Holiday rentals in Osceola County

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Top-rated holiday rentals in Osceola County

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Guest favourite

Cottage in Lake Wales

4.97 out of 5 average rating, 110 reviews

Charming, renovated 1917 Cottage

Charming, renovated 1917 cottage in beautiful neighborhood. One block from large lake with walking/running trail, 3.5 miles to Bok Tower, 12 miles to Legoland, 38 miles to Disney World, 47 miles to Universal Studios, and 63 miles to Busch Gardens. Pet friendly! King size bed in bedroom, double sofa bed in living area. Newly renovated kitchen has full size refrigerator, sink, microwave, stove top and large toaster oven. Big backyard with beautiful landscaping. Separate driveway. Lots of privacy!

Guest favourite

Home in Kissimmee

4.86 out of 5 average rating, 224 reviews

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.

Guest favourite

Villa in Lake Wales

4.98 out of 5 average rating, 190 reviews

Lakefront, Dock, 2 Kayaks, near Bok & Legoland

** New Construction ** Breathtaking view of lake, private dock (2 kayaks for guests included), beach/swim area, outdoor shower, large private balcony w/gas grill and gorgeous sunsets! 2 Bedrooms each w/walk in closet, two full baths, full kitchen w/all amenities. All new furnishings, (3) 4K Smart TV's, FAST free wifi. Gorgeous location, quiet street, private free parking, 2 private entrances. Villa is detached from main house. Near Disney, LegoLand, Bok Tower. WEEKLY & MONTLY DISCOUNTS

Guest favourite

Tiny home in Kissimmee

4.95 out of 5 average rating, 386 reviews

Sunny Tiny House Cottage near all Attractions!!

Our Tiny House in Mill Creek RV Resort is minutes away from Disney, Universal, Sea World & most area attractions. Our cozy cottage has vaulted ceilings, one bedroom, loft bedroom (40” high), full kitchen, dining table/chairs, living room, free washer/dryer, and the perfect front porch. There is a private drive and free parking. The resort is peaceful with plenty of amenities! We have four tiny house cottages - please check us out on Facebook under Tiny Mouse Houses to find the Airbnb links.

Guest favourite

Cottage in Lake Wales

4.89 out of 5 average rating, 114 reviews

The "Little ‘Toa" Ideal for short & long stays!

Welcome to the Little TOA, Central Florida's fishing, hunting and winter get away. The house sits just off the Kissimmee River which is part of the Kissimmee chain of lakes, connecting Lake Hatchineha and Kissimmee. This will be a great spot for you and your buddies or family for a short weekend trip or an extended stay. Come see old Florida, the area holds many things to occupy your vacation time. *Your pet is welcome, please let me know ahead of time. There is a one time fee for pets.

Guest favourite

Serviced apartment in Kissimmee

4.92 out of 5 average rating, 269 reviews

Modern APT W/ Patio 15 mins from Theme Parks & MCO

Beautiful space where you can spend a beautiful vacation with your loved ones, the space is created with immense love and for you to feel at home. El acceso será autónomo, con llavín inteligente y una entrada completamente independiente y sin restricción de horario . Ofrecemos un patio exterior diseñado para tiempo de descanso,para compartir un café y también para fumar si fuera de su agrado El parqueo está concebido para dos autos y tenemos cámara de seguridad las24h Todo climatizado

Superhost

Rental unit in Kissimmee

4.81 out of 5 average rating, 544 reviews

1BR w/Kitchenette near AdventHealth Orlando

A family holiday in the place where the magic begins. Melia Orlando Celebration is an oasis of comfort right next to the kingdom of dreams to be discovered with your family. Attractions await you: ✔Disney’s magical kingdom ✔Learn about space at Kennedy Space Center ✔Breathtaking sceneries at Lake Eola ✔Spend the day relaxing in the water and snorkeling with tropical fish at Discovery Cove ✔Take a tour at Universal Orlando Resort and see Harry Potters Hogwarts Castle

Guest favourite

Tiny home in Kissimmee

4.94 out of 5 average rating, 160 reviews

Disney Tiny House Getaway!

Unleash your Orlando Holliday adventure in our captivating 1-bedroom + loft tiny house! Perfectly situated for thrilling escapades at Disney, Universal, and Sea World, it's just 15 miles from the heart of the action. Whip up culinary delights in the full kitchen, relax on the charming porch, and dive into resort-style amenities including a sparkling pool, brand new fitness center, exciting playground, pickleball court, and so much more. Your unforgettable getaway starts here!

Guest favourite

Tiny home in Babson Park

4.92 out of 5 average rating, 322 reviews

Lil cedar tiny home, on crooked lake

Newly constructed tiny home.locatedon one of Florida's most prestigious lakes.crooked lake in s central floridais noted for its spring fed,clear water and white sand beaches,as well as it's amazing fishing and boating opportunities.the tiny house sits on 3/4 acre property overlooking crooked lake.the "million dollar view" as it's been called is spectacular at sunrise.the tiny house has an open ,airy, feel,with its comfortable roomy bedroom loft,and all the amenities of home.

Guest favourite

Treehouse in Saint Cloud

4.96 out of 5 average rating, 871 reviews

TreeHouse in the Cloud, (Close toTheme Parks

The treehouse is a private getaway for a couple that want to experience the magic. Check out video tours on U-Tube. Type in Treehouse in the Cloud. There have been several movie and other photo shoots done on property. Please text request and details, and we can negotiate fees. Our other AirBnB is just next door; Country gem horses close to Theme parks [link] Which is 1,000 sq ft and sleeps six.

Guest favourite

Guest suite in Kissimmee

4.86 out of 5 average rating, 604 reviews

Private Studio in POOL home

Hello travelers! We offer a portion of our home with a King sized bed, a large private bathroom with a Jacuzzi tub, and a Harry Potter play area accessed by rock climbing wall. The mini kitchen has a microwave, bread toaster, coffee maker, and refrigerator. There's an internet TV in the apartment with access to Prime. The pool and garden areas are shared with my family and another set of travelers. We are happy to offer our studio to travelers.

Guest favourite

Cottage in Kissimmee

4.95 out of 5 average rating, 450 reviews

Bright & Cozy Cottage Near Disney

My place located within 10 miles of: Disney World, Celebration, Universal, Water Parks, Old Town & Fun Spot USA's More than 70 Restaurants and Dining, Gifts Shop. My place is good for couples, solo adventurers, business travelers, and families (with kids). You’ll love my place because of In Our Cozy and Comfortable Sand Castle Cottage You'll discover that perfect Mix of High-Energy Fun and Laid Back Florida Lifestyle Right Here.