabod
Exceptional
(27 reviews)

Walk to Clubhouse | Tron Game Room | Tiki Bar | Private Pool | 7BR Villa

Kissimmee

7% off
AU$4,390
for 7 nights, 1 villa
AU$627 per night
includes taxes & fees
Walk to Clubhouse | Tron Game Room | Tiki Bar | Private Pool | 7BR Villa
Private kitchen
Pool
Outdoor dining
Exterior
Exceptional
(16 reviews)

Beautiful villa, 7 bedroom, 6 bath home with private pool and game room.

Kissimmee

7% off
AU$3,381
for 7 nights, 1 villa
AU$483 per night
includes taxes & fees
Beautiful villa, 7 bedroom, 6 bath home with private pool and game room.
  • 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)
  • 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)
  • Disney's Animal Kingdom® Theme Park (10 mi / 16.1 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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