Windermere Vacation Packages 2026 from $205

Windermere flight + hotel vacation packages

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

Westgate Vacation Villas Resort

Save 100% on your flight

$205

per person

May 5 - May 9

found 12 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 Palace Hotel / Universal / I-Drive

International Drive District

$486

per person

Apr 15 - Apr 20

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Orlando (MCO)

This resort features an outdoor pool, a gym, and a restaurant. Bring the family and enjoy the children's pool, free theme park shuttle, and kid-friendly dining. Relax with a drink at the bar/lounge and enjoy perks like free self parking and free WiFi.

Flamingo Inn Beachfront

$238

per person

Mar 23 - Mar 28

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. Enjoy the outdoor pool and conveniences like a garden and barbecue grills.

Westgate Blue Tree Resort in Lake Buena Vista

Save 100% on your flight

$340

per person

Apr 23 - Apr 28

found 20 hours ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

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

Westgate Cocoa Beach Resort

$1,649

per person

Apr 18 - Apr 25

found 24 hours 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.

Top Windermere hotels deals

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

8800 Vistana Centre Dr Orlando FL

Free Cancellation

Reserve now, pay when you stay

$131 nightly

$148 total

Mar 15 - Mar 16

Total with taxes and fees

This smoke-free hotel features 3 restaurants, 6 outdoor pools, and 10 outdoor tennis courts. There's fun for all ages with a free kid's club and mini golf, and barbecue grills are available on site. Enjoy the 8 hot tubs and perks like free WiFi.

Pool

Hot Tub

Hyatt Regency Orlando International Airport

9300 Jeff Fuqua Boulevard Orlando FL

Free Cancellation

Reserve now, pay when you stay

$249 nightly

$280 total

Feb 22 - Feb 23

Total with taxes and fees

This smoke-free hotel includes 2 restaurants, an outdoor pool, and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a bar/lounge on site, and laundry facilities and concierge services are also provided.

The Grove Resort & Water Park Orlando

14501 Grove Resort Avenue Winter Garden FL

Free Cancellation

Reserve now, pay when you stay

$218 nightly

$245 total

Feb 22 - Feb 23

Total with taxes and fees

Free water park access, 3 restaurants, and 6 outdoor pools are all featured at this resort. Bring the family and enjoy the lazy river, children's club, and mini golf. Enjoy the 2 hot tubs and perks like free WiFi.

Universal's Cabana Bay Beach Resort

6550 Adventure Way Orlando FL

Free Cancellation

Reserve now, pay when you stay

$155 nightly

$174 total

Feb 25 - Feb 26

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

Marriott's Grande Vista

5925 Avenida Vista Orlando FL

Free Cancellation

Reserve now, pay when you stay

$135 nightly

$152 total

Feb 22 - Feb 23

Total with taxes and fees

This smoke-free 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

DoubleTree by Hilton Hotel Orlando at SeaWorld

10100 International Drive Orlando FL

Free Cancellation

Reserve now, pay when you stay

$114 nightly

$129 total

Mar 8 - Mar 9

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

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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

Universal Orlando Resort

4.5/5(4,155 reviews)

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.

Walt Disney World® Resort

4.5/5(2,427 reviews)

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 acclaimed theater scene in this walkable area.

Disney Springs™

4.5/5(11,529 reviews)

You can search for that perfect souvenir when you visit Disney Springs™, a favorite shopping spot in Lake Buena Vista. Experience the entertainment choices and acclaimed theater scene 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 $205. 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.