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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Top 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, 200 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, 617 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, 391 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 modern living space is highlighted by a plush grey sofa and mid-century styled furniture. A large window invites natural light, showcasing views of the outdoors. Decorative elements, including a small plant and artwork, add character to the room while maintaining a clean aesthetic.
Loft in Orlando
4.92 out of 5 average rating, 683 reviews

Contemporary Loft Near Downtown

Conveniently located between the foodie-friendly Milk District and Downtown Orlando, this impeccably thought-out space features a spacious loft style open floor plan perfect for a couple or small group. The floor to ceiling windows allow natural light to fill the space while providing complete privacy during your stay. Upscale Winter Park restaurants and the vibrant Thornton Park art scene are only a short drive away. Universal is only 20 minutes away, Disney is 35 minutes, MCO 20 minutes.

Guest favorite
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, 160 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 favorite
A stylish kitchen is equipped with modern stainless steel appliances, including a refrigerator and microwave. A central island features two metallic stools, and the cabinetry is finished in a soft gray. A small potted plant adds a touch of greenery to the space.
Guesthouse in Orlando
4.99 out of 5 average rating, 126 reviews

Location, Location, Location!

Enjoy a stylish experience at this centrally-located Guest House. It is located in an excellent area close to the downtown Orlando, excellent restaurants, and much more. It is fully furnished and equipped with new appliances (washer and dryer included) and furniture. It is located minutes from Winter Park, Downtown Orlando and theme parks. Downtown Orlando 3 miles (6 min) Advent Health Hospital 0.6 miles (2 min) Walt Disney World 20 miles (23 min) Universal Studios 11 miles (18 min)

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, 313 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 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, 186 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
4.99 out of 5 average rating, 124 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.

Top guest favorite
Cottage in Winter Park
4.95 out of 5 average rating, 460 reviews

Winter Park Pearl 6 min drive to historic Park Ave

This Winter Park cottage was built in 1954 with original hardwood flooring. Take a 5 min drive to and through historical Winter Park to access shops and restaurants on the coveted Park Ave. It is the perfect central location to access beaches, Universities, Orlandos events, and the best restaurants. The house is tucked away into a quiet neighborhood with lots of sleepy old big oaks. If you have any questions I am always available, so please ask. My response time is immediate!

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, 242 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, 236 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.

Popular amenities for Maitland vacation rentals

When is the best time to visit Maitland?

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Avg. priceﺩ.ﺇ 411ﺩ.ﺇ 411ﺩ.ﺇ 400ﺩ.ﺇ 316ﺩ.ﺇ 294ﺩ.ﺇ 239ﺩ.ﺇ 327ﺩ.ﺇ 327ﺩ.ﺇ 342ﺩ.ﺇ 356ﺩ.ﺇ 375ﺩ.ﺇ 353
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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.

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 ﺩ.ﺇ 73 per night before taxes and fees

  • Verified guest reviews

    Over 5,380 verified reviews to help you choose

  • Family-friendly vacation rentals

    40 properties offer extra space & 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

  • Wi-Fi availability

    120 of Maitland vacation rentals include wi-fi 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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