Holiday rentals with outdoor seating in Windsor Hills

A cozy living area features a light-colored sofa adorned with cushions, accompanied by a vibrant orange accent chair. A round wooden coffee table holds decorative items, and plants add natural greenery. The space is softly illuminated by a stylish pendant light above.

4.93 out of 5 average rating, 114 reviews

Boho Bliss Escape• Poolside•Minutes from Adventure

🌿✨ Welcome to Boho Bliss Townhouse! ✨🌿 Your boho-chic retreat near Kissimmee ’s top attractions! 🏰 8 min Walt Disney World w/o traffic!!!! 🎢 25 min Universal ✈️ 25 min Orlando Airport 🐊 Gatorland 🛍️ Old Town Kissimmee 🎡 ICON Park features The Wheel, dining, and SEA LIFE Aquarium 🌊 Lake Tohopekaliga 🍖 Medieval Times offers dinner and a show. 🎢 Fun Spot America provides amusement park fun 🌿 Kissimmee Lakefront Park offers a relaxing lakeside experience 🌳 Shingle Creek Park is perfect for nature

A modern kitchen features stainless steel appliances, bright white cabinets, and a clean countertop. In the background, large windows provide a view of the outdoor space. The cozy living area showcases a comfortable seating arrangement and tropical-themed decor, with light streaming through the glass doors.

4.94 out of 5 average rating, 195 reviews

Private Pool & Arcade | Family Disney Townhome

Just 4 miles from Disney, our luxury townhome is your family’s perfect escape! With a private splash pool, brand-new 65” Smart TV, and family-friendly gear (stroller, pack n’ play, high chair), you’ll have everything needed for a carefree stay. Located across from Windsor Hills Resort’s clubhouse, enjoy resort perks like a pool, splash pad, fitness center, and theater! Sleeps 8 comfortably with 3 en-suite bedrooms, including a themed Disney beach kids’ room. Fun, comfort, and convenience await!

4.95 out of 5 average rating, 182 reviews

An outdoor dining area features a large custom-built farmhouse table surrounded by seating options. Flower arrangements are placed on the table, and a blue pool is visible in the background. The space is sheltered with a screen enclosure, allowing for a spacious view of the yard.

Villa in Kissimmee

★Completely New★ 3 miles to Disney + Free Resort!

Closest FREE resort to Disney Parks! Plumeria Place is a 6 bedroom 4 bathroom luxury villa that sleeps 14. Completely renovated in March 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 & 9' custom-built farmhouse table to seat the whole family! Every detail has been thought of!

A spacious living area is showcased, featuring a large sectional sofa with decorative pillows. A flat-screen TV is mounted on a media console, while a coffee table sits in the center. Light from nearby windows enhances the open atmosphere leading into the dining area.

4.93 out of 5 average rating, 244 reviews

Tito's Beachy Townhouse, 1.5 miles from Disney

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 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. Absolutely the best unit in the entire community!

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.

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.

A bright bedroom features a spacious bed adorned with colorful bedding and a throw pillow. Two bedside lamps are positioned on dark nightstands. Natural light flows through large windows, and an ensuite bathroom is visible in the background.

4.87 out of 5 average rating, 381 reviews

Splendid house 1, 5 miles to Disney

Crestwynd Bay condominium is only 1,5 miles to Disney Parks entrance. Walmart is 0,3 miles,very near. Beautiful and complete townhouse with 3 bedrooms, 3 bathrooms, kitchen equipped, laundry room, free WIFI, exterior area . Self check-in. This condo has community pool and children playground. Parking for car in front of the house. Is five minutes from target ,pharmacies , restaurants and fast foods. Ten minutes of outlets and 15 min from Universal parks and sea world. Great location!

4.92 out of 5 average rating, 106 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!

Aerial view captures the expansive Windsor Hills water park, with colorful slides and pools. The lower images showcase a family-friendly living room, brightened by wall murals featuring iconic Disney characters and cozy furnishings, including a spacious bed with vibrant bedding.

4.74 out of 5 average rating, 151 reviews

Toy Story Retreat Near Disney

Immerse yourself in the magic of Disney and create lifelong memories at your very own Toy Story Retreat. - Newly remodeled 3-bedroom, 2-bathroom condo - Family-friendly atmosphere with Disney-inspired design - Access to Windsor Hills Clubhouse with pools and gym - Ground-floor unit with greenspace views - Fully equipped kitchen and in-unit washer/dryer - Free WiFi and parking - Kid-friendly amenities like high chair and stroller - No extra fees, including resort fees

4.96 out of 5 average rating, 153 reviews

A recreational game room is presented, featuring an air hockey table and a pool table centered in the space. Two gaming chairs are positioned near flat-screen monitors on the wall. Colorful LED lighting creates an engaging atmosphere in the room.

Villa in Kissimmee

Mr. Clean's Cozy Disney Home w/ Luxury Finishes

• Newest house in the #1 resort community in the Disney Area, Windsor Hills • ALL Mattresses & Pillows are encased in waterproof SANITIZED covers. • 2 FUN children themed rooms (Star Wars, & Frozen) • Onsite, driveway parking for 3 vehicles • FREE pool heat + BBQ with ALL rentals • Fully equipped + stocked kitchen; including Keurig machine • Self check-in with digital lock • Super FAST Wi-Fi wireless internet speed at +1,000 Mbps!! • Property is managed directly by owner

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.

4.94 out of 5 average rating, 106 reviews

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.

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 outdoor seating rentals in Windsor Hills

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

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 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 clear view of a spacious outdoor pool area is presented, surrounded by a landscaped garden. Comfortable white lounge chairs are positioned around the pool, which features a water feature. Colorful umbrellas provide shade, enhancing the inviting atmosphere of the community.

4.94 out of 5 average rating, 154 reviews

Luxury and Perfect Family Vacay 3 min from Disney!

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

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

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, 253 reviews

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

The exterior of a charming home is presented with a red front door and neat landscaping. A palm tree is visible in the yard, and the garage doors feature a clean design. The image showcases a welcoming pathway leading to the entrance.

4.95 out of 5 average rating, 171 reviews

Disney home w/ Pool, Hot Tub & 2 King En-Suites ❤️

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, 108 reviews

Luxury Resort Style Condo Near Disney-103

5 out of 5 average rating, 17 reviews

Joyful Disney Getaway with Kids Room & Heated Pool

4.92 out of 5 average rating, 122 reviews

Condo in Kissimmee

An open living area features a modern design with a spacious layout. A comfortable sofa with accent pillows and a coffee table is set in front of a large window. The adjacent kitchen is equipped with sleek cabinetry and modern appliances, complemented by a dining space visible in the background.

4.93 out of 5 average rating, 108 reviews

3180-207 Resort Pool View Disney Universal Orlando

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 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!

An aerial view reveals a sprawling lagoon-style pool surrounded by lush green landscapes, highlighted by winding water features. A well-appointed bedroom presents a spacious bed framed by modern decor and natural light filtering through a window. The living area showcases an elegant dining setup alongside a stylish sofa, while a vibrant children's room features a bunk bed and playful accents.

4.82 out of 5 average rating, 215 reviews

2Bedrooms/2 Bathrooms Storey Lake Resort 3150-404

A bright and inviting living and dining area features a large table set for dinner, surrounded by colorful decorations. A blue mural and modern light fixtures enhance the atmosphere. Nearby, playful artifacts and themed elements add charm, contributing to a family-friendly environment.

4.91 out of 5 average rating, 55 reviews

Walt’s Vision – Disney-Inspired 3BR Condo

Apartment rentals with outdoor seating

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, 134 reviews

Oakwater Resort, Kissimmee , 1.5 Miles to Disney

4.94 out of 5 average rating, 231 reviews

Andy's Toy Chest at Resort Minutes from Disney!

4.91 out of 5 average rating, 254 reviews

Disney Oasis by the lake

A patio area is presented under a covered porch, featuring a round table set for two with a white tablecloth and colorful cups. Two comfortable chairs with blue cushions are positioned around the table. A scenic view of a lake with greenery can be seen in the background.

4.84 out of 5 average rating, 147 reviews

Stunning view, near Disney.

A modern living area features a cozy sofa facing a mounted TV, displaying a serene landscape. Behind the sofa, an electric fireplace adds ambiance. The open layout connects to a well-equipped kitchen, enhancing a sense of space within the inviting atmosphere. Accessibility to dining areas is evident.

4.91 out of 5 average rating, 164 reviews

Chic Disney Resort Condo • Pool Access Near Parks

An outdoor poolside area is depicted, featuring several round tables with dark wicker chairs. A tiki bar is visible, surrounded by lush greenery and palm trees. The sky is bright, with fluffy clouds, creating a relaxed atmosphere for guests to enjoy.