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.

Pool Spa + Outdoor Entertainment | Golf Retreat

Escape to a one-of-a-kind golf retreat in Davenport, where resort-style outdoor living meets family-friendly entertainment. Spend your days relaxing by the private pool & spa, enjoying movies on the outdoor TV, and challenging the family in the Super Mario game room, all just minutes from Disney Whether you're planning a family vacation, golf getaway, or long weekend with friends, this beautifully renovated 4-bedroom home was designed for connection, comfort, and unforgettable Florida memories.

6 miles from Disney ! Private pool ! 4 bedrooms

This Beautiful newly renovated 4 bedroom 3 bathroom luxury townhouse has a private pool with complimentary resort facilities. The house has a bedroom and a full bathroom in the first floor for accesibility. The house is close to the Resort and Clubhouse, which has a lobby/reception, snack bar, all-year heated pools, training facilities, and a game room. It is 15 minutes from all Disney parks and close to Orlando attractions. Very relaxing. Newly renovated with new appliances and furniture.

Elegant 15BR 16BA, Sleeps 40, Theater, Game Room

Welcome to this elegant 15-bedroom home, featuring 16 bathrooms, nestled in the prestigious Sonoma Resort. Recently renovated, this home showcases a meticulously crafted design with exceptional attention to detail throughout. Each of the 15 bedrooms boasts its own private bathroom, ensuring ultimate comfort and convenience for all guests. Perfect for group getaways, this stylish retreat comfortably accommodates up to 40 guests, making it an unforgettable destination for your next gathering!

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!

10 Min to Disney | Kings | Heated Pool | Games

✨ Perfect family getaway just minutes from Disney magic! ✨ This spacious 4-bedroom home sleeps 9 and features 2 king beds, 4 full beds, and 1 twin, plus fun Mickey Mouse & Minion themed rooms kids love. Unwind in your private screened pool, enjoy the game room with arcade games, ping pong, foosball & pool table, or relax with cozy board-game nights. 🏰 Animal Kingdom 10 mins Epcot & Hollywood Studios 15 mins Book now and start making unforgettable family memories!

Orlando Dream Escape | Piscina Privada | Disney

Welcome to your perfect Orlando getaway! Enjoy this beautifully renovated home with a private pool, just 20 minutes from Disney, Universal, and SeaWorld. Perfect for families and groups of up to 8 guests. Features 3 bedrooms, 2 full bathrooms, a fully equipped kitchen, fast Wi-Fi, washer & dryer, free parking, and self check-in. Relax, unwind, and create unforgettable memories close to Orlando’s best attractions, shopping, and restaurants. 🏊‍♀️ Private Pool

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!

Luxury Home w/ Pool & 6 Beds near Disney

Welcome to your modern escape in Kissimmee! Just 15 minutes from Orlando International Airport, this beautifully renovated 3-bedroom, 2-bath home offers the perfect blend of comfort and luxury. Every detail has been thoughtfully upgraded—from the brand-new kitchen and spa-like bathrooms to the pristine private pool area—ensuring a relaxing stay. With sleeping arrangements for up to 9 guests across six beds, there’s plenty of space to unwind.

Montego Bay Retreat | 15 Min to Disney

Enjoy a stylish stay in this newly renovated 3-bedroom, 2-bath home, perfect for families and groups of up to 9 guests. Located only 15 minutes (8 miles) from Disney and close to Orlando’s top attractions, restaurants, and shopping. Relax in modern, comfortable spaces after a fun day at the parks. Outdoor grill available for $30/day (gas included). The perfect mix of location, comfort, and convenience for your Florida vacation! ✨

Cozy House with Pool. Kissimmee/Orlando

Travelers will love staying at this home for its perfect mix of comfort and fun. Enjoy a private pool to relax after a long day, plus a gas BBQ included for easy outdoor meals with family or friends. The spacious and cozy layout is ideal for unwinding, while the peaceful setting makes it feel like a true getaway. Whether you’re here to relax or explore, this home offers everything you need for an unforgettable stay.

Luxe Family Retreat | Pool Villa Near Disney & MCO

Escape to this beautifully designed family retreat featuring a private screened pool, BBQ gazebo, foosball table, spacious open-concept living areas, and a fully equipped kitchen. Ideally located near Disney, MCO Airport, outlets, shopping, restaurants, and Orlando’s top attractions. Perfect for family vacations, group trips, or a relaxing getaway with all the comforts of home.