Orlando showing dining out and theatre scenes as well as a couple

Maitland holiday rentals

We found 13,823 holiday rentals — enter your dates for availability

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July 2025

August 2025

Discover a selection of 13 homes and other holiday rentals in Maitland that are perfect for your trip. Whether you're travelling with your children and pets, with friends or just your children, holiday rentals have the best amenities for spending time at your holiday home, including Wi-Fi and parking. At the end of the day, you'll be sure to find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - Maitland

Showing deals for:10 Oct - 17 Oct

Exceptional

(18 reviews)

Escape to Paradise! Luxury Waterfront Heated Pool House in Tranquil Neighborhood

Kissimmee, FL

12% off

S$335 per night

includes taxes & fees

Wonderful

(19 reviews)

Winter Park Citrus Escape; sleeps 8, relaxing pool, family & pet friendly

Winter Park, FL

8% off

S$461 per night

includes taxes & fees

living room/ dinette area, screened/ and or enclosed furnished porch in rear

Exceptional

(56 reviews)

Home away from Home Luxury 2 bed/2bath Country Club Condo

Orlando, FL

8% off

S$186 per night

includes taxes & fees

Great table for family dinners and game nights!

Exceptional

(147 reviews)

Family Friendly home with Fenced in Backyard to enjoy with kids & pets

Maitland, FL

7% off

S$246 per night

includes taxes & fees

Exceptional

(32 reviews)

Orlando 5 Star-Disney, By Convention Center-Penthouse, Excellent for Large Group

Orlando, FL

7% off

S$428 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find properties near top attractions in Maitland

Enzian Theater

Find the best place to stay - Maitland

Showing deals for: 6 Oct - 9 Oct

Family Friendly home with Fenced in Backyard to enjoy with kids & pets

Sleeps 8 · 3 bedrooms · 2 bathrooms

for 3 nights, 1 home

S$317 per night

includes taxes & fees

Temporary living that feels like home where you can relax and be yourself.

Sleeps 6 · 4 bedrooms · 2 bathrooms

for 3 nights, 1 home

S$308 per night

includes taxes & fees

Travel Themed Property with Backyard Oasis

Sleeps 14 · 6 bedrooms · 3 bathrooms

for 3 nights, 1 home

S$647 per night

includes taxes & fees

Top rated rentals - Maitland

Together with friends

Peace of mind
Our Book with Confidence guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

The picturesque setting of Maitland is ready to explore

Come and experience Maitland and its art galleries, temples and entertainment. This welcoming city attracts visitors thanks to its restaurants and shopping. Universal Studios Florida and Universal Orlando Resort are just a couple of the must-see attractions in the area. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in Maitland

Are you hoping to find attractions to see in the area? Venture out of your cosy holiday rental and experience everything that makes Maitland a one-of-a-kind holiday spot. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

Universal Studios Florida (12.2 mi / 19.7 km)
Universal Orlando Resort (12.4 mi / 20 km)
The Wizarding World of Harry Potter™ (12.1 mi / 19.5 km)
Universal’s Islands of Adventure (12.6 mi / 20.3 km)
Universal’s Volcano Bay (13.3 mi / 21.4 km)
Aquatica (15.7 mi / 25.3 km)

Exploring the natural landscape of Maitland

Whether you're looking for adventure or just want to take in the scenery, Maitland is a great place to spend some time outside. These are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

Cranes Roost Park (2.9 mi / 4.6 km)
Harry P. Leu Gardens (4 mi / 6.5 km)
Sanlando Park (4.1 mi / 6.6 km)
Red Bug Lake Park (4.7 mi / 7.5 km)
Lake Eola (5.8 mi / 9.4 km)
Lake Eola Park (5.8 mi / 9.4 km)

Transport to and around Maitland

The nearest airport is in Orlando, FL (SFB-Orlando Sanford Intl.), located 12.5 mi (20.1 km) from the city centre. If you can't find a flight that's convenient for your trip, you could book a flight to Orlando International Airport (MCO), which is 14 mi (22.5 km) away.

Catch a ride on the metro at Maitland Station for ease of access to the rest of the city.

Frequently asked questions

What is the most popular type of holiday rental accommodation in Maitland?

The most sought-after types of holiday rentals in Maitland are houses. Looking for something different? Vrbo has many options to match our guests' diverse needs, so you'll see holiday properties in all sizes, and for all budgets. The ideal fit is ready and waiting for you --- grab yours today.

How much does it cost to rent a holiday rental in Maitland?

Different factors can determine what you'll pay for your holiday rental in Maitland, such as the time of year, length of stay and property type. Still, all our holiday homes have one thing in common --- exceptional value. Just add your travel dates to find your ideal match.

How much does it cost to rent a beach house in Maitland?

Prices for beach houses in Maitland can vary depending on the type and size of the property and time of year you're travelling. Just enter your travel dates into Vrbo and the number of guests to see available options and prices. From there you can use the filters to tailor your search results by ratings, amenities, nearby activities and more.

Are there pet-friendly holiday rentals in Maitland?

Yes, there are. You can pick from four holiday rentals that cater to pets in Maitland. Some of our pet-friendly holiday rentals come with a backyard for your furry pal to play around in, complimentary treats, doggie beds and proximity to parks. Apply the "Pets allowed" filter to find a pad that'll set tails wagging on Vrbo.

Can I rent a house with a pool in Maitland?

Mark the "pool" box in our filter tool and pick from two houses with private pools in Maitland on Vrbo. Morning soak, afternoon splash or midnight swim? Free time is up to you when your holiday home comes with its own swimming pool.

What are popular rental amenities in Maitland?

When it comes to rental amenities that guests search for in Maitland, tennis, a fireplace and a garden are the most popular. With Vrbo holiday homes, you'll enjoy choices to fit your taste and style, whether you're planning to get away with family members, friends or even pets.

Are there large group holiday rentals in Maitland?

Yes, there are two properties in Maitland that can host a group of five or more people. From family getaways to events like birthday parties, these stays have enough room to hang out with the people that matter the most.

Are there holiday rentals in Maitland that welcome kids?

Maitland has four family-friendly holiday homes to choose from. And booking a stay that welcomes kids is a breeze with Vrbo's "Properties good for families" filter. On top of having the whole place to yourselves, you'll get access to perks and amenities like living rooms, full kitchens and yards.

What are the top attractions for families in Maitland?

Keeping the kiddos entertained during your Maitland holiday is a cinch with these top family-friendly attractions:

Orlando Science Centre
Church Street Station
Boardwalk Bowl Entertainment Centre

How can I find holiday rentals with air conditioning in Maitland?

Decide on your travel dates and then use the filter tool to search for holiday rentals with ac in Maitland on Vrbo. With four air-conditioned properties available, you can enjoy a cool and comfortable trip.

How old do you have to be to rent a holiday rental in Maitland?

The minimum required age is usually 16, 18 or 21. It can differ between properties on Vrbo, so look at the rules of your chosen Maitland holiday rental before booking your trip.

How long can I rent a holiday rental in Maitland for?

The amount of time you can rent a Maitland holiday home for is down to the property. Simply put in your travel dates to see options that offer long-term stays. They have the things you need to make your extended holiday more comfortable such as kitchens and laundries. Some properties might also offer discounted weekly or monthly prices, so you can stay even longer for less.