Holiday rentals with outdoor seating in Windsor Hills

4.97 out of 5 average rating, 104 reviews

Disney Pool Villa | Windsor Hills | Sleeps 8

BOOK EARLY! Rated top 1% & Guest Favorite. Our popular home fills up 3-4 months in advance. 3BR/3BA Private Pool Villa in Windsor Hills Resort, Kissimmee! Newly renovated, gated resort, 3 miles to Disney World. Modern beach-coastal design, updated kitchen, family-friendly layout. Free parking, Wi-Fi, full resort access (pool, splash park, gym, playground). Near Universal (20 min), SeaWorld (18 min), Legoland (40 min). Perfect location for vacations Disney trips, sports events, and conventions.

A playful bedroom features twin beds with a colorful 'Aloha' theme. The living area showcases a dining table for six and a comfortable seating arrangement. A screened patio displays a private pool. An entertainment room is equipped with game tables and superhero-themed decor.

5 out of 5 average rating, 24 reviews

Disney Family Fun Villa

Windsor Hills - NEW Fully Renovated 6Bed&4Bath Villa with FREE pool heat - Private South Facing Pool and Spa - Smart TVs in every room - Free WIFI - Fully renovated & equipped kitchen with granite countertops & new appliances - 1.5 Miles to Disney - Close to Universal Studios, Shopping,Restaurants,Waterparks - Gated Community - Free Clubhouse Access with New Waterpark, Basketball, Tennis & Volleyball Courts & Putting Green - Newly renovated Marketplace Bar & Grill, Games Room & Convenience Store

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, 152 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.

A spacious living area is seen, featuring a large sectional sofa adorned with decorative pillows. Natural light enters through expansive glass doors, providing a view of the backyard and pool area. Elegant light fixtures hang from the ceiling, complementing the neutral color palette.

5 out of 5 average rating, 112 reviews

Cinderella's HolidayVilla-Minutes from Disney-NEW!

• 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 FULLY REMODELED in Sept 2022!

4.97 out of 5 average rating, 159 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!

The living room features a playful Disney-themed design with a comfortable sectional sofa and an entertainment unit. A light-filled bedroom showcases a large bed with subtle Disney accents. The kitchen is equipped with modern appliances, and a dining area presents seating for multiple guests. A bird's-eye view reveals a sparkling pool area surrounded by lounge chairs.

4.97 out of 5 average rating, 101 reviews

NEW Stunning Villa located 5-10 Min from Disney

Welcome to this BRAND-NEW dreamscape Vacation Villa with private views. Located at the desirable Summerville Resort offering a PRIME location, only 10 minutes from Disney World and 20 minutes from Universal Orlando, Sea World and Aquatica. Amazing entertainment and dining within minutes from your Villa, Disney Springs, Sunset Walk, City Walk, Disney’s Boardwalk, Walmart, Starbucks and more. This Villa is hypoallergenic and carefully cleaned and sanitized. The perfect getaway for your family!

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, 145 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!

4.98 out of 5 average rating, 122 reviews

11 am checkout, Windsor Hills, Family, Disney.

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.

4.99 out of 5 average rating, 104 reviews

Villa in Kissimmee

Cozy Themed Villa 6 BR | Close to Disney

🏖️☀️🏄‍♀️Stay just minutes from Disney in this spacious 6-bedroom home, perfect for a family getaway. It comfortably sleeps up to 14 guests and is designed for both kids and adults to enjoy. Located in Windsor Hills Resort — one of the closest communities to Disney World — you’ll have quick and easy access to the parks. Enjoy themed bedrooms, a game room, and your own private patio and pool — great for relaxing after a fun day at Disney.🌴👙🩳🥽🩴 ❤️❤️We'd love to welcome you here!

4.97 out of 5 average rating, 117 reviews

A light-filled living area features a gray sectional sofa with accent pillows, arranged around a low coffee table. A patterned rug sits beneath, while a tall floor lamp adds warmth. Large sliding glass doors provide views of the outdoor patio, framed by sheer curtains.

Townhouse in Kissimmee

Star Wars Bungalow | 4 Mi to Disney | Waterpark

Enjoy your stay at this gorgeous, freshly renovated home! MINUTES to Walt Disney World. • 🎢 WATER SLIDES • 🌟THEMED Star Wars Retreat •🍴 Entertainer's Kitchen • 🤱 BOB Jogger Stroller available • 🏖️ Private patio with HEATED POOL • ☕️ **Latte and Coffee Bar** • 📶 Fiber High Speed Wi-Fi Thoughtfully curated for your ultimate ENJOYMENT. Beautiful modern interior, ceramic tile floors, and high quality decor throughout. This impeccable 3 bedroom, 3 bath home sleeps up to 8.

4.78 out of 5 average rating, 67 reviews

Villa in Kissimmee

Villa | Game Room & Summer Kitchen | 8 min Disney

Welcome to your dream Orlando getaway! Perfectly located just minutes from Disney, this beautiful 6-bedroom home is designed for families and groups seeking both comfort and fun. Enjoy a private pool with spa and summer kitchen, spacious living areas, and a fully equipped kitchen for family meals. Everyone will love can gather in the game room for entertainment. The clubhouse with resort-style amenities is just a short walk away for even more vacation fun.

A spacious living area features a contemporary design with a large flat-screen TV mounted on the wall, surrounded by comfortable seating. A stylish coffee table is centered on a soft area rug, and decorative plants add a touch of greenery. The bright space is complemented by warm lighting.

4.96 out of 5 average rating, 26 reviews

Hibiscus Villa w/ themed rooms, game room and pool

Welcome to your luxurious single story 4-bedroom getaway in the heart of a gated resort just 2.6 miles from the magic of Disney World! This meticulously designed vacation home offers not only comfort and convenience but also an array of resort amenities that promise an unforgettable stay. Your dream vacation home is not just a place to stay; it's a gateway to a world of enchantment and relaxation. Book your stay now and let the magic begin!

Popular amenities for Windsor Hills outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with Outdoor Seating

A screened-in pool area features a clear blue pool with floatation devices, surrounded by a sunlit deck. A Tiki bar with seating stands to one side, while lounge chairs are arranged along the edge. Lush greenery is visible beyond the enclosure.

4.95 out of 5 average rating, 124 reviews

Disney Retreat | Huge Pool with Spa | 2 King beds

A home theater room features plush reclining sofas arranged for optimal viewing. Colorful murals of trees and a moon adorn the walls, complemented by vibrant blue ambient lighting. A large screen is mounted on the front wall, enhancing the immersive experience.

5 out of 5 average rating, 6 reviews

Hilltop 6BR Disney Villa: Theater, Pool/Spa, View

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.

4.93 out of 5 average rating, 159 reviews

Luxury and Perfect Family Vacay 3 min from Disney!

An open-plan living area features a comfortable sofa beside a wooden coffee table, set against a backdrop of a vibrant landscape artwork. A well-equipped kitchen with modern cabinetry and bar seating is visible, illuminated by natural light flowing through large windows.

4.97 out of 5 average rating, 177 reviews

Luxury 2 Master Suite Pool Hot Tub Pool Table BBQ

The outdoor patio features a private heated swimming pool surrounded by lounge chairs and a dining area. A screened enclosure provides protection while allowing plenty of natural light. The spacious deck offers a relaxing space for families to enjoy the warm weather and nearby views.

4.92 out of 5 average rating, 13 reviews

Disney Vacation Home w/ Pool, Hot Tub + GameRoom

An outdoor seating area features vibrant blue chairs and a shaded patio overlooking a private pool. Surrounded by a screened enclosure, the view includes manicured grass and trees, creating a serene setting for relaxation and enjoyment.

4.9 out of 5 average rating, 20 reviews

Themed Luxury 6BR Getaway with Resort Amenities Pr

A private backyard oasis features a heated pool and hot tub, framed by a screened enclosure. Large sun loungers are placed on the pool deck, offering a relaxing space. The scenic view includes lush greenery with no rear neighbors, ensuring privacy for guests.

4.86 out of 5 average rating, 42 reviews

Family Disney Home | Pool | Game Room | Hot Tub

4.9 out of 5 average rating, 42 reviews

Elegant Lake Villa - Game Room, Pool & Spa!

Apartment rentals with outdoor seating

The image features a resort-style swimming pool, surrounded by lush greenery and palm trees. Lounge chairs are positioned near the water, with vibrant red umbrellas providing shade. The clubhouse is visible in the background, completing the inviting outdoor space.

4.9 out of 5 average rating, 158 reviews

14-206 Legacy Dunes, Lake View, Free Wifi/Parking

4.89 out of 5 average rating, 112 reviews

Cozy Apartment Close to Disney

Superhost

A whimsical room features two full-sized beds adorned with colorful bedding inspired by a popular animated theme. The walls are decorated with snowflake motifs and soft, twinkling lights, creating a playful atmosphere. A connecting ensuite bathroom is visible in the background.

4.75 out of 5 average rating, 130 reviews

Luxury 2BR-2BA Windsor Hills Condo - Direct Entry

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, 80 reviews

Modern Disney Condo

4.97 out of 5 average rating, 105 reviews

A private balcony is showcased with a round table and two woven chairs, providing a serene view of the lake and surrounding landscape. Soft morning light reflects on the water, while a small potted plant adds a touch of greenery to the setting.

Apartment in Orlando

2-Bedroom Renovated Lakeside Condo Near Disney

The landscaped pathway leading to Sunshine Bliss Villa showcases vibrant tropical plants and well-maintained hedges. Two people are seen walking together, framed by lush greenery and flowering shrubs, creating a welcoming entrance to the villa.

4.98 out of 5 average rating, 84 reviews

Cozy 3bdrm/2bath unit Just Minutes to Disney World

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.

4.83 out of 5 average rating, 223 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.

4.92 out of 5 average rating, 64 reviews

Themed Condo · Ground Floor · Walk to Waterpark

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, 127 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, 216 reviews

Magical Stay Near Disney & ESPN

4.88 out of 5 average rating, 105 reviews

Condo in Davenport

A luxurious living just 15 min/Disney!

A bright living area features a comfortable brown sofa and loveseat, accented with decorative pillows. A modern coffee table is centered on tiles that enhance the spaciousness. Natural light filters through large windows, while a flat-screen TV is mounted on the wall, framed by stylish light curtains.

4.86 out of 5 average rating, 161 reviews

Star Wars Condo in Windsor Hills 3 bdrm, 2 baths

4.94 out of 5 average rating, 238 reviews

Andy's Toy Chest at Resort Minutes from Disney!

A view of a spacious resort-style pool area featuring various sections including a water park with slides and a splash pad. Surrounding palm trees offer shade, while lounge chairs are positioned around the pool's edge, creating an inviting atmosphere for relaxation.

4.94 out of 5 average rating, 101 reviews

Poolside 3 Bed Vacation Retreat in Windsor Hills

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.

4.96 out of 5 average rating, 160 reviews

Disney Oasis