Guesthouse holiday rentals in Kissimmee

Guesthouse in Winter Garden

4.9 out of 5 average rating, 105 reviews

A place with a view

Welcome to Your Secluded Getaway Enjoy a quiet retreat minutes from supermarkets and Florida’s top attractions. Urgent care , Emergency room & Hospital are all nearby Top Attractions Island H2O: 23m | Epcot: 27m | SeaWorld: 32m Disney Springs: 34m | Universal: 36m Legoland: 1h | Busch Gardens: 1h 27m Shopping & Dining Winter Garden/Clermont14m Outlets 28m | Florida Mall 35m | I-Drive 40m Travel MCO Airport 40m Oversized Parking: Dedicated space for boats, RVs, and moving trucks. storage only

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.

4.94 out of 5 average rating, 160 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

4.9 out of 5 average rating, 289 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.

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.

4.98 out of 5 average rating, 529 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.

4.9 out of 5 average rating, 168 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

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.

4.85 out of 5 average rating, 123 reviews

Historic lakefront guesthouse

Relax and enjoy the serenity of this historic guesthouse with large grounds and a beautiful lake. Start out your day with a cup of your favorite coffee out on the balcony or shoreside, watching the sun reflect off the lake and listening to nature. Then take out a kayak or paddle board for a bit of cardio before heading out to the parks, or enjoy some of Orlando’s hidden secrets for a bit of local fun.

Guesthouse in Buenaventura Lakes

4.99 out of 5 average rating, 125 reviews

cozy Fully self-contained/ kitchen and bathroom

Casa Venice, cozy, ideal for a short stay or an unforgettable vacation in Kissimmee, close to the best tourist attractions, restaurants and natural parks Clean, quiet 30 minutes to Disney parks, Old Town, lots of great food locations nearby. 9 minutes to Walmart, 7 minutes to Aldi 7 minutes to Ross, and more Safe and secure entrance. Private parking

A comfortable sleeping area features a spacious bed covered with a floral-patterned blanket. Two bedside lamps provide soft lighting. A small dining table with four chairs is positioned nearby, and a kitchenette is seen in the background with modern appliances and cabinetry.

4.99 out of 5 average rating, 115 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.

4.93 out of 5 average rating, 102 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

Beauty & Beast Guest House, Near Disney, Sleeps 4

Magical Beauty & the Beast guest house with queen bed + hidden pull-out Twin XL, sofa bed, themed decor, coffee bar, and in-suite washer/dryer. Quiet cul-de-sac location near Disney & Orlando theme parks. Perfect for families, couples, or small groups seeking comfort, convenience, and a magical stay!

4.98 out of 5 average rating, 337 reviews

"Little Blue House" Getaway Near the Disney Parks

Blue House, 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.

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.

4.95 out of 5 average rating, 138 reviews

Modern & Cozy Retreat - Orlando City Center Epic

Welcome to your ultimate Orlando retreat! Our beautifully decorated guesthouse offers a blend of luxury and comfort- designed to make your stay unforgettable. Spacious and elegantly appointed, this home features high-end finishes, tasteful decor & all the amenities you could desire.

4.95 out of 5 average rating, 223 reviews

A well-equipped kitchen is visible, featuring modern cabinetry and stainless steel appliances. A small dining table is positioned in the foreground, adorned with a vase of fresh flowers. The backsplash adds a touch of elegance, complementing the overall clean and bright design.

Guesthouse in Clermont

Modern efficiency ~ Great location

Modern and very comfortable efficiency with private entrance, 1 free parking at driveway, equipped kitchen, 1 queen bed & 1 futon. Only 20 min drive to Magic Kingdom, 35 min to Universal, 25 min to Disney Springs and close to many other attractions.

Popular amenities for Kissimmee guesthouses

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-Friendly guesthouses

A bright living area is shown featuring a large flat-screen TV on a dark dresser, accompanied by a blue and white patterned area rug. A small dining table with tall chairs is positioned near a window, with a decorative plant and artwork adding a touch of color to the space.

4.92 out of 5 average rating, 306 reviews

Cozy Guesthouse Getaway

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, 669 reviews

Little Studio, Small studio.

Guesthouse in Williamsburg

A modern kitchen area features white cabinetry with brass knobs and open shelving that displays decorative items. Stainless steel appliances, including a refrigerator and microwave, are visible. A coffee maker and cooking utensils are arranged on the countertop, contributing to a functional cooking space.

4.87 out of 5 average rating, 153 reviews

Great accommodation in Orlando!

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!

Guesthouse in Doctor Phillips

4.81 out of 5 average rating, 278 reviews

Modern 1BR Guesthouse • Prime Orlando Location

4.88 out of 5 average rating, 197 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

4.95 out of 5 average rating, 121 reviews

•The Sapphire Luxury Suite•Near Epic~MCO~Disney

Guesthouse in Meadow Woods

4.96 out of 5 average rating, 48 reviews

Guest Home_ Orlando Airport and Disney

Guesthouses with a patio

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.

4.84 out of 5 average rating, 348 reviews

Couples Oasis *Heated Pool* and Lake View

Guesthouse in Buenaventura Lakes

4.94 out of 5 average rating, 190 reviews

Beautiful brand new apartment

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, 194 reviews

King-size Studio 4 min to Universal

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.

4.9 out of 5 average rating, 173 reviews

Vintage Florida Vibes House

Guesthouse in Meadow Woods

5.0 out of 5 average rating, 11 reviews

Modern Boutique Retreat Near MCO Airport

5.0 out of 5 average rating, 11 reviews

Cozy Guest House Near MCO & Theme Parks

4.81 out of 5 average rating, 48 reviews

The Villa Stay

4.98 out of 5 average rating, 45 reviews

Guesthouse in Belle Isle

~ Luxe Modern Suite • Heated Pool • 2BR Gem

Guest house rentals with a washing machine and dryer

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, 538 reviews

Bungalow Close to Attractions and Downtown Orlando

The modern kitchen features a spacious island with seating for four. A vibrant yellow door adds a pop of color to the neutral decor. Stainless steel appliances and pendant lighting enhance the contemporary design, complemented by white tile backsplash and wooden accents.

4.93 out of 5 average rating, 349 reviews

CLEAN & Modern 2BR w/ sunny yard, close to Disney

4.82 out of 5 average rating, 173 reviews

Cozy Tiny House Near Orlando Airport & Theme Parks

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

4.88 out of 5 average rating, 217 reviews

A bright living space features a comfortable sofa and a vintage trunk as a coffee table. This area includes a dining table set for four and a compact kitchen with bar seating. Natural light fills the room through large windows, highlighting colorful wall art.

Guesthouse in Davenport

Winsome Farm Guest House

5.0 out of 5 average rating, 20 reviews

Brand New Cozy Space - 15 Min From Disney & Shops.

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.

5.0 out of 5 average rating, 34 reviews

Orange Blossom Apartment