Vacation rentals with a pool in Windsor Hills, Four Corners

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Top-rated rentals with a pool in Windsor Hills, Four Corners

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Guest favorite

Home in Kissimmee

4.94 out of 5 average rating, 171 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, 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. Absolutely the best unit in the entire community!

Mar 24 – 31

R2,930 ZAR per night

Guest favorite

Condo in Kissimmee

4.97 out of 5 average rating, 104 reviews

Windsor Hills Pool View-Waterpark-2mi to Disney

As close to the pool as you can get! Don't miss out on this top rated condo with amazing views of the heated pool & waterslides, and just 10-minutes from Disney World! With new appliances and updated furnishings this 3rd floor condo sleeps 8, with plenty of space to unwind after a long day at the parks. The screened-in balcony can’t be beat, overlooking the pool and waterpark with huge waterslides! The clubhouse is steps away, with a small store, food, drinks, game room, and fitness center.

Sep 8 – 15

R2,951 ZAR per night

Guest favorite

Condo in Kissimmee

4.82 out of 5 average rating, 150 reviews

Heated Waterpark 10 mins to Disney in Windsor Hill

Welcome to Windsor Hills' Gated Vacation Community! Perfect for an adventurous family vacation or a relaxing getaway in the sun. I am excited to host your stay. Your unit is located on the 3rd floor. Get a quick exercise and hike up (39 stairs) to the front door or catch a break and use the elevator located on the ground level. Once inside, enjoy the newly remodeled 2Bdr, 2Bth condo, fully equipped to accommodate your stay. We are a PET and SMOKE-FREE property. Additional cleaning fee applied.

Jan 17 – 24

R2,746 ZAR per night

Guest favorite

Townhouse in Kissimmee

4.98 out of 5 average rating, 117 reviews

DISNEY R US! UNIVERSAL IS TOO!!!

This Is The Way!!! 🗡️ Our Magic is your Magic, only 3 Miles from the park and in a gated community with all the amenities needed to stay and rest a day if you want to. Head off to take a journey on the back of a banshee. Maybe try some grey stuff at Be Our Guest restaurant in Magic Kingdom. Travel only 15 minutes to wave a wand like Harry Potter in Universal Studios. Then come back and relax in the gated community pool/spa area for an night of rest. We want your trip to be Magical and Epic!

Oct 2 – 9

R2,972 ZAR per night

Guest favorite

Home in Kissimmee

4.93 out of 5 average rating, 131 reviews

NEW! Star Wars Room, Frozen Room, close to Disney

This fantastic 4 bedroom, 4 bathroom house is located a few miles from Disney World in the highly coveted (and gated) Windsor Hills Resort. You will have access to all that Windsor Hills has to offer including A NEW WATER PARK, double Olympic sized pool, play grounds, clubhouse, gym, video arcade, marketplace and grill, tennis courts, and more! This home features two amazing themed bedrooms with a Twin/Full bunk bed for your little ones to enjoy and to help get into the spirit of the magic!

Jan 29 – Feb 5

R6,524 ZAR per night

Guest favorite

Condo in Kissimmee

4.89 out of 5 average rating, 152 reviews

Disney's Doorstep, 3 Bed 2 Bath, Waterslides!

Welcome to your dream vacation! This 3 bedroom, 2 bath, is right on Disney's doorstep, this amazing vacation rental has all the amenities you'd put on your dream list. Two water slides, a kids splash park, walk in pool, movie theater with wheelchair access, game room, fitness center, putting green, playground, shop for snacks, and more! This condo also comes fully furnished with a washer/dryer, WiFi, elevator for wheelchair access, and more. This is sure to be your relaxation destination.

Aug 7 – 14

R3,277 ZAR per night

Guest favorite

Townhouse in Kissimmee

4.88 out of 5 average rating, 125 reviews

*** Newly furnished 3 BDR/3Bath next to Disney ***

Newly 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 !

Jan 5 – 12

R2,576 ZAR per night

Guest favorite

Condo in Kissimmee

4.94 out of 5 average rating, 133 reviews

Minutes from the Magic - Windsor Hills 3br 2ba

**PLEASE NOTE** Pool will be closed for maintenance 9/5/2024 to 10/5/2024 Beautiful condo with incredible amenities just minutes from Walt Disney World. Plenty of room for the entire family with three bedrooms and two full baths. Windsor Hills is a gated resort community with all of the amenities you can imagine! Beautiful, zero-entry pool, splash pad, and water slides will help you beat the heat. A fitness center, arcade, shop, cafe, sports courts, and movie theater are on site!

Nov 15 – 22

R2,739 ZAR per night

Guest favorite

Condo in Kissimmee

4.96 out of 5 average rating, 112 reviews

Windsor Hills Resort - Disney Pool View Condo

Location, location, location! Windsor Hills pool view condo and only 2 miles to Disney World! This newly updated 3 bedroom pool view condo is in the beautiful Windsor Hills Resort gated community. The single level condo is located in the closest building to the pool, water park, clubhouse, hot tub, movie theater, and arcade. The condo has one of the best balcony views in the entire resort. Located on the third floor, the balcony looks directly over the resort pool and lake.

May 20 – 27

R3,483 ZAR per night

Guest favorite

Condo in Kissimmee

4.85 out of 5 average rating, 133 reviews

WH Condo. Pool/Waterpark and close to Disney!

Take an elevator to unit 302 and witness beautifully decorated Disney themed rooms. Directly outside is a lovely pool and kid-friendly waterpark. Other amenities include: game room, theater, exercise room, tennis courts, play grounds, sand volleyball, putting green, basketball court and a marketplace and grill. Located 15 minutes to all 4 Disney parks and Sea World! Looking for more space? Check out our townhome also located in Windsor Hills at 7668 Fitzclarence

Sep 24 – Oct 1

R2,952 ZAR per night

Guest favorite

Home in Kissimmee

5.0 out of 5 average rating, 175 reviews

Windsor Orlando Private Arcades,Theater,Pool-Spa

Orlando, Disney, Arcade, Movie Theater, Massage Chair, Pool, Hot Tub, 2 King Beds, Kids Bunk Bed, Kissimmee. Upgraded games room IN the private home, theater for evenings home and your private lanai with pool and hot tub. Choose from including Pump It Up dance, Sponge Bob Racing, NASCAR racing, Legends 3, Pac-Man's Arcade Party, an 80-inch TV, and an Xbox 360. Watch your favorite movies on the 92-Inch projection screen, surround sound, and stadium style seating.

Nov 27 – Dec 4

R11,446 ZAR per night

Guest favorite

Condo in Kissimmee

4.98 out of 5 average rating, 100 reviews

Disney Oasis

Enjoy Disney Oasis, our 3-bedroom, 2-bath condo, ideal for families! Nestled in a gated community with 24/7 security, we're just 3 miles from Walt Disney World® and close to other theme parks. Indulge in our resort-style amenities: a double Olympic-sized pool, thrilling waterslides, and a fun splash pad. Enjoy the convenience of nearby shopping, dining, and entertainment. Our condo is not just a place to stay, but a gateway to an unforgettable vacation!

Sep 3 – 10

R3,030 ZAR per night