House holiday rentals in Osceola County

Lakefront home near Disney/Beach

Relax after a long day visiting the beaches, Disney, or springs in this peaceful lakefront home. Enjoy your morning coffee on the front patio overlooking the lake or wind down with a glass of wine underneath the pergola soaked with tropical flora. A paved walking path is just a few steps from the front door with quick access to the local marina. Downtown St Cloud is minutes away where you can enjoy local eats, drinks, shopping and other amenities! 30 minutes from Disney, an hour to the beaches.

Location · Value · Getting around

3 bedroom Villa in Kissimmee

The villa is in a residential area within a 5-min drive to local amenities including, a pharmacy, 3 supermarkets and 2 gas stations. The property is between 15 - 40 mins drive from Disney, Epic Universe, SeaWorld, Gatorland & Universal Studios. Orlando International Airport is only about 17 mins drive away. Osceola Heritage Park, the home of the world’s largest collector car auction is only 4 mins drive from the villa. The Florida Turnpike that runs through Miami is 6 mins from the property.

Value · Location · View

Premium location - Near Disney

Beautiful modern home with 3 full suites and 3 bathrooms — a rare find in the area! Located in the gated community THE HUB, featuring new construction, an American-style kitchen integrated with the TV room, and pet-friendly accommodations (rules apply). The community also offers a swimming pool and a small gym for guests. Guests enjoy: 🕒 24h self check-in 🔐 Unique access code valid only during the stay 🛏️ Linens and towels provided 🐾 Pet-friendly (check rules) 🏊 Community pool & small gym

Value · Family · Parking

La Casita Redonda (The little round house)

Enjoy a memorable visit when you stay in this unique and historical place in Lake Wales, FL. Constructed in 1936 this home is nestled within a quiet and friendly neighborhood just minutes from the downtown area and just a short walk to Lake Wailes itself. Although the current owner updated the home with practical renovations, the peculiar house still has the character and features from the time it was built, features that once granted it a place among the pages of Ripley’s Believe it or Not.

Value · Family · Hiking

New Gtd community Sleeps 6 - 3B/2 bth near Disney

NEWLY BUILT private home. Enjoy a stylish experience with fully equipped kitchen and EVERYTHING brand new. Sleeps up to 6 in 3bed/2bath. Includes 1 KING and 4 Twin beds with a tv in each room. Enjoy the arcade game and lounge in the relaxing open space. Connect to WiFi and enjoy the dedicated workspace. Safe & secure smart house in gated community. Access to resort style pools, sports courts & more. Minutes from several entertainment spots including Disney, shopping & restaurants all close by.

Location · Family · Walkability

Sunshine on the Lake | Boat Slip+Lakefront Fishing

Welcome to Florida Lakefront Paradise! ⭐️ Breathtaking Sunsets ⭐️ Bass Fishing ⭐️ Reserved Boat Slip ⭐️ Fish Cleaning Station ⭐️ Boat Wash Station ⭐️ Marina with Ice/Gas ⭐️ Large Fire Pit Area ⭐️ Located on Kissimmee Chain of Lakes ⭐️ Smart TV's ⭐️ Screened Lakefront Back Patio ⭐️ High Speed Internet ⭐️ Spacious ⭐️ Balcony Facing the Lake ⭐️ 30 minutes to Lego Land ⭐️ 20 minutes to Bok Tower Gardens ⭐️ 1 hour to Disney World ⭐️ 18 minutes to Spook Hill ⭐️ 18 minutes to Kissimmee State Park

Family · Location · Accuracy

New Listing! Casita Bonita Pool House

Bring the whole family to this great place with lots of room for fun. Beautiful house in Kissimmee. Perfect home to relax and enjoy quality time with the family. Airport (Orlando International): 15 - 20 Minutes Lake Nona 10-12 Min Taking a cruise? 🚢 Port Cañaveral 45min Disney Springs: 25 - 30 Min Disney's Magic Kingdom & Disney's parks:35-45Min Florida Mall: 20 - 25 Min Islands of Adventure: 25 - 30 Min Premium Outlets (Vineland Ave): 20 - 25 Min Universal Studios & Volcano Bay 25 - 30 Min

Family · Location · Quiet

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!

Value · Location · Backyard

Cozy House with Pool. Kissimmee/Orlando

Welcome to Your Kissimmee Getaway! 🏠 Enjoy a relaxing stay in beautiful Kissimmee, conveniently located near Orlando’s world-famous theme parks, restaurants, shopping, and entertainment -Pet friendly home🐾( pet fees may apply) Please make sure to include your pet(s) when making your reservation so any applicable fees can be reflected in your booking. -No parties or events of any kind -No smoking inside the property Please respect the home, neighbors, and community during the stay

Family · Value · Walkability

Large Private Home on Golf course by Disney

Bring the whole family to this great place with lots of room for fun. With fantastic views of the 4th hole on the Tom Watson golf course and your own private pool and hot tub everyone will enjoy this stylish and modern vacation home. Located in premier Reunion Resort and only 10 minutes to Disney you can have it all! This home boats over 4000sq feet, two very large masters suites, 2 additional bedrooms and plenty of space throughout the home. There are 6 tvs! Pets are welcome too!

Family · Location · Comfort

"Cutty Shack" Waterfront Kissimmee River House 3/3

"Cutty Shack" is the perfect fishing retreat. It is a 3 bedroom, 3 bath home built by our family in 1969. The Cutty Shack will sleep 6-7. This large stilt home (all living area is upstairs) is situated directly over Kissimmee River and right next door to Camp Mack River Resort. You and your group can enjoy peaceful evenings in the house, or walk next door to grab a drink and watch a "weigh-in". Our family has enjoyed this retreat for five generations and we hope you will too!

Location · Family · Bathroom

Villa Resort Club

LUXURIOUS VILLA - SUPER BEAUTIFUL NEIGHBORHOOD POOL HEATER HOUSE - Have fun with the whole family in this modern style home, you will love the picnic area in front of the house , the play area and pool with heater , a spacious artificial grass place to play your children and in a very trankila area near the Disney parks and the MCO airport. YOU WILL LOVE THE HOUSE Local utility or county personnel may access exterior areas for maintenance without prior notice.

Family · Location · Pool