Windermere Vacation Packages 2026 from $257

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

$257

per person

May 15 - May 19

found 19 hours ago

Roundtrip flight included

New York (LGA) 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 Lakes Resort & Spa Universal Studios Area

Save 100% on your flight

$415

per person

May 3 - May 9

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 Town Center Resort

Save 100% on your flight

$375

per person

May 3 - May 9

found 1 day 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 mini golf, and families will appreciate the onsite laundry facilities. Enjoy the 14 outdoor pools and perks like free self parking and free WiFi.

Westgate Towers Resort

Save 100% on your flight

$260

per person

May 15 - May 19

found 19 hours ago

Roundtrip flight included

New York (LGA) to Orlando (MCO)

2 outdoor pools, 2 hot tubs, and a gym are all featured at this smoke-free hotel. There's fun for all ages with a children's pool and a playground, and barbecue grills are available on site. Relax with a drink at the bar/lounge and enjoy perks like free self parking.

Westgate Cocoa Beach Resort

Save 100% on your flight

$685

per person

May 1 - May 4

found 21 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

The Grove Resort & Water Park Orlando

14501 Grove Resort Avenue Winter Garden FL

Free Cancellation

Reserve now, pay when you stay

$229 nightly

$257 total

Apr 13 - Apr 14

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.

Pool

Hot Tub

Hyatt Regency Orlando International Airport

9300 Jeff Fuqua Boulevard Orlando FL

Free Cancellation

Reserve now, pay when you stay

$229 nightly

$258 total

Mar 16 - Mar 17

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.

Pool

Free WiFi

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

8800 Vistana Centre Dr Orlando FL

Free Cancellation

Reserve now, pay when you stay

$147 nightly

$166 total

Apr 10 - Apr 11

Total with taxes and fees

This smoke-free condo resort 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

Universal's Cabana Bay Beach Resort

6550 Adventure Way Orlando FL

Free Cancellation

Reserve now, pay when you stay

$133 nightly

$150 total

Apr 12 - Apr 13

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

Rosen Inn at Pointe Orlando

9000 International Drive Orlando FL

Free Cancellation

Reserve now, pay when you stay

$78 nightly

$88 total

Mar 15 - Mar 16

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

Westgate Lakes Resort & Spa Universal Studios Area

9500 Turkey Lake Rd Orlando FL

$143 nightly

$161 total

Apr 12 - Apr 13

Total with taxes and fees

Pool

Hot Tub

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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

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.

Universal Studios Florida

4.5/5(9,273 reviews)

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

Vibrant street scene at Universal Studios Florida with families and attractions under a cloudy sky

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.

Frequently asked questions

How much are vacation packages to Windermere?

Enjoy a memorable experience in Windermere with a vacation package starting from just $257. 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.