Maitland Vacation Packages 2026 from $274

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Your Maitland Vacation

Lock in a Maitland vacation package that has everything you need and nothing you don't. Good for dining, bars and pubs and shopping, think about basing yourself in the neighborhood of Ivanhoe Village. Make your trip to Maitland even more fun by including some sightseeing. Rollins College, Full Sail University and Altamonte Mall are among the leading attractions you'll want to explore. Expedia is here to help you escape the everyday. Tailor your vacation to Maitland to suit your style of travel, whatever that may be!

The Latest Maitland vacation packages

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

Palazzo Lakeside Hotel

$274

per person

Dec 13 - Dec 16

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

8.4/10 Very Good! (5,343 reviews)

Westgate Palace Hotel / Universal / I-Drive

International Drive District

Save 100% on your flight

$901

per person

Dec 23 - Dec 29

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

9/10 Wonderful! (1,334 reviews)

I called the front desk to request more towels and to let them know that the shower water was only lukewarm and not hot at all. Within five minutes a whole bag of assorted towels was delivered! Literally, about one minute after that, a service worker showed up to address the water temperature issue. He had it resolved within an hour! This hotel was great to stay in. The price was lower than I would expect for this level of accommodation. I saw hotel security several times which made it feel safe and the controlled automobile entrance was a huge plus. Convenient to everything and very courteous staff make this resort hotel definitely worth it.

Reviewed on Oct 13, 2026

Westgate Leisure Resort

International Drive District

Save 100% on your flight

$324

per person

Dec 3 - Dec 8

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

8.6/10 Excellent! (1,001 reviews)

The room was exceptionally clean and well organized, and well stocked. The only dislike was that the stove was gas. The grounds were beautiful and I love the water feature two areas of the resort.

Reviewed on Oct 12, 2026

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Save 100% on your flight

$674

per person

Dec 13 - Dec 16

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

9.2/10 Wonderful! (1,001 reviews)

The Delaney Hotel

South Orange

Save 100% on your flight

$631

per person

Jan 6 - Jan 11

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Orlando (MCO)

9.6/10 Exceptional! (1,213 reviews)

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Stay near popular Maitland attractions

A marquee with "ENZIAN CINEMA CAFE" and "MORE THAN A MOVIE" written on it.

Enzian Theater

6.4/10 (21 reviews)

Central Florida's only full-time independent cinema showcases diverse films in a unique theater-café setting. Enjoy a craft cocktail at Eden Bar before settling in for dinner and a movie under centuries-old oak trees.

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A wooden boardwalk over a calm lake with trees and a clear sky.

Lake Lily Park

7.4/10 (24 reviews)

This peaceful 10-acre park offers a half-mile lakeside trail where you can spot herons and limpkins. Visit Sunday mornings for the vibrant farmers market featuring local produce and artisanal goods.

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A large tree overhanging a calm lake with a dock in the background.

Maitland Community Park

7.6/10 (22 reviews)

This 25-acre green sanctuary features tennis courts, playgrounds and a scenic boardwalk through lush Florida vegetation. Enjoy shaded trails or reserve a pavilion for family gatherings away from the midday heat.

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Maitland Art Center

7.6/10 (23 reviews)

Maitland Art Center showcases intricate Mayan Revival architecture with sculptural reliefs from 1937. Explore tranquil gardens and historic studios while enjoying contemporary exhibitions in this National Historic Landmark.

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Telephone Museum

This unique museum showcases telecommunications evolution through interactive exhibits and antique equipment. Try a vintage switchboard and experience early 20th-century communication systems firsthand.

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Kewannee Park

Kewannee Park offers a peaceful six-acre retreat with a scenic boardwalk overlooking native Florida wetlands. The connecting 1.7-mile paved Kewannee Trail links to local schools and the library.

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Village Plaza Shopping Center

7.4/10 (16 reviews)

This local shopping hub offers diverse restaurants, services, and specialty shops in a convenient Maitland setting. Browse the antique market or refresh at the salon in this community-focused plaza.

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Holocaust Memorial Resource and Education Center of Florida

7.4/10 (13 reviews)

This powerful center preserves Holocaust history through moving exhibits, artifacts, and survivor testimonies. Explore thought-provoking displays that promote understanding and human rights education.

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What to do in Maitland

LEGOLAND® Florida Tickets

$33

per traveler

86% of travellers recommend

Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options

$31

per adult

92% of travellers recommend

Universal Orlando Resort Express Passes

$128

per traveler

80% of travellers recommend

See all activities in Maitland

Maitland Hotel Deals

Hyatt Regency Orlando International Airport

9300 Jeff Fuqua Boulevard Orlando FL

Fully refundableReserve now, pay when you stay

$219 nightly

$246 total

Nov 2 - Nov 3

Total with taxes and fees

9.4/10 Exceptional! (4,549 reviews)

"Excellent hotel, quiet and comfortable"

Reviewed on Oct 13, 2026

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

8800 Vistana Centre Dr Orlando FL

Fully refundableReserve now, pay when you stay

$137 nightly

$154 total

Nov 3 - Nov 4

Total with taxes and fees

9.2/10 Wonderful! (7,047 reviews)

"We would definitely stay here again the sprawling grounds were great for a morning or evening walk. The marketplace, pools, and recreational activities were easy to find and close in proximity. We had issues with our unit’s electricity and staff were quick to respond to remedy the matter. Newly renovated, ..."

Reviewed on Oct 13, 2026

Marriott's Grande Vista

5925 Avenida Vista Orlando FL

Fully refundableReserve now, pay when you stay

$96 nightly

$108 total

Nov 3 - Nov 4

Total with taxes and fees

See all 8,483 properties in Maitland

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.

Find the Best Maitland Vacation Packages

Things to do in and around Maitland

Maitland, Florida, offers a delightful mix of family-friendly activities and entertainment options, making it an ideal vacation spot. Enjoy a stay at local resorts, explore educational attractions, or indulge in shopping at nearby malls. Whether you're seeking memorable experiences, a fun-filled family vacation, or a day trip to a theme park, Maitland has something for everyone to enjoy.

Shopping

For shopping in Maitland, visit Winter Park Village, just 2 miles away, offering a lively atmosphere with various shops and entertainment options. Altamonte Mall, 3 miles from Maitland, features a mix of stores and family-friendly activities. If you're up for a drive, explore more malls further out for additional options.

Recreation

The Kia Center offers an energetic atmosphere for sports enthusiasts, while the Enzian Theater provides a cozy setting for family and romantic film experiences. The Plaza Theatre showcases cultural performances, making it a delightful spot for family entertainment and romantic outings.

Adventure

Experience thrilling races at Lil 500 Go-Karts in Maitland, perfect for adrenaline seekers. For family fun, visit Boardwalk Bowl Entertainment Center, an arcadeAdventureZone located 9 miles away. Challenge yourself at Aiguille Rock Climbing Center, just 4 miles from Maitland, offering an exciting outdoor climbing experience.

Nightlife

Maitland offers a vibrant nightlife with options like the lively Maitland Tavern, perfect for a laid-back evening, or the chic Blue Bamboo, known for its live music and cocktails. For a unique experience, check out the local breweries for craft beers and a friendly atmosphere.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions near Maitland

Maitland, Florida, offers a perfect blend of family-friendly activities, cultural experiences, and outdoor fun. Visitors can explore urban parks, art museums, and scenic lakes. The Maitland Showground hosts exciting events, while nearby beach destinations provide a relaxing escape. Whether you’re seeking luxury travel or a day out at Maitland Gaol, this charming city has something for everyone, making it an ideal spot for entertainment-themed vacations.

Orlando Science Center: Located 4 miles from Maitland, the Orlando Science Center offers a family-friendly environment filled with interactive exhibits and engaging science demonstrations. Explore the wonders of the universe, biology, and technology while enjoying hands-on activities that inspire curiosity and learning.
Rollins College: Just 3 miles from Maitland, Rollins College boasts a beautiful campus with historic architecture and lush landscapes, creating a vibrant city vibe. Visitors can stroll through the grounds, enjoy art galleries, and soak in the academic atmosphere of this prestigious liberal arts college.
Dr. Phillips Center for the Performing Arts: Situated 6 miles away, this stunning arts center is a cultural hub featuring world-class performances ranging from Broadway shows to concerts. Experience the artistic flair and vibrant atmosphere that make it a must-visit for art enthusiasts.

Best time to go to Maitland

The best time to visit Maitland is dependent on what kind of holiday you are seeking. August is its hottest month on average. At this time, visitor numbers are slightly low and weather is mostly sunny with moderate rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	60.3°F (15.7°C)	Light Rain	Mostly Sunny	Average	Average
February	64.0°F (17.8°C)	Light Rain	Mostly Sunny	Average	Average
March	67.5°F (19.7°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
April	72.5°F (22.5°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
May	77.0°F (25.0°C)	Light Rain	Mostly Sunny	Average	Average
June	81.0°F (27.2°C)	Light Rain	Mostly Sunny	Average	Average
July	82.4°F (28.0°C)	Light Rain	Mostly Sunny	Average	Average
August	82.6°F (28.1°C)	Moderate Rain	Mostly Sunny	Slightly Low	Slightly Low
September	80.2°F (26.8°C)	Light Rain	Mostly Sunny	Slightly High	Slightly Low
October	75.0°F (23.9°C)	Light Rain	Mostly Sunny	Slightly Low	Average
November	68.2°F (20.1°C)	No Rain	Mostly Sunny	Slightly Low	Slightly Low
December	64.0°F (17.8°C)	No Rain	Mostly Sunny	Average	Slightly High

Tips to save on your trip to Maitland

Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
Consider traveling to Maitland during the low season (August to September and November) for more affordable options.
Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Maitland Essential Information

Language	English
Currency	U.S dollars
Closest Airport	Orlando Intl. Airport (MCO)
Population	17,500
Max Temp Winter	70ºF
Max Temp Summer	90ºF
Top Sights	The Wizarding World of Harry Potter™, Universal CityWalk and Orlando Science Center

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Frequently asked questions

How much does a Maitland vacation package cost?

Offering great value package deals from $274 on Expedia, you'll be thrilled with how little a vacation to Maitland costs! Our packages simplify travel planning and maximize your savings.

What are the cheapest months to go to Maitland?

You're likely to find lower rates and greater availability in January, May and December. Take a look at our cheap Maitland vacation packages and you could land some great off-season discounts.

How many days is enough for Maitland?

To fully enjoy your Maitland vacation, we suggest booking for 3 days. Divide your time between visiting Lake Lily Park, Maitland Community Park and other top attractions, as well as exploring neighborhoods like Northeast Orlando and Downtown Orlando. If you've got some time to spare, include a day trip or tour in your Maitland vacation itinerary.

Is it worth booking a vacation package to Maitland?

It's no wonder a Maitland vacation is on the must-do list of many travelers. Leading attractions like Maitland Art Center are just the beginning of things to see and do here.

How to find the best Maitland package deals?

Start your search for a Maitland package deal by entering your travel dates and destination under our "Packages" tab. Then apply a few filters, like "Property type" and "Guest rating," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the perfect Maitland package deal straight away, just tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Maitland escape off to a flying start.

Is it cheaper to book a Maitland vacation as a package?

An Expedia vacation package could land you significant savings when compared to booking flights and hotels individually. Better still, you can tailor your Maitland trip to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.

When to book a vacation package to Maitland?

If you're planning a spontaneous Maitland trip, browse our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can land sensational deals on your hotels and flights by booking ahead.

How to plan a trip to Maitland?

Pick your dates: The things you'd like to do in Maitland and your favorite season will help you decide when to go.
Budget wisely: As well as the price of your stay, you should factor in other expenses. These include transportation, flights and food. Also, put aside a little extra for unexpected costs that may come up during your trip to Maitland.
Organize your Maitland getaway with our trip planning tool: Search for and book hotels and activities all in one place. You can also collaborate with friends and family to plan an unforgettable trip to Maitland together.
Set the duration of your trip: Start by listing all the sights and activities you'd like to experience in Maitland. Then, estimate how long you'll need at each, along with any travel time.
Bundle your hotel and flights: Awesome destination, check. Length of stay, check. Now all that's left is to pick a Maitland vacation package that brings all your bookings together.
Book any excursions or activities: Here's the fun part — locking in everything you want to do and see. Explore some of the exciting things to do in Maitland in Maitland and book your tickets early to save time (and maybe some dollars too!).

Does Expedia offer Book Now, Pay Later Maitland vacation packages?

If you're anything like us, you love traveling the world but are not a fan of the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the cost of your Maitland trip across 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can snap up cheap vacation packages with payment plans as soon as you see them.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

Maitland Vacations from $274

Book a Hotel + Flight or Car together to unlock savings

Plan, book, travel with confidence

Better together

Find the right fit

Rest easy

Your Maitland Vacation

The Latest Maitland vacation packages

Palazzo Lakeside Hotel

Westgate Palace Hotel / Universal / I-Drive

Westgate Leisure Resort

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

The Delaney Hotel

Stay near popular Maitland attractions

Enzian Theater

Lake Lily Park

Maitland Community Park

Maitland Art Center

Telephone Museum

Kewannee Park

Village Plaza Shopping Center

Holocaust Memorial Resource and Education Center of Florida

What to do in Maitland

LEGOLAND® Florida Tickets

Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options

Universal Orlando Resort Express Passes

Maitland Hotel Deals

Hyatt Regency Orlando International Airport

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Marriott's Grande Vista

Find the Best Maitland Vacation Packages

Things to do in and around Maitland

Find the best attractions near Maitland

Best time to go to Maitland

Tips to save on your trip to Maitland

Maitland Essential Information

More vacations you might like

Frequently asked questions

Explore a world of travel with Expedia

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