Cottage vacation rentals in Kissimmee

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Top-rated cottage rentals in Kissimmee

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Guest favorite

Cottage in Kissimmee

4.89 out of 5 average rating, 209 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

Dec 4 – 11

G$20,410 GYD per night

Guest favorite

Cottage in Kissimmee

4.98 out of 5 average rating, 139 reviews

Runaway Beach Resort Pet Friendly: Magic Kingdom

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.

Aug 2 – 9

G$28,596 GYD per night

Guest favorite

Cottage in Kissimmee

4.93 out of 5 average rating, 169 reviews

Cozy Private Cottage 5 miles from Disney!

This cottage is located on a 4 star resort and has been freshly painted and completely renovated from top to bottom to enhance your experience and stay. This home has been completely decorated in a beach teme decor and has everything you will need for a short or long stay. And is conveniently located in the heart of Kissimmee, Florida. -4 miles to Disney World -4 miles to medieval times dinner -.2 miles to ALDI, Dollar Tree, CVS, Krispy Kreme -2 miles to Walmart & Old Twn -7 miles to Sea World

Oct 14 – 21

G$19,951 GYD per night

Guest favorite

Cottage in Kissimmee

4.99 out of 5 average rating, 139 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!!

Nov 11 – 18

G$38,691 GYD per night

Guest favorite

Cottage in Kissimmee

4.98 out of 5 average rating, 121 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".

Jul 15 – 22

G$49,955 GYD per night

Guest favorite

Cottage in Winter Garden

4.99 out of 5 average rating, 106 reviews

Come Stay In The Heart Of Winter Garden

Stay in a completely renovated 1937 cottage that's located in the heart of historic downtown Winter Garden. It's walking distance from all of the shops, restaurants, and events (including the #1 rated farmers market in the nation every Saturday) that make Winter Garden one of the most desirable cities in Florida. Sit on the front porch and watch as people bike and jog on the famous West Orange Trail, or rent a bike from the corner and join them. The home is close to all major highways.

Jul 19 – 26

G$36,762 GYD per night

Guest favorite

Cottage in Kissimmee

4.81 out of 5 average rating, 142 reviews

Cozy cottage close to Theme parks and shopping.

Our home is close to all area theme park attractions. 1 1/2 hrs. from each coast line. Outlet shopping near by. Our home is well kept cozy 2 bedroom place with an outdoor private patio with a gazebo with a great view of the pond. We are a short walk to outdoor pool and hot tub. Great restaurants just a short drive or walk away. Aldi's grocery store and C.V.S pharmacy close by. Disney World is 4.5 miles away Universal Studios is 13.6 miles away Sea World is 8.4 miles away

Sep 11 – 18

G$23,177 GYD per night

Guest favorite

Cottage in Saint Cloud

4.93 out of 5 average rating, 260 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. A list of some of the local favorites along with directions and numbers is provided.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.

Aug 24 – 31

G$20,662 GYD per night

Guest favorite

Cottage in Kissimmee

4.94 out of 5 average rating, 371 reviews

Entire Cottage close to Disney, Universal, Airport

A full cottage for 4! The perfect place stay. Located just 20 minutes from Disney and Universal. Shopping and Restaurants are less than 5 minutes from the cottages. All new furnishings, fresh linens, fresh paint! Privately owned. This cottage is our favorite!!! We also just updated the A/C. Check out unit We also have three other cottages on property, the Bitty Bungalow, Bitty Bliss, and the Bitty Blossom. All cottages are within 70 yards of each other.

Dec 4 – 11

G$17,299 GYD per night

Guest favorite

Cottage in Davenport

4.92 out of 5 average rating, 129 reviews

$79! 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!

Jul 5 – 12

G$19,728 GYD per night

Guest favorite

Cottage in Kissimmee

4.86 out of 5 average rating, 391 reviews

Yay! Cool Tiny Home Near All the Parks (98)

Located in the middle of it all. Hundreds of restaurants/shopping/grocery stores/pharmacies. You will love our great porch and the quiet atmosphere. One awesome thing about our neighborhood is that even though it is centrally located, you cannot hear any noise. 15 minutes from Disney, Sea World and Universal!! Deer, raccoons, and large water birds walk down the streets. Our cottage is great for families, couples, solo adventurers or business travel.

Apr 2 – 9

G$23,589 GYD per night

Guest favorite

Cottage in Kissimmee

4.98 out of 5 average rating, 100 reviews

Margaritaville 1BD Cottage "Limoncello" nr. Disney

Welcome to your own island-inspired oasis. Our charming cottage is the perfect home base for your next dream Orlando vacation. The unit comes with all the comforts from home but worlds away. Conveniently located minutes from the Disney parks, a state-of-the art water park and newly opened 196,000 square foot shopping and dining district with multiple dining food and beverage options & brand-new movie theater. All Pets Must Be Preapproved :)

Mar 4 – 11

G$41,455 GYD per night