Vacation rentals with outdoor seating in Windsor Hills

Find and book unique outdoor seating rentals on Airbnb

Top-rated outdoor seating rentals in Windsor Hills

Guests agree: these outdoor seating rentals are highly rated for location, cleanliness, and more.

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Top guest favorite
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
4.95 out of 5 average rating, 178 reviews

★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!

Guest favorite
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
4.95 out of 5 average rating, 182 reviews

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.

Top guest favorite
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.
Condo in Kissimmee
4.98 out of 5 average rating, 114 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.

Top guest favorite
The room features two twin beds with gray quilted covers, positioned next to a nightstand with a lamp. A colorful wall art piece is displayed above one bed, and natural light enters through a window adorned with white blinds.
Townhouse in Kissimmee
4.89 out of 5 average rating, 168 reviews

* Quiet and cozy 3 Bedroom/3 Bath next to Disney !

Nicely furnished and decorated 3 BDR/3 bath townhome in a gated, secured community less than 2 miles from Disney area. This is a prime location for visitors. Walmart is less than a mile away, and lots of restaurants, shops and tourist attractions are available nearby on US-192. Disney and Universal Studios theme parks are only a short drive away. Otherwise relax in the living room sofa and enjoy Netflix and DISNEY+ on the 4K 60" TV, take a dip in the pool, or read a book on the patio !

Superhost
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.
Condo in Kissimmee
4.73 out of 5 average rating, 146 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

Top guest favorite
The living area features a comfortable gray sofa adorned with accent pillows, complemented by a wooden coffee table. A large TV is mounted on the wall, with a stylish chair placed nearby. Natural light enters through glass doors, which lead to a balcony.
Apartment in Kissimmee
4.99 out of 5 average rating, 130 reviews

Chic Vibes Comfy King Bed Next to Parks/Food/shops

Welcome to our stylish oasis in Kissimmee, which seamlessly blends sophistication with a laid-back vibe. Your stay begins in a professionally cleaned apartment for your full enjoyment. Discover resort-style amenities – a sparkling pool, a fitness center, and hammocks, offering the luxuries of a five-star retreat. Conveniently located with in walking distance of theme parks, restaurants, and shopping. Book now. We can't wait to host you in our little slice of paradise!

Guest favorite
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
4.95 out of 5 average rating, 101 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.

Guest favorite
The open living and dining area features a large L-shaped sofa and a glass table, with natural light flowing through French doors. A wall mural showcases a Star Wars theme, while the private balcony offers expansive views of the Arnold Palmer PGA golf course and sunset skies.
Condo in Kissimmee
4.91 out of 5 average rating, 109 reviews

Gorgeous Views: Golf Front, StarWars, XBox, 2Pools

This modern 3-bedroom luxury condo has one of the most PICTURESQUE VIEWS in the Reunion Resort of the Arnold Palmer PGA golf course. Combining STYLISH DESIGN and LUXURIOUS COMFORT, there are 2 KING bedrooms and a playful STAR WARS themed bedroom with a classic Arcade machine & Xbox. 4 TVs with DirecTV, free high-speed wifi, your own washer & dryer, access to 6 resort pools, 2 of which are only a 3 minute walk away, and only a short drive to Disney.

Top guest favorite
The cottage features a charming exterior with bright yellow siding and a classic gabled roof. Lush palm trees and manicured hedges frame the entrance, which includes a welcoming porch with yellow chairs. Large windows allow natural light to enhance the inviting facade.
Cottage in Kissimmee
4.98 out of 5 average rating, 124 reviews

1BD Cottage "Limoncello" in Margaritaville

Welcome to your own island-inspired oasis. Our charming cottage is the perfect home base for your next dream Orlando vacation. The unit comes with all the comforts from home but worlds away. Conveniently located minutes from the Disney parks, a state-of-the art water park and newly opened 196,000 square foot shopping and dining district with multiple dining food and beverage options & brand-new movie theater. All Pets Must Be Preapproved :)

Top guest favorite
The spacious living area features a light-filled environment with comfortable seating arrangements, including a sofa and armchair. A coffee table sits in the center, accompanied by a decorative bowl of sunflowers. A large television is positioned against a wall, complemented by neutral-toned decor.
Home in Kissimmee
4.89 out of 5 average rating, 103 reviews

4BD 2BA Kissimmee Pool House near Disney

This 4BD 2BA house is in a quiet part of Kissimmee less than 5 miles south of Disney! The master suite features a king bed and attached bath with double sinks and walk-in shower. The second room contains a queen bed and the last two rooms have two twins each. There is a fully equipped kitchen and two work spaces, each containing a desk, office chair and computer monitor. Shops, entertainment, and restaurants are just a few minutes away.

Top guest favorite
A Star Wars themed bedroom features two twin beds with themed bedding. A decorative quilt with a pattern of star fighters is placed over one bed, while the other is dressed in a space-themed cover. A bedside table holds a lamp shaped like a lightsaber, with blue walls adorned with framed artwork.
Condo in Kissimmee
4.91 out of 5 average rating, 187 reviews

Themed Resort Condo | Pool | Spa | Mins to Disney

The Magic Galaxy – an affordable 3 bedroom, 2 bath condo in the gated Windsor Palms resort, known for its cleanliness and thematic charm. The retreat features themes from Star Wars, Mickey Mouse, Jurassic World, and Harry Potter. Enjoy resort amenities like a pool, spa, splash pad, courts for basketball, tennis, and volleyball, a movie theater, game room, gym, Tiki bar and grill, and a sundry shop.

Top guest favorite
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.
Home in Kissimmee
4.95 out of 5 average rating, 168 reviews

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

Welcome to Sunset Palms 2, a Safe Private and Updated Pool and Hot Tub Home, Within 4 Miles to Disney!!! Large stand alone Hot Tub. House is updated with Themed bedrooms. 2 Master EnSuites both with King sized Beds and their own private bathroom. Game Room includes Pool Table and Ping Pong Table Two King master bed En-Suites and Themed Bedrooms (STAR WARS AND MICKEY MOUSE)

Popular amenities for Windsor Hills outdoor seating rentals

When is the best time to visit Windsor Hills?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$47,430 GYDG$48,892 GYDG$52,653 GYDG$53,907 GYDG$47,012 GYDG$48,266 GYDG$51,818 GYDG$45,967 GYDG$41,788 GYDG$47,848 GYDG$48,057 GYDG$54,325 GYD
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Quick stats about vacation rentals with outdoor seating in Windsor Hills

  • Total vacation rentals

    Explore 340 vacation rentals in Windsor Hills

  • Nightly prices starting at

    Windsor Hills vacation rentals start at G$14,626 GYD per night before taxes and fees

  • Verified guest reviews

    Over 8,920 verified reviews to help you choose

  • Family-friendly vacation rentals

    320 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Vacation rentals with a pool

    340 properties feature pools

  • Rentals with dedicated workspaces

    220 properties have a dedicated workspace

  • Wi-Fi availability

    340 of Windsor Hills vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Windsor Hills rentals

  • 4.8 Average rating

    Windsor Hills stays are highly rated by guests—averaging 4.8 out of 5!