Windermere Vacation Packages 2026 from $301

Windermere flight + hotel vacation packages

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

Westgate Towers Resort

Save 100% on your flight

$301

per person

Oct 15 - Oct 20

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) 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 Palace Hotel / Universal / I-Drive

International Drive District

$579

per person

Oct 28 - Nov 4

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.

Westgate Lakes Resort & Spa Universal Studios Area

Save 100% on your flight

$444

per person

Nov 4 - Nov 9

found 1 day ago

Roundtrip non-stop 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 mini golf and a children's pool, and barbecue grills are available on site. Enjoy the 7 outdoor pools and get free valet parking.

Westgate Vacation Villas Resort

Save 100% on your flight

$305

per person

Oct 16 - Oct 20

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 a children's pool, and families will appreciate the onsite laundry facilities. Enjoy the 14 outdoor pools and get free self parking.

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

International Drive District

Save 100% on your flight

$504

per person

Oct 28 - Nov 4

found 1 day ago

Roundtrip non-stop 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.

Top Windermere hotels deals

Rosen Inn Lake Buena Vista

8442 Palm Parkway Orlando FL

Free Cancellation

Reserve now, pay when you stay

$62 nightly

$70 total

Aug 19 - Aug 20

Total with taxes and fees

This hotel features 2 outdoor pools, a restaurant, and a bar/lounge. Bring the family and enjoy the children's pool, free theme park shuttle, and playground. Guests will appreciate perks like free WiFi and a free shopping center shuttle.

Pool

Pet friendly

DoubleTree by Hilton at the Entrance to Universal Orlando

5780 Major Blvd Orlando FL

Free Cancellation

$78 nightly

$88 total

Sep 1 - Sep 2

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

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

8800 Vistana Centre Dr Orlando FL

Free Cancellation

Reserve now, pay when you stay

$123 nightly

$139 total

Sep 7 - Sep 8

Total with taxes and fees

This smoke-free aparthotel 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

$150 nightly

$169 total

Aug 16 - Aug 17

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

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

Aug 18 - Aug 19

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

Walt Disney World Swan

1200 Epcot Resort Blvd Lake Buena Vista FL

Free Cancellation

Reserve now, pay when you stay

$249 nightly

$280 total

Aug 16 - Aug 17

Total with taxes and fees

This smoke-free resort features a private beach, 3 hot tubs, and a restaurant. Bring the family and enjoy the children's pool, free theme park shuttle, and waterslide. Enjoy the outdoor pool and perks like free WiFi.

On private beach

Pool

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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.

Stay near popular Windermere attractions

Tibet Butler Preserve

Explore the lovely green spaces of Tibet Butler Preserve and enjoy the golf courses in Windermere. Check out the shops and top-notch restaurants in this family-friendly area.

See properties

Frequently asked questions

How much are vacation packages to Windermere?

Enjoy a memorable experience in Windermere with a vacation package starting from just $301. 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.