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Guesthouse vacation rentals in Osceola County

Find and book unique guesthouse rentals on Airbnb

Top-rated guesthouse rentals in Osceola County

Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

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Top guest favorite
A serene bedroom features a queen bed with light blue linens and an elegant headboard. A cozy wingback chair and a full-length mirror offer additional comfort. A woven rug complements the space, while windows allow natural light to brighten the room.
Guesthouse in Kissimmee
5 out of 5 average rating, 16 reviews

The Forrestry

The Forrestry is the ideal launching pad for visits to the parks. Perfectly priced so you can enjoy Disney, SeaWorld, Legoland & Universal's Epic Universe. The garden gate opens to a spacious patio. This cozy retreat is a great room concept. A coffee bar with snacks greets you on entry into the living room, with a comfortable sofa bed and a multi-use table for games and dining. A well-equipped kitchen and laundry room flank it. The bedroom suite has a spacious walk-in closet and bathroom.

Guest favorite
Guesthouse in Kissimmee
4.91 out of 5 average rating, 143 reviews

Cozy & 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

Top guest favorite
A tranquil pool area reflects the softly illuminated surroundings created by string lights overhead. Sliding glass doors lead to an inviting interior space, framed by palm trees that gently sway in the evening breeze.
Guesthouse in Davenport
4.96 out of 5 average rating, 45 reviews

Thousand Oaks Peaceful Studio with Private Pool

Take a break in your private pool and unwind at this peaceful oasis! Escape to this serene studio, just a short drive from the magic of Disney World and Universal Studios. Enjoy the exclusive use of the pool, perfect for relaxation and sunbathing. The house next door is a completely separate unit and does not have use of the pool. If you are traveling with friends and/or family, we also have another studio right next door! Check it out here: https://www.airbnb.com/l/AY7X1u4B

Top guest favorite
A brightly painted tiny home is showcased against a serene backdrop. The exterior features red and yellow hues with a blue door and window. Two blue chairs are positioned beside a small table, creating an outdoor seating area surrounded by lush greenery.
Guesthouse in Kissimmee
4.98 out of 5 average rating, 53 reviews

Orlando Private Tiny Guest House

*Quiet, safe neighborhood Premium location *20 minutes to Orlando Airport *20 minutes to Disney parks & Disney Springs *25 minutes to Universal Studios & CityWalk *7 minutes to shopping plaza with top outlets and diverse dining *5 minutes to super Walmart *Local minimarkets. Inside your tiny home: *Queen-size bed *Coffee, fridge & microwave *Private entrance + patio *Modern shower *Air conditioning, Wi-Fi & Smart TV *Need transportation or special arrangements? Let us know

Guest favorite
A bright bedroom features a spacious bed with white linens and decorative pillows. Light-colored walls are complemented by a ceiling fan. Natural light enters through a nearby window, and simple decor adds a relaxed feel. A chair is placed beside the bed for added comfort.
Guesthouse in Lake Hamilton
4.89 out of 5 average rating, 265 reviews

Luxury Cottage Near Legoland & Chain of Lakes

The Old Florida Cottage, in the quaint community of Lake Hamilton, just 5-miles from Legoland, less than an hour from Disney, and minutes away from the only public boat access to Lake Hamilton, is your perfect getaway! Enjoy a fully-equipped kitchen, a luxurious suite and modern bathroom, surrounded by Old Florida decor. We look forward to welcoming you to the cottage, with its own entrance and dedicated parking, located on a quiet street. Your home away from home!

Top guest favorite
A spacious bed is dressed in a patterned duvet with a combination of navy and white colors. Soft coral pillows add a pop of color. A small nightstand is positioned beside it, featuring a unique lamp. The room is softly illuminated, creating a cozy ambiance.
Guesthouse in Kissimmee
4.96 out of 5 average rating, 103 reviews

Bello apartamento a estrenar

Disfruta de la sencillez de este alojamiento tranquilo, céntrico y acogedor . Es un apartamento espectacular tipo estudio con entrada independiente a la casa . Y todo el alojamiento está disponible solo para los huéspedes . Con área de parrilla . A 15 min del aeropuerto de orlando y 20 min de los parques . Cerca de los outlets y del convención center. Contamos con estacionamiento y si deseas traslado también podríamos ayudarte

Top guest favorite
A cozy bedroom features a tufted gray headboard above a neatly made bed with white linens. Decorative pillows are arranged on the bed, and whimsical letters spelling 'DREAM' adorn the wall above. Two bedside tables with lamps provide a soft glow.
Guesthouse in Four Corners
4.98 out of 5 average rating, 498 reviews

Quiet Room Close to Disney and Attractions

Quaint and quiet retreat just minutes from attractions. Private in-law suite and bathroom, detached from main house. Features all the basic amenities of a hotel room with the feeling of home. Room is perfect for up to three persons. Queen bed and additional sleeper sofa. Located in Reunion Resort. There is a pool, gym, and spa located within the resort but not on the property and is for Reunion club members only.

Superhost
Large sliding glass doors provide a view of the outdoor scenery, showcasing lush greenery and a peaceful lakeside. A small table is positioned beside the bed, with direct access to the refreshing natural light filtering through the screen.
Guesthouse in Kissimmee
4.75 out of 5 average rating, 65 reviews

Tiny Lakeview Suite Near Disney & Universal

Our cozy Tiny suite offers a stunning lake view right from the bed, thanks to the large sliding windows. Enjoy the sunrise in the morning without even getting up – pure relaxation. You’re just 20-25 minutes away from top attractions like Disney World, Universal Studios, outlet malls, and the airport. Perfect for couples or solo travelers who value comfort and privacy. An ideal retreat after a fun-filled day.

Superhost
A well-appointed bedroom features a spacious bed centered against a stylish black headboard. Two bedside tables with sconces provide soft lighting. A bench with a textured fabric sits at the foot of the bed, and natural light enters through a covered window, creating a calm ambiance.
Guesthouse in Kissimmee
4.78 out of 5 average rating, 9 reviews

Hermosa habitación para pareja

En este lugar encontrarás todo lo esencial para pasar una estancia agradable y acogedora disfrutando su viaje con total privacidad, con entrada propia, baño, cocina y lavandería solo para usted. Ideal para parejas, a solo 20 minutos de casi todas las atracciones de Disney World, Sea World, Universal Orlando, Volcano Bay, Fun Spot y mucho más. Lo sentimos, no se permiten camiones grandes ni remolques.

Top guest favorite
A contemporary living area features a comfortable sofa, accentuated by a decorative coffee table. A wall-mounted television displays vibrant artwork, while natural light filters through the window with blinds. A well-equipped kitchenette is visible, promoting a sense of functionality and modern design.
Guesthouse in Kissimmee
5 out of 5 average rating, 19 reviews

Orange Blossom Apartment

Welcome to the Orange Blossom Apartment - Your Private Oasis! Escape to your own private oasis at Orange Blossom Apartment, a charming and comfortable guest suite nestled within a tranquil home. Enjoy complete privacy with a dedicated entrance, making your stay truly independent and relaxing. Centrally located so you are just a few miles away from all of Central Florida’s major attractions!

Top guest favorite
A spacious sleeping area is presented with a modern bed adorned with a patterned blanket and vibrant yellow accents. An armchair in a bright tone complements the decor. Artistic cityscape images are displayed on the walls, enhancing the contemporary ambiance.
Guesthouse in Kissimmee
4.99 out of 5 average rating, 102 reviews

a nice place near Disney! Kissimmee, FL!

Casa Venice, acogedora, ideal para pasar una corta estancia o tener unas vacaciones inolvidables en Kissimmee, cerca a las mejores atracciones turísticas, restaurantes y parques naturales Clean, quiet 30 minutes to Disney parks, Old Town, lots of great food locations near by. 9m walmart, 7m Aldi 7m Ross, and more Safe and secure entrance. privateparking

Top guest favorite
Guesthouse in Kissimmee
4.98 out of 5 average rating, 285 reviews

"Little Blue House" Getaway Near the Disney Parks

Your home away from home! Enjoy a comfortable and relaxing stay in our Casa Azul. Spacious and modern, it features a bedroom with a double bed, a private bathroom, a living room with a sofa bed, a dining room, and a fully equipped kitchen. Ideal for vacations with family or friends.

Popular amenities for Osceola County guesthouse rentals

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