Holiday 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.

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Guest favourite

Epic stay at Vista Cay!

This 2-bedroom, 2-bathroom apartment at Vista Cay Resort, Orlando, offers an exceptional location for enjoying the best of the city. Just minutes from Orlando International Airport and Walt Disney World, it provides unparalleled convenience for both travelers and residents. Additionally, its proximity to the Convention Center, Universal Studios, SeaWorld, and International Drive grants easy access to major attractions, dining, and shopping, offering a complete experience in the heart of Orlando.

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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!

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Guest favourite

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!

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Guest favourite

12BR Disney Luxury Retreat - Pool, Theater & Fun!

Welcome to our magical vacation home in Orlando, just minutes from Universal Studios, located on International Dr, less than 2 miles from SeaWorld! Featuring 12 themed bedrooms inspired by beloved movies like Harry Potter, Frozen, and Aladdin, and a Tiana-themed kitchen, every detail is designed to delight guests of all ages. With 21 beds, it’s perfect for families and groups. Enjoy a prime location, unique decor, and ultimate comfort for an unforgettable stay. All themed environments.

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Guest favourite

Haunted Mansion-inspired Ghoulish Sanctuary

Welcome, Foolish Mortals... To the Ghoulish Sanctuary: An immersive Haunted Mansion-themed stay just 15 minutes from Walt Disney World, where candlelights flicker, and the air is deathly still... Experience a one-of-a-kind Haunted Mansion-themed stay for up to 6 people. This spooky rental in Kissimmee lets you inhabit your favorite ghostly estate... if you dare. Ready to play your next campaign and need a place to gather for your DnD weekend? The sanctuary and its spirits await.

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!

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4BR Disney & Universal Themed Villa Reunion Resort

Welcome to our newly remodeled 4BR/4BA luxury villa in Reunion, designed for families and groups seeking comfort, style, and a magical Orlando escape. Enjoy brand-new furnishings, modern finishes, Toy Story and Mickey themed bedrooms, a spacious open living area with massage chair, and a fully equipped game room featuring air hockey, arcade basketball, and PlayStation. Relax in your private screened pool with optional heating after unforgettable park days.

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.

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Guest favourite

Near Disney • 4BR • Perfect for Families

Guests love this home! It’s usually fully booked! Location is incredible! Heart our property and save it to your wishlist! IMPORTANT: parking available only for one car. 9 min - Hollywood Studios (6 mi) 10 min - Animal Kingdom (8 mi) 12 min - Disney Springs (5 mi) 15 min - Magic Kingdom (10 mi) Just 3’ from Walmart, Publix, and a big strip mall full of restaurants, grocery stores, and shopping! Experienced host, 10 years on Airbnb!

Luxury Reunion Retreat Patio Views Near Disney

Located in the desirable Spectrum Condo at Reunion Resort, this comfortable 5‑bedroom, 4‑bathroom condo offers a relaxing and convenient home base for families and groups looking to explore all that Orlando has to offer. With a well‑designed layout and comfortable furnishings, this condo provides the perfect balance of privacy and togetherness, making it an ideal choice for your next getaway.

Brand new luxury near clubhouse / lake view (405)

STOREY LAKE - 6 GUESTS - 2 BEDROOMS - 2 BATHROOMS - LAKE AND CLUB VIEW DON'T MISS OUT! BE ONE OF THE FIRST TO RENT!! Modern Lake View Apartment – Near Disney, Universal , Outlets This beautiful apartment was fully redecorated with all-new furniture by B & Design (By Barbara Costa), featuring a modern, clean, and airy design. Enjoy relaxing moments on the balcony overlooking the lake.