Windermere Vacation Packages 2026 from $396

Windermere flight + hotel vacation packages

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

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

International Drive District

Save 100% on your flight

$396

per person

Sep 3 - Sep 8

found 24 hours 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.

Westgate Lakes Resort & Spa Universal Studios Area

Save 100% on your flight

$551

per person

Aug 21 - Aug 28

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

The Delaney Hotel

South Orange

Save 100% on your flight

$689

per person

Aug 20 - Aug 27

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Orlando (MCO)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking, a terrace, and a snack bar/deli are also offered.

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Save 100% on your flight

$1,176

per person

Aug 18 - Aug 24

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

Free water park access, 4 restaurants, and 2 outdoor pools are all featured at this smoke-free hotel. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like free self parking and WiFi in public areas. You'll appreciate the hot tub, poolside bar, and snack bar/deli.

Dune House Hotel & Spa

$660

per person

Sep 9 - Sep 14

found 8 hours ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

An outdoor pool, valet parking, and concierge services are featured at this hotel. WiFi in public areas is free. A snack bar/deli, a communal living room, and express check-in are also on offer.

Top Windermere hotels deals

Hyatt Regency Orlando International Airport

9300 Jeff Fuqua Boulevard Orlando FL

Free Cancellation

Reserve now, pay when you stay

$169 nightly

$190 total

Jul 1 - Jul 2

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

$135 nightly

$152 total

Jul 19 - Jul 20

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

DoubleTree by Hilton at the Entrance to Universal Orlando

5780 Major Blvd Orlando FL

Free Cancellation

Reserve now, pay when you stay

$89 nightly

$101 total

Jul 12 - Jul 13

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

The Grove Resort & Water Park Orlando

14501 Grove Resort Avenue Winter Garden FL

$257 nightly

$289 total

Jul 28 - Jul 29

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

Universal's Cabana Bay Beach Resort

6550 Adventure Way Orlando FL

Free Cancellation

Reserve now, pay when you stay

$150 nightly

$169 total

Jun 30 - Jul 1

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

$124 nightly

$140 total

Jul 19 - Jul 20

Total with taxes and fees

This smoke-free aparthotel 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.

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

A castle with multiple spires and a central tower.

Walt Disney World® Resort

4.5/5(2,451 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.

A globe with the word "UNIVERSAL" and a theme park in the background.

Universal Studios Florida

4.5/5(9,415 reviews)

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

A colorful street with various shops and a Ferris wheel.

Universal Orlando Resort

4.5/5(4,207 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 $396. 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.