Windermere Vacation Packages 2025/2026 from $313

Windermere flight + hotel vacation packages

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

Westgate River Ranch Resort & Rodeo

Save 100% on your flight

$313

per person

Oct 24 - Oct 26

found 1 day ago

Roundtrip flight included

Philadelphia (PHL) to Orlando (MCO)

This smoke-free resort features free water park access, a marina, and 2 restaurants. There's fun for all ages with mini golf and a playground, and barbecue grills are available on site. Relax with a drink at one of the 3 bars/lounges and enjoy perks like free self parking.

Hilton Garden Inn Jacksonville Ponte Vedra Sawgrass

Palm Valley

Save 100% on your flight

$410

per person

Nov 10 - Nov 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

This hotel features an outdoor pool, a hot tub, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. You'll appreciate the gym, bar/lounge, and snack bar/deli.

Westgate Cocoa Beach Resort

Save 100% on your flight

$607

per person

Nov 21 - Nov 24

found 1 day ago

Roundtrip flight included

Boston (BOS) 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.

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

International Drive District

Save 100% on your flight

$448

per person

Nov 12 - Nov 18

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

This hotel features an outdoor pool and a rooftop terrace. Enjoy the hot tub and free perks like continental breakfast and free self parking. A business center, free WiFi in public areas, and a terrace are also on offer.

Parkway International Resort

Save 100% on your flight

$411

per person

Nov 8 - Nov 15

found 17 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Orlando (MCO)

This hotel features an outdoor pool, a hot tub, and a restaurant. There's fun for all ages with a children's pool and a playground, and barbecue grills are available on site. Enjoy the gym and perks like free self parking and free WiFi.

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

$93 nightly

$104 total

Sep 25 - Sep 26

Total with 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

Marriott's Grande Vista

5925 Avenida Vista, Orlando, FL

Free Cancellation

Reserve now, pay when you stay

$87 nightly

$98 total

Sep 28 - Sep 29

Total with 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

$136 nightly

$153 total

Sep 29 - Sep 30

Total with 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

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

12401 International Dr, Orlando, FL

Free Cancellation

Reserve now, pay when you stay

$84 nightly

$95 total

Oct 1 - Oct 2

Total with taxes and fees

This smoke-free hotel features 2 restaurants, 5 outdoor pools, and 2 outdoor tennis courts. Bring the family and enjoy the children's club, children's pool, and waterslide. Enjoy the 4 hot tubs and perks like free WiFi.

DoubleTree by Hilton Hotel Orlando at SeaWorld

10100 International Drive, Orlando, FL

Free Cancellation

Reserve now, pay when you stay

$96 nightly

$108 total

Sep 14 - Sep 15

Total with taxes and fees

This smoke-free resort features 2 restaurants, 2 outdoor pools, and a 24-hour gym. There's fun for all ages with mini golf and a children's pool, and families will appreciate the onsite laundry facilities. Relax with a drink at one of the 3 bars/lounges and get perks like free WiFi.

Pool

Pet friendly

Rosen Inn at Pointe Orlando

9000 International Drive, Orlando, FL

Free Cancellation

Reserve now, pay when you stay

$65 nightly

$74 total

Sep 14 - Sep 15

Total with 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

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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 $313. 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.