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 favourite

Cottage in Lake Wales

4.97 out of 5 average rating, 111 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

Guest suite in Kissimmee

4.93 out of 5 average rating, 134 reviews

Newly renovated near Disney and Universal Orlando

Entire suite , new ultra comfortable king size bed, free wifi, 64"TV with Netflix and Amazon Prime. Private bath, Living room and kitchen, shared laundry room, free parking 13 miles or 21 minutes from Disney World, Disney Springs shops and restaurants and Orlando Premium Outlets 16.6 miles or 23 minutes from Universal Orlando. 12.6 miles or 22 minutes from Aquatica and SeaWorld Orlando 11.6 miles or 22 minutes from Orlando International Airport 15 miles or 25 minutes from the Convention Center

Guest favourite

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 favourite

Villa in Osceola County

4.98 out of 5 average rating, 103 reviews

*Private Resort Oasis: Golf-Front, Pool/Spa/Cinema

The perfect balance of STYLISH DESIGN, LUXURIOUS COMFORT, & ENDLESS ENTERTAINMENT, beautifully situated with stunning views in the sprawling 3.5 square mile Reunion Resort. You will have your own private pool, spillover spa, STAR WARS cinema-game room with pinball, classic arcade games, and karaoke, MARVEL kids room with tube slide and double bunks, the latest Xbox Series S, a sprawling 2000 ft2 pool deck, fire pit, and even a HARRY POTTER cupboard hidden under the stairs, minutes to Disney.

Guest favourite

Cottage in Lake Wales

4.89 out of 5 average rating, 116 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

Guesthouse in Kissimmee

4.93 out of 5 average rating, 108 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 favourite

Tiny homes in Babson Park

4.92 out of 5 average rating, 327 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, 893 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.

Superhost

Home in Lake Wales

4.91 out of 5 average rating, 102 reviews

Hidden Gem - Hot Tub/ Fire pit/Hammock/Grill Area

Take it easy at this unique and tranquil getaway. Come and enjoy a piece of heaven with friends and family. Take a soak on the hot tub, fire up the grill, make some smores on the fire, sit back and relax. Close to lakes and state parks. Bring your boat or rent our available kayaks to have a great day at Lake Pierce less than a mile away. Drive 45Mins to Disney and 20mins to Legoland. We'll see you soon! Events Available upon request.

Guest favourite

Cabin in Davenport

4.93 out of 5 average rating, 208 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 favourite

Guest suite in St. Cloud

4.93 out of 5 average rating, 330 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.

Guest favourite

Guest suite in Kissimmee

4.98 out of 5 average rating, 215 reviews

Little Blue House with private entrance & parking

The Blue House is very spacious, with a bedroom with a queen bed, a private bathroom, a small living room with a sofa bed, a dining room and a kitchen equipped with all the necessary amenities for a relaxing stay. Perfect for vacationing with your children or friends!