
Vacation rentals in Maitland
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Quick stats about vacation rentals in Maitland

Total vacation rentals
Explore 130 vacation rentals in Maitland

Nightly prices starting at
Maitland vacation rentals start at R 325 ZAR per night before taxes and fees

Verified guest reviews
Over 5,560 verified reviews to help you choose

Family-friendly vacation rentals
40 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 50 rentals that welcome pets

Vacation rentals with a pool
40 properties feature pools

Rentals with dedicated workspaces
80 properties have a dedicated workspace

Wi-Fi availability
130 of Maitland vacation rentals include wi-fi access

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

4.7 Average rating
Maitland stays receive an average rating of 4.7 out of 5 from guests
Top-rated vacation rentals in Maitland
Guests agree: these stays are highly rated for location, cleanliness, and more.

Orlando Poolside Oasis
Welcome to the Orlando Poolside Oasis!! This property is located in a quiet suburb of Orlando, with easy access to both theme parks and the beaches. This 3 bedroom 2 bathroom pool home will allow you to vacation in comfort and style. We have recently completed many upgrades to the property, including a newly renovated kitchen and bathrooms. We hope you love this property as much as we do! The home is also very baby friendly (crib upon request, stroller, baby bath,etc)!We can’t wait to host you!😊
4.95 out of 5 average rating, 112 reviews
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.
4.88 out of 5 average rating, 632 reviews
Atmospheric Studio in the Garden
Enjoy a little piece of Florida's lush paradise. Full studio suite lives elegantly & comfortably for longer-term stays. We've taken such pride in the opportunity to allow old Florida to intersect with compelling modern design and styling. Relax in this fully furnished studio apartment with kitchenette nestled among a verdant garden. Home boasts modern kitchen, comfy memory foam bed, separate shower and bath & spacious living and entertaining areas. Available for stays of one month or longer.
4.97 out of 5 average rating, 261 reviews
Lakefront Home•screened deck, dock•Long Stays OK
Water-ski, swim, boat, and fish in the pristine, spring-fed waters of the 310-acre Bear Lake beside this expansive home. Canoe and paddle boards provided! Enjoy the sunset from the swing on the boat dock, watch the sunrise from the screened deck while lounging in the hammock, or spend a lazy afternoon with the family playing board games. The guest suite is the private half of a duplex, completely separated from the owner's side with no shared areas. (2 kings, 2 queens, 2 futons, 3.5 baths)
5.0 out of 5 average rating, 107 reviews
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!
4.85 out of 5 average rating, 167 reviews
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)
4.99 out of 5 average rating, 137 reviews
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.
4.95 out of 5 average rating, 188 reviews
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.
4.98 out of 5 average rating, 132 reviews
St. Hemingway Suite
Very tranquil Romantic Suites with views and access to large lake. PRIVATE ENTRANCE and private bathroom. Amenities include, private dock, pool, large manicured lawns, private parking, breakfast kitchenette and much more. Close to theme parks and beaches. Ample shopping and award winning restaurants very nearby. Peaceful setting to read, do Yoga, enjoy quiet moments by the lake, watch the boats sail by or watch the sun rise. Peace and tranquility at its best. We welcome you
4.97 out of 5 average rating, 358 reviews
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.
4.97 out of 5 average rating, 254 reviews
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.
4.96 out of 5 average rating, 246 reviews
Stunning Orlando Getaway w/Spa & Heated Pool
The whole group will enjoy easy access to everything from this centrally located Orlando location. This 1950s beautifully designed space has all modern amenities with an amazing outdoor living space. Located in College Park situated close to many amenities Orlando has to offer. Only 9 Minutes to downtown Orlando or 15 Minutes to Universal. The Acre & The Cottage Wedding venues are both within Walking Distance. Dubsdread is only 4 Minutes Away.
4.92 out of 5 average rating, 181 reviewsPopular amenities for Maitland vacation rentals
Stay near Maitland's top sights
Other great vacation rentals in Maitland

Elegant, Spacious Three Bedroom Residential House.
4.86 out of 5 average rating, 224 reviews
New Mid Century-Modern Studio
4.97 out of 5 average rating, 341 reviews
Renovated Winter Park Home | Work & Family
4.85 out of 5 average rating, 102 reviews
Recharging Lakeview Oasis w/Pool centrally located
4.88 out of 5 average rating, 112 reviews
Fern Park Retreat
4.96 out of 5 average rating, 69 reviews
Casa Bella
5.0 out of 5 average rating, 22 reviews
Joe's Bar and Grill
5.0 out of 5 average rating, 92 reviews
*Travel Themed Property with Backyard Oasis*
4.97 out of 5 average rating, 70 reviewsWhen is the best time to visit Maitland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | R 1,820 ZAR | R 1,820 ZAR | R 1,772 ZAR | R 1,885 ZAR | R 1,950 ZAR | R 1,642 ZAR | R 1,447 ZAR | R 1,447 ZAR | R 1,512 ZAR | R 1,577 ZAR | R 1,658 ZAR | R 1,560 ZAR |
| 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.
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