Holiday rentals with outdoor seating in Windsor Hills

The spacious living area features comfortable seating arrangements, large windows, and a decorative area rug. The view leads to the private screened-in pool, providing a seamless indoor-outdoor experience. The room is illuminated by natural light and complemented by a modern ceiling fan.

4.99 out of 5 average rating, 145 reviews

Game & Theater Room, Castle Bunks, Pool & Spa

Vacation at Windsor’s Best located in Windsor Hills Resort just 2 miles from Walt Disney World. This one-story 4 bed, 4 bath vacation villa has everything you need for a wonderful getaway with family or friends. Situated on an elevated corner lot, this spacious villa with it's private pool and spillover spa offers a beautiful view overlooking the resort community. Plus, guests have access to the family-friendly Windsor Hills Resort amenities, including the water park, playgrounds, gym and more.

4.92 out of 5 average rating, 157 reviews

New Luxury Condo near Disney

A passos da piscina e parque aquático. Covid-19 safe. Wi-fi de 500 megabytes! O apartamento possui localização privilegiada: está no condomínio fechado Windsor Hills, o mais próximo dos parques. A 10 minutos do Animal Kingdom, Epcot, Hollywood Studios e Magic Kingdom e a 25 minutos dos parques da Universal. Além disso, possui fácil acesso ao aeroporto (US 192, FL 417 e I-4), Downtown Orlando, Miami e a todos os atrativos da região da Central Flórida (Daytona Beach, Clearwater, St. Petersburg).

4.97 out of 5 average rating, 151 reviews

An outdoor dining area features a large, custom-built wooden table surrounded by black chairs. Blue plates and glassware are meticulously arranged for an inviting meal. A bright blue pool glimmers in the background, enclosed by a mesh screen to ensure privacy.

Villa in Kissimmee

*Brand New!* Minutes to Disney + Free Resort!

Closest FREE resort to Disney Parks! Hibiscus Hideaway is a 6 bedroom 4 bathroom luxury villa that sleeps 14. Completely renovated in October 2022! * Kitchen is loaded & all baby gear provided. * Custom game room with A/C, LED panel lighting & ROCK CLIMBING WALL! * New Roku smart TVs & NEST tech throughout. * Outdoor space includes your own private pool, hot tub, overhead lighting, NEW BBQ grill & 10' custom-built farmhouse table to seat the whole family! Every detail has been thought of!

A home theater room is equipped with red stadium seating for eight, positioned toward a large screen displaying vibrant visuals. An arcade game machine is set beside the screen, with ambient blue lighting accentuating the dark walls, creating an engaging entertainment space.

4.86 out of 5 average rating, 137 reviews

Resort Home 3.5 miles to Disney with home theater

We welcome you to stay in our home located in the Windsor Hills community with a water park, slides, theatre and so much more! The house is just 3.5 miles from Disney’s Animal Kingdom. Our home has 6 large bedrooms including laundry in the home, an 8 seat home theatre, TVs in every room, a large swimming pool & spa with a large patio cover, plus a large kitchen fully equipped with everything you need for your stay. Please message us if you have any questions, we look forward to hosting you!

The aerial view showcases a spacious pool area surrounded by lush palm trees and lounge chairs. A bright water slide is visible in the background, leading to the pool. A serene lake serves as a picturesque backdrop, enhancing the resort's atmosphere.

4.85 out of 5 average rating, 203 reviews

One in a Minion condo your kids will love +450Mbps

Enjoy of sophisticated and modern accommodations on your next visit to Orlando. This One in a Minion themed two bedroom condo boasts 1082 SQ FT of living space and it's fully equipped for 6 guests. Conveniently located on the ground floor and a short stroll to the clubhouse, pool and dueling water slides. It features a smart lock, High-speed WIFI Internet +450Mbps, cable TV, telephone line, linens & towels and washer/dryer. Slide and Water Park will not reopen until Wednesday, February 18th.

4.95 out of 5 average rating, 185 reviews

An open-plan living area features a spacious seating arrangement with two patterned chairs and a gray sofa. A large wooden dining table with blue chairs is visible, alongside a TV mounted on the wall. Light pours in through multiple windows, enhancing the inviting atmosphere.

Townhouse in Kissimmee

Jackies’s Jungle View Vacation Villa

ALL NEW fully remodeled and updated! One of the closest and newest communities to Walt Disney World! Located just 5 minutes from Disney, our freshly updated townhouse is the perfect location for your next Florida adventure. A fully equipped kitchen, super-fast Wifi, heated community pool, and a brand new Walmart just down the street are only a few of the many amenities you will find with this incredible rental. Our 1600 sq. ft. home is bright, fresh, and waiting to welcome our next guests.

The community pool area features a winding pool surrounded by palm trees and lounge chairs. A colorful water slide is visible, along with shaded cabanas. The well-maintained grounds include lush greenery and pathways leading to residential buildings in the background.

4.98 out of 5 average rating, 116 reviews

Family, Windsor Hills, Sleep In with 11AM Checkout

Walk into your home away from home. Enjoy a relaxing stay. Located on 4th floor. Enjoy morning coffee on a screened-in balcony or a late snack. Pet-free home. Please NO Smoking. Children are always welcome. Come enjoy all of the accommodating facilities at Windsor Hills with a top-notched 24/7 gated security. FREE parking & leisure activities! Maximum of 3 cars allowed per reservation. This includes all guest that are visiting. All unregistered drivers will be denied access by HOA.

4.92 out of 5 average rating, 105 reviews

A decorative lantern is suspended from an artistic wall hanger, featuring a hummingbird design. The lantern's glass enclosure houses a candle, creating an inviting aesthetic. In the background, softly blurred greenery contributes to a serene outdoor atmosphere.

Guest suite in Kissimmee

It's too much like a elegant mini-hotel (1)

It's too much like a elegant mini hotel with rich artistic atmosphere！ All the pictures on this page are a reflection of the real condition of the house. All the furniture has been carefully selected, and comfortable mattress and pillows will quickly accompany you into sweet dreams. The biggest feature of this house are comfort, economy and convenience. All of my houses have hosted countless guests from South America, including Brazil and Argentina. You will always be welcome here!

4.94 out of 5 average rating, 105 reviews

A modern living area boasts high ceilings and large windows that invite natural light. Elegant furnishings include two gray sofas and a wooden dining table set against a backdrop of neutral tones. A flat-screen TV is mounted on the wall, and vibrant artwork decorates the space.

Townhouse in Kissimmee

A Refined Modern Oasis next to Disney World

An architecturally stunning 2400 square foot corner villa next to Disney World Orlando that is privately owned and designed by the world-renowned Pininfarina Group of Italy embodies modern sophistication with open-concept living, high ceilings, 4 bedrooms (2 master bedrooms – one on each floor), 4 en-suite bathrooms, and a downstairs half bath. All bathrooms each have their own bath and shower supplies. THERE ARE NO CAMERAS ANYWHERE ON OR IN THE PROPERTY.

4.82 out of 5 average rating, 160 reviews

A screened-in private splash pool is surrounded by comfortable seating, featuring playful Minion characters on the walls of the adjoining rooms. The layout includes vibrant décor and modern furnishings, creating a family-friendly space with direct access to outdoor relaxation.

Townhouse in Kissimmee

Themed Pool Home 2 Miles to Disney

Welcome to your dream vacation home! - Newly remodeled 3 bedroom, 3 bathroom townhome with themed rooms - Private splash pool, fully screened-in - Prestigious Windsor Hills Resort with no resort fee - Access to a new kids water park, clubhouse, gym, and more - Free Wifi and fast internet for your Zoom meetings - 24 hour security and gated access - Have a pet? $150 pet fee on 1st; $75 each additional pet - Check out our 5 Star Reviews!

A cozy living room is shown with a brown sofa and bright orange throw pillows. A coffee table with yellow legs sits on a plush area rug. Large windows allow natural light, complemented by a ceiling fan and decorative wall art.

4.88 out of 5 average rating, 132 reviews

Contemporary Stay 10 min to Parks Pets Friendly

Welcome to Your Magical Gateway – Just 10 Minutes from Orlando's Magical Parks! Location: Perfectly located for Disney and Universal, our apartment offers a peaceful retreat with all the comforts of home. Whether you’re here to explore the magic unwind, or even stay for longer terms, you’ll love every moment of our cozy space. The property sleeps 4 people! PLEASE CONTACT US TO INQUIRY ABOUT ADDITIONAL POTENTIAL DISCOUNTS FOR MULTIPLE DAYS STAY

A game room is presented with a red and neutral color scheme, featuring a billiard table with a set of colorful pool balls arranged on it. A television is mounted on the wall, and a dartboard is visible. The space is accented with vibrant wall art and seating areas.

4.9 out of 5 average rating, 134 reviews

No Airbnb Fee | Newly Renovated 4BR w/ Pool!

**We offer EV Charger for FREE!!! The magic of Orlando starts at home! This incredible house has much more than you need; it has everything you WANT! We offer guests comfort, convenience and an amazing experience!! Transparency and communication is very important to us! We want to make it clear, that we are here at your disposal for any doubts or suggestions. We can't wait to have you here enjoying peace and quiet and having lots of fun!

Popular amenities for Windsor Hills outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with Outdoor Seating

A cozy living area features a large sectional sofa with decorative pillows, positioned near a wall-mounted flat-screen television. A light-colored coffee table and a woven basket are present. Natural light fills the room through the large window, adorned with white blinds, creating a welcoming ambiance.

4.91 out of 5 average rating, 101 reviews

Resort 2 bedroom Townhome near Disney World

A charming two-story cottage is featured, exhibiting a cheerful yellow exterior. A small balcony is visible above the entrance, flanked by white railings. Lush palm trees and landscaped foliage surround the property, enhancing the inviting open space in a sunny environment.

5 out of 5 average rating, 147 reviews

Margaritaville Cottage 10 Minutes to DisneyWorld!

A well-furnished living area is present, featuring a light-colored sectional sofa adorned with patterned cushions. A soft area rug lies beneath a rectangular ottoman, complemented by decorative artwork on the walls. Natural light filters through vertical blinds, creating a bright atmosphere.

4.83 out of 5 average rating, 110 reviews

Equipped HOUSE near Disney/Orlando 4BR

A spacious living area features a comfortable sectional sofa adorned with decorative pillows, alongside a coffee table with a small potted plant. Natural light floods the space through large sliding doors, revealing a view of the outdoor area, while a dining table is positioned in the background.

4.96 out of 5 average rating, 114 reviews

Best Location! Best Location! Villa in Kissimmee

A large swimming pool is surrounded by lounge chairs and palm trees, reflecting bright blue skies. Nearby, a well-maintained lawn is visible through the screened lanai, enhancing the outdoor experience.

4.95 out of 5 average rating, 138 reviews

No Stairs!-Beside Pool-No Rear Neighbors!

A private splash pool is enclosed within a screened patio, featuring a stone surface for easy movement. Two red lounge chairs are positioned alongside the pool, with greenery visible in the background, creating a sense of openness and tranquility.

4.81 out of 5 average rating, 16 reviews

Perfect Townhome Near Disney!

The exterior of the home displays a welcoming front porch, accompanied by a bright red door. Lush greenery lines the pathway, with neat shrubs creating a private ambiance. The light beige facade is complemented by a well-maintained lawn leading up to the entrance.

4.83 out of 5 average rating, 252 reviews

Disney’s Home Away From Home (5 miles from Disney)

5 out of 5 average rating, 108 reviews

The image features a private pool surrounded by lounge chairs, with a basketball hoop and a lush green backdrop. An entertainment area is visible in the foreground, showcasing a game table, a digital pinball machine, and a large screen for movies and games, including a fun tube slide.

Home in Four Corners

*NEW* Space Odyssey: Pool, Spa, Cinema, Games+PS5

Apartment rentals with outdoor seating

A spacious bedroom features a comfortable bed with decorative pillows and a modern ceiling fan. An open kitchen area showcases stylish cabinetry and stainless steel appliances. A living area is equipped with ample seating and large windows allowing natural light. Another bedroom is similar in style with neutral tones.

4.85 out of 5 average rating, 107 reviews

Luxury Resort Style Condo Near Disney-103

4.92 out of 5 average rating, 122 reviews

Condo in Kissimmee

A living room is presented with light wood flooring, featuring a comfortable sofa and loveseat adorned with tropical-themed cushions. A glass coffee table sits centrally, complemented by two lamps on side tables. Natural light filters through the large window, enhancing the inviting ambiance.

5 out of 5 average rating, 31 reviews

Everlasting Memories: 10 Min. From Disney!

Superhost

A well-lit bedroom features two spacious beds positioned side by side, each adorned with neutral-toned bedding. Decorative wall art with abstract designs enhances the ambiance. Natural light filters through the window, illuminating the minimalist decor and adding to the room's inviting atmosphere.

4.71 out of 5 average rating, 72 reviews

Modern Disney Condo

A modern living room is depicted with a full sofa, coffee table, and a smart TV. Natural light enters through the sliding glass door leading to the balcony. Three framed botanical prints decorate the wall, while a floor lamp adds soft illumination.

4.98 out of 5 average rating, 54 reviews

Modern Condo: 10 Min to Disney + Fireworks Views!

A cozy living area features dark leather sofas and a glass coffee table. A ceiling fan hangs above, while natural light filters in through sliding glass doors leading to an outdoor view. A television is mounted on the wall opposite the seating.

4.96 out of 5 average rating, 45 reviews

3/2 unit by Disney, Walmart

5 out of 5 average rating, 9 reviews

My Disney Grandview

4.96 out of 5 average rating, 95 reviews

Disney Spring Break–Windsor Hills Waterpark+Pool

Condo rentals with outdoor seating

Superhost

A large condominium structure stands under a clear blue sky. Several palm trees frame the entrance, and well-maintained landscaping lies around the building. Vehicles are parked in designated spaces in front, with a visible path leading to the entrance.

4.72 out of 5 average rating, 125 reviews

Minutes to Disney best of Home, with a Resort feel

The living area features a comfortable sofa facing a large smart TV mounted on the wall. Natural light enters through windows, enhancing the space. A round coffee table sits in the center, surrounded by potted plants, with a dining area and a modern kitchen visible in the background.

4.93 out of 5 average rating, 213 reviews

Magical Stay Near Disney & ESPN

A spacious living area is designed with light-colored walls and a large sectional sofa adorned with decorative pillows. A round coffee table sits in the center on a patterned area rug. Large sliding doors provide access to a balcony, framed by greenery.

4.96 out of 5 average rating, 133 reviews

Oakwater Resort, Kissimmee , 1.5 Miles to Disney

An aerial view of the community water park features vibrant water slides and a children's water play area. Lounge chairs are arranged around the expansive pool, surrounded by lush greenery. Additional seating is provided near the water slides, creating an inviting space for relaxation and fun.

4.84 out of 5 average rating, 206 reviews

Heated Waterpark 10 mins to Disney in Windsor Hill

4.94 out of 5 average rating, 231 reviews

Andy's Toy Chest at Resort Minutes from Disney!

A children's bedroom is decorated with a vibrant Lion King theme. Two twin beds are covered with colorful bedding featuring characters from the movie. A bedside table with a lamp sits between the beds, and a large, eye-catching curtain depicting a jungle scene enhances the playful atmosphere.

4.95 out of 5 average rating, 221 reviews

Close To Disney! 3 Bedroom Condo in Windsor Palms

4.91 out of 5 average rating, 254 reviews

Disney Oasis by the lake

A spacious living area features a large leather sofa and wall art, creating an inviting space. The open-concept layout connects to the kitchen and dining area, while large windows allow natural light to fill the room. A vibrant resort-style pool area and water slides are visible outside.