Cottage vacation rentals in Osceola County

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Top-rated cottage rentals in Osceola County

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Guest favorite

Cottage in Kissimmee

4.98 out of 5 average rating, 165 reviews

Runaway Beach Club- Lakeview, Patio, Near Disney!

Welcome to our 2/2 PET FRIENDLY villa just 8 minutes to Disney! Nearby you will find Lake Buena Vista Outlets, Universal Studios, Disney Springs, Old Town, restaurants and more! Stay includes: Disney Costumes Wi-Fi Washer/Dryer Free Parking Access to shuttle to Disney 4 pools including kids area/Calypso Cay Pools withTiki Bar 24 HR Gym, Volleyball/Basketball Court Mini Putt Putt Kids items available upon request. Strollers, etc. Small Pet Fee added for fur friends with complimentary pet food.

Guest favorite

Cottage in Kissimmee

4.9 out of 5 average rating, 110 reviews

Modern Vacation Cottage near Walt Disney World

Our cozy, modern vacation cottage is nestled in a quiet, private community just 4 miles from Walt Disney World and convenient to all the fun that Orlando has to offer. The cottage features 1 bedroom with a high-quality queen bed, a living room, a full bathroom, and a fully-stocked kitchen with a new dishwasher, refrigerator, microwave, and oven. Centrally located to all of the Orlando attractions, our cottage is a very comfortable and special place to enjoy all of the magic and sunshine of FL!

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

Cottage in Kissimmee

4.9 out of 5 average rating, 232 reviews

Be Our Guest Sandcastle Cottage 81

Located-Encore Tropical Palms RV Resort 5 min to Disney property and minutes away from various restaurants. Old Town and Fun Spot are right next to the property. New renovated floors just installed! (May 2023) Has private bedroom with queen bed and upstairs loft with 2 twin beds for the kids. Newer sofa and recliner and washer/dryer. Stainless Steel Appliances and granite tile counter tops in kitchen. Smart TV in living room. Resort style pool with kiddie area. Miniature Golf area. Free WiFi

Guest favorite

Cottage in Saint Cloud

4.93 out of 5 average rating, 278 reviews

Country Gem, Horses, Close to theme parks

Our place is good for couples, solo adventurers, business travelers, and families (with kids). The cottage is handicapped friendly. We have available two ramps, elevated toilet and toilet chair, and hand bars. The shower has a shower chair, and pedestal sink. There are two sliding barn doors which will make the common areas into two semi private rooms. Check in is 3pm, check out is 11am. Canaveral National Seashore is 44 miles away. An island on the Atlantic Ocean, is a National Park.

Guest favorite

Cottage in Kissimmee

4.99 out of 5 average rating, 149 reviews

Tahiti Gil’s Mananui: Disney Poly & Tiki Inspired!

Aloha Adventurers! Welcome to Faré Mananui. Your passport to a far away tropical hideaway awaits, so get ready to grab your favorite Aloha shirt! Mananui was made for the Disney/Tiki ADULT in mind! Imagined by artist @TahitiGil & designed by @TyphoonTommy (Former Disney/Universal creative team & designer of the Suffering Bastard Tiki Bar in Sanford, Fl. Experience your next Adventureland/ Enchanted Tiki Room “story dwelling” adventure from the moment you step thru the door! - Kungaloosh!!

Guest favorite

Cottage in Kissimmee

4.99 out of 5 average rating, 135 reviews

Margaritaville cottage minutes from Disney

Gorgeous 2 bedroom/2bath cottage located in gated Margaritaville Resort just 6 miles from the Magic Kingdom. This immaculate cottage sleeps six people and has everything you will need to enjoy your vacation. Sunset Walk is an easy 10 minute stroll with plenty of shopping and unique restaurants to choose from. Orlando's newest waterpark, Island H2O Live, is right next to Sunset Walk to enjoy on a hot day. It's time to waste away in Margaritaville, and come enjoy a little "Peace of Paradise".

Guest favorite

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 favorite

Cottage in Davenport

4.93 out of 5 average rating, 151 reviews

$69! Cozy Cottage + Outdoor Fun -Close to Disney!

Book with us now and receive access to all of these amenities✨: •Lightning Fast Internet ⚡️ •Outdoor Movie Theater 🎥 •Ping Ping Table/Pool Table 🏓🎱 •Complimentary Coffee & Breakfast ☕️ •Safe Gated Location •Large Enclosed Covered Patio •Comfortable Queen Sized Bed •Cable TV (Adjustable) •Modernized Brand New Full Bathroom •Nearby All Major Attractions •Outdoor Dining Area •Kitchen, Fridge/Freezer, & Breakfast Nook •And Much More! Book with us now!

Superhost

Cottage in Kissimmee

4.83 out of 5 average rating, 245 reviews

Private Cottage. Only 5 miles from Disney.

Welcome to our private cottage on a 4 star resort only 5 miles from Disney World in Kissimmee, Florida. This home has some smart home features such as Alexa, smart thermostat that Alexa can control. It has a smart lock that makes it convenient for you when you stay your are given a confidential code for your stay only. The cottage is a one bedroom one bathroom with a queen size bed. Also the sectional couch turns into a full size bed.

Guest favorite

Cottage in Kissimmee

4.95 out of 5 average rating, 451 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.

Superhost

Cottage in Kissimmee

4.8 out of 5 average rating, 103 reviews

Cozy Cottage 5mins From Disney Parks!

Comfortable little cottage nestled in one of the nicest RV Resorts Kissimmee has to offer. Whether you're here for the Orlando Attractions (Disney, Universal, Sea World, etc.), random getaway, or escaping the Great White North, you will enjoy staying here. Lots of friendly people as well as activities galore. You will have access to all of the amenities of the RV park (Pool, Gym, Sport Facilities, Clubhouse, etc).