Maitland Accommodations

Stylish Boutique Guest house in Winter Park

Highly Rated

Apartment

Stylish Boutique Guest house in Winter Park

10.0

Exceptional

(109 Reviews)

3 Bedrooms 1 Bath 4 Guests

CA $268/Night 7 Nights - CA $1,876

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House

Spacious Casselberry House with Backyard Pool

10.0

Exceptional

(1 Review)

4 Bedrooms 2 Baths 8 Guests 1689.93 ft²

CA $337/Night 7 Nights - CA $2,360

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House

Altamonte-4 bed

1 Bedroom 1 Bath

CA $613/Night 7 Nights - CA $4,290

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House

Home away from home in the heart of charming Winter Park!

10.0

Exceptional

(4 Reviews)

2 Bedrooms 2 Baths 4 Guests 1266 ft²

CA $226/Night 7 Nights - CA $1,579

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Affordable, convenient pet-friendly family space

Apartment

Affordable, convenient pet-friendly family space

9.0

Exceptional

(3 Reviews)

1 Bedroom 1 Bath 4 Guests 495.14 ft²

CA $179/Night 7 Nights - CA $1,250

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House

LOCATION! COZY COMFORT 2 BLOCKS FROM PARK AVE W POOL, HOT TUB AND GRILL STATION!

10.0

Exceptional

(4 Reviews)

2 Bedrooms 1 Bath 4 Guests 850 ft²

CA $186/Night 7 Nights - CA $1,300

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Spacious Modern Japandi Retreat - Winter Park

House

Spacious Modern Japandi Retreat - Winter Park

9.0

Exceptional

(1 Review)

1 Bedroom 3 Baths 12 Guests 2002.09 ft²

CA $654/Night 7 Nights - CA $4,580

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House

Cozy Comfort Just 2 Blocks From Park Ave!

10.0

Exceptional

(4 Reviews)

2 Bedrooms 1 Bath 4 Guests 850 ft²

CA $167/Night 7 Nights - CA $1,167

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House

3BR Entire Home | Near Orlando Downtown & Parks

8.6

Fabulous

(7 Reviews)

1 Bedroom 2 Baths 7 Guests

CA $262/Night 7 Nights - CA $1,837

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6 Mi to Downtown Orlando: Quiet Home w/Sunroom

Price Dropped

House

6 Mi to Downtown Orlando: Quiet Home w/Sunroom

10.0

Exceptional

(4 Reviews)

2 Bedrooms 1 Bath 4 Guests 890 ft²

CA $142/Night 7 Nights - CA $997

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3brdrm home near Downtown Orlando and Winterpark

House

3brdrm home near Downtown Orlando and Winterpark

8.2

Excellent

(23 Reviews)

3 Bedrooms 1 Bath 8 Guests 968.75 ft²

CA $240/Night 7 Nights - CA $1,683

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Apartment

LUXURY AND LOCATION!

10.0

Exceptional

(3 Reviews)

2 Bedrooms 2 Baths 5 Guests 1252 ft²

CA $204/Night 7 Nights - CA $1,429

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More Top-Rated Accommodations in Maitland Area

Why Choose Rent By Owner for your Maitland Accommodations?

What makes our Accommodations special?

Verified Listings

Book with confidence knowing every property meets our quality and safety standards.

Unbeatable Value

Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.

Diverse Options

From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Maitland

When should you plan your Accommodations stay?

To make the most of your stay here, consider planning your vacation during the region's optimal seasons when the weather is most favorable, ensuring a comfortable and enjoyable experience in this destination.

Peak Season Highlights

Spring (March to May)

During the spring, this area sees pleasant weather, making it an ideal time for exploring outdoor activities and local events in Maitland.

Average Temperature Daytime: 75°F - Nighttime: 55°F

Fall (September to November)

The fall months offer cooler temperatures and fewer crowds, providing a peaceful environment for enjoying the region's natural beauty and seasonal festivities.

Average Temperature Daytime: 78°F - Nighttime: 60°F

Off-Season Highlights

Summer (June to August)

Summer brings hotter weather, with a higher chance of rain, making it a quieter time to visit if you prefer less crowded accommodations in the area.

Average Temperature Daytime: 89°F - Nighttime: 72°F

Winter (December to February)

During winter, the region experiences mild temperatures and lower visitor numbers, offering affordable lodging options for those seeking a tranquil escape.

Average Temperature Daytime: 65°F - Nighttime: 45°F

Weekly Weather Forecast for Maitland

How to Book Your Maitland Accommodations

What's our booking process?

Our platform allows you to browse a curated selection of accommodations. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

Search Properties

Use our filters to find the right property that fits your needs.

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Maitland

More Top-Rated Accommodations in Maitland Area

Common Accommodations Amenities

What amenities can you expect?

Our Accommodations are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

Fully-equipped kitchens with modern appliances
Comfortable living areas with flat-screen TVs
Free Wi-Fi for staying connected
Air conditioning and heating for year-round comfort
In-unit washers and dryers for convenience
Luxurious bedrooms with premium bedding
Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

Enjoy a private outdoor pool to relax and unwind during your stay in this area.
Take advantage of spacious patios or decks perfect for outdoor dining or entertaining guests.
Experience lush gardens and landscaped yards that add natural beauty to your outdoor space.
Make use of outdoor grills for barbecues and cookouts in the region’s pleasant climate.
Benefit from access to private or community tennis courts, ideal for staying active.
Relax in hammocks or seating areas designed for enjoying the sunny Florida weather.
Utilize outdoor fire pits or fireplaces for cozy evenings beneath the stars.

Top Attractions Around Maitland

What attractions are nearby?

In this vibrant area, you can enjoy a variety of outdoor activities and cultural experiences, making it an ideal destination for exploring nearby parks, lakes, and entertainment venues that showcase the best of Maitland, Florida.

Family Activities

Lake Lily Park Enjoy a family picnic or explore walking trails around the scenic Lake Lily, offering outdoor fun in a peaceful setting.
The Maitland Art Center Engage with local culture through interactive exhibits and family-friendly art workshops at this historic art destination.
Enzian Theater Experience family movie nights and special screenings in an intimate theater setting that caters to all ages.
Rest Haven Park Make lasting memories with playgrounds, open fields, and shaded picnic areas perfect for relaxing family outings in the region.

Adult Activities

Lake Lily Park Enjoy a relaxing day by the water at this scenic park, perfect for picnics, walking trails, and outdoor activities in the area.
Maitland Art Center Explore local culture and creativity through distinctive art exhibits and engaging workshops hosted at this historic arts center.
Winter Park Scenic Boat Tour Discover the natural beauty of nearby Winter Park with a guided boat tour through its picturesque canals and lakes.
The Enzian Theater Experience independent films and cinematic events at this charming theater that offers a unique entertainment atmosphere in the region.

Other Places to Stay in Maitland, FL

Audubon Center for Birds of Prey

Explore 341 Properties

Maitland Art Center

Explore 329 Properties

Lake Maitland Terrace Marina

Explore 329 Properties

Maitland Historical Society

Explore 327 Properties

Enzian Theater

Explore 323 Properties

Village Plaza Shopping Center

Explore 320 Properties

Lake Lily Park

Explore 315 Properties

Holocaust Memorial Resource and Education Center of Florida

Explore 297 Properties

Maitland Community Park

Explore 269 Properties

AdventHealth Care Center

Explore 266 Properties

Lil 500 Go-Karts

Explore 238 Properties

Kewannee Park

Explore 168 Properties

More Places to Stay Near Maitland

Maitland Travel Tips

How Can You Make the Most of Your Stay?

Plan Your Visit Around Local Events: Check the area's event calendar to align your stay with festivals or community gatherings that showcase the region's vibrant culture and enhance your experience.
Explore Nearby Natural Attractions: Take advantage of the local parks and outdoor spaces to enjoy recreational activities and get a true sense of the area's natural beauty.
Discover Authentic Dining Options: Seek out highly-rated restaurants and cafes in the vicinity to immerse yourself in the regional culinary scene and try local specialties.
Utilize Convenient Transportation: Familiarize yourself with available transit services or consider renting a vehicle to seamlessly explore the region at your own pace.

Transportation Options

Orlando International Airport This major airport offers convenient access to the region, with numerous domestic flights and transportation options for quick travel here.
Public Transit - Lynx Bus System The local bus network provides affordable and reliable transportation across the area, making it easy to explore without a car.
Rental Car Services Numerous rental companies operate at or near the airport, giving you flexible options to explore the region at your own pace.
Taxi and Ride-Sharing Services Taxis and popular ride-sharing apps like Uber and Lyft are readily available, offering quick and direct routes throughout the area.

Local Customs Options

Local Festivals and Parades: Participating in community festivals and parades is a cherished tradition that reflects the area's vibrant cultural scene.
Honoring Native American Heritage: Respect for Native American history is evident through local educational events and commemorations held throughout the year.
Southern Hospitality: Warm welcomes and polite greetings are customary, creating a friendly atmosphere for visitors exploring here.
Regional Cuisine: Sampling locally inspired dishes at nearby eateries offers an authentic taste of the area's culinary traditions.

Frequently Asked Questions about Maitland Accommodations

1. What are the top Accommodations in Maitland?

There are a lot of options in Maitland. If you plan on staying in the Maitland area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Accommodations in Maitland:

2. How many Accommodations are available in Maitland?

Currently, the total number of properties listed by RBO in 2026 is over 244 in the Maitland area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Accommodations in Maitland. 

3. What is the cancellation policy for accommodations in the area?

Cancellation policies vary depending on the property listing. You should review the specific terms outlined on the listing page or contact the property owner directly to understand any fees or restrictions associated with cancellations.

4. How do I find available dates and book my stay in this destination?

You can check the availability calendar on each property listing and proceed with the booking process online. For best results, consider reaching out to the property owner if you have specific dates or special requests.

5. Are there any amenities included with the accommodations in the region?

Amenities differ from one listing to another. Please read the detailed description of the property or contact the host to confirm the amenities offered during your stay.

6. Is there a security deposit required when booking here?

Many properties may require a security deposit or damage waiver. Details about deposits are typically listed on the property page, or you can inquire directly with the owner for clarification.

7. What should I know about checking in and checking out at these accommodations?

Check-in and check-out procedures vary by property. Instructions are usually provided in your reservation confirmation or by the host. It's advisable to review these details before arrival to ensure a smooth check-in experience.