House vacation rentals in Kissimmee

2026 BRAND NEW 10 Bedrooms At Windsor Cay

🏡 The Space Welcome to this stunning and beautifully designed 10-bedroom vacation villa located in the amazing Windsor Cay Resort, perfect for large families and group getaways. Combining spacious accommodations, themed bedrooms, and resort-style amenities, this home was thoughtfully designed to create an unforgettable Orlando vacation experience. With a private screened-in pool, spacious gathering areas, and themed bedrooms inspired by Tangled, Mickey Mouse, Spider-Man, and Harry Potter, this property comfortably accommodates up to **24 guests** while offering comfort, entertainment, and convenience for everyone. Bedrooms First Floor Bedroom 1: King Bed Suite Master – Private en-suite bathroom Bedroom 2: King Bed – Bathroom located outside the bedroom Second Floor Bedroom 3: King Bed Bedroom 4 – Tangled (Rapunzel) Themed Room: 3 Twin Bunk Beds Bedroom 5: King Bed Suite – Shared bathroom with Bedroom 6 Bedroom 6 – Mickey Mouse Themed Room: 1 Twin Bunk Bed + 2 Twin Beds – Shared bathroom with Bedroom 5 Bedroom 7: King Bed Suite – Private en-suite bathroom Bedroom 8:King Bed Suite – Private en-suite bathroom Bedroom 9 – Spider-Man Themed Room: 2 Twin Bunk Beds (4 Twin Beds) Suite – Private en-suite bathroom Bedroom 10 – Harry Potter Themed Room:** 1 Full Bed + 1 Twin Bed Suite – Private en-suite bathroom 🎮 Entertainment & Living Areas Designed with families and groups in mind, the home offers spacious and comfortable gathering areas, including: -TVs in all bedrooms -TV in the living room and family room -Complimentary Wi-Fi and cable -Central air conditioning throughout the home -Spacious open-concept living areas -Fully equipped kitchen for home-cooked meals and group dining -Laundry room with washer and dryer 🏊 Outdoor Area Enjoy your own private outdoor retreat after a long day at the parks: -Private screened-in swimming pool -Child safety pool fence -Outdoor patio furniture with sun loungers -Spacious outdoor seating area for relaxing and entertaining OPTIONAL Services -Pool heating: $45 per day (minimum of 3 consecutive days) -BBQ grill rental: $100 per stay (up to 1 week) -Mid-stay cleaning service: $499 🏠 Property Features -Gated resort community -Access to Windsor Cay Resort amenities -Fully equipped kitchen -Washer and dryer in unit -Hair dryers, iron, and ironing board -Linens and towels provided according to occupancy -Pack ’n Play and high chair available upon request -Clubhouse access included 🌴 Windsor Cay Resort Amenities Guests have access to a wide variety of premium resort amenities, including: -Community room for meetings and activities -24-hour manned gated community -Fitness center -Resort-style pool with zero-entry access and lazy river -Children's splash pad -Sports courts -Full-service concierge and activities director -Water slides -Private cabanas -Onsite tavern and grill -Community playground -9-hole putt-putt golf course 📍 Prime Location Conveniently located near Orlando's top attractions with easy access to major highways and shopping. Check-in / Check-out -Check-in: 4:00 PM -Check-out: 10:00 AM 🚫 House Rules -Parties are NOT allowed -Pets are NOT allowed -Smoking inside the home is strictly prohibited Smoking is permitted only in designated outdoor areas such as the balcony and pool area. *A $250 fee will apply if smoking occurs inside the property.* 📝 Additional Information This is a self-catering vacation home. To help guests settle in comfortably, we provide a starter set of supplies, including: -One roll of toilet paper per bathroom -One paper towel roll -Two trash bags -Dish sponge and dish detergent -Dishwasher pods -Laundry detergent and fabric softener -Basic toiletries (soap, shampoo, conditioner) No food, condiments, or seasonings are provided for hygiene and contamination prevention purposes. 🧺 Housekeeping -No daily housekeeping service is included -The property is professionally cleaned and inspected before check-in -Clean sheets and towels will be available in the unit -Mid-stay cleaning service available upon request for an additional fee -No washcloths are provided Bath towels, hand towels, and pool towels will be provided according to the number of guests staying. 🗑️ Trash Disposal Please observe trash collection days and place trash in the resort dumpster daily to help maintain a clean and pleasant environment. 📦 Online Deliveries -USPS does not deliver to vacation homes -Only UPS, FedEx, and DHL are recommended -Some resorts may charge package handling fees or decline deliveries entirely *We are not responsible for lost, delayed, or returned packages.* 🔥 Pool Heating Important Information** -$45 per day (minimum of 3 consecutive days) -Must be requested at least 48 hours in advance -Maximum temperature is 95°F -The attached spa is **NOT** a jacuzzi and does not have jets -The spa heats only when the pool heating service is activated -Pool heaters operate through heat exchange and may not perform efficiently during cold weather conditions -Refunds are not provided if cold weather affects heating performance Our pool heating system includes automatic safety controls that may temporarily shut down the system during extreme weather conditions to prevent equipment overheating and ensure proper functionality. Additional Charges Additional fees may apply if house rules are violated, damages occur, or excessive cleaning is required after check-out.

Top guest favorite

Guest favorite

DISNEY 🎉 Game rm, heated Pool, Spa, Lazy rvr, BBQ

House for rent next to DISNEY Windsor at Westside features a grand 10,000 square foot resort clubhouse FREE FOR GUEST USE filled with amenities for active families that include multiple sports courts, children's playgrounds as well as a resort-style swimming pool and lazy river with splash water park. Tu Casa is an onsite restaurant and bar and there's even an ice cream shop to refresh yourself with some sweet treats. GAME ROOM- air hockey, basketball, themed rooms, billiards, designer bedrooms!

Top guest favorite

Guest favorite

Encanto at Emerald Island-Pool House by Disney

POOL HEATER OPTION!! Make some memories at this unique and family-friendly place. A guarded Resort- neighborhood awaits! As you enter this magical place you will fall in love with the unique landscaping full of palm trees surrounding the neighborhood. This secluded place has everything you need! 5 star location, security, private pool, and also a clubhouse with many activities for the young ones. You will be next to restaurants, shopping and more. Only 3 miles aways from Disney's exit & parks!

Top guest favorite

Guest favorite

10 Minutes to Disney | Heated Pool, Arcade, Kings

🏡 Tucked inside a gated community near Kissimmee’s top attractions, this bright, themed home is made for memorable family getaways. Enjoy friendly competition in the game room, unwind in the heated private pool (available upon request), or relax on the covered patio beneath the Florida sun. Just 11 minutes to Fun Spot America, 11 minutes to Old Town, and 12 minutes to Disney World, it’s the perfect home base for your Florida adventure. Book now and start creating unforgettable memories!

Top guest favorite

Guest favorite

Sunny-All-Day Pool Vacation Home

Welcome to our Sunny 3-Bedroom Retreat! This inviting home features 3 spacious bedrooms, a south-facing pool for all-day sun, and a private fenced yard. Enjoy the bright living space, modern kitchen, and outdoor oasis with comfortable seating. Conveniently located near local attractions, dining, and shopping. Additional amenities include high-speed Wi-Fi, smart TV, air conditioning, washer and dryer, and free parking. Book now for a perfect getaway! **No parties ($500 fine) and no smoking**

Top guest favorite

Guest favorite

Near Disney | Heated Pool, King Bed, Arcade

✨ Family-Friendly Retreat Near Disney in a gated, safe & quiet community 🏰 Loved by guests for its cleanliness, comfort, and fast communication. 🏊‍♂️ Unwind after park days in your private HEATED pool 🍔 Enjoy the outdoor BBQ for easy family meals 🎮 Have fun in the upgraded game room with pool table, ping pong, foosball, and a retro arcade ⭐ Hosted by 3 experienced Superhosts known for quick, reliable replies. A perfect balance of fun and relaxation. Book now as dates fill fast!

Magical 6BR at Encore Resort next to Disney - 453

Modern 3,300sf luxury home, with 6 en-suites, at world's renowned Encore Resort at Reunion. It features a movie room with PS4, a beautiful backyard, a private pool and spa, and a garage with ping-pong and foosball tables. 6 Minutes away from Super Walmart and Publix supermarket 15 Minutes away from Disney Parks 15 minutes away from Disney Springs 15 Minutes away from Premium Outlets 20 Minutes away from Universal Studios 20 Minutes away from International Drive attractions

NEW Modern Villa Near Disney w/ Pool & Spa!

Create unforgettable memories of a lifetime and enjoy a vacation you’ll remember for years to come. This spectacular home is ideally located within the Sonoma Resort and only 8 miles to Disney, and within a short drive to Universal, Disney Springs, and many beaches! With 6000sqft of luxury living space, a private pool/spa, movie theater, and a game room for the kids, your family can enjoy the relaxing and fun atmosphere together! We can't wait to welcome you!

Top guest favorite

Guest favorite

Royal Retreat Disney Themed Pool Home, Arcade, Theater

Welcome to The Royal Retreat. Located just 10 miles away from the entrance of WDW, our rental is the perfect place to stay for your Disney vacation. Our 5 star home features 8 themed bedrooms and 5 bathrooms, a fully-equipped kitchen, private heated pool, private arcade, home theater & BBQ! Free Pool heat & the 1st tank of propane for the BBQ are included. Booking with us includes full access to the Champions Gate Clubhouse, Oasis Resort and Retreat Club!

Modern 12 BR 11.5 BA, Sleeps 32, 15 mins to Disney

Welcome to this modern 12-bedroom, 11.5-bath home—perfect for your next family getaway! Comfortably sleeping up to 32 guests, this centrally located retreat is just 15 minutes from the Disney parks. Enjoy fantastic amenities including a private pool and spa, a home theater for movie nights, and a fun-filled game room. With plenty of space and entertainment for all ages, it’s the ideal spot for family reunions, group vacations, and special get togethers.

12BR Disney Beach house 34 ppl Pool Theater Arcade

Stay near Walt Disney World in this luxury 12-bedroom Orlando vacation home, perfect for large families and groups. Enjoy a private pool and hot tub, movie theater, Transformers game room, poker table, outdoor kitchen, and themed Minions, Moana, Scooby-Doo, Inside Out, and Lilo & Stitch bedrooms. With multiple king suites and space to relax, play, and reconnect, it’s the perfect Disney-area getaway for reunions and unforgettable group vacations.

Villa Resort Club

Welcome to Villa Resort Club! Lovely 4BR/2.5BA for 8 with a screened private pool and game room. Full kitchen, workspace, washer/dryer, parking, and Wi-Fi. Pet-friendly. Minutes from Disney. Quiet, comfy home base! Welcome to Villa Resort Club! House with 4 bedrooms/2.5 bathrooms for 8, pool with enclosure and games. Full kitchen, workspace, washer/dryer, parking, Wi-Fi. Pets OK. Minutes from Disney. Quiet and comfortable!