Windermere Vacation Packages from $248

Flight and hotel packages to Windermere

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

Palazzo Lakeside Hotel

Save 100% on your flight

per person

Jul 26 - Jul 29

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

This hotel features an outdoor pool, a gym, and a restaurant. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and a picnic area are also on offer.

Westgate Palace Hotel / Universal / I-Drive

Florida Center

per person

Jul 3 - Jul 7

Roundtrip 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

per person

Jun 24 - Jun 29

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 get free valet parking.

Westgate Blue Tree Resort in Lake Buena Vista

Save 100% on your flight

per person

Jul 3 - Jul 9

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 spa tub and perks like free self parking.

Barefoot'n Resort

Save 100% on your flight

per person

Jul 24 - Jul 30

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

This hotel features an outdoor pool and a spa tub. There's fun for all ages with a children's pool and a playground, and families will appreciate the onsite laundry facilities. WiFi in public areas is free.

Top Windermere hotel deals

The Grove Resort & Water Park Orlando

14501 Grove Resort Avenue, Winter Garden, FL

Free Cancellation

Reserve now, pay when you stay

$199

per night

May 23 - May 24

Free water park access, 3 restaurants, and 3 outdoor pools are all featured at this resort. Bring the family and enjoy the lazy river, children's club, and mini golf. Relax with a drink at one of the 2 poolside bars and get perks like free WiFi.

DoubleTree by Hilton Hotel Orlando at SeaWorld

10100 International Drive, Orlando, FL

$76

per night

May 29 - May 30

This smoke-free hotel 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. Unwind with a drink at one of the 3 bars/lounges and enjoy free perks like buffet breakfast and WiFi in public areas.

Hyatt Regency Orlando International Airport

9300 Jeff Fuqua Boulevard, Orlando, FL

Free Cancellation

$189

per night

May 29 - May 30

This smoke-free aparthotel 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.

Breakfast available

Pool

DoubleTree by Hilton at the Entrance to Universal Orlando

5780 Major Blvd, Orlando, FL

Free Cancellation

Reserve now, pay when you stay

$102

per night

May 28 - May 29

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.

Holiday Inn Resort Orlando Suites - Waterpark, an IHG Hotel

14500 Continental Gateway, Orlando, FL

Free Cancellation

$84

per night

May 27 - May 28

A water park, 2 outdoor pools, and 2 spa tubs are all featured at this smoke-free hotel. There's fun for all ages with mini golf and a waterslide, and families will appreciate the onsite laundry facilities. Enjoy the gym and perks like free WiFi.

Universal's Endless Summer Resort - Dockside Inn and Suites

7125 Universal Boulevard, Orlando, FL

Free Cancellation

Reserve now, pay when you stay

$144

per night

May 23 - May 24

This smoke-free hotel features 2 outdoor pools, a gym, and a restaurant. 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 3 bars/lounges and get perks like free WiFi.

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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 in Windermere

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.

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?

Travelocity has flight and hotel packages starting from just $248. With such huge savings, you’ll be saying hello to Windermere before you know it.

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

There are awesome Windermere package deals to score with Travelocity. Did you know we partner with 400 airlines and 1,000,000 properties across the globe? Remember this the next time you’re ready to check another place off your travel bucket list.

Why should I book my Windermere vacation bundle via Travelocity?

You’ll not only save lots, but you can also access our 24/7 support, high-quality service and a Price Match Guarantee. Explore every nook-and-cranny across the world, uncover lesser-known sights and forge unforgettable memories — we’ll take care of the little details.

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

Bundling your flight, hotel and car into a Windermere vacation package is an excellent way to land the best prices. Plus, having your own set of wheels gives you absolute freedom to make your way to all those famous sights you’re itching to explore. Sitting 55 mi away from Windermere, Daytona International Speedway is one attraction that should have a place on your itinerary. Buckle up and make a day trip of it.

What is the best time of year to go to Windermere?

You can avoid the tourist crowds and save some cash in September, October and December, which are the quietest times to visit. The peak season months of January, February and March are naturally busier and more expensive, but more will be happening around Windermere. Book a hotel in and you’ll see your budget go further. Room rates are usually highest in .

Which airport is best for Windermere?

For plenty of visitors, heading to Windermere means getting off the plane at Orlando Intl. Airport (MCO). This busy airport sits 14 mi east of the downtown area. You could also choose to fly into Orlando Melbourne Intl. Airport (MLB) (60 mi away from central Windermere) or Orlando Sanford Intl. Airport (SFB) (25 mi away from central Windermere).

What is there to do in Windermere?

You’ll sense a particular magic in the air as you roam the streets of Windermere. Isleworth Golf and Country Club and Tibet Butler Preserve are just two famous attractions that lure visitors to this fantastic city, so put them on your to-do list.

Where should I stay when visiting Windermere?

If you’re after someplace comfortable to spend your nights, check out the Beautiful 5 Br. Single_family (419004) by Houzlet. It’s the top choice for many travelers.