House holiday rentals in Maitland

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Top-rated house rentals in Maitland

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Guest favourite
The inviting pool area is framed by a wooden deck, featuring two lounge chairs and a large umbrella for shade. The clear water reflects the blue sky and surrounding greenery, creating a serene atmosphere for relaxation.
Home in Altamonte Springs
4.94 out of 5 average rating, 100 reviews

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!😊

Superhost
A bright sleeping area features a spacious bed with light grey bedding. A woven blanket is draped casually across the foot of the bed. A piece of art depicting hands is mounted above the bed, while a floor lamp stands beside it, illuminating the room.
Home in Park Lake/Highland
4.73 out of 5 average rating, 128 reviews

Cozy Vintage Bungalow @Mills50 District

This special place is close to everything, making it easy to plan your visit. Location at this vintage duplex is second to none. You'll enjoy being walking distance to MILLS50 district food, dive bars, entertainment, breweries and so much more! The property has received a makeover while retaining its original vintage charm. Still original and preserve are some accents in the bathroom, vanity mirror is original steel, as is the flooring and more 😎 ✅26 Min to DisneyWorld 🌏 ✅️15 Min Univervsal

Top guest favourite
A spacious living area features a large, deep-seated sectional couch adorned with decorative pillows. A wooden tray rests on the couch. A dining table with chairs is positioned near bright windows, enhancing the natural lighting in the room.
Home in Winter Park
4.98 out of 5 average rating, 168 reviews

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)

Top guest favourite
A serene bedroom features a spacious bed dressed in crisp white linens, flanked by modern bedside lamps. A vibrant floral accent wall adds a pop of color, while light filters through plantation shutters, creating a calming atmosphere.
Home in College Park
4.96 out of 5 average rating, 101 reviews

Yale House in College Park 2 mi from Downtown

Yale House is a charming, historic 1927 home. This happy place is a stylish mix of nostalgia and modern life. The home is only steps away from shops & restaurants. The full kitchen and laundry have everything one needs for longer stays and includes a dedicated workspace with ethernet. There is wifi & 4 streaming TV’s with a huge comfy couch. Two bedroom choices provide for a peaceful rest. Driveway parking, outdoor spaces and a top of the line home gym make this unique for long term comfort.

Guest favourite
The cozy sleeping area features a spacious bed adorned with luxurious cotton sheets and coordinating pillows. A rattan headboard complements the tropical-themed wallpaper. A small seating area with a brown couch and decorative pillows is visible, adding to the inviting atmosphere.
Home in College Park
4.94 out of 5 average rating, 155 reviews

The Boho Jungalow - Private | HotTub | Downtown

This relaxing 1 bed 1 bath space in Downtown Orlando boasts a lush fenced-in private yard, hot tub, and fully equipped kitchen. We pride our studio on comfort, wellness, and delicate attention to detail to experience the magic of a trendy space in the heart of Orlando. Enjoy brand-new remodeling, furnishings, and appliances. This is the back unit of a 2-unit property. We include: ✅50" TV ✅Luxury mattress ✅Fiber optic Wi-Fi ✅Decaf Coffee & Tea ✅Disney Plus, Hulu, Max, Netflix ✅ Free Parking

Guest favourite
A spacious game room features a blue pool table at its center, surrounded by light wooden flooring. To one side, seating options include modern chairs and a couch, with natural light filtering through large windows. The kitchen and dining area are visible in the background.
Home in Orlando
4.94 out of 5 average rating, 136 reviews

Lake House Retreat w/ Firepit - Centrally Located

Our cozy lakefront retreat in the heart of Orlando boasts a fenced-in backyard with stunning lake views. Relax around the fire pit/wood-burning grill or enjoy a game of corn hole or ping pong on the porch. With a pool table in our game room and comfortable sleeping arrangements for up to 8 guests, this is the perfect place to relax and unwind. Located just minutes from downtown, Disney World, Universal Studios, and the airport, this is an ideal spot to experience all the area has to offer.

Guest favourite
A spacious living area features a modern sectional sofa arranged facing a stone fireplace. Large glass doors provide natural light and views of the outdoor space. Decorative plants and a wall-mounted mirror add elegance to the cozy atmosphere.
Home in Maitland
4.86 out of 5 average rating, 140 reviews

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!

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, 179 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.

Top guest favourite
An open living area includes a modern kitchen with white cabinetry and stainless steel appliances alongside a spacious seating area. A black sectional sofa faces a large window, allowing natural light to brighten the space. Decorative plants are arranged on a nearby shelf.
Home in Altamonte Springs
4.97 out of 5 average rating, 218 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.

Superhost
A serene bedroom features a spacious bed with white linens and decorative pillows against a backdrop of warm wooden paneling. Modern pendant lights hang symmetrically above the bedside tables, and a soft area rug is placed beneath the bed, enhancing the calming atmosphere.
Home in Winter Park
4.83 out of 5 average rating, 112 reviews

Sleeps 3, Winter Park & Downtown

Welcome to gorgeous Winter Park! Enjoy this stylish centrally-located 1/1 home with newly renovated bedroom and fully remodeled bathroom. Just a few minutes from the beautiful cobblestone Park Avenue with the best restaurants, shops and Rollins College, always happening downtown Orlando (Kia Center, Camping World Stadium, Orlando City Stadium etc) and vibrant College Park neighborhood. Take a 25 min drive to south and you'll reach all major theme parks.

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, 143 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.

Guest favourite
An outdoor space features a heated pool and a hot tub, surrounded by stone masonry. A custom bar, crafted from wood, is visible alongside tropical plants. Two built-in TVs are fitted above the bar area, enhancing the outdoor living experience.
Home in Orlando
4.91 out of 5 average rating, 148 reviews

Stunning Orlando Getaway w/Spa & Heated Pool

The whole group will enjoy easy access to everything from this centrally located Orlando location. This 1950s beautifully designed space has all modern amenities with an amazing outdoor living space. Located in College Park situated close to many amenities Orlando has to offer. Only 9 Minutes to downtown Orlando or 15 Minutes to Universal. The Acre & The Cottage Wedding venues are both within Walking Distance. Dubsdread is only 4 Minutes Away.

Popular amenities for house rentals in Maitland

When is the best time to visit Maitland?

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Quick stats about house rentals in Maitland

  • Total holiday rentals

    Explore 60 holiday rentals in Maitland

  • Nightly prices starting at

    Maitland holiday rentals start at $26 SGD per night before taxes and fees

  • Verified guest reviews

    Over 1,480 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wifi availability

    60 of Maitland holiday 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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