
Holiday rentals in Maitland
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Top-rated holiday rentals in Maitland
Guests agree: these stays are highly rated for location, cleanliness and more.

Maitland-Orlando Area, FL. Pool House Bungalow
Large open space adjacent to a beautiful pool, waterfall, and fantastic lake view. 27 miles to Disney World, close to Park Avenue, local hospitals, Universities, and less than an hour to local beaches. Only 18 miles to MCO-Orlando International Airport. Great shopping within 3 miles. Location is secluded with large trees, lakeside, and adjacent to the commuter train track. The train runs by on regular basis. Please note in the pictures the pool creates the ambiance to make your stay complete.

St. Augustine suite
Luxurious space with PRIVATE ENTRANCE, PRIVATE BATHROOM and breakfast kitchenette. Located on a large lake front property with amenities that include private dock, pool, large manicured lawns and much more. Ideal for canoeing, watching the sun rise or doing nothing at all. Close to theme parks and beaches. Spring Valley is a peaceful community with age old oak tree , Ample shopping and award winning restaurants very nearby. Come play or rejuvenate your soul in this picturesque setting

Contemporary Loft Near Downtown
Conveniently located between the foodie-friendly Milk District and Downtown Orlando, this impeccably thought-out space features a spacious loft style open floor plan perfect for a couple or small group. The floor to ceiling windows allow natural light to fill the space while providing complete privacy during your stay. Upscale Winter Park restaurants and the vibrant Thornton Park art scene are only a short drive away. Universal is only 20 minutes away, Disney is 35 minutes, MCO 20 minutes.

"Winnie's Place" A Peaceful Guesthouse with Pool.
Share the quiet yard and pool with hosts. 1 hr. from Disney & the beaches. 12 yr & older only. Single Sofa bed for 3rd guest. NOT a heated pool. Not Handicap Certified, but most wheelchair guests have not had issues. Narrowest opening 32" Ramp into unit by pool. Shower no steps. Queen bed height 29"-standard cabinets. Grab bars in bathroom. Airbnb's Accessibility Policy has exempted this listing from accepting Service & Emotional Support Animals due to owner's severe health condition.

Bonheur Ala Maison
Bonheur A la Maison is the home that offers a beautiful, comfortable, spacious, convenient and all around happy feeling with the little extras and attention to detail to make you feel like you're basking in a lot of luxury for a simple price! Its everything you need from your blow dryer, to your plush robe and from your USB outlets at all bedsides to your built in wireless speakers for your music of choice. We tried to think of it all. Conveniently located near lots of shops and parks!

Location, Location, Location!
Enjoy a stylish experience at this centrally-located Guest House. It is located in an excellent area close to the downtown Orlando, excellent restaurants, and much more. It is fully furnished and equipped with new appliances (washer and dryer included) and furniture. It is located minutes from Winter Park, Downtown Orlando and theme parks. Downtown Orlando 3 miles (6 min) Advent Health Hospital 0.6 miles (2 min) Walt Disney World 20 miles (23 min) Universal Studios 11 miles (18 min)

Orlando area pool home in Maitland
Everyone finds our home fun & relaxing. We are close to tons of restaurants & shopping. Only 1 mile from the intersection of I-4 & 414 (Maitland Blvd). Home, it is fully stocked. Plus a gas grill. Towels & linens provided. Games and toys for all ages. Pets are welcome with pet fee. Guests have private use of property, 2 bedrooms & 2 full baths and all living areas, back yard and porch with pool . There is an optional third bedroom available for an additional $35 a night fee.

Florida Poolside Paradise a Great Place to Unwind!
Welcome to our exquisite 4-bedroom vacation rental in the heart of Maitland, Florida – a true gem where luxury meets convenience. This upscale home boasts fine furnishings and a private pool, making it the ideal retreat for families or groups seeking both comfort and style during their Sunshine State getaway. The house is located in a residential neighborhood with plenty of restaurants and shopping within a 5 minute drive. Convenient location off Rt 436. and half hour to the airport.

3/1 house conveniently located in central Florida!
Relax with your whole family in this peaceful quiet home. Your home away from home is Conveniently Located close to all the attraction and beaches. It's a small 800 sq ft 3 bed 1 bath House with Casper beds and flat screen in every room. 10 Minutes away from the Altamonte Springs hospital. Full Stocked kitchen with everything you need to cook a home cooked meal. It's a perfect place to stay with your family instead of a Hotel for a more comfortable stay and peace of mind.

Private entrance/bathroom 10 min from DT Orlando
Welcome to your home away from home! Our cozy room with a attached bathroom is the perfect retreat for your visit to Orlando. Located just 10min from downtown Orlando, 30min from MCO and Disney, and 20 min from Universal, you'll have the best of both worlds - convenience and comfort. Whether you're here for business or pleasure, our room is the perfect place to call your temporary home. Book your stay with us today and experience the best of our city.

Elegant, Spacious Three Bedroom Residential House.
Get the best experiences of Central Florida in this stylish, newly renovated centrally-located house. Minutes from top restaurants, beautiful Wekiva Springs and Rock Springs, Altamonte Mall, and Cranes Roost Area. Minutes from Super I-4 which can take you straight to downtown Orlando, Universal Studios, Walt Disney World. If you decide to go east enjoy beautiful downtown Daytona Beach, NASCAR, and New Smyrna Beach.

Chez Bienvenu
Close proximity to Park Avenue in Winter Park! Sunny and Adorable Vintage Guest House ...entire spacious guest house; with private entrance and driveway* Just a couple of blocks off Park Avenue to enjoy Shopping! Cafes! Museums! Nestled in quiet family community* •Smart TV •Stackable washer and dryer included in the unit. •Grill, Beach Chairs, Fishing Poles available •750 square feet of living space
Popular amenities for Maitland holiday rentals
Other great holiday rentals in Maitland

10 min to Winter Park, Games, Gym, King bd, Coffee

WINTER PARK TOWNHOUSE - NEAR DOWNTOWN & PARKS

Top 1% Modern Japandi Retreat - Jacuzzi No Fee

Recharging Lakeview Oasis w/Pool centrally located

2 Min to Park Ave | Charming Winter Park Bungalow

Serene private home near the fun

The Briarcliff

Sleeps 6 | Car Rental | Prime DTO Location
When is the best time to visit Maitland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £83 | £83 | £81 | £64 | £59 | £48 | £66 | £66 | £69 | £72 | £76 | £71 |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 17°C |
Frequently Asked Questions
What are the best places to stay in Maitland?
Neighborhoods near lakes and parks, such as areas around Lake Lily and community green spaces, are often suggested for vacation rentals. Homes with outdoor patios or gardens can offer a comfortable retreat.
What are the best things to do in Maitland with kids?
Children often enjoy playgrounds at local parks, community art workshops, and educational exhibits at the area’s history museum. Lake Lily Park is a favorite for families, combining walking trails, wildlife, and play areas.
What are some of the best things to do in Maitland?
Explore the Maitland Art Center, walk around Lake Lily Park, and discover the city’s local history museum. Neighborhood cafes and outdoor spaces create opportunities for both relaxation and creativity.
How is the weather in Maitland?
Maitland has mild winters around 49–72°F (10–22°C) and warm, humid summers near 72–92°F (22–33°C) with frequent afternoon rain. Spring and autumn bring comfortable temperatures and lower humidity, making outdoor activities a popular choice.
When is the best time to visit Maitland?
Spring and autumn are frequently suggested, with milder temperatures between 58–84°F (15–29°C) and fewer rainy days. Summer brings warmer weather and higher humidity, popular for local outdoor festivals and lake activities.
What are the best places to visit in Maitland?
The Maitland Art Center, Lake Lily Park, and the local history museum are frequently suggested places to explore. Art galleries and lakeside spaces offer a mix of culture and natural beauty.
What are some hiking trails in Maitland?
Stroll the paths at Lake Lily Park or wander through neighborhood nature preserves featuring shaded trails and native plants. Locals often enjoy trails around area lakes for birdwatching and peaceful views.
What are some family activities we can do in Maitland?
Families can explore lakeside parks, visit the area’s art museum, and enjoy playgrounds or nature walks. Seasonal festivals and community events often include activities for children of many ages.
What are some of the best day trip ideas from Maitland?
Consider exploring nearby nature reserves, visiting botanical gardens, or discovering the area’s science museum in a neighboring city. Many travelers enjoy checking out theme parks and cultural landmarks just outside Maitland.
Are there any pet friendly accommodations available in Maitland?
Many vacation rentals near lakes and parks welcome pets, especially in neighborhoods with access to walking trails. Checking for homes with fenced yards or pet amenities is often suggested for those traveling with animals.
What are some local tips for visiting Maitland?
Maitland has several lakes and parks, so bringing comfortable walking shoes is often recommended. Locals often suggest exploring neighborhood eateries with Southern-inspired cuisine and checking out community art spaces for a feel of the area’s creative spirit.
What is Maitland known for?
Maitland is known for its distinctive art center with historic architecture, lakeside parks, and a creative community spirit. The city’s history museum and neighborhood festivals reflect both local culture and artistic traditions.
What are the best hidden gems to explore in Maitland?
Neighborhood galleries and small community gardens tucked near the lakes offer quieter experiences. Attending local art workshops and discovering historic architecture are often recommended for visitors seeking lesser-known highlights.
What are the best foods to try in Maitland?
Locally rooted cuisine highlights Southern-inspired dishes, fresh lake fish, and bakery treats. Neighborhood cafes and family-run restaurants are often recommended for regional specialties and comfort foods.
What should I bring for a trip to Maitland?
Pack light clothing for warm weather, comfortable shoes for exploring parks and walking paths, and a rain jacket during summer months. A reusable water bottle and sunscreen are often suggested for outdoor activities.
What is the nightlife in Maitland like?
Maitland’s nightlife centers on neighborhood eateries, casual bars, and community events featuring live music. Locals sometimes gather at lakeside venues and art spaces for relaxed evenings.
What are the most popular events or festivals in Maitland?
Art and cultural festivals at the Maitland Art Center are often recommended, with community celebrations in spring and autumn drawing visitors. Seasonal food festivals and outdoor events sometimes feature local music and crafts.
Are there family friendly vacation rentals in Maitland?
Family-friendly vacation rentals are available in many Maitland neighborhoods, often featuring multiple bedrooms, kitchens, and proximity to parks or playgrounds. Properties with outdoor spaces make it easier for families to relax together.
Quick stats about holiday rentals in Maitland

Total holiday rentals
Explore 130 holiday rentals in Maitland

Nightly prices starting at
Maitland holiday rentals start at £15 per night before taxes and fees

Verified guest reviews
Over 5,380 verified reviews to help you choose

Family-friendly holiday rentals
40 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 40 rentals that welcome pets

Holiday rentals with a pool
40 properties feature pools

Rentals with dedicated workspaces
70 properties have a dedicated workspace

Wifi availability
120 of Maitland holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Maitland rentals

4.8 Average rating
Maitland stays are highly rated by guests – averaging 4.8 out of 5!
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