Vacation rentals in Maitland

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Quick stats about vacation rentals in Maitland

  • Total vacation rentals

    Explore 130 vacation rentals in Maitland

  • Nightly prices starting at

    Maitland vacation rentals start at R 320 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 5,560 verified reviews to help you choose

  • Family-friendly vacation rentals

    40 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 50 rentals that welcome pets

  • Vacation rentals with a pool

    40 properties feature pools

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wi-Fi availability

    130 of Maitland vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Maitland rentals

  • 4.7 Average rating

    Maitland stays receive an average rating of 4.7 out of 5 from guests

Top-rated vacation rentals in Maitland

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

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Guest favorite
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
4.95 out of 5 average rating, 111 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!😊

Guest favorite
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, 204 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 favorite
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
4.88 out of 5 average rating, 630 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 favorite
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, 394 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 favorite
A charming lakefront cottage is viewed from across the water, showcasing its blue exterior. The porch area includes a deck with seating, and two light-colored lounge chairs are positioned on the grassy lawn, surrounded by lush greenery and trees.
Cottage in Altamonte Springs
4.99 out of 5 average rating, 155 reviews

Charming Private Lakefront Cottage Retreat

You can fully relax in this adorable lakefront cottage. We're sure you'll enjoy all of the wonderful amenities this peaceful property has to offer. Our incredibly unique cottage is nestled under a large grand oak tree and tucked away behind climbing jasmine vine clad fencing and security gates. Inside, you will find a new remodeled fully stocked kitchen and luxury bathroom. Our cozy cottage has all the comforts of home and more. Reserve your stay today and enjoy this special property.

Top guest favorite
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, 331 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, zip code 32804. 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 add the pet to the reservation.

Top guest favorite
The exterior of the two-story cottage is captured, showcasing a red and white color scheme with black shutters. Lush green landscaping and a well-maintained lawn surround the home, while a concrete driveway leads to a detached garage nearby. A white picket fence adds charm to the property.
Guesthouse in College Park
4.91 out of 5 average rating, 198 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.

Top guest favorite
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, 187 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 favorite
The screened-in pool area features a tranquil pool with a soft blue hue, surrounded by white decking. A small table holds a lit lantern beside two lounge chairs, providing a serene space for relaxation under the evening sky.
Home in Maitland
4.98 out of 5 average rating, 130 reviews

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.

Guest favorite
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, 250 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.

Top guest favorite
Guest suite in Eatonville
4.96 out of 5 average rating, 242 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 favorite
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
4.97 out of 5 average rating, 118 reviews

1927 Bungalow · Walk to College Park Shops

A 1927 bungalow in College Park with its original character intact — plantation shutters, wood floors, a record player and a wall of albums worth digging through. A walk-everywhere address: Publix, Starbucks and the shops on Edgewater are two minutes away. Inside, a full kitchen with dishwasher, in-unit laundry, 1000 Mbps fiber and a real desk with ethernet — a week here works as easily as a weekend. Private patio and driveway parking for two.

Popular amenities for Maitland vacation rentals

When is the best time to visit Maitland?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceR 1,794 ZARR 1,794 ZARR 1,746 ZARR 1,859 ZARR 1,923 ZARR 1,618 ZARR 1,426 ZARR 1,426 ZARR 1,490 ZARR 1,554 ZARR 1,634 ZARR 1,538 ZAR
Avg. temp16°C18°C20°C22°C25°C27°C28°C28°C27°C24°C20°C17°C

Frequently Asked Questions

  • What are the best places to stay in Maitland?

    Neighborhoods near lakes and parks, such as areas around Lake Lily and community green spaces, are often suggested for vacation rentals. Homes with outdoor patios or gardens can offer a comfortable retreat.

  • What are the best things to do in Maitland with kids?

    Children often enjoy playgrounds at local parks, community art workshops, and educational exhibits at the area’s history museum. Lake Lily Park is a favorite for families, combining walking trails, wildlife, and play areas.

  • What are some of the best things to do in Maitland?

    Explore the Maitland Art Center, walk around Lake Lily Park, and discover the city’s local history museum. Neighborhood cafes and outdoor spaces create opportunities for both relaxation and creativity.

  • How is the weather in Maitland?

    Maitland has mild winters around 49–72°F (10–22°C) and warm, humid summers near 72–92°F (22–33°C) with frequent afternoon rain. Spring and autumn bring comfortable temperatures and lower humidity, making outdoor activities a popular choice.

  • When is the best time to visit Maitland?

    Spring and autumn are frequently suggested, with milder temperatures between 58–84°F (15–29°C) and fewer rainy days. Summer brings warmer weather and higher humidity, popular for local outdoor festivals and lake activities.

  • What are the best places to visit in Maitland?

    The Maitland Art Center, Lake Lily Park, and the local history museum are frequently suggested places to explore. Art galleries and lakeside spaces offer a mix of culture and natural beauty.

  • What are some hiking trails in Maitland?

    Stroll the paths at Lake Lily Park or wander through neighborhood nature preserves featuring shaded trails and native plants. Locals often enjoy trails around area lakes for birdwatching and peaceful views.

  • What are some family activities we can do in Maitland?

    Families can explore lakeside parks, visit the area’s art museum, and enjoy playgrounds or nature walks. Seasonal festivals and community events often include activities for children of many ages.

  • What are some of the best day trip ideas from Maitland?

    Consider exploring nearby nature reserves, visiting botanical gardens, or discovering the area’s science museum in a neighboring city. Many travelers enjoy checking out theme parks and cultural landmarks just outside Maitland.

  • Are there any pet friendly accommodations available in Maitland?

    Many vacation rentals near lakes and parks welcome pets, especially in neighborhoods with access to walking trails. Checking for homes with fenced yards or pet amenities is often suggested for those traveling with animals.

  • What are some local tips for visiting Maitland?

    Maitland has several lakes and parks, so bringing comfortable walking shoes is often recommended. Locals often suggest exploring neighborhood eateries with Southern-inspired cuisine and checking out community art spaces for a feel of the area’s creative spirit.

  • What is Maitland known for?

    Maitland is known for its distinctive art center with historic architecture, lakeside parks, and a creative community spirit. The city’s history museum and neighborhood festivals reflect both local culture and artistic traditions.

  • What are the best hidden gems to explore in Maitland?

    Neighborhood galleries and small community gardens tucked near the lakes offer quieter experiences. Attending local art workshops and discovering historic architecture are often recommended for visitors seeking lesser-known highlights.

  • What are the best foods to try in Maitland?

    Locally rooted cuisine highlights Southern-inspired dishes, fresh lake fish, and bakery treats. Neighborhood cafes and family-run restaurants are often recommended for regional specialties and comfort foods.

  • What should I bring for a trip to Maitland?

    Pack light clothing for warm weather, comfortable shoes for exploring parks and walking paths, and a rain jacket during summer months. A reusable water bottle and sunscreen are often suggested for outdoor activities.

  • What is the nightlife in Maitland like?

    Maitland’s nightlife centers on neighborhood eateries, casual bars, and community events featuring live music. Locals sometimes gather at lakeside venues and art spaces for relaxed evenings.

  • What are the most popular events or festivals in Maitland?

    Art and cultural festivals at the Maitland Art Center are often recommended, with community celebrations in spring and autumn drawing visitors. Seasonal food festivals and outdoor events sometimes feature local music and crafts.

  • Are there family friendly vacation rentals in Maitland?

    Family-friendly vacation rentals are available in many Maitland neighborhoods, often featuring multiple bedrooms, kitchens, and proximity to parks or playgrounds. Properties with outdoor spaces make it easier for families to relax together.