Winter Springs Vacation Packages 2026 from $338

Winter Springs flight + hotel vacation packages

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

Boardwalk Inn and Suites

Davis

$338

per person

May 6 - May 9

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

This hotel features a bar/lounge, a poolside bar, and an outdoor pool. Enjoy the gym and perks like free valet parking and free WiFi. There's a hot tub on site, and a 24-hour front desk and a communal living room are also provided.

Westgate Vacation Villas Resort

$1,572

per person

Mar 17 - Mar 24

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.

Westgate Palace Hotel / Universal / I-Drive

International Drive District

$1,450

per person

Mar 17 - Mar 24

found 1 day ago

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.

Extended Stay America Suites Orlando Conv Ctr Universal Blvd

International Drive District

$448

per person

May 3 - May 9

found 18 hours ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

This hotel features an outdoor pool and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like on-the-go breakfast and free self parking.

Westgate Blue Tree Resort in Lake Buena Vista

Save 100% on your flight

$340

per person

Apr 23 - Apr 28

found 1 day 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.

Top Winter Springs hotels deals

DoubleTree by Hilton at the Entrance to Universal Orlando

5780 Major Blvd Orlando FL

Free Cancellation

$125 nightly

$141 total

Mar 12 - Mar 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

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

Orlando International Drive North Hotel

5859 American Way Orlando FL

Free Cancellation

Reserve now, pay when you stay

$79 nightly

$89 total

Feb 23 - Feb 24

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. There's fun for all ages with a theme park shuttle and a playground. There's no skimping on freebies - guests receive free buffet breakfast, free WiFi, and free self parking.

Pool

Breakfast included

Sonesta Essential Orlando Airport

8101 Aircenter Ct Orlando FL

Free Cancellation

Reserve now, pay when you stay

$101 nightly

$114 total

Feb 24 - Feb 25

Total with taxes and fees

This hotel features an outdoor pool and a gym. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A computer station, dry cleaning, and luggage storage are also on offer.

Pool

Breakfast included

Avanti International Resort

8738 International Dr Orlando FL

Free Cancellation

Reserve now, pay when you stay

$117 nightly

$132 total

Feb 22 - Feb 23

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Bring the family and enjoy the children's pool, free theme park shuttle, and arcade/game room. Enjoy the gym and perks like free WiFi.

Pool

Hot Tub

Rosen Inn at Pointe Orlando

9000 International Drive Orlando FL

Free Cancellation

Reserve now, pay when you stay

$75 nightly

$85 total

Feb 21 - Feb 22

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

Don't see what you're looking for?

See all available properties in Winter Springs

View all properties

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

Central Winds Park

After visiting Central Winds Park, make a plan to see the other sights and activities in Winter Springs. Amble around the area's lakeside or attend a sporting event.

Trotwood Park

After visiting Trotwood Park, make a plan to see the other sights and activities in Winter Springs. Experience the area's entertainment choices or attend a sporting event.

Tuscawilla Golf Course

Enjoy a round of golf in Winter Springs at Tuscawilla Golf Course. Stroll along the lakeside or attend a sporting event in the area.

Frequently asked questions

How much are vacation packages to Winter Springs?

With a Travelocity vacation package, you can experience the sights and sounds of Winter Springs for as low as $338. Hotels, flights and experiences — we have it all. You'll make great savings just for combining your bookings. And with all of that taken care of before you even set off, you can sit back, relax and enjoy the adventure.

Where can I get the best vacation package deals for Winter Springs?

You'll find a fantastic range of Winter Springs package deals on Travelocity. With as many as 400 partner airlines and 1,000,000 worldwide properties, putting together your dream escape will be simple.

Why should I purchase my Winter Springs vacation bundle via Travelocity?

Because life is all about the journey, and we've got everything you could hope for to get you on your way. With our high-quality service and Price Match Guarantee, you can organize your trip with confidence. And you can sleep easy while you're away knowing you can reach us with our 24/7 customer support.

Can I save on my Winter Springs car rental if I bundle it with my hotel or flight?

Sure can — bundle your flight, hotel and car into a Winter Springs vacation package and you can save plenty. With so many places to explore in Winter Springs, that rental vehicle will make it easy to explore. Once you're in the driver's seat, turn up the tunes and make your way to Daytona International Speedway, a famous attraction about 35 mi from Winter Springs.

Which airport is best for Winter Springs?

Many travelers fly into Orlando Intl. Airport (MCO), 19 mi south of downtown Winter Springs. Others prefer Daytona Beach Intl. Airport (DAB) (35 mi away from central Winter Springs) or Orlando Sanford Intl. Airport (SFB) (7 mi away from central Winter Springs).

What is there to do in Winter Springs?

While venturing off the beaten track can be rewarding, you really shouldn't miss the well-known sights that make a destination famous. Tuscawilla Golf Course and Central Winds Park are a couple of them in Winter Springs.

Where should I stay when visiting Winter Springs?

Many travelers check in to the Cozy Home 4 bedroom 5 bed with Jet Tub.. It's sure to be a great base for your Winter Springs escape.