Holiday houses in Maitland

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Top-rated holiday rentals in Maitland

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
A spacious pool house is visible behind a lush, green lawn, surrounded by trees. A paved path leads to the inviting pool area, while a gated fence provides added privacy. Sunlight filters through the leaves, creating dappled patterns on the grass.
Bungalow in Maitland
4.87 out of 5 average rating, 594 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.

Top Guest favourite
A cozy bedroom showcases a queen bed with an orange floral duvet cover and matching pillows. Three pieces of wall art in soft hues are displayed above the headboard. A door leading to the private entrance is visible, providing easy access.
Apartment in College Park
4.94 out of 5 average rating, 273 reviews

College Park/Winter Pk 1 bed/bath private entrance

255 sq ft studio- queen bed, workspace, kitchenette, large bathroom, private yard area & entrance. This gem is clean & quiet w/ complete blackout in bedroom. Bathroom has tons of natural light & 3 shower heads. There’s TV w/Roku, microwave, fridge & Keurig. Comfy, peaceful at I-4 Par exit # 44. $20 pet fee No cleaning fee. Universal 11 mi Kia Center 3 mi Airports (MCO) (SFB) 23 mi Orlando City Soccer 4.6 AdventHealth Orlando 0.6 mi Orlando Health, Arnold/Winnie Palmer 3.8 Rollins College 1.9

Top Guest favourite
A serene pool area features a clear blue pool surrounded by elegant tile flooring. Comfortable lounge chairs are arranged around the pool, providing ample space for relaxation. Potted plants add a touch of greenery to the setting, contributing to a calming atmosphere.
Guest suite in Altamonte Springs
4.96 out of 5 average rating, 370 reviews

St. Augustine suite

Luxurious space with PRIVATE ENTRANCE, PRIVATE BATHROOM and breakfast kitchenette. Located on a large lake front property with amenities that include private dock, pool, large manicured lawns and much more. Ideal for canoeing, watching the sun rise or doing nothing at all. Close to theme parks and beaches. Spring Valley is a peaceful community with age old oak tree , Ample shopping and award winning restaurants very nearby. Come play or rejuvenate your soul in this picturesque setting

Top Guest favourite
The front porch features two wicker chairs with bright orange cushions, inviting relaxation. Potted plants and hanging baskets add greenery, while a gentle overhang provides shade. A pathway leads to the entrance and a nearby guest house, framed by well-maintained shrubs.
Guesthouse in Orlando
4.97 out of 5 average rating, 359 reviews

Oasis Garden Cottage -cozy, chic, near everything!

Our cozy cottage is located within minutes of some of the best areas, restaurants, bars, and attractions Orlando has to offer. Winter Park and College Park are 3-5 minute drives, Disney and Universal only 20 minutes, etc. The interior is chic and inviting, with a homey feel. Enjoy the fireplace, play some board games, soak in bath salts in the claw foot tub, curl up on the porch with a coffee and read one of our provided books— it’s so peaceful you’ll have a hard time leaving for the day!

Top Guest favourite
A white door with a glass panel leads into the studio, framed by a decorative welcome mat on stone pavers. Lush green plants are positioned beside the door, adding a natural touch to the entrance. Soft shadows from nearby foliage create a calming atmosphere.
Guest suite in College Park
4.97 out of 5 average rating, 246 reviews

New Mid Century-Modern Studio

Enjoy your stay in this beautifully decorated studio with all the conveniences of home. The bed is Queen. We are located in College Park of Orlando. On Edgewater Drive there are restaurants, bars, and boutique shops. Close to downtown , 30 min. from all the attractions, and 5 min. from one of the city’s largest hospitals, 23 miles from ORMC airport. Walking distance from the historic Dubsdread Golf Club and restaurant. Pet fee required. Please make sure to add the pet to the reservation.

Top Guest favourite
A private pool area is surrounded by lush tropical landscaping, featuring tall palm trees and vibrant greenery. The sparkling blue water of the pool reflects the sky, while a paved pathway leads to the entrance. A serene atmosphere is created by the nearby plants and outdoor decor.
Home in Maitland
4.95 out of 5 average rating, 178 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.

Guest favourite
A small, private room features a comfortable bed with a patterned blanket. A desk is positioned against the wall, accompanied by a chair. Natural light enters through a window, with decorative plants and simple wall décor enhancing the space.
Guest suite in Orlando
4.92 out of 5 average rating, 126 reviews

Adorable, private studio in College Park

Currently opening up this space for long term rentals (20-60 days). Perfect for travel nurses- about 10 min drive to Orlando Advent Health Hospital. This spot is perfect for 1 or 2 people looking for a private, welcoming place to stay! It is completely separate but does share a wall with the owners unit, so you could potentially hear some noises through there. The fenced in back yard is shared as well, both back doors open up to the yard. Its about 10 mins from downtown Orlando

Guest favourite
A cozy bedroom features a black platform bed dressed in a navy and white patterned duvet. A wooden dresser stands adjacent to the bed, and a small desk is positioned nearby. Natural light illuminates the space, highlighting the serene beach artwork on the wall.
Guest suite in Eatonville
4.95 out of 5 average rating, 208 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.

Top Guest favourite
A spacious guest suite is presented with a queen bed and a comfortable seating area featuring a gray sofa and coffee table. A kitchenette is visible in the background, complemented by natural light from the window. Decorative elements include subtle artwork and indoor plants.
Guest suite in Altamonte Springs
4.93 out of 5 average rating, 378 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!

Top Guest favourite
A bright bedroom features a spacious bed with a plush headboard and soft linens. Natural light enters through two windows, illuminating the room. A round mirror is mounted on the wall above a minimalistic desk with a chair, adding functionality to the cozy space.
Home in College Park
4.94 out of 5 average rating, 142 reviews

Priv. Modern Cozy CP 1B/1Ba Suite near DT Orl & WP

Private & Comfortable 1 bd/ba suite in a 2021 townhome with front view windows, queen size bed, walk-in shower& private entrance. Equipped w/ ceiling and portable fans, Roku smart TV, mini fridge/freezer, microwave, and Keurig. Located in a safe, quiet, walkable neighborhood. 5 minutes of College Park shops, 10 minutes from downtown Orlando, 25 minutes to Universal Studios, 30 minutes to Orlando International Airport, & 40 minutes to Disney.

Top Guest favourite
An efficient layout showcases the interior of the airstream, featuring a modern kitchenette with a sink and seating area. Along one wall, sleek bar stools are positioned in front of a counter. Soft lighting creates a cozy atmosphere, enhancing the vintage charm.
Campervan/RV in Orlando
4.91 out of 5 average rating, 154 reviews

Unique and modern airstream near UCF

Our airstream has all the amenities you need. It is located in our one acre property behind our house (very private) the parking is on the side of our house next to our carport and you will go through a gate and follow the path to the airstream. MCO Airport 12 miles Disney parks 25 mil Universal Studios 16 mil beaches 50 mil UCF 2.4 mil Full Sail 2.4 mil Valencia 3.5 mil Dining, Shopping entertainment and much more!

Top Guest favourite
An outdoor deck features a round table with two chairs beneath a vibrant orange umbrella. The entrance to the container studio is framed by glass doors, surrounded by plants. String lights are visible overhead, providing a cozy ambiance.
Shipping container in College Park
4.92 out of 5 average rating, 179 reviews

Cozy container in College Park and near Downtown

This is a unique stay in a container that has been transformed into a studio. Similar to a tiny home but without climbing into a loft. The Container is outfitted with a Kitchen, Bath and sleeping area. Cozy and quaint is the best way to describe it. The location is in my backyard in College park, near major roadways for easy travel to the theme parks, Winter Park restaurants and Downtown entertainment.

Popular amenities for Maitland holiday rentals

When is the best time to visit Maitland?

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Frequently Asked Questions

  • Are there house rentals with a dedicated workspace in Maitland?

    Yes! Work meets play with ease at over 30 house rentals in Maitland featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • 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.

  • What are the most popular amenities for Apartment Rentals in Maitland?

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 30 homes with air conditioning, over 30 homes with wifi, over 10 homes with a kitchen, over 20 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there family-friendly house rentals in Maitland?

    Maitland has more than 30 family-friendly house rentals. 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 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!

  • Are there pet-friendly house rentals in Maitland?

    Four-legged friends are welcome in Maitland. Choose from more than 20 house rentals for guests traveling with pets.

  • Do apartment rentals in Maitland have wifi?

    Absolutely! We offer over 30 apartment rentals with wifi in Maitland. Enjoy a tailored experience with all the comforts you desire.

  • Where should I stay in Maitland?

    Make yourself at home in Maitland by choosing from our most frequently booked neighborhoods. We have over 460 vacation rentals in Eatonville, and over 730 vacation rentals in Maitland.

Quick stats about holiday rentals in Maitland

  • Total holiday rentals

    Explore 110 holiday rentals in Maitland

  • Nightly prices starting at

    Maitland holiday rentals start at $30 AUD per night before taxes and fees

  • Verified guest reviews

    Over 5,220 verified reviews to help you choose

  • Family-friendly holiday rentals

    40 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 40 rentals that welcome pets

  • Holiday rentals with a pool

    40 properties feature pools

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

  • Wi-Fi availability

    110 of Maitland holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi 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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