Villa vacation rentals in Osceola County

Find and book unique villas on Airbnb

Top-rated villa rentals in Osceola County

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Guest favorite

Villa in Kissimmee

4.87 out of 5 average rating, 142 reviews

Minutes from Disney Gated LakeView Pvt Heated Pool

Lowest Cleaning fee! Special wkly, military & AirBnB Host discnts. New Sofa set, Dolby Home theatre, new 65" HD LED TV w/ Airplay. A separate Remote office setup! Sunset Lakes is a secured gated community ~12 min from Disney & other parks. Updated Villa offers Lake View pvt pool, gorgeous sunset, BBQ Grill, Fishing dock. Fully furnished & sparkling clean with 4 beds - 1 King, 1 Quen, 3 baths, kitchen & laundry. Come & enjoy your next trip to Disney & leave everything to a fantastic experience!

Dec 13 – 20

G$34,066 GYD per night

Guest favorite

Villa in Kissimmee

4.78 out of 5 average rating, 406 reviews

7BD with Movie Theater Pool & Jacuzzi near Disney!

Have your own private Movie Theater, Pool and Spa 4miles from Disney. 7 Bedrooms and heated Pool this is the house of your dreams in a DISNEY vacation. Placed at The Emerald Island Resort, one of the most traditional and beautiful community in the DISNEY AREA, house is surrounded by nature since the community was build in a preservation area, your kids and family will gonna love every minute of your stay, fun and relax are waiting. Comfort with huge space... We hope that you enjoy our house!

Feb 3 – 10

G$67,615 GYD per night

Guest favorite

Villa in Lake Wales

4.99 out of 5 average rating, 179 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

Jan 5 – 12

G$31,965 GYD per night

Guest favorite

Villa in Kissimmee

4.98 out of 5 average rating, 102 reviews

Sleeps 24✦Free Pool Heat✦15 min to Disney✦Hot Tub

Make memories to last a lifetime in our luxurious 9-bedroom home (sleeps 24) at Orlando's premier vacation community. Enjoy your own Star Wars game room, private pool (heated at no extra charge*), and hot tub. Our 100% Five-Star rating from previous guests and our generous cancellation policy means you can book with confidence. Only 15 minutes to Disney and just a short walk to a fabulous resort clubhouse with free access to a lavish pool, kids waterpark, restaurant, playground, gym, and more!

Nov 10 – 17

G$84,385 GYD per night

Guest favorite

Villa in Kissimmee

5.0 out of 5 average rating, 11 reviews

Between Disney and Legoland Gated Resort

30 miles South of Disney World and about 20 miles NE of Legoland and only a 5 minute walk to beautiful Lake Marion. After a day at Disney World or Legoland, come back to relax in the hot tub while the kids play in one of two pools, kiddy pool or playground. You can play basketball, shuffle board, tennis, pickle ball. shoot pool in the clubhouse or workout in the gym. Take a short walk through the preserve area to the lake, where you might see eagles, bob cats, armadillos or even an alligator.

Oct 3 – 10

G$24,029 GYD per night

Guest favorite

Villa in Kissimmee

4.85 out of 5 average rating, 370 reviews

Amazing Cozy 4Bed/3Bath, Disney Area, Private Pool

A modern, comfortable, cozy and spacious house with a lot of and amenities. 4 bedrooms, 3 full bathrooms, game room/PS4, private pool, 3 parking spaces, WiFi, Smart TVs, well equipped Kitchen and Laundry. The house is located at Crystal Cove, a gated community, considered one of the best location at Disney area. The house is perfect! You’ll be at Walmart block and few minutes from Target, Sams Club, Publix, restaurants and Celebration. Are you going to MAGIC KINGDOM? Only 20 minutes driving!

Mar 31 – Apr 7

G$40,549 GYD per night

Guest favorite

Villa in Kissimmee

4.96 out of 5 average rating, 167 reviews

4 bed villa w/private pool near Disney, sleeps 6+

Lovely, updated Vacation Villa, near Disney & Universal Studios. Located on the beautiful, resort-style property of Trafalgar Village. It's your "home-away-from-home" equipped with complimentary high-speed Wifi and flat-screen TVs in every bedroom. You can relax at the home's private pool w/spa or venture off to the clubhouse's community pool, spa, fitness center, game room, and movie theater, just steps away from the villa. The home is 10mins in both directions to shops and restaurants.

Aug 22 – 29

G$31,948 GYD per night

Guest favorite

Villa in Kissimmee

4.92 out of 5 average rating, 181 reviews

Mad Men Magic Kingdom House*FAB POOL*OutdoorMOVIE

AMAZING Pool Deck Extension cira 2023! Its the BIGGEST pool deck at the resort! Plus JAW DROPPING, Fancy, Fun, Fountain Jets w/ LED lighting, high-end glass tile & a Mickey Mosaic giving you an ULTIMATE luxury pool experience. This SALT WATER POOL/SPA will leave your skin feeling soft w/ no eye-sting & it has botanical qualities for your muscles after long days at the parks! Enjoy all this plus our unique OUTDOOR MOVIE EXPERIENCE & FIRE-PIT for the BEST vacay ever only 6 miles to Disney!

Mar 28 – Apr 4

G$125,437 GYD per night

Guest favorite

Villa in Kissimmee

4.9 out of 5 average rating, 123 reviews

Waterfront Retreat,King Bed,Heated Pool & Fire Pit

Sit back and relax in this stylish home with all the amenities you need for a fun family getaway. This home has a spacious layout with 3 bedrooms and 2 baths. We have thought of everything so you don't have to-toiletries,washer/dryer, and wifi. Enjoy your morning coffee in the screened in pool area with a beautiful sunrise and lake view or sip a glass of wine while floating in the pool. Just minutes to Theme Parks and major highways, this is the dream home you have been waiting for!

Dec 17 – 24

G$66,141 GYD per night

Guest favorite

Villa in Kissimmee

4.97 out of 5 average rating, 130 reviews

Close To The Mouse: Something for Everyone!

Are you ready for four amazing bedrooms, three full baths, a fully equipped kitchen, formal dining area, reclining seats on the new couch and love seat, Tempur-Pedic mattresses on every bed, a beautiful pool, and a game room that will make you want to stay home for the day? Everything is close by: Disney World, Universal , and Sea World. No need to share the space with others, this is your own private oasis for your time here. Additional health and safety standards in place.

Jan 13 – 20

G$36,663 GYD per night

Guest favorite

Villa in Davenport

4.94 out of 5 average rating, 112 reviews

Beautiful 4 Bedroom Pool Villa Near Disney World

This sunny single story home has 4 beautiful bedrooms (2 master suites) and 3 full bathrooms with its own private screened pool. It is an ideal accommodation for 2 families to share, or one large family. This villa is located in the gated community, a small peaceful community set away from any main road traffic. The home is situated approximately 15 minutes from the Walt Disney World, and is conveniently located from all major Orlando attractions, nearby restaurants and shopping.

Oct 14 – 21

G$39,133 GYD per night

Guest favorite

Villa in Kissimmee

4.91 out of 5 average rating, 33 reviews

Disney Pool Home Kissimmee

Remodel complete. Located in the beautiful Crescent Lakes of Kissimmee. Just minutes (12 miles) to Disney. Our 3 Bed, 2 full bath Villa will be sure to make your vacation enjoyable. Relax under the sun or the stars in the south/west facing pool. Lounge and dine on the oversized pool deck. 3 bed, 2 full bath Villa.

Feb 8 – 15

G$38,251 GYD per night