House holiday rentals in Maitland

4.97 out of 5 average rating, 133 reviews

A heated pool surrounded by lush greenery features a stone ledge and a small waterfall. Hammocks are placed for relaxation. The screened patio allows for unobstructed views of the sunset, creating a tranquil setting. Warm lighting highlights the natural textures of the landscape.

Home in Lake Formosa

Spacious Home with Pool & Hot Tub near Downtown

Nestled in one of the most coveted neighborhoods near Downtown Orlando (Ivanhoe Village), you'll be within a 5-min walk to tons of restaurants, bars, breweries, and boutique shops. Boasting a heated pool, hot tub, tiki bar, patio area w/seating & two living areas -you'll have ample room to play, entertain or relax in your Tropical Oasis! ☀ Harry P. Leu Gardens – 4 mins ☀ Orlando Museum of Art – 4 mins ☀ Universal Studios – 19 mins ☀ Walt Disney World – 24 mins ☀ The Mall at Millenia – 16 mins

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.

4.98 out of 5 average rating, 161 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)

An outdoor space features a large pool surrounded by a patio area. Comfortable seating and an umbrella are positioned under a shaded area. Lush greenery lines the back and sides, providing privacy, while the main house showcases a welcoming design with large doors leading out to the pool.

4.86 out of 5 average rating, 119 reviews

Charming Retreat In Winter Park

“Welcome to our renovated Winter Park home! This modern one-story property features 3 bedrooms plus a loft, comfortably sleeping 6 guests. Enjoy the large backyard with an extra-large pool and outdoor shower. Conveniently located near Orlando’s attractions, including Disney And Universal Studios as well as Rollins Collage and the Kia Center. Indulge in over 60 restaurants with in 10 min. Winter Park Village and Park Ave. Shopping. Experience comfort and style in this charming Florida retreat!”

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.

4.93 out of 5 average rating, 149 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

4.89 out of 5 average rating, 118 reviews

A spacious living area features a large sectional couch and a stylish coffee table. Natural light filters through the windows, highlighting modern décor. An arcade game stands in the background, and a laundry area is visible to the left, contributing to the home's functionality.

Home in Casselberry

Cozy 4/2, King Beds, Pergola, Hot Tub & Pool

Newly renovated farmhouse gem centrally located in the beautiful Casselberry / Orlando area. Stylish and thoughtful touches throughout will make you feel right at home. 2 king beds, 1 queen and 1 bunk room (2 doubles & 2 twins) along with an 8' farmhouse table (seats 8) makes this home great for both small & larger groups alike. Complete with a hot tub, amazing walk-in shower, Marvel Arcade, Private patio with pergola outdoor furniture & gas grill, it's great for both the adults and kiddos!

The living area features a modern sectional sofa arranged around a textured coffee table. A colorful area rug adds warmth. A dining table with black chairs is set nearby, illuminated by pendant lights. Large windows provide ample natural light, and contemporary wall art enhances the ambiance.

4.94 out of 5 average rating, 124 reviews

Luxurious and modern cottage near UCF

This is peaceful and quiet place in a country seating yet in the middle of the city. It has been renovated and decorated in a luxurious and modern style by professionals. It’s better than the pictures. From here you can easily access the theme parks, beaches, downtown Orlando and all mayor attractions. Disney 24 miles. Universal studios 21 mi. Sea World 18 mi. Airport 12 mi. Beaches 50 mi. Downtown Orlando 15 mi. UCF 2.4 mi. And tons of restaurants! Come and experience Florida at its best

The light-filled living room features a stylish gray sofa, wooden side tables, and a coffee table. Natural light enters through the large window, illuminated by soft curtains. Decorative plants enhance the inviting ambiance, complemented by warm wooden flooring.

4.93 out of 5 average rating, 123 reviews

Charming 2BR Cottage, Downtown Orlando

Bright, cozy 1940’s cottage located in a quiet, safe, family-friendly Downtown Orlando neighborhood. 2 bedroom, 1 bath, onsite parking, full kitchen, washer and dryer, fenced-in back yard and patio area, working desk space in bedroom. Walking distance to the local gems and eateries of Audubon Park and the Mills 50 District! Central location minutes away from Winter Park and Downtown local attractions. 20-30 minutes from Universal, Disney and MCO. Great for a work trip or an Orlando getaway!

4.86 out of 5 average rating, 138 reviews

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

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!

4.95 out of 5 average rating, 177 reviews

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

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.

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.

4.97 out of 5 average rating, 211 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.

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.

4.83 out of 5 average rating, 109 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.

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.

4.95 out of 5 average rating, 139 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.

Popular amenities for house rentals in Maitland

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A serene pool area is surrounded by lush landscaping and tall palm trees, with sunlight glistening on the clear water. The pool features a gentle curve, and a white fence encloses the backyard, providing privacy and a sense of tranquility.

4.87 out of 5 average rating, 149 reviews

3 BR/2BA Home w Private Pool~12 min to Airport!

4.99 out of 5 average rating, 155 reviews

A welcoming living area features comfortable seating arrangements around a central ottoman. A large television is placed on a stylish console, with decorative plants and artwork enhancing the space. Natural light streams through windows, contributing to a bright, inviting environment.

Home in Sanford

The Cypress House

The private pool is surrounded by a spacious patio, featuring a gentle curve and inviting turquoise water. A covered dock is visible in the background, with lush greenery and a fence enhancing the outdoor space.

4.96 out of 5 average rating, 109 reviews

Private Pool 4/2 Waterfront Oasis Weekly Discounts

4.97 out of 5 average rating, 178 reviews

A grand living area showcases a striking stone wall adorned with an extensive collection of framed artwork. Soft seating is arranged around a fireplace, providing a cozy yet elegant atmosphere. A staircase leads to the upper level, while rich drapery frames the large windows, allowing natural light to flow in.

Home in Kissimmee

Waterfront Wizarding Near Universal's Harry Potter

4.9 out of 5 average rating, 270 reviews

A spacious pool area is surrounded by tropical landscaping, featuring tall palm trees and flourishing plants. The pool includes a spa with cascading water features. A bright red umbrella provides shade over a seating area, creating an inviting outdoor space for relaxation.

Home in Lake Mary

Gated community XL pool Home 2500sq/f

A large, inviting pool glistens under the sun, surrounded by a spacious patio and palm trees. A stylish, shaded cabana is positioned nearby, offering a retreat for relaxation. The pool area is enclosed and features a clean white fence, enhancing the tranquil outdoor atmosphere.

4.88 out of 5 average rating, 231 reviews

Pool-Jacuzzi & Palm Trees/ 8 Universal/ 15 Disney

4.86 out of 5 average rating, 138 reviews

An open-concept living area features a modern kitchen with a central island and stainless steel appliances. A comfortable sectional sofa is paired with wooden armchairs, and a round coffee table sits in the center. Large windows bring natural light into the space, enhancing the clean, neutral decor.

Home in Apopka

2-bedroom home with pool near Kings Landings!

4.98 out of 5 average rating, 122 reviews

A spacious bedroom features a large bed dressed in neutral tones, accented by decorative pillows. Natural light filters through angular windows, illuminating the space. A seating area with a gray bench is positioned at the foot of the bed, and wooden walls provide a warm backdrop.

Home in Longwood

Private 4-Bedroom home with pool!

Weekly house rentals

4.97 out of 5 average rating, 36 reviews

10 min to Winter Park, Games, Gym, King bd, Coffee

5 out of 5 average rating, 8 reviews

Cozy quiet 1 bedroom home with office!

The kitchen features white cabinetry and a large island with two cushioned stools. Stainless steel appliances, including a refrigerator and oven, are included. Natural light is provided by multiple windows, enhancing the bright and functional space.

4.87 out of 5 average rating, 70 reviews

Stylish Bungalow

4.97 out of 5 average rating, 63 reviews

A modern kitchen features white cabinetry and granite countertops, complemented by stainless steel appliances. Bright, natural light streams through the windows, illuminating the open layout. Pendant lights hang above the central island, while a dining area is visible in the background.

Home in Orwin Manor

Charming Bungalow in Winter Park

4.96 out of 5 average rating, 27 reviews

A hot tub is positioned beside a gazebo, with comfortable seating and decorative lighting. Lounge chairs are arranged around a spacious pool deck, surrounded by green foliage and palm trees. The evening sky is visible in the background, creating a tranquil outdoor environment.

Home in Casselberry

Wana Chill Spot *Pool *Spa *Bar *Ping Pong *BBQ

4.91 out of 5 average rating, 82 reviews

A spacious living room features a large grey sectional sofa facing a modern fireplace. Natural light fills the area through multiple windows, while a ceiling fan provides airflow. The room includes a smart TV mounted on the wall and is connected to the dining area with a sleek table.

Home in Maitland

Lake Front Home near Winter Park!

The image captures the serene lakeside view of a spacious property surrounded by lush greenery and cypress trees. A wooden dock extends over the calm water, highlighting the landscape and offering access to canoes and kayaks. A well-maintained lawn features inviting outdoor seating areas.

4.9 out of 5 average rating, 60 reviews

Lakefront Paradise Near Attractions

5 out of 5 average rating, 69 reviews

Joe's Bar and Grill

Private house rentals

The exterior of the estate is showcased at twilight, featuring a circular driveway with a central fountain. Lush landscaping is visible around the entrance, complemented by soft lighting in the windows. A colorful sky adds warmth to the serene setting.

5 out of 5 average rating, 17 reviews

Luxurious 5,778 Sq Ft Estate · Helipad · 3+ Acres

The exterior of the bungalow is surrounded by lush greenery and colorful flowering plants. A manicured lawn leads to the front entrance, where a modern black door is framed by large windows. Tall trees provide additional shade and natural beauty.

4.85 out of 5 average rating, 39 reviews

Cozy Blue Bungalow

The living area showcases a spacious sectional sofa adorned with accent pillows, positioned near a sleek electric fireplace. A large Smart TV is mounted above the mantel. Light wood flooring complements the modern design, while a vibrant green accent wall enhances the atmosphere.

4.89 out of 5 average rating, 19 reviews

Spacious Modern Japandi Retreat - Winter Park

4.96 out of 5 average rating, 53 reviews

A modern living room features two green accent chairs and a light-colored sofa, arranged around a small coffee table. A wall-mounted TV is positioned above a wooden media console. Large windows provide views of the green outdoor space, enhancing the bright interior.

Home in Casselberry

Luxurious Lakefront Home | Near DT & Winter Park

A spacious living area is displayed, featuring a large sectional sofa adorned with decorative pillows. A wooden coffee table sits at the center, with candles positioned on it. Soft lighting illuminates the room, and a dining area is seen in the background, complemented by art on the walls.

5 out of 5 average rating, 5 reviews

Beautiful 2 Bed/1 Bath College Park Home

5 out of 5 average rating, 47 reviews

The Winter Park Experience

A modern living area features a spacious sectional sofa, a round coffee table, and a dining table with high-backed chairs. Natural light fills the space, highlighting the open kitchen with stainless steel appliances and stylish pendant lighting.

4.87 out of 5 average rating, 23 reviews

3BD in Winter Park, 10 min Park Ave/Rollins, Pets

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.