Holiday rentals in Osceola County

Guest suite in Haines City

4.92 out of 5 average rating, 87 reviews

1 BR 1BA Lake Apt. Boat slip, Deck, Pets, Laundry

Come wake up to birds singing, looking out your windows to a nice deep water canal view. The canal leads to Lake Hatchineha (great fishing). TVs in every room. Fully loaded kitchen; private entrance. There is a porch, laundry and deck area shared with one other apt. Free laundry . We are 45 min from MCO(airport) 45 min from Disney and 15 minutes to Legoland. Bok Towers is a unique park that is 18 miles away. Star gazing and bicycling or fishing. Pets $35 per trip with a fenced in area for them.

4.96 out of 5 average rating, 57 reviews

Home in Osceola County

Large Private Home on Golf course by Disney

Bring the whole family to this great place with lots of room for fun. With fantastic views of the 4th hole on the Tom Watson golf course and your own private pool and hot tub everyone will enjoy this stylish and modern vacation home. Located in premier Reunion Resort and only 10 minutes to Disney you can have it all! This home boats over 4000sq feet, two very large masters suites, 2 additional bedrooms and plenty of space throughout the home. There are 6 tvs! Pets are welcome too!

4.82 out of 5 average rating, 72 reviews

Guest suite in Kissimmee

Elegant 1-Bdrm Near Disney - FREE Parking ✨️

Unwind at this stunning, clean, and modern home. The apartment has a luxurious yet charming feel that makes you feel right at home. Enjoy a cup of coffee on the porch in the morning while enjoying the Florida sunshine. The apartment is located only 25 minutes away from Disney and 30 minutes away from the airport. This space is truly a peaceful, secluded gem. Kick back and relax in this calm, stylish space. LONG TERM STAY DISCOUNTS AVAILABLE!! Send message for more details.

4.99 out of 5 average rating, 104 reviews

Home in Kissimmee

Suite con entrada independiente

suite con totalmente independiente * 1 cama Queen. * 1 sofá cama individual *Cocina equipada * baño privado * estacionamiento gratis. * WIFI * terraza La ubicación es perfecta para disfrutar de todos los parques temáticos que Orlando tiene para ofrecer: disney estudios Universales Acuática y Sea World. (están a solo unos minutos). Está convenientemente cerca de restaurantes, supermercados, outlets, gasolineras, excelente ubicación para sus vacaciones

4.96 out of 5 average rating, 982 reviews

Treehouse in St. Cloud

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.

4.87 out of 5 average rating, 39 reviews

Flat in Kissimmee

“Cozy Studio apartment “

Welcome to our charming studio! Here’s what makes it special: Lake Views: Wake up to serene lake vistas right outside your window. Sparkling White Quartz Countertops Private Parking: Park conveniently right by your door—no hassle after a day of exploring. Nearby Attractions: Disney Park: Just 11 miles away, experience the magic of Disney. Universal Studios: A short 12-mile drive for thrilling adventures. Orlando International Airport: Only 9.6 miles—ideal for travelers

4.99 out of 5 average rating, 105 reviews

Home in Kissimmee

Traveler's Dream - King Bed, Pool, Games, Disney+

Welcome to our enchanting home, where magic and comfort collide! Nestled just moments away from the Disney parks, this whimsical haven is perfect for families and Disney enthusiasts alike. Dive into the magic with our sparkling pool, relax in our luxurious bedrooms, and enjoy the convenience of being a short stroll from the enchantment of Disney. Make your vacation a fairy tale come true – book your stay TODAY and let the memories begin!

Shipping container in Osceola County

4.96 out of 5 average rating, 49 reviews

Beautiful off-grid tiny home cottage #3

Retreat to the food covered grounds of this off-grid oasis in Central Florida, reconnect to the beauty and vibrancy of nature, and experience the magnitude of freedom and abundance it has to offer on your sustainable getaway. Your shipping container has a full kitchen, mini-split cooler and spacious shower with an on-demand water heater fed by pristine well water... you would never know you're off-grid!

4.96 out of 5 average rating, 109 reviews

Guest suite in Kissimmee

It's too much like a elegant mini-hotel (4)

It's too much like a elegant mini hotel with rich artistic atmosphere！ All the pictures on this page are a reflection of the real condition of the house. All the furniture has been carefully selected, and comfortable mattress and pillows will quickly accompany you into sweet dreams. The biggest feature of this house are comfort, economy and convenience.

5 out of 5 average rating, 26 reviews

Home in Osceola County

The Modern Retreat by Disney

The Azur Resort, a luxurious and family-friendly community, is ideally situated close to Disney World, offering the perfect balance of comfort and convenience for your vacation home needs.This stunning three-bedroom townhome at The Azur Resort exemplifies modern elegance and thoughtful design, ensuring a memorable stay for all.

4.88 out of 5 average rating, 42 reviews

Guest house in Kissimmee

Luxury Suite, only 15 miles to Disney World

Luxury room to enjoy your travel completely private with own entrance, bathroom, kitchen and laundry just for you, ideal space to couples at only 20 minutes away from almost all Disney World attractions, Sea World, Universal Orlando, Volcano Bay, Fun Spot and to much more Sorry don’t allow big truck and/or trailers

4.98 out of 5 average rating, 259 reviews

Guest house in Kissimmee

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!

Holiday rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Houses

A space that's all yours, with room for everyone

Villas

Luxurious estates for the ultimate escape

Popular amenities for Osceola County holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Osceola County

Private room in Davenport

4.99 out of 5 average rating, 70 reviews

Private room near Disney

LaurelRating, 5 stars2 weeks ago

I greatly enjoyed my stay with Rebecca, her son, Tyler, and their adorable dog, Lily. They were incredibly friendly and helpful, the room was cozy and comfortable, and the extra included snacks were a lovely treat! I felt right at home and was able to have some great conversations with Rebecca and Tyler. I would definitely recommend staying with them, and I hope I’ll have the chance to do so again sometime!

4.86 out of 5 average rating, 36 reviews

Suíte Master Privativa Disney

PatriciaRating, 5 stars3 days ago

Die Kommunikation mit Juliana war großartig – sogar spät in der Nacht hat sie noch schnell geantwortet. Besonders herzlich fand ich, dass sie sich proaktiv nach meiner Ankunft erkundigt und gefragt hat, ob alles in Ordnung sei. Die Ausstattung der Wohnung hat mich begeistert: eine hervorragend ausgestattete Küche, viele kleine Annehmlichkeiten im Bad (es gab sogar Wattestäbchen!) und hilfreiche, liebevoll platzierte Hinweise in der ganzen Wohnung. Ich habe mich rundum wohlgefühlt und konnte wunderbar entspannen. Einziger kleiner Kritikpunkt war die etwas laute Lüftung im Schlafzimmer, die direkt aufs Bett gerichtet war – aber das ist Jammern auf hohem Niveau.

4.88 out of 5 average rating, 49 reviews

9. Small room in paradise Resort+ FREE waterpark

StephanyRating, 5 stars2 weeks ago

La estadía fue excelente, Sofi siempre pendiente de todo, mucho gracias por todo, mi hijo y yo nos vamos muy satisfechos, volveremos.

4.89 out of 5 average rating, 121 reviews

Queen/Heated Pool/Gym/Kitchen/Free parking #3

Luiz HenriqueRating, 5 stars2 weeks ago

A casa é simplesmente linda — do tipo que eu adoraria morar! Tudo estava impecável: limpeza, organização, decoração e conforto. Me senti em casa desde o primeiro momento. O Carlos foi atencioso e prestativo, o que tornou a experiência ainda melhor. Com certeza voltaria e recomendo para qualquer pessoa que esteja procurando um lugar especial para ficar!

Superhost

4.72 out of 5 average rating, 101 reviews

Private room near Disney

RodrigoRating, 5 stars5 days ago

Shuoyan é uma anfitriã excelente, atenciosa, paciente uma excelente pessoa, sempre pronta a ajudar! Uma pessoa flexível e muito educada! Esteve sempre pronta para ajudar durante minha estadia! Foram excelentes dias!