Guesthouse vacation rentals in Kissimmee

A spacious studio contains a king-size bed with a light-colored quilt, flanked by two bedside lamps. A small refrigerator and kitchenette are visible in the corner, while a ceiling fan provides airflow. Windows are adorned with light curtains, allowing natural light into the room.

4.9 out of 5 average rating, 202 reviews

King-size Studio 4 min to Universal

Amazing location! king-size private studio, perfectly situated in the desirable Dr. Phillips area, You'll be just 4 minutes from the excitement of Universal Studios and CityWalk. "Restaurant Row," home to some of Orlando’s finest dining only 7 minutes away. The Orlando Convention Center is a quick 10-minute drive, MCO Airport is about 20 minutes away, and Disney is just 18 minutes from your doorstep. Newly remodeled bathroom, a convenient kitchenette, a fridge, a microwave, and a 65-inch TV

An outdoor patio area is furnished with a seating set featuring turquoise cushions, under a shaded pergola. A private pool reflects the blue sky, and a built-in grill is positioned nearby, enhancing the inviting atmosphere for relaxation and outdoor dining.

4.85 out of 5 average rating, 360 reviews

Couples Oasis *Heated Pool* and Lake View

Have a romantic getaway in this SODO Couples Oasis Retreat with private pool or come work alone in this peaceful oasis. Perfect for couples or the busy profesional who want privacy and quiet with lake view while relaxing by the pool. Centrally located in SODO by downtown Orlando. Close to everything. Walk to great nearby places like Kelly’s Hand Made Ice Cream only a 5-minute walk from the house. *Heated Pool* - Premium Linen Upgrade - Early Check In & Late Check Out - see details for fees

4.98 out of 5 average rating, 353 reviews

"Little Blue House" Getaway Near the Disney Parks

"Blue House" , Your Home Away from Home! Enjoy a comfortable and relaxing stay in our cozy Blue House. This completely independent accommodation features a bedroom with a Queen bed, private bathroom, living room with a sofa bed, dining area, and fully equipped kitchen. One designated parking space is included for 1 vehicle only. The vehicle must be parked only in the designated Blue House parking space. Parking on the grass or on the neighboring property is not permitted.

4.9 out of 5 average rating, 291 reviews

An open kitchen area features modern appliances, including a stainless steel refrigerator and stacked washer/dryer units. A round dining table surrounded by black chairs is illuminated by a decorative light fixture. A wall-mounted TV sits across from the dining space, enhancing practicality.

Guesthouse in Bay Hill

Modern Guest Studio with pool access

Private Guest Studio in a Perfect Orlando location, 5 minutes from I-Drive, Universal Studios, Disney World & Premium Shopping Outlets. Very Quiet lovely neighborhood with Biking distance to "Restaurant Row" where all your favorite restaurants are located. All major highways at your finger tips / ride 15 min to Disney! This space has an industrial modern look with high ceilings, Stay and cook with all the amenities including a Washer and Dryer.

An aerial view of the resort's main pool area showcases a large swimming pool with a surrounding patio. Sun loungers are arranged neatly, while additional shaded seating areas are provided. Lush palm trees and well-manicured landscaping enhance the tranquil ambiance.

4.9 out of 5 average rating, 100 reviews

Magical vacation getaway - 3 miles from Disney!

Located just a few miles of Disney World and minutes away from Universal Studios, SeaWorld, and all major convention centers in the Orlando area. This studio is located in an exclusive gated resort with high-end amenities including two pools, fitness center, spa, sauna, tennis courts, paved nature walk and more! Private Suite has an outside entrance with keypad. No shared spaces. (ALL SERVICES AND AMENITIES ARE INCLUDED IN YOUR STAY)

4.98 out of 5 average rating, 103 reviews

The Palm Oasis 2•Free Parking•Near Epic•MCO•Disney

🌴 The Palm Oasis 2 is not just a place to sleep—it's part of your Orlando experience. We create a private, impeccable, and carefully prepared space, where the small details make a difference. Just 7 minutes from Orlando International Airport, with free parking and a convenient location. Arrive, drop off your bags, and unwind. We prepare the space; you just enjoy your stay. ✨ We look forward to welcoming you to The Palm Oasis.

Guesthouse in Four Corners

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.

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.

4.98 out of 5 average rating, 538 reviews

4.9 out of 5 average rating, 171 reviews

Charming Studio | Near Disney & Universal

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. 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

Guesthouse in Buenaventura Lakes

cozy Fully self-contained/ kitchen and bathroom

Casa Venice: Your ideal Kissimmee retreat. Enjoy a peaceful, cozy stay near top attractions. Location & Proximity:Disney Parks & Old Town: 25 mins away. Shopping: 9 mins to Walmart, 7 mins to Aldi & Ross.Dining: Minutes from great local restaurants. Comfort & Safety:Quiet environment. Secure entrance.Private parking on-site.Perfect for a quick getaway or an unforgettable vacation!

4.99 out of 5 average rating, 127 reviews

A modern studio space is highlighted by a spacious bed with a grey wooden frame and blue accents. A kitchenette equipped with stainless steel appliances is visible, alongside a compact dining area. Natural light enters through window coverings, complementing the cozy atmosphere.

4.93 out of 5 average rating, 147 reviews

Modern & Cozy Retreat - Orlando City Center Epic

PRIVATE ORLANDO STUDIO — FULL KITCHEN + GREAT LOCATION! Enjoy a modern and comfortable private studio conveniently located between Downtown Orlando and the theme parks. With a queen bed, brand-new full kitchen, free laundry, fast WiFi + Ethernet, private entrance, and dedicated parking, this is a great home base for couples, solo travelers, business guests, or longer stays.

Guesthouse in Doctor Phillips

Universal Getaway Private Guesthouse + Kitchen

Your comfortable, modern Orlando home away from home is just 3 minutes from Universal and minutes from Epic Universe, Disney, SeaWorld, dining, and shopping. This private 1-bedroom guesthouse features a full kitchen, private entrance, cozy living space, and dedicated parking — perfect for couples, solo travelers, business travelers, or small families.

4.8 out of 5 average rating, 281 reviews

4.99 out of 5 average rating, 123 reviews

Beautiful garage suite w/washer and dryer

Enjoy a peaceful, centrally-located garage suite in Southwest Orlando—perfect for convention goers! Just 15 minutes from the airport, and Universal theme parks, 25 min drive to Disney theme parks , 10 min to Sea World and only a 20-minute walk to the JW Marriott and Ritz Carlton. Washer and dryer inside of the unit.

Popular amenities for Kissimmee guesthouse rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly guest house rentals

4.89 out of 5 average rating, 209 reviews

A stone pathway lined with gravel extends between two white fences, leading toward a small, dark wooden structure. Lush greenery is positioned beside the path, adding a natural touch to the tranquil setting.

Guesthouse in Oak Ridge

Tiny House behind Millenia Mall

4.8 out of 5 average rating, 619 reviews

Guesthouse in Oak Ridge

Cozy Private Studio Near Universal & Disney

A small outdoor seating area features two chairs with tropical-themed cushions and a metal table between them. A green decorative flower hangs on the wall, and the tiled floor reflects a light color. A door is positioned nearby, leading to the interior.

4.78 out of 5 average rating, 676 reviews

Little Studio, Small studio.

Guesthouse in Meadow Woods

Guest Home| Orlando Airport & Florida Mall 15 min

5.0 out of 5 average rating, 12 reviews

4.98 out of 5 average rating, 52 reviews

Private Suite Independent Entrance, All Amenities

4.95 out of 5 average rating, 44 reviews

Modern private studio | Full Kitchen | laundry

The entrance to Storey Lake is marked by a prominently displayed sign featuring colorful icons and a tropical design. Lush green grass surrounds the sign, complemented by vibrant pink flowers and several palm trees, all set against a bright blue sky with scattered clouds.

4.62 out of 5 average rating, 84 reviews

Steps from the Magic World! The best accomodation!

Guesthouse in Meadow Woods

Modern Private Studio near Orlando attractions

5.0 out of 5 average rating, 3 reviews

Guest house rentals with a patio

An outdoor pool is centered within a landscaped patio area, surrounded by lush greenery and mature plants. Two teak lounge chairs are positioned in the foreground, facing the calm water, while sun umbrellas and vibrant seating are visible nearby.

4.89 out of 5 average rating, 179 reviews

Vintage Florida Vibes House

4.95 out of 5 average rating, 107 reviews

comfortable stay

4.99 out of 5 average rating, 98 reviews

A heated saltwater pool is set within a landscaped backyard, featuring paver stones and surrounded by a white privacy fence. Colorful pool floats rest on the water's surface. Multiple lounge chairs and shade umbrellas are positioned around the pool, enhancing the relaxing outdoor space.

Guesthouse in Belle Isle

~Elegant Suite • Luxe Pool • Prime Orlando Stay

A bright living area is presented with vaulted ceilings and hardwood floors. Comfortable seating is arranged around a central coffee table, with soft lighting provided by table lamps. Natural light filters through the windows, illuminating the decor and creating a welcoming atmosphere.

4.86 out of 5 average rating, 127 reviews

Historic lakefront guesthouse

A bright sleeping area features a white metal bed adorned with a yellow blanket and decorative pillows. Two bedside lamps provide soft lighting, while round wall art pieces add a touch of color. A ceiling fan is mounted above for air circulation.

4.9 out of 5 average rating, 101 reviews

Cozy new guesthouse to yourself.

5.0 out of 5 average rating, 20 reviews

Cozy Guest House Near MCO & Theme Parks

4.82 out of 5 average rating, 57 reviews

The Villa Stay

Guesthouse in Buenaventura Lakes

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.

Orange Blossom Apartment

5.0 out of 5 average rating, 35 reviews

Guest house rentals with a washer and dryer

A living area is presented with a comfortable gray sofa adorned with decorative pillows. A white coffee table is centered in front, accompanied by a minimalist glass side table. Tall plants bring a touch of greenery, while a television completes the space.

4.93 out of 5 average rating, 159 reviews

Kyle's Place - Private Unit, Pool + Laundry Room

Guesthouse in Winter Garden

A place with a view

4.9 out of 5 average rating, 107 reviews

4.93 out of 5 average rating, 104 reviews

A cozy sleeping area is highlighted by a vibrant yellow bedspread. Decorative pillows in shades of blue and red accent the bed, complemented by a colorful wall art piece overhead. A stylish blue chair with a red pillow is positioned to the side, alongside a doorway.

Guesthouse in Davenport

Near Disney world, Beauty & Beast Theme, Sleeps 4

A comfortable living area is furnished with a dark sofa and an armchair. A light-colored throw blanket is draped over the sofa, and a patterned area rug adds warmth to the tiled floor. Natural light streams through the windows, illuminating the dining area in the background.

4.86 out of 5 average rating, 112 reviews

1/1 Private Guesthouse in Orlando (South Downtown)

The studio features a spacious sleeping area with a queen bed dressed in soft linens. A cozy seating area with striped chairs and a wooden desk is visible. The kitchen area includes modern appliances, while natural light enters through the nearby windows, illuminating the warm terracotta tile floor.

4.89 out of 5 average rating, 291 reviews

Cozy Guest Home 1.8 Miles from City Center

A cozy corner of a bedroom features a nightstand with a decorative lamp casting a warm glow. A vibrant artwork of a flamingo is displayed on the wall, complementing the colorful pillows atop the spacious bed. Natural light filters in from a nearby window.

4.88 out of 5 average rating, 546 reviews

Bungalow Close to Attractions and Downtown Orlando

4.83 out of 5 average rating, 185 reviews

Cozy Tiny House Near Orlando Airport & Theme Parks

A spacious outdoor area features a fire pit surrounded by seating options, including loungers and umbrellas. Lush greenery adds a natural backdrop, and the setting is illuminated by a warm evening glow, creating a welcoming environment for relaxation.