
Vacation rentals in Maitland
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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!😊

Stylish newly updated home in Winter Park
Sleeps 8 people comfortably but can fit 10. This home has VERY CONVENIENT ACCESS TO I-4 making it easy to get to Orlando's most sought after attractions, including Park Avenue, Downtown Orlando, Rollins College, Leu Gardens, Mills Ave, Baldwin Park, College Park, Camping World Stadium, Amway Arena, SunRail, and many hospitals. SHORT WALK to 3 notable restaurants Also nearby: Universal Studios (20 min) Outlet Mall (20 min) International Drive (25 min) Orlando Airport (30 min) Disney (~30-40 min)

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.

8th Green Cottage - A relaxing oasis in the city
The 8th Green Cottage is a relaxing oasis in the heart of Orlando. Located 5 minutes from downtown. Sitting on the historic 1924 Dubsdread golf course. Enjoy the great views, pleasant and quiet neighborhood all with easy access to everything Orlando has to offer. Location is key when traveling and the 8th Green Cottage delivers! Disney, Universal, and Sea World all within a straight shot down I4. Free play Arcade with 3500 games included in spare bedroom Pets are welcome and stay Free.

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!

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.

Orlando, spacious, quiet, centrally located, suite
This suite includes private entrance, living room, kitchen with utensils and cookware, one bedroom with king bed and private bath. Third and fourth persons may be accommodated with recliner that lays flat into a queen-size bed in living room. Also a queen size air mattress and portacrib is available. Excellent location for Disney, Universal, SeaWorld, and beaches. Approx. 35 min. to Disney; 27 min. to Universal; 23 min. to convention center; 45 min. to beach; and 35 min. to Airport.

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.

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

The Little Treehouse 2 at Country Club of Orlando
With rustic urban charm, The Little Treehouse "2" is a perfect relaxation spot for your stay in the City Beautiful. This completely renovated 1926 carriage house downstairs unit is a 260 sq. ft. blend of cosmopolitan comfort and enchantment. Located 5 minutes from Downtown, Amway Arena, Camping World Stadium, 15 minutes to Universal Studios, 25 minutes to Disney and an hours drive to Florida's beautiful beaches! *Search "Little Tree House Orlando" in your browser for more info.

TreeHouse in the Cloud, (Close toTheme Parks
The treehouse is a private getaway for a couple that want to experience the magic. Check out video tours on U-Tube. Type in Treehouse in the Cloud. There have been several movie and other photo shoots done on property. Please text request and details, and we can negotiate fees. Our other AirBnB is just next door; Country gem horses close to Theme parks [link] Which is 1,000 sq ft and sleeps six.

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.
Popular amenities for Maitland vacation rentals
Other great vacation rentals in Maitland

Charming 2/1 Condo on a Lake in Winter Park

Serene private home near the fun

Joe's Bar and Grill

The Winter Park Experience

Garden Cottage Swim/Spa, Ctrl Orlando, Disney, 2/2

May Special, Spring the best time of the year!

3BR DT ORL | Fenced Yard + On-Site Car Rental

Golf Car Fun ,Spring & Swing Retreat
When is the best time to visit Maitland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $141 CAD | $128 CAD | $126 CAD | $120 CAD | $112 CAD | $91 CAD | $124 CAD | $124 CAD | $130 CAD | $135 CAD | $142 CAD | $134 CAD |
| 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
Are there family-friendly vacation rentals in Maitland?
Maitland has more than 50 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in house rentals in Maitland?
Experience the best of Maitland with our house rentals, starting at about $20 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there pet-friendly vacation rentals in Maitland?
Four-legged friends are welcome in Maitland. Choose from more than 40 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Maitland?
Yes! Work meets play with ease at over 70 vacation rentals in Maitland featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there Maitland house rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 house rentals with pools in Maitland, available on Airbnb. Make a splash and soak up the sun in style!
Where should I stay in Maitland?
Make yourself at home in Maitland by choosing from our most frequently booked neighborhoods. We have over 470 vacation rentals in Eatonville, and over 760 vacation rentals in Maitland.
Do apartment rentals in Maitland have air conditioning?
Absolutely! We offer over 30 apartment rentals with air conditioning in Maitland. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Maitland have a kitchen?
Absolutely! We offer over 50 house rentals with a kitchen in Maitland. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Maitland have wifi?
Absolutely! We offer over 60 house rentals with wifi in Maitland. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Maitland have free parking?
Absolutely! We offer over 60 house rentals with free parking in Maitland. Enjoy a tailored experience with all the comforts you desire.
Quick stats about vacation rentals in Maitland

Total vacation rentals
Explore 120 vacation rentals in Maitland

Nightly prices starting at
Maitland vacation rentals start at $28 CAD per night before taxes and fees

Verified guest reviews
Over 5,110 verified reviews to help you choose

Family-friendly vacation rentals
50 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Vacation rentals with a pool
40 properties feature pools

Rentals with dedicated workspaces
70 properties have a dedicated workspace

Wifi availability
110 of Maitland vacation 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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- Walt Disney World Resort
- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Walt Disney World Resort Golf
- Disney Springs
- SeaWorld Orlando
- Magic Kingdom Park
- Universal's Volcano Bay
- Ocean Center
- Orlando / Kissimmee KOA
- Daytona Beach Bandshell
- Discovery Cove
- ESPN Wide World of Sports
- Epcot
- Disney's Animal Kingdom Theme Park
- Daytona International Speedway
- Kia Center
- Old Town
- Reunion Resort Golf Courses - Palmer & Watson
- Camping World Stadium
- Aquatica
- Playalinda Beach
- Disney's Hollywood Studios




