Windermere Vacation Packages 2025/2026 from $191

Windermere flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Westgate Lakes Resort & Spa Universal Studios Area

Save 100% on your flight

per person

Oct 23 - Oct 25

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

This smoke-free hotel features a full-service spa, a water park, and a marina. There's fun for all ages with a lazy river and a children's club, and barbecue grills are available on site. Enjoy the 7 outdoor pools and perks like free valet parking and a free theme park shuttle.

Westgate Towers Resort

Save 100% on your flight

per person

Sep 26 - Oct 1

found 1 day ago

Roundtrip flight included

Philadelphia (PHL) to Orlando (MCO)

This hotel features an outdoor pool and a gym. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the hot tub and perks like free self parking.

Ocean Sands Beach Boutique Inn - 1 Acre Private Beach

Vilano Beach

Save 100% on your flight

per person

Oct 15 - Oct 19

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

The private beach and full-service spa are among the highlights at this hotel. Relax with beach cabanas, sun loungers, and beach umbrellas. Enjoy the outdoor pool and free perks like buffet breakfast and WiFi in public areas.

Westgate Vacation Villas Resort

Save 100% on your flight

per person

Sep 20 - Sep 27

found 7 hours ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

This smoke-free resort features a water park, a marina, and 2 restaurants. There's fun for all ages with a children's club and a children's pool, and families will appreciate the onsite laundry facilities. Enjoy the 14 outdoor pools and get free self parking.

Westgate Cocoa Beach Resort

per person

Sep 10 - Sep 14

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

Free water park access and an outdoor pool are featured at this smoke-free condo resort. Spend a day at the beach surfing, or relax with sun loungers and beach umbrellas. There's fun for all ages with a lazy river and a children's pool, and barbecue grills are available on site.

Top Windermere hotels deals

DoubleTree by Hilton at the Entrance to Universal Orlando

5780 Major Blvd, Orlando, FL

Free Cancellation

Reserve now, pay when you stay

$98 nightly

$110 total

Aug 17 - Aug 18

Total includes taxes and fees

This smoke-free hotel includes 2 restaurants, an outdoor pool, and a 24-hour gym. There's fun for all ages with a children's pool and an arcade/game room, and families will appreciate the onsite laundry facilities. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi.

Pool

Hot Tub

Rosen Inn at Pointe Orlando

9000 International Drive, Orlando, FL

Free Cancellation

Reserve now, pay when you stay

$70 nightly

$79 total

Aug 25 - Aug 26

Total includes taxes and fees

This hotel features 3 outdoor pools, a gym, and a restaurant. Bring the family and enjoy the free theme park shuttle, playground, and kid-friendly dining. Enjoy a meal in one of the 2 coffee shops/cafes and perks like free WiFi.

Pool

Pet friendly

Marriott's Grande Vista

5925 Avenida Vista, Orlando, FL

Free Cancellation

Reserve now, pay when you stay

$87 nightly

$98 total

Sep 1 - Sep 2

Total includes taxes and fees

This eco-certified hotel features a golf course, a full-service spa, and 3 restaurants. There's fun for all ages with mini golf and a children's pool, and barbecue grills are available on site. Enjoy a meal in one of the 2 coffee shops/cafes and perks like free WiFi.

Pool

Hot Tub

Universal's Cabana Bay Beach Resort

6550 Adventure Way, Orlando, FL

Free Cancellation

Reserve now, pay when you stay

$135 nightly

$152 total

Sep 1 - Sep 2

Total includes taxes and fees

This smoke-free hotel features 2 restaurants, 2 outdoor pools, and 2 hot tubs. There's fun for all ages with a lazy river and a bowling alley, and families will appreciate the onsite laundry facilities. Unwind with a drink at one of the 2 poolside bars and enjoy freebies like WiFi in public areas and a theme park shuttle.

Pool

Hot Tub

Home2 Suites by Hilton Orlando at Flamingo Crossings

341 Flagler Ave, Winter Garden, FL

Free Cancellation

Reserve now, pay when you stay

$110 nightly

$123 total

Aug 20 - Aug 21

Total includes taxes and fees

This hotel features an outdoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy freebies like buffet breakfast and a theme park shuttle

Pool

Breakfast included

Kompose Boutique Resort at Theme Parks

7491 W Irlo Bronson Memorial Hwy, Kissimmee, FL

Free Cancellation

Reserve now, pay when you stay

$68 nightly

$78 total

Aug 17 - Aug 18

Total includes taxes and fees

2 hot tubs, an outdoor pool, and a 24-hour gym are all featured at this smoke-free resort. Enjoy the sauna and perks like free WiFi. A bar/lounge, a 24-hour front desk, and a poolside bar are also provided.

Pool

Hot Tub

Don't see what you're looking for?

See all available properties in Windermere

View all properties

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.

Popular places to visit

Walt Disney World® Resort

Have a fun-filled day at Walt Disney World® Resort and find out why this is a popular theme park in Lake Buena Vista. Discover the top-notch restaurants and entertainment choices in this family-friendly area.

Universal Studios Florida

Movie sets and thrill rides combine to create this internationally acclaimed theme park.

Universal Studios Orlando showing street scenes, a city and rides

Universal Orlando Resort

Have a fun-filled day at Universal Orlando Resort and see why people love this theme park in Orlando. Check out the shops and top-notch restaurants in this family-friendly area.

Frequently asked questions

How much are vacation packages to Windermere?

Enjoy a memorable experience in Windermere with a vacation package starting from just $191. Booking your tours, hotels and flights with Travelocity is easy. On top of that, our deals will leave you with more savings for plenty of fun times.

Where can I get the best vacation package deals for Windermere?

Walking away with an amazing package deal to Windermere is a cinch with Travelocity. With around 400 airlines and 1,000,000 properties all over the world, you're flush with choice when picking your hotels and flights.

Why should I book my Windermere vacation bundle with Travelocity?

Incredible savings, an abundance of breathtaking destinations and 24/7 customer service — that's why. And with our Price Match Guarantee, you can rest assured knowing that you'll always score the best possible deal with Travelocity.

Will I save money on my Windermere car rental if I combine it with hotels and flights?

With a Windermere vacation package, you can bundle your hotel, flight and car bookings and save a ton. If you can't wait to explore the best of this fantastic destination, why not make a beeline for Daytona International Speedway? This famous sight is 55 mi from Windermere. With your own rental car, you'll be there in a flash.

Which airport is best for Windermere?

Orlando Intl. Airport (MCO) is a main hub. You'll find it approximately 14 mi east of Windermere. Other options worth checking out are Daytona Beach Intl. Airport (DAB) (55 mi away from central Windermere) and Orlando Sanford Intl. Airport (SFB) (25 mi away from central Windermere).

What is there to do in Windermere?

Windermere has plenty of places to explore, like Isleworth Golf and Country Club and Tibet Butler Preserve. These two fantastic attractions top most tourists' itineraries.

Where should I stay when visiting Windermere?

If you're after someplace comfortable to spend your nights, take a look at the 1 Bedroom Lofted, Private entrance, dedicated parking, W/D, WiFi, dog friendly. It's the top choice for many travelers.