Windermere Holidays

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Windermere Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
per person
24 Jul - 27 Jul
found 14 hours ago
Return flight included
Singapore (SIN) to Orlando (MCO)
7.8/10 Good! (1,262 reviews)
Speedy and very cordial. The water park was an additional $25 per person and I wasn't expecting that; neither the surprised additional $70 resort fee at check in

Reviewed on 10 Jun, 2025

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
Florida Center
per person
24 Jul - 27 Jul
found 14 hours ago
Return flight included
Singapore (SIN) to Orlando (MCO)
8.6/10 Excellent! (1,000 reviews)
Great amenities from inside your hotel room to the pool area! A little inconsistent with what kitchen tools each room has but enough for a family to be comfortable and make a meal! The only negative experience was the highly offensive marketing team. We were offered a free gift and the opportunity to learn more about Westgate properties. That dude did not do well. We were offered a late check out but the key card stopped working at 10 am. Otherwise, no issues. My family members from CA and TX booked other suites. We all agreed we would stay here again!

Reviewed on 11 Jun, 2025

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
per person
24 Jul - 27 Jul
found 14 hours ago
Return flight included
Singapore (SIN) to Orlando (MCO)
8.2/10 Very Good! (4,996 reviews)
I had great time at the West Gate resort i didn't want to leave. Its a great place for the kids.

Reviewed on 11 Jun, 2025

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

4 out of 5
per person
24 Jul - 27 Jul
found 14 hours ago
Return flight included
Singapore (SIN) to Orlando (MCO)
9/10 Wonderful! (1,001 reviews)
I did not enjoy my stay at the hose for the time i had to call the office and could never get it was some inconvenience anyone to seevice my washing maxhine.

Reviewed on 11 Jun, 2025

Vintage At Horizon West Apartments By Barsala

Vintage At Horizon West Apartments By Barsala

4 out of 5
per person
24 Jul - 27 Jul
found 14 hours ago
Return flight included
Singapore (SIN) to Orlando (MCO)
9.4/10 Exceptional! (3 reviews)
Enjoyed the stay. It was quiet and clean

Reviewed on 11 May, 2025

Top hotels in Windermere

Marriott's Grande Vista
Marriott's Grande Vista
4 out of 5
5925 Avenida Vista, Orlando, FL
Fully refundableReserve now, pay when you stay
The price is S$149 per night from 6 Jul to 7 Jul
S$149
6 Jul - 7 Jul
includes taxes & fees
8.8/10 Excellent! (2,491 reviews)
"All good"

Reviewed on 9 Jun, 2025

Marriott's Grande Vista
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
4 out of 5
8800 Vistana Centre Dr, Orlando, FL
Fully refundableReserve now, pay when you stay
The price is S$110 per night from 7 Jul to 8 Jul
S$110
7 Jul - 8 Jul
includes taxes & fees
9.2/10 Wonderful! (3,038 reviews)
"Everything was nice and clean beautiful home"

Reviewed on 10 Jun, 2025

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Rosen Inn Lake Buena Vista
Rosen Inn Lake Buena Vista
3.5 out of 5
8442 Palm Parkway, Orlando, FL
Fully refundableReserve now, pay when you stay
The price is S$96 per night from 13 Jul to 14 Jul
S$96
13 Jul - 14 Jul
includes taxes & fees
8.4/10 Very Good! (5,124 reviews)
"Staff very friendly"

Reviewed on 10 Jun, 2025

Rosen Inn Lake Buena Vista
See all 51,865 properties in Windermere
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.

Frequently asked questions

How much does a Windermere holiday package cost?
You’ll find cheap prices from S$1,802 on Expedia for your Windermere getaway. However, factors like the season, choice of hotel and length of stay will influence how much your holiday to Windermere costs.
What are the cheapest months to go to Windermere?
Plan your trip for the off-peak season and you’re likely to get cheap Windermere holiday packages. Bear in mind that public holidays and local events and festivals can have an impact on prices, so do some research before booking.
How many days is enough for Windermere?
Windermere holidays can be short or long, but to really sink your teeth into this destination, we reckon 3 days is a good ballpark. This will mean you can fit in top attractions like Windermere Country Club and Windermere Country Club and seek out some hidden gems. Don’t forget to explore neighbourhoods such as Florida Centre and Lake Buena Vista North either. If you’re smart with your time, you can even schedule a day trip or two from Windermere too.
Is it worth booking a holiday package to Windermere?
Windermere is a good holiday destination with attractions like Isleworth Golf and Country Club among the many things to keep you entertained. Whether you’re travelling with the family or getting away with friends, a Windermere holiday promises a good time for everyone.
How to find the best Windermere package deals?
Use Expedia’s handy filters to help you find some tempting Windermere package deals. When you start your search, just set your maximum budget and then order the results by “Price: low to high.” If you’re looking to save, plan your adventure for midweek, or browse for Windermere package deals in the off-peak season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it’s typically best to book your holiday package well in advance.
Is it cheaper to book a Windermere holiday as a package?
You can enjoy significant savings on your Windermere getaway by booking a personalised holiday package. Click on the “Package” heading, then select your travel dates and destination to see the best hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a holiday package to Windermere?
If you have your Windermere holiday dates confirmed, book as soon as you can to snap up some awesome deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spontaneous adventures? Our last-minute deals are perfect for quick escapes.
How to plan a trip to Windermere?

  1. Choose your dates: What you want to do in Windermere and your preferred season will help you decide when to travel.
  2. Figure out your budget: Ensure you have enough money to cover everything from food and transportation to activities and airfares. Your accommodation will likely be the largest expense during your trip to Windermere.
  3. Decide your trip length: Think about how much time you’d like to spend exploring Windermere. Plan your itinerary so you can get to all the attractions and activities you’re interested in at a leisurely pace.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, hotels, car rental and more into a tailored Windermere holiday package.

Popular places to visit

Walt Disney World® Resort

Walt Disney World® Resort

4.5/5(63 reviews)

Walt Disney World® Resort is part of Orlando. It makes up part of bustling metropolis that is home to 240,000 inhabitants. Walt Disney World® Resort is approximately 15 miles (24 kilometers) from Orlando’s city center. If you are flying in, Walt Disney World® Resort is approximately 15 miles (24 kilometers) from Orlando International Airport.

Walt Disney World® Resort
Universal Studios Florida

Universal Studios Florida

4.5/5(273 reviews)

Exhilarating rides and world class film sets are brought together to create this outstanding world-renowned theme park.

Universal Studios Florida
Universal Studios Florida® featuring rides, street scenes and a city

Universal Orlando Resort

4.5/5(166 reviews)

Make your Florida vacation one to remember with a stay at this hotel and theme park complex.

Universal Orlando Resort

What to do in Windermere

LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

S$87
per traveller
84% of travellers recommend
LEGOLAND® Florida Tickets
Bamboo Dune Buggy Tour

Fort Meade: Bamboo Dune Buggy Tour

S$90
per adult
100% of travellers recommend
Fort Meade: Bamboo Dune Buggy Tour
Old Town Kissimmee: Attraction and Meal Combo Offers

Old Town Kissimmee: Attraction and Meal Combo Offers

S$19
per adult
80% of travellers recommend
Old Town Kissimmee: Attraction and Meal Combo Offers
See all activities in Windermere

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.