Best Vacation rentals and Airbnb offers in Maitland, FL
10 1 review
Maitland, FL
07/31 – 08/02
$312/nighttotal: $624 (2 )
Cute 5-bedroom House In Peaceful Winter Park
5 9
apartment , Casselberry
This 5-bedroom house is located in Winter Park, providing proximity to the Central Florida Fairgrounds and Kraft Azalea Gardens, with the Mall at Millenia and Winter Park Village also nearby. This accommodation offers space for 11 guests with 5 bedrooms, 2 bathrooms, air conditioning, and internet, and is a short drive from Casselberry attractions.
9.4 11 reviews
Maitland, FL
06/27 – 07/04
$97/nighttotal: $679 (7 )
Traveler's Dream: Refresh & Recharge Poolside
1 2
apartment , Casselberry
This Casselberry apartment rental is conveniently located near Secret Lake Park (2.2 miles) and Red Bug Lake Park (2.8 miles), with easy access to Winter Park Village and Altamonte Mall (under 6 miles). This one-bedroom, one-bathroom unit sleeps two guests and features a private pool, free WiFi, a fully equipped kitchen with a refrigerator, microwave, and stovetop, a smart TV, and access to a community pool; nearby parks offer walking and jogging trails.
9.2 20 reviews
Maitland, FL
07/31 – 08/02
$817/nighttotal: $1634 (2 )
Walk Into Tropical Paradise - Pool - Gym - Hot Tub
4 9
apartment , Altamonte Springs
This Altamonte Springs vacation home, near I-4, offers easy access to Orlando's theme parks and Altamonte Springs' shopping and dining. This four-bedroom, two-bathroom rental boasts a private backyard oasis with a pool, hot tub, waterfalls, mini golf, and yard games, accommodating up to nine guests and featuring a fully equipped kitchen, home gym, and multiple large TVs.
10 4 reviews
Maitland, FL
06/27 – 07/04
$125/nighttotal: $875 (7 )
The Blue Accent Retreat
2 2
apartment , Lockhart
This private 2-bedroom guest unit is located in Orlando, a short 2-mile drive from Downtown Orlando and within 7 miles of Universal Studios and Walt Disney World. This apartment offers a fully equipped kitchen, air conditioning, and accommodates up to 5 guests, making it ideal for families, couples, and business travelers visiting Orlando.
9.5 227 reviews
Maitland, FL
06/27 – 07/04
$90/nighttotal: $630 (7 )
Lake Front Suite -Close To All Attractions
1 2
apartment , Forest City
This waterfront vacation home is located in Forest City, within 6 miles of major attractions like RDV Sportsplex, Altamonte Mall, and Cranes Roost Park. The house has excellent user, location, and cleanliness ratings. The house has a floor area of 650 square feet, 1 bedroom, and a guest capacity of 4. It features a well-equipped kitchenette, free WiFi, two bathrooms, and a sofa bed. Guests can enjoy amenities such as an outdoor pool, spa tub, water park, private fenced yard, balcony, and free parking.
9.4 10 reviews
Maitland, FL
07/31 – 08/02
$427/nighttotal: $854 (2 )
The Secret Garden Games Getaway 4 Bedroom Home
4 9
apartment , Orlando
This Orlando apartment rental, ideally situated near Universal Studios (16-minute drive) and Walt Disney World Resort (32-minute drive), provides easy access to major theme parks, Camping World Stadium, and the Orlando International Premium Outlets. Offering a unique 'Secret Garden' theme, this spacious 4-bedroom, 3-bathroom dwelling accommodates up to 14 guests and includes amenities such as a fully equipped kitchen, free internet, and a private garden with a tennis court; plus, enjoy an on-site 'Secret Garden Quest'.
8.8 74 reviews
Maitland, FL
06/27 – 07/04
$109/nighttotal: $763 (7 )
Suites By The Wellborn
1 2
apartment , Orlando
Vacation rental listing with an excellent rating of 88% based on 74 reviews. Your accommodation will be based in Orlando. Facilities and services include free parking, a garden and a bar. This apartment also has air conditioning!
10 1 review
Maitland, FL
07/31 – 08/02
$7566/nighttotal: $15132 (2 )
5/4 King Bed Lux Arcade Near Wp/cp & Dt Orlando ️
5 9
apartment , Orlando
This 5-bedroom, 4-bathroom Orlando residence is located in the College Park neighborhood, offering convenient access to Winter Park and downtown Orlando's dining and entertainment options. This expansive vacation home accommodates over 20 guests and features a dedicated movie room with a 4K projector, a screened-in patio with a Jacuzzi, a private backyard with a BBQ area, and a garage gym.
9.8 57 reviews
Maitland, FL
06/27 – 07/04
$154/nighttotal: $1078 (7 )
Entire Townhome | Stylish & Cozy | Peaceful
1 2
apartment , Casselberry
This Casselberry townhome offers easy access to Universal Studios (approximately 30 minutes away) and Disney World (about 40 minutes away). The two-bedroom, one-bathroom property sleeps six guests and includes a fully equipped kitchen, in-unit laundry, and private parking; nearby restaurants and shops provide additional convenience.
Maitland, FL
06/27 – 07/04
$75/nighttotal: $525 (7 )
Chic Studio Near Downtown & Theme Parks
1 2
studio , Orlando
This studio apartment in Orlando is located 5.3 miles from Church Street Station and 5.4 miles from the Kia Center, offering convenient access to downtown attractions. This 400 sq ft pet-friendly accommodation sleeps up to 3 guests and features a kitchenette with a microwave, air conditioning, free WiFi, and an on-site garden.
9.9 113 reviews
Maitland, FL
06/27 – 07/04
$152/nighttotal: $1064 (7 )
Cottage Retreat In The City
1 2
cottage , Orlando
This charming cottage is located in College Park, a historic neighborhood in Orlando, just a short drive from Universal Studios, Walt Disney World, and Downtown Orlando. The cottage consistently receives excellent ratings for location, cleanliness, and overall guest experience. The cozy cottage has one bedroom and one bathroom, comfortably accommodating up to two guests. Enjoy a private outdoor space with a large front porch, a fully equipped kitchen, a modern HD TV, and free Wi-Fi.
9.6 117 reviews
Maitland, FL
06/27 – 07/04
$109/nighttotal: $763 (7 )
Renovated ✓Nature ✓Cozy ✓Walk To Mall Park Publix
1 2
studio , Altamonte Springs
This studio apartment is located in a peaceful area of Altamonte Springs, within walking distance of the mall, park, and Publix, and close to Orlando attractions and Uptown Altamonte Springs. It has consistently received excellent ratings for cleanliness, location, and user satisfaction. The studio comfortably accommodates up to three guests with a queen bed, rollaway bed, couch, and even a baby crib. You'll enjoy amenities like a private patio, laundry access, a fully equipped kitchen, and a fitness center.
Our Favorite Family-Friendly Vacation Rentals in Maitland, FL
Booking a family-oriented vacation rental in Maitland, FL keeps you close to top city attractions for a stress-free getaway.
9.8 38 reviews
Maitland, FL
07/31 – 08/02
$969/nighttotal: $1938 (2 )
*Travel Themed Property With Backyard Oasis*
6 9
apartment , Casselberry
Centrally located in Maitland, within walking distance of Walmart Supercenter and various restaurants, "The Terminal" is a highly-rated 6-bedroom apartment that offers a unique travel-themed experience. With a floor area of 2500 square feet, it can accommodate up to 14 guests and features a private screened-in pool, an outdoor kitchen, a fire pit, a game room with an 85" TV, air hockey table, and Atari arcade console, as well as nine HD TVs throughout the apartment.
9.6 25 reviews
Maitland, FL
07/31 – 08/02
$524/nighttotal: $1048 (2 )
Quiet Retreat 15 Minutes From Downtown Orlando, Orlando Airport International!
3 9
apartment , Azalea Park
This apartment is located in the quiet residential neighborhood of Azalea Park, just a short walk from Capehart Park and a half mile from a shopping mall with Walmart, Publix, and Walgreens. It has received very good user ratings. This 3-bedroom, 2-bathroom home comfortably sleeps 10 guests. The apartment offers amenities like a fully equipped kitchen, air conditioning, a garden, a tennis court, parking, and internet access, making it ideal for families or groups.
9.0 3 reviews
Maitland, FL
06/27 – 07/04
$407/nighttotal: $2849 (7 )
Spacious And Relaxing Home - Longwood, Florida
5 2
house , Longwood
This 5-bedroom, 4-bathroom house in Longwood is located just 15 miles from downtown Orlando and its attractions, offering a peaceful retreat with easy access to the city's excitement. The house has received excellent user ratings and very good ratings for location and cleanliness. The spacious home can accommodate up to 10 guests and features a fully equipped kitchen, a relaxing patio with garden views, a hot tub, and free Wi-Fi. Enjoy a peaceful garden, private parking, and the convenience of being close to Orlando Sanford International Airport.
10 1 review
Maitland, FL
06/27 – 07/04
$288/nighttotal: $2016 (7 )
Virelli Apartments Upscale King Suite In The Heart Of Orlando W Pool
1 2
apartment , Orlando
This one-bedroom rental is located in a central Orlando district, 1.2 miles from the city center and a 16-minute walk from Kia Center. This 800 sq ft residence accommodates up to 7 guests, offering a full kitchen, air conditioning, a swimming pool, and on-site parking, with proximity to Church Street Station and Camping World Stadium.
Best Maitland, FL vacation rentals with parking
Maitland, FL
06/27 – 07/04
$143/nighttotal: $1001 (7 )
New Boho 1br Steps To Lake Eola - Thornton Park
1 2
apartment , Orlando
This one-bedroom condo in Orlando's South Eola district offers waterfront living with Lake Eola views, just a short walk to the Amway Arena and Dr. Phillips Center, and convenient to downtown attractions and shopping. This private condo accommodates two guests and features a queen-size bed, a 55-inch flat-screen TV, and is located near essential amenities including a Publix grocery store, with complimentary transportation options available to major theme parks.
8.7 6 reviews
Maitland, FL
06/27 – 07/04
$86/nighttotal: $602 (7 )
Botanical Tranquility
1 2
apartment , Casselberry
This Casselberry apartment rental is conveniently located approximately 11-15 miles from Orlando Sanford International Airport and within a 12-20 mile radius of attractions like the Addition Financial Arena and Camping World Stadium. The one-bedroom, one-bathroom unit sleeps three guests and features a private pool, free Wi-Fi, private parking, a fully equipped kitchen, and an outdoor dining area.
Maitland, FL
06/27 – 07/04
$127/nighttotal: $889 (7 )
Lake Eola Thornton Park Studio With Balcony
1 2
studio , Orlando
This studio apartment is situated in Orlando's Thornton Park district, just steps from Lake Eola and within a 19-minute walk of Church Street Station, with the Kia Center located 1.2 miles away. This 750 sq ft studio accommodates up to 3 guests and features a private balcony, free WiFi, air conditioning, and a kitchen with a fridge and microwave oven.
9.8 188 reviews
Maitland, FL
06/27 – 07/04
$128/nighttotal: $896 (7 )
Lake Marion Apt W/ Canoe In Altamonte Springs!
1 2
apartment , Altamonte Springs
This Altamonte Springs house is conveniently located just 11 miles from Church Street Station and 11 miles from Orlando Sanford International Airport, providing easy access to both downtown Orlando and the airport. The house has received excellent ratings for its location, cleanliness, and overall experience. The one-bedroom, one-bathroom vacation rental offers 450 square feet of space, comfortably accommodating up to 2 guests. Enjoy the fully equipped kitchen, private patio, and access to Lake Marion for canoeing and relaxing in the peaceful setting.
Frequently Asked Questions about vacation rentals in Maitland, FL
What should a first-time visitor not miss in Maitland, FL?
Maitland is known for its beautiful parks, so a visit to the scenic Lake Lily Park is a must. You can enjoy a stroll along the lake, rent a paddleboat, or simply relax on the lawn. For a taste of history, head to the Maitland Art Center, a beautiful building showcasing local and regional art.
What are the best Airbnb and vacation rentals in Maitland, FL?
Which neighborhood in Maitland, FL should you consider for a vacation rental?
The area around Lake Lily is popular with visitors, and you'll find a good selection of vacation rentals there. It's a short walk to the park and within easy reach of restaurants and shops.
What are the most popular Airbnbs in Maitland, FL?
What are the top family-friendly attractions in Maitland, FL?
The Maitland Art Center has family-friendly activities and events, and the Leu Gardens is a great place for a stroll, with beautiful botanical displays and kids' activities. You can also visit the Wekiwa Springs State Park for a day of swimming, kayaking, or hiking.
What are the best vacation rentals with a pool in Maitland, FL?
When is the best time to book a vacation rental in Maitland, FL?
Booking in advance is always a good idea, especially during peak season, which runs from late fall to early spring. If you're looking for better deals, consider visiting during the shoulder seasons, like spring or fall.
What are the best rentals for families and kids in Maitland, FL?
What events or festivals should visitors check out in and around Maitland, FL?
The Maitland Art Center hosts several events throughout the year, including art exhibitions and workshops. The city also has a vibrant farmers market every Saturday, offering local produce and crafts.
What are the best rentals or Airbnbs with a jacuzzi in Maitland, FL?
What are the best budget-friendly activities in Maitland, FL?
A walk or bike ride along the scenic Maitland Trail is a great way to enjoy the outdoors for free. You can also visit the free-admission Maitland Public Library for a quiet afternoon or browse the books at the used bookstore on Horatio Avenue.
What are the best restaurants with local dishes in Maitland, FL?
For a taste of Florida, try the fresh seafood at The Rusty Spoon. If you're looking for something a little more casual, The Boathouse at Lake Lily is a great spot for lunch or dinner with waterfront views.
What are the best walking or cycling routes in Maitland, FL?
The Maitland Trail is a popular walking and cycling route that runs for miles, offering scenic views of the city. You can also explore the paved paths around Lake Lily Park or take a leisurely bike ride through the residential streets of the downtown area.
Are there pet-friendly attractions in Maitland, FL?
Lake Lily Park is dog-friendly, and you can often see people walking their dogs along the trails. The Maitland Art Center also hosts occasional pet-friendly events.
What are the benefits of choosing a vacation rental in Maitland, FL?
Vacation rentals offer more space and privacy than hotels, and they can often be more affordable, especially for families or groups. Many rentals also have kitchens, allowing you to prepare your own meals.
What are the top sports attractions and facilities in Maitland, FL?
Maitland is home to the Maitland Community Center which offers a variety of fitness classes, a swimming pool, and a gymnasium. The city also has several parks with sports fields and courts.
Destinations nearby
Find the Best Vacation Rentals with Balconies in Maitland, FL
Elevate your stay in Maitland, FL with a vacation rental featuring a private balcony and stunning city skyline views.
Maitland, FL
07/31 – 08/02
$1243/nighttotal: $2486 (2 )
Next Level Orlando: Spacesurfsprings Pool+games
4 9
apartment , Fairview Shores
This 4-bedroom, 2-bathroom vacation rental is located in Fairview Shores, Orlando, approximately 5 miles from Universal Orlando Resort and 10 miles from Walt Disney World. This family-friendly house features unique themed rooms, a private resort-style backyard with a heated pool and mini-golf, an indoor game room, and parking for up to six vehicles, accommodating up to 13 guests.
10 7 reviews
Maitland, FL
07/31 – 08/02
$961/nighttotal: $1922 (2 )
The Soundwave Retreat Pool, Spa & Golf Oasis
4 9
apartment , Casselberry
This Casselberry vacation home, near the Casa Feliz Historic Home Museum and Orlando Science Center, offers easy access to local attractions and parks. This 2,460-square-foot rental boasts four bedrooms, two bathrooms, sleeps fourteen guests, and includes a private water park, hot tub, and fully equipped kitchens in each bedroom.
9.0 9 reviews
Maitland, FL
06/27 – 07/04
$146/nighttotal: $1022 (7 )
Lake Eola Thornton Park Studio With Balcony
1 2
studio , Orlando
This Thornton Park studio apartment is centrally located in Orlando, Florida, within walking distance of Lake Eola, the Amway Center, and the Dr. Philips Center for the Performing Arts. This 750-square-foot unit sleeps two guests and features a full kitchen, private balcony, free parking, and access to the Lynx bus system; nearby amenities include Publix and various restaurants and bars.
8.4 9 reviews
Maitland, FL
06/27 – 07/04
$129/nighttotal: $903 (7 )
Modern Oasis Near Lake Eola
1 2
apartment , Orlando
This Lake Eola Heights apartment rental is conveniently located less than a mile from Lake Eola Park, and within three miles of the Kia Center and Camping World Stadium. This one-bedroom, one-bathroom unit sleeps three guests and features a fully equipped kitchen, in-unit laundry, a balcony, and access to community amenities including a garden and grills; enjoy nearby attractions and public transportation via the Lynx Central Station, a 21-minute walk away.
Neighborhoods and points of interest in Maitland, FL
Top Dog-Friendly Vacation Rentals in Maitland, FL
Discover pet-friendly vacation rentals in Maitland, FL that prioritize comfort for both you and your dog.
9.1 23 reviews
Maitland, FL
06/27 – 07/04
$373/nighttotal: $2611 (7 )
Resort Like House, 4 Bedrooms, 3 Bathrooms
4 2
house , Longwood
This Longwood house is located 15 miles from Church Street Station and Amway Center, offering a convenient base for exploring Orlando's attractions. The house has received excellent ratings for cleanliness, location, and user experience, ensuring a comfortable and enjoyable stay. This 4-bedroom, 3-bathroom home comfortably accommodates 8 guests with a spacious 80 square feet of living space. The house features a fully equipped kitchen, a hot tub, a patio with garden views, and a private parking space, providing everything you need for a relaxing and enjoyable vacation.
8.9 15 reviews
Maitland, FL
06/27 – 07/04
$109/nighttotal: $763 (7 )
Apartment| Downtown Orlando 10 Min & Disney 25 Min
1 2
apartment , Fairview Shores
This Winter Park condo offers a 1-bedroom, 1-bathroom unit with a 3-guest capacity, featuring air conditioning, a kitchen, and internet, located 25 miles from Disney World and 19 miles from Universal Orlando. Conveniently situated in Winter Park, this apartment is 10 miles from the Kia Center and Downtown Orlando, and 6 miles from Downtown Winter Park's shops and restaurants, with on-site parking available.
9.6 25 reviews
Maitland, FL
06/27 – 07/04
$263/nighttotal: $1841 (7 )
Amazing Five-star Luxury Thornton Park Two Bedroom Apt - Close To Kia Center.
2 2
apartment , Orlando
This two-bedroom apartment is located in Thornton Park, a lively neighborhood just a short walk from Lake Eola and a quick drive to the Kia Center and Camping World Stadium. Guests rave about the apartment's excellent location and amenities. The apartment comfortably sleeps four guests and is equipped with a full kitchen, in-unit laundry, and a private patio. Enjoy the on-site swimming pool, spa, and water park, or take advantage of the free Wi-Fi and relax in the garden.
10 36 reviews
Maitland, FL
06/27 – 07/04
$261/nighttotal: $1827 (7 )
Charming Clean Home Near East End Market Large Fenced Yard
3 2
apartment , Orlando
This family-friendly vacation home is located in the heart of Orlando, within walking distance of Harry P. Leu Gardens and Lake Virginia. Guests have consistently rated this property as excellent, making it a popular choice for families visiting the city. The 3-bedroom, 2-bathroom house can comfortably accommodate up to 6 guests and features a fully equipped kitchen, a garden with barbecue grills, and a terrace for outdoor relaxation. Amenities include a washer and dryer, air conditioning, free Wi-Fi, and a Smart TV with a DVD player for entertainment.
