Guesthouse holiday rentals in Kissimmee

4.82 out of 5 average rating, 181 reviews

Cozy Tiny House Near Orlando Airport & Theme Parks

Orlando International Airport (MCO) 8 miles away. Distance Parks and more: The Florida Mall 4.4 millas. Orlando Kart Center 4.4 millas. Aquatica (8.3 millas). Orange County Convention Center (9.9 millas.), Icon Park Orlando (11 miles). Lake Eola Park. (8.6 m). ✨Amway Center. (9.1 millas) Discovery Cove (7.5 millas).🐬 SeaWorld (9 millas.) Perfect for vacations, business trips, Disney, Universal & Orlando adventures. Conveniently located from MCO airport, shopping, restaurants & attractions.

ValueFamilyOutdoor spaces

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, 198 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

LocationFamilyCleanliness

4.98 out of 5 average rating, 351 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.

LocationValueAccess

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.

LocationValueComfort

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)

LocationFamilyLong stay

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.

FamilyValueCleanliness

4.98 out of 5 average rating, 535 reviews

4.91 out of 5 average rating, 169 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

LocationFamilyWalkability

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, 126 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.

FamilyLocationParking

Guesthouse in Buenaventura Lakes

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

ValueLocationBathroom

4.99 out of 5 average rating, 125 reviews

4.99 out of 5 average rating, 121 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.

ValueFamilyHospitality

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

Beauty & Beast Theme, Near Disney world, Sleeps 4

Magical Beauty & the Beast guest House with a 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!

FamilyLocationHospitality

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.

Great accommodation in Orlando!

Private home with exceptional location in the city of Orlando - Florida📍 The house has a smart front door, kitchen and bathrooms equipped with everything you need! It also has free parking. Just minutes from Orlando and Universal water parks!

FamilyValueKitchen

4.87 out of 5 average rating, 156 reviews

Popular amenities for Kissimmee guesthouses

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-Friendly guesthouses

4.94 out of 5 average rating, 228 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

LocationFamilyQuiet

4.88 out of 5 average rating, 206 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

FamilyLocationAmenities

A cozy living area features a dark gray sofa with bright yellow accent pillows and a matching ottoman. There are two wooden side tables with potted plants placed on them, and a wall art piece displaying the word 'FAMILY' hangs above.

4.82 out of 5 average rating, 642 reviews

Spacious getaway close to Universal and Outlets!

ValueFamilyWalkability

Guesthouse in Doctor Phillips

Modern 1BR Guesthouse • Prime Orlando Location

LocationFamilySolo travel

4.8 out of 5 average rating, 279 reviews

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, 674 reviews

Little Studio, Small studio.

LocationValueGetting around

Guesthouse in Meadow Woods

Guest Home| Orlando Airport & Florida Mall 15 min

LocationBathroomCleanliness

5.0 out of 5 average rating, 7 reviews

4.76 out of 5 average rating, 74 reviews

A house near Disney and Universal - mikeyfl-1

LocationFamilyBathroom

5.0 out of 5 average rating, 8 reviews

Magic Stay Cozy Studio near Disney & Universal

FamilyAmenitiesComfort

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, 354 reviews

Couples Oasis *Heated Pool* and Lake View

FamilyLocationCondition

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, 178 reviews

Vintage Florida Vibes House

LocationValueWalkability

5.0 out of 5 average rating, 18 reviews

Cozy Guest House Near MCO & Theme Parks

LocationIndoor spacesQuiet

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

LocationValueQuiet

5.0 out of 5 average rating, 35 reviews

Guesthouse in Meadow Woods

Modern Boutique Retreat Near MCO Airport

ValueLocationHospitality

5.0 out of 5 average rating, 21 reviews

4.85 out of 5 average rating, 41 reviews

Nature Escape

ValueFamilyHospitality

The collage displays four areas of the guesthouse. A clear pool reflects light under a shaded umbrella. A cozy bedroom features a full-over-queen bunk bed with bright wall decorations. The kitchen counter showcases a well-stocked drawer of snacks and essentials. Greenery adds warmth throughout.

4.94 out of 5 average rating, 34 reviews

Private 2BR Guesthouse + Pool-Heart of Kissimmee!

ValueFamilyGetting around

A well-lit bedroom features a spacious bed with gray and white linens. A lamp with a warm glow stands on a nightstand. A large sliding door provides a view of the outdoor space, complemented by sheer curtains that allow natural light to filter in.

4.76 out of 5 average rating, 51 reviews

Guest Suite w/ Private Pool Near Disney

ValueLocationHospitality

Guest house rentals with a washing machine and dryer

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, 350 reviews

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

FamilyValueCleanliness

Guesthouse in Winter Garden

A place with a view

FamilyValueAccuracy

4.9 out of 5 average rating, 107 reviews

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, 544 reviews

Bungalow Close to Attractions and Downtown Orlando

FamilyValueComfort

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

ValueLocationCheck-in

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)

ValueFamilyCheckout

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.

4.92 out of 5 average rating, 145 reviews

Modern & Cozy Retreat - Orlando City Center Epic

LocationValueKitchen

4.88 out of 5 average rating, 219 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

LocationValueGetting around