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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.

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Guest suite in Altamonte Springs

4.96 out of 5 average rating, 159 reviews

Comfortable Guest Suite-Stylish Altamonte Springs!

Enjoy a stylish guest experience at this centrally-located Altamonte Springs Florida guest suite. This luxury 830 sq ft unit offers a living room, kitchenette, bedroom, bathroom and large pool in the peaceful Spring Valley Farms residential community. It is located 8 miles north of downtown Orlando, a primo location close to downtown, both ocean coasts, Wakiwa Springs State Park, theme parks (Disney, Universal, SeaWorld, more), Crane's Roost, and many other great destinations in central Florida!

Bungalow in Maitland

4.87 out of 5 average rating, 527 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.

Guesthouse in College Park

4.93 out of 5 average rating, 107 reviews

Beautiful 1 Bed/1 Bath in College Park Orlando

College Park is a great residential neighborhood of Orlando close to all the action, but also far enough away if you are looking for peace and quiet. There are several bars, breweries, and restaurants within minutes by car and you can also Uber downtown within 5-10 minutes. The Advent Health Hospital is within walking distance just 3 blocks away. Everything from Disney and Theme Parks to nightlife and nature are about a 30 minute drive away. If you need any help deciding what to do, just ask.

Guesthouse in College Park

4.91 out of 5 average rating, 163 reviews

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.

Bungalow in College Park

4.98 out of 5 average rating, 277 reviews

Cozy 2/2 Home - Downtown Winterpark/Orlando

You will be close to everything when you stay at this centrally-located bungalow. Located right off I-4, 5 minutes from Advent Health Hospital, you will be 5 minutes from Downtown Orlando an, 10 min from Downtown Winter Park, 15 min from Universal Studios, and 25 min from Disney! Dubsdread golf course within walking distance! Large 70 inch 4K tv with surround sound, large sofa to enjoy watching your favorite movies, 2 rooms with queen beds, and 2 bathrooms equipped with bluetooth music

Home in Winter Park

4.94 out of 5 average rating, 137 reviews

Modern, Quiet & Cozy - Entire house 2/2

Embrace Tranquil Living in Winter Park, Florida. Located in a quiet neighborhood NE of downtown this recently renovated house is modern, clean, and cozy. Short drive to other great attractions in Orlando. Its central location is minutes away from Park Ave, the University of Central Florida, Rollins College, Full Sail University, Downtown Orlando, MCO Airport, Amway Center, Dr. Phillips, Science Center, Orlando City Stadium, and much more! You need to be at least 18 years old to book.

Guesthouse in College Park

4.97 out of 5 average rating, 113 reviews

New Mid Century-Modern Studio

Enjoy your stay in this beautifully decorated studio with all the conveniences of home. We are located in College Park of Orlando. The main road here is Edgwater Drive which offers restaurants, bars, and boutique shops. This location is 15 min. from downtown, 30 min. from all the attractions, and 5 min. from one of the city’s largest hospitals in central Florida. Also, you are within walking distance from the historic Dubsdread Golf Club and restaurant. Perfect home away from home.

Home in Maitland

4.96 out of 5 average rating, 140 reviews

The Butterfly Bungalow near Park Ave

This 1950s bungalow has been lovingly restored to maintain it's Florida charm and offer simple comforts. Located in a family-friendly neighborhood just a few blocks from the Enzian Theater, the bungalow is close to restaurants and shops lining the cobblestone streets of Park Ave, and centrally located to historic areas of both Winter Park and Maitland. Park Ave shopping district - 1.5 miles Whole Foods - 0.8 miles Publix - 0.8 miles SunRail - 1.7 miles Downtown Orlando - 8 miles

Guest suite in Altamonte Springs

4.96 out of 5 average rating, 314 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

Home in Altamonte Springs

4.96 out of 5 average rating, 135 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.

Guest suite in Eatonville

4.98 out of 5 average rating, 117 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.

Guest suite in Altamonte Springs

4.92 out of 5 average rating, 333 reviews

The Bungalow

Welcome to your home away from home! Enter through a private driveway and enjoy the ease of keyless entry. Located across the street, Sanlando Park offers walking trails, basketball and popular tennis courts. Whether your interests are peace and quiet or adventure, you are only 30 minutes or less away from our beautiful natural springs, beaches and all major attractions. Wake up with the sunshine, put on a pot of coffee and welcome to Florida!

Vacation rentals for every style

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Stylish accommodations and amenities

Popular amenities for Maitland vacation rentals

Free parking on premises

Air conditioning

Stay near Maitland's top sights

Charles Hosmer Morse Museum of American Art168 locals recommend

Enzian Theater77 locals recommend

Winter Park Village68 locals recommend

Regal Cinemas Winter Park Village43 locals recommend

Starbucks39 locals recommend

Whole Foods Market34 locals recommend

Other great vacation rentals in Maitland

Townhouse in Altamonte Springs

4.85 out of 5 average rating, 26 reviews

Cheerful 2 bedroom home in Altamonte Springs.

Home in Altamonte Springs

5 out of 5 average rating, 13 reviews

Cozy Blue Bungalow

Home in Baldwin Park

5 out of 5 average rating, 43 reviews

Stunning Luxury Oasis + Nintendo-themed Game Room

Rental unit in Winter Park

4.9 out of 5 average rating, 88 reviews

The Lake House

Guest suite in Casselberry

5 out of 5 average rating, 30 reviews

2B/2B Close to Orlando,Winter Park&Winter Springs

Home in Winter Park

4.97 out of 5 average rating, 112 reviews

Relax on a private lake in Winter Park!

Bungalow in College Park

4.98 out of 5 average rating, 62 reviews

Cozy Cottage in College Park.

Guest suite in Casselberry

4.9 out of 5 average rating, 72 reviews

Orlando, spacious, quiet, centrally located, suite

Quick stats about vacation rentals in Maitland

Total rentals
80 properties
Total number of reviews
2.3K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
30 properties have a pool
Rentals with dedicated workspaces
40 properties have a dedicated workspace

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Maitland?
Yes! Work meets play with ease at over 40 vacation rentals in Maitland featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Maitland have air conditioning?
Absolutely! We offer over 40 house 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 30 house rentals with a kitchen in Maitland. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Maitland?
Enhance your stay in our House Rentals with the most popular amenities: over 40 homes with air conditioning, over 30 homes with a kitchen, over 40 homes with free parking, over 40 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there family-friendly vacation rentals in Maitland?
Maitland has more than 30 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in apartment rentals in Maitland?
Experience the best of Maitland with our apartment 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 Maitland vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 30 vacation homes with pools in Maitland, available on Airbnb. Make a splash and soak up the sun in style!
Are there pet-friendly vacation rentals in Maitland?
Four-legged friends are welcome in Maitland. Choose from more than 20 vacation rentals for guests traveling with pets.
Do apartment rentals in Maitland have wifi?
Absolutely! We offer over 20 apartment 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 40 house rentals with free parking in Maitland. Enjoy a tailored experience with all the comforts you desire.

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