Some info has been automatically translated. Show original language

Holiday rentals with outdoor seating in Windsor Hills

Find and book unique rentals with outdoor seating on Airbnb

Top-rated rentals with outdoor seating in Windsor Hills

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

%{current} / %{total}1 / 1
Top guest favourite
A spacious bedroom features a tranquil tree mural on the dark wall, complemented by a large window allowing natural light. The inviting living area includes modern seating and a wall-mounted TV. A rooftop view shows the community, highlighting its green spaces and swimming pool.
Apartment in Kissimmee
4.93 out of 5 average rating, 134 reviews

The Tree House, only 1.5 Miles From Disney!

What You’ll Love About The Tree House The Location! Just 1.5 miles from Walt Disney World, the fun begins right away! Dozens of other attractions, golf courses, restaurants, and cafés are also conveniently located just minutes away from our 2 bed/2 bath townhome-style condo for 6 guests, located on the second floor and nestled in a quiet gated community. Keep in mind that when parks close for the day, traffic can be something else, so being that close to home gives you another great advantage.

Guest favourite
A shaded lounging area features comfortable seating and a glass-top table, set with refreshments. In the background, a large pool glistens under the sun, surrounded by palm trees and various seating options, including cabanas and sun loungers.
Townhouse in Kissimmee
4.84 out of 5 average rating, 214 reviews

Orlando Disney ºoº 3BD in Resort | Kissimmee

Modern Townhouse in Resort w/ preserve area and Amazing Clubhouse. (NO resort fees!) | 1 min | Old Town Kissimmee | 3 min | Publix®, McDonald's®, Wendy's®, Miller's Ale House® and more | 6 min | Walmart® & Target® | 7 min | Celebration | 9 min | DISNEY® AREA (All Theme Parks) | 9 min | Premium Outlet® | 11 min | Disney Springs | 11 min | ESPN® Sports | 13 min | Convention Center | 15 min | UNIVERSAL® STUDIOS | 26 min | Orlando Airport | 70 min | Bush Garden's® | 95 min | Sarasota & Clearwater

Top guest favourite
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.
Townhouse in Kissimmee
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!

Guest favourite
Apartment in Kissimmee
4.92 out of 5 average rating, 156 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).

Top guest favourite
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.
Home in Kissimmee
5 out of 5 average rating, 103 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!

Top guest favourite
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.
Townhouse in Kissimmee
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!

Top guest favourite
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.
Apartment in Kissimmee
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.

Guest favourite
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
4.92 out of 5 average rating, 105 reviews

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!

Top guest favourite
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.
Flat in Kissimmee
4.99 out of 5 average rating, 138 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 favourite
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
4.94 out of 5 average rating, 105 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 favourite
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
4.82 out of 5 average rating, 159 reviews

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!

Guest favourite
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.
Home in Kissimmee
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

When is the best time to visit Windsor Hills?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price£168£173£187£191£167£171£184£163£148£164£181£208
Avg. temp16°C18°C20°C22°C25°C27°C28°C28°C27°C24°C20°C17°C

Quick stats about holiday rentals with outdoor seating in Windsor Hills

  • Total holiday rentals

    Explore 340 holiday rentals in Windsor Hills

  • Nightly prices starting at

    Windsor Hills holiday rentals start at £52 per night before taxes and fees

  • Verified guest reviews

    Over 8,920 verified reviews to help you choose

  • Family-friendly holiday rentals

    320 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 30 rentals that welcome pets

  • Holiday rentals with a pool

    340 properties feature pools

  • Rentals with dedicated workspaces

    220 properties have a dedicated workspace

  • Wifi availability

    340 of Windsor Hills holiday rentals include wifi 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!