Best Vacation rentals and Airbnb offers in Maitland, FL
9.8 16 reviews
Maitland, FL
06/27 – 07/04
$106/nighttotal: $742 (7 )
Yania's Cozy Getaway
1 2
apartment , Azalea Park
This Azalea Park apartment rental is minutes from Waterford Lakes Town Center and major highways, offering easy access to Orlando's theme parks, including Universal Studios' Wizarding World of Harry Potter. The one-bedroom, one-bathroom unit sleeps two guests and features a private patio, internet, air conditioning, parking, and a kitchen with a fridge and microwave; nearby attractions include the Florida Mall and Central Florida Fairgrounds.
9.7 52 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.
9.6 5 reviews
Maitland, FL
06/27 – 07/04
$81/nighttotal: $567 (7 )
Stylish & Cozy Retreat | Modern Comfort
1 2
apartment , Altamonte Springs
This Altamonte Springs condo offers suburban comfort with quick access to Orlando's attractions, situated near Altamonte Springs Mall and within a short drive to theme parks and nature parks. This one-bedroom, one-bathroom apartment accommodates up to three guests and features a full kitchen, air conditioning, Wi-Fi, and access to a swimming pool and fitness center, with driveway parking available.
Maitland, FL
06/27 – 07/04
$78/nighttotal: $546 (7 )
Virbo Host Website Is Not Working For Me. Do Not Book This Property. Thank You
1 2
apartment , Fairview Shores
This apartment in Fairview Shores, Winter Park, is a 3-minute drive from Mead Garden and 4 minutes from Lake Ivanhoe, with Lee Road Shopping Center a 10-minute walk away. This rental offers Wi-Fi, air conditioning, and toiletries, and is a short drive to Florida Mall, Orlando International Premium Outlets, and Universal Orlando Resort attractions.
9.4 6 reviews
Maitland, FL
06/27 – 07/04
$133/nighttotal: $931 (7 )
Retro Lake Eola 1 Bedroom Condo Thornton Park
1 2
apartment , Orlando
This South Eola District condo offers stunning Lake Eola views, walking distance to Thornton Park's restaurants and the Dr. Philips Center for the Performing Arts, and easy access to Amway Center via various transportation options. The one-bedroom, one-bathroom apartment sleeps two guests and features a 55" flat-screen TV, queen-size bed, and a full kitchen with a refrigerator and microwave, plus one designated parking spot (additional parking available for a fee).
9.5 69 reviews
Maitland, FL
06/27 – 07/04
$128/nighttotal: $896 (7 )
Historic Home- Downtown Orlando
1 2
apartment , Orlando
This two-bedroom, self-contained apartment near Lake Formosa in Orlando offers easy access to I-4, placing you within 300 yards of major attractions like Disney and Daytona Beach, and walking distance from the Orlando Science Center and Mennello Museum of American Art. The 1927 Mediterranean Revival-style rental features a full kitchen with dishwasher, in-unit laundry, air conditioning, parking, and accommodates two guests; a park-like setting and jogging trail along Lake Formosa are nearby.
10 3 reviews
Maitland, FL
06/27 – 07/04
$138/nighttotal: $966 (7 )
Thornton Park Paradise 1 Bedroom Lake Eola
1 2
apartment , Orlando
This downtown Orlando apartment is conveniently located within walking distance of Lake Eola, the Amway Center, and the Dr. Philips Center for the Performing Arts. This 750-square-foot unit features one bedroom, one bathroom, and accommodates two guests, offering amenities such as free Wi-Fi, a kitchen with a fridge and microwave, air conditioning, a private garden, and one off-street parking space.
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.
9.6 117 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.
8.8 19 reviews
Maitland, FL
06/27 – 07/04
$105/nighttotal: $735 (7 )
Sunshine Escape Guesthouse
1 2
apartment , Maitland
This Eatonville vacation rental is conveniently located near the RDV Sportsplex (1.7 miles) and Enzian Theater (2 miles), with easy access to Lee Road Shopping Center and the Casa Feliz Historic Home Museum within a 6-mile radius. This one-bedroom, one-bathroom house comfortably sleeps two guests and features a kitchenette with a refrigerator and microwave, in-unit laundry, free WiFi, and a Smart TV, making it ideal for a Maitland getaway.
9.2 7 reviews
Maitland, FL
06/27 – 07/04
$110/nighttotal: $770 (7 )
Renovated Nature Cozy Walk To Mall Park Publix
1 2
house , Altamonte Springs
This Altamonte Springs villa is conveniently located within one mile of Altamonte Mall and Cranes Roost Park, and two miles from Sanlando Park. This one-bedroom, one-bathroom vacation rental offers in-unit laundry, high-speed Wi-Fi, a fitness center, and comfortably accommodates up to three guests.
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. This accommodation is located in Orlando. Services and facilities include a restaurant, a fridge and free parking. This apartment also has air conditioning!
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.
9.3 133 reviews
Maitland, FL
06/27 – 07/04
$381/nighttotal: $2667 (7 )
Spacious And Relaxing Home - North Of Orlando In Longwood, Florida
5 2
apartment , Longwood
This Longwood home is located in a peaceful neighborhood, just a short walk from downtown Longwood and the Commuter Station (Sunrail), and is 20 minutes from Orlando. It has consistently received excellent ratings for user experience, location, and cleanliness. The 5-bedroom, 4-bathroom home offers 1840 square feet of space and can comfortably accommodate up to 10 guests. Amenities include a fully equipped kitchen, air conditioning, a Jacuzzi, a garden, a spa, parking, and internet access.
9.8 197 reviews
Maitland, FL
06/27 – 07/04
$321/nighttotal: $2247 (7 )
Lake House Pets Allowed
2 2
apartment , Orlando
This family-friendly vacation rental is located near downtown Orlando, within a mile of Lake Eola and its park, and within three miles of Camping World Stadium. This property has received excellent ratings for location, cleanliness, and overall experience. This two-bedroom, two-bathroom home comfortably accommodates four guests. The house features a full kitchen, a swimming pool, a jacuzzi, a sauna, a spa, a fitness center, a tennis court, and a garden, offering a variety of amenities and activities for relaxation and entertainment.
Maitland, FL
06/27 – 07/04
$143/nighttotal: $1001 (7 )
93 M² Hus ∙ 2 Sovrum ∙ 6 Gäster
2 2
house , Orlando
This pet-friendly, family-friendly house in Orlando offers 2 bedrooms, 1 bathroom, and accommodates up to 6 guests with 1000 square feet of living space, featuring a full kitchen with a fridge, freezer, microwave, and dishwasher, plus air conditioning and internet access. Located in a district providing convenient access to Orlando's attractions, this residence has a primary front door entry with a separate key for a side door, and includes a shoe ottoman near the front entrance.
10 7 reviews
Maitland, FL
06/27 – 07/04
$407/nighttotal: $2849 (7 )
Modern Home With Sport Court & Wellness Amenities
1 2
apartment , Orlando
This 2-bedroom, 2-bathroom condo is located in a well-situated Orlando district, offering a 10-minute drive to Downtown Orlando. This family-friendly residence accommodates up to 4 guests and features a private screened-in patio with an outdoor kitchen and bar, a hot tub, an infrared sauna, a cold plunge, red light therapy, and a shared semi-private basketball/pickleball court.
Best Maitland, FL vacation rentals with parking
9.4 10 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.
9.8 188 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.
Maitland, FL
06/27 – 07/04
$130/nighttotal: $910 (7 )
Modern Lake Eola Condo In The Heart Of Thornton Park
1 2
apartment , Orlando
This apartment is located in Orlando's Thornton Park district, 0.7 miles from downtown and Church Street Station, 1.1 miles from the Kia Center, 2.4 miles from Camping World Stadium, 6.3 miles from Holy Land Experience, and within 10 miles of Universal Studios Orlando and Universal Studios' Islands of Adventure. This 700 sq ft condo accommodates up to 3 guests with 1 bedroom, a living room, a fully equipped kitchen with a fridge and microwave, air conditioning, and free WiFi, offering a private entrance for convenience.
9.6 306 reviews
Maitland, FL
06/27 – 07/04
$155/nighttotal: $1085 (7 )
Cute Guest House In Winter Park Minutes From Downtown In Car
1 2
apartment , Fairview Shores
This guest house is located in Winter Park, Florida, just minutes from the Park Ave strip and Winter Park Village, offering easy access to shopping, dining, and entertainment. This property has received excellent ratings for user experience, location, and cleanliness. The studio is approximately 320 square feet and comfortably accommodates two guests. It features a kitchenette, refrigerator, AC, smart TV, Wi-Fi, a queen-size bed, a full bathroom with toiletries, a private entrance, and a backyard 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.
8.0 1 review
Maitland, FL
06/27 – 07/04
$383/nighttotal: $2681 (7 )
3 Bedroom Corner Suite
3 2
apartment , Orlando
This Orlando condo is located in the South Eola district, offering a 10-minute walk to the Dr. Phillips Center for the Performing Arts and a few minutes' walk to Lake Eola, with Church Street Station accessible in a 13-minute walk for public transport connections. This 2000 square foot apartment accommodates up to 6 guests with 3 bedrooms and 2 bathrooms, featuring a balcony, fitness center, barbecue area, and in-unit amenities including free Wi-Fi, air conditioning, and a washer/dryer, all supported by a concierge service.
9.6 135 reviews
Maitland, FL
06/27 – 07/04
$279/nighttotal: $1953 (7 )
Charming Heated Pool Home In Altamonte Springs
3 2
apartment , Altamonte Springs
This vacation rental is conveniently located in Altamonte Springs, within a 5km radius of Altamonte Mall, Maitland Art Center, and Cranes Roost Park, offering easy access to shopping, art, and outdoor activities. Guests consistently rate the location, cleanliness, and overall experience as excellent. The 3-bedroom, 2-bathroom house comfortably accommodates up to 6 guests within its 1650 square feet of living space. The home features a fully equipped kitchen, a private garden with barbecue grills, a swimming pool, and a terrace/balcony for relaxing and enjoying the Florida sunshine.
10 1 review
Maitland, FL
06/27 – 07/04
$5102/nighttotal: $35714 (7 )
5/4 King Bed Lux Arcade Near Wp/cp & Dt Orlando ️
5 2
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.
9.4 3 reviews
Maitland, FL
06/27 – 07/04
$228/nighttotal: $1596 (7 )
Luxury 1260sq Ft 2 Bd/2bth In Dt
2 2
apartment , Orlando
This Thornton Park rental is centrally located in South Eola, Orlando, within walking distance of Lake Eola, the Amway Center, and the Dr. Phillips Center for the Performing Arts. This 860-square-foot, two-bedroom, two-bathroom apartment sleeps four and includes amenities such as free internet, cable, and parking, plus a 24-hour doorman.
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.
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.
9.9 9 reviews
Maitland, FL
06/27 – 07/04
$304/nighttotal: $2128 (7 )
2 Bdrm Penthouse With Billiards
1 2
apartment , Orlando
This two-bedroom penthouse apartment is located in downtown Orlando, less than half a mile from the city center and 8.7 miles from Orlando International Airport. The 1,610-square-foot unit sleeps seven guests and features two bathrooms, a fully equipped kitchen, in-unit laundry, a billiards table, free Wi-Fi, and access to an on-site fitness center and concierge services.
9.6 80 reviews
Maitland, FL
06/27 – 07/04
$146/nighttotal: $1022 (7 )
Great Location + Pickleball / Basketball Court!
1 2
house , Orlando
This two-story duplex is located in a safe neighborhood close to downtown Orlando, offering easy access to the city's attractions, restaurants, and entertainment. The property consistently receives excellent ratings for location, cleanliness, and overall user experience. This home features two bedrooms and two bathrooms, comfortably accommodating up to six guests. Amenities include a fully equipped kitchen, a designated workspace, free parking, Wi-Fi, and pet-friendly accommodations.
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.
