Vacation rentals in Osceola County

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Top-rated vacation rentals in Osceola County

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite

Barn in St. Cloud

4.96 out of 5 average rating, 134 reviews

Rustic Barn Retreat

Experience the rustic elegance of this beautifully remodeled 1,800 sq. ft. barn nestled on a serene 12-acre property. Unwind in the private heated hot tub and soak up the peaceful surroundings. The prime location offers convenient access to major attractions—just a 35-45 min drive west will take you to Disney, Universal, SeaWorld, and gator parks, while a 45-60 min drive east leads you to the breathtaking Atlantic beaches and the Space Coast. Plus, the property is only 30 min from the airport.

Guest favorite

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 favorite

Villa in Lake Wales

4.98 out of 5 average rating, 191 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 favorite

Cottage in Lake Wales

4.89 out of 5 average rating, 115 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 favorite

Farm stay in Kissimmee

4.83 out of 5 average rating, 311 reviews

Container home -near Disney WIFI Bamboo Farm

Looking for something off the beaten path that is unique and private? Come stay in our container home in the bamboo forest. We have designed it to be comfortable for up to two people with a large shower, a queen size bed, and even a kitchen equip with a toaster oven, keurig coffee maker, and a refrigerator. The deck has a covered screened in space and a hammock for relaxing in this tranquil environment close to everything and yet it feels miles from anything. Now with excellent WIFI

Guest favorite

Serviced apartment in Kissimmee

4.92 out of 5 average rating, 272 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

Guest favorite

Guesthouse in Kissimmee

4.92 out of 5 average rating, 102 reviews

Entire deluxe studio for 2 near Disney & parks

Welcome to my independent apartment in my house, I have a great location and you can enjoy easy access to popular shops, restaurants and parks from this charming place to stay with a great location. I also offer the ride from/to the airport just for $30 each ride from home. MCO 30 Min Kissimmee gateway Airport 3 miles-7min Osceola hospital 2.7 miles-7min Disney world and Disney parks are 11-12 miles Universal Studios/ aventure Island is 18 miles The Loop Shopping center is 5.7 miles

Guest favorite

Guesthouse in Kissimmee

4.89 out of 5 average rating, 117 reviews

Cozy 1BR apt-Pool/Tennis/Gym/Near attractions

Welcome to The Lopes Cozy Apt! We are delighted to have you. This gorgeous and safe garage/apt, has been renovated renovated and furnished in a peaceful neighborhood with great community amenities. Pack your bags and get ready to escape to NE Kissimmee, just 6 miles from MCO Airport, 12 miles from Sea World, 18 miles from Universal. Disney World is #1 in the US tourism, only 15 miles from the apt. adittionally Coco a beach Florida only 58 miles to get your sun kissed look.

Guest favorite

Tiny home in Babson Park

4.92 out of 5 average rating, 324 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 favorite

Treehouse in Saint Cloud

4.96 out of 5 average rating, 887 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 favorite

Cabin in Davenport

4.93 out of 5 average rating, 201 reviews

$69! Cozy Cabin- Disney 20 Miles Away!

Book with us now and receive access to all of these amenities✨: •Fast Internet •Covered Patio •Safe Gated Location •Keypad Entry Door •Comfortable Queen Sized Bed •Cable TV (Adjustable) •Modernized Brand New Full Bathroom •Nearby All Major Attractions, Theme Parks, and Malls •Outdoor Dining Area •Kitchen, Fridge/Freezer, & Breakfast Nook •Complimentary Coffee & Breakfast •Cooking Equipment •And Much More! Book with us now!

Guest favorite

Guest suite in St. Cloud

4.93 out of 5 average rating, 327 reviews

LAKE FRONT Suite with FREE USE of Kayaks & Canoes

Private Master Suite with it's own exclusive entry. It has a convenient kitchenette complete with mini refrigerator, microwave, toaster, toaster oven and an outside grill. Comfy Queen size bed with overhead ceiling fan. Private Bathroom and shower. Lake view from the front of property, unit is in the back overlooking wetlands. Plenty of parking, with enough room to bring a boat.