Guesthouse holiday 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.

4.87 out of 5 average rating, 148 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 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, 160 reviews

Vintage Florida Vibes House

Enjoy a peaceful & stylish getaway in this detached Guesthouse with private entrance, gardens, kitchen & pool. Sip coffee in the shade of our Oak trees. Grill out while you watch TV and cool off in the pool after a day at the parks. Sit under the stars and string lights and nestle into your cozy beds, with your own dedicated central AC unit and ceiling fans to keep you comfortable. Only 2 miles from downtown Orlando and directly off the I4 highway that takes you to every park & attraction.

4.9 out of 5 average rating, 150 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

Guesthouse in Wadeview Park

A spacious bedroom features a large bed with white bedding and decorative pillows. Two soft bedside lamps illuminate the area, complemented by a cozy armchair and a decorative bench at the foot of the bed. Exposed brick wall accents the room.

4.98 out of 5 average rating, 120 reviews

The Cottage A Pet Friendly Guesthouse

Welcome to The Cottage! A pet friendly, super cute, and quiet studio apartment built in 2016, located above the detached garage behind my house. Pets always stay for free, and no additional cleaning fees are charged. Private self access is provided so you come and go as you please. The unit has a full kitchen, king sized bed, 4 pillows, 100% cotton sheets and coverlet. Laundry detergent and dish soap are provided. Trash is located on the west sideof the building.

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, 502 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.

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, 331 reviews

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

Our place is a 2BR, one-bath entire home, with a cozy fire pit and patio furniture space, a fun kids playground area, and a large sunny yard with mature trees for you and guests to explore and enjoy. Excellent location within 15 mins driving distance to the main Disney amusement parks. Free WiFi and HDTV with streaming services available. Please read “Guest Access” for note on other house in the property.

Guesthouse in Southern Oaks

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, 111 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.

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.

4.94 out of 5 average rating, 118 reviews

Brand new beautiful apartment

Enjoy the simplicity of this quiet, central and cozy place to stay . It is a spectacular studio apartment with independent entrance to the house . And the entire home is available only for guest use . With grill area. 15 min from the orlando airport and 20 min from the parks . Close to outlets and the center convention. Parking is available and if you want a transfer we could also help you

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.

4.91 out of 5 average rating, 286 reviews

Cozy Guesthouse Getaway

Welcome to our private studio guesthouse with queen mattress, full bath, kitchenette, mini fridge, microwave, coffee maker, WiFi, and cable TV. Convenient access to downtown, theme parks, beaches, and the turnpike. Perfect for the traveling business person or the amusement park visitor!

4.98 out of 5 average rating, 296 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.

4.95 out of 5 average rating, 201 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.

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.

4.86 out of 5 average rating, 117 reviews

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!

Popular amenities for Kissimmee guesthouses

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-Friendly guesthouses

4.84 out of 5 average rating, 49 reviews

The living room is spacious with comfortable seating arrangements, including a dark gray sofa and a light gray couch facing a wall-mounted TV. A coffee table is centered on a patterned area rug, while natural light enters through large windows leading to the back patio.

Guesthouse in Davenport

Inviting 3 br haven: vaca/work

A two-story building is set in a green yard with shade from large trees. The exterior features a staircase leading to an upstairs unit, complemented by various plants and shrubs along the base. Clear blue skies provide a bright backdrop.

4.89 out of 5 average rating, 9 reviews

Upstairs cottage room by airport

A cozy room features a blue upholstered bed, complemented by a decorative pillow. Two abstract art pieces adorn the wall above. A kitchenette with modern appliances is visible in the background, alongside light-toned cabinetry and a small dining area.

4.92 out of 5 average rating, 49 reviews

Spectacular Relaxing Blue Moon-EPIC,OIA,Fl Mall

Guesthouse in Winter Garden

4.89 out of 5 average rating, 91 reviews

A place with a view

4.94 out of 5 average rating, 35 reviews

A two-story home features a mix of wood and siding on its facade. Large windows enhance natural light, while a spacious garage is visible beneath the front entry. The driveway is paved with stone and bordered by manicured landscaping, providing an inviting approach.

Guesthouse in Reunion fl

BeachGuyDave's Reunion Guesthome

A kitchenette area is visible, featuring a black refrigerator, a sink with storage cabinets above, and a coffee machine on the countertop. A wooden table with a light finish and a chair can be seen, along with a large mirror reflecting part of the room.

4.88 out of 5 average rating, 34 reviews

Convenient Getaway Near Orlando Hotspots

A modern kitchenette is showcased, featuring white cabinetry and a sleek countertop. A microwave is positioned above the sink, which is paired with a stylish faucet. A single-serve coffee maker and an induction cooktop are also present on the countertop, complemented by a compact refrigerator.

4.87 out of 5 average rating, 23 reviews

Modern & Cozy Studio|Private Retreat w Kitchenette

A private patio area features a round glass table surrounded by two white chairs. A large blue umbrella provides shade, and small potted plants are placed on either side, enhancing the tranquil setting. The space is enclosed with a white fence.

5 out of 5 average rating, 9 reviews

BRAND NEW! 1 Bedroom APT

Guesthouses with a patio

4.9 out of 5 average rating, 42 reviews

Crystal-clear water is visible in the pool, with water features gently cascading into the inviting surface. The surrounding area includes a spacious outdoor living space, offering a calming blend of greenery and comfortable seating.

Guesthouse in Davenport

Privatepool studio near Disney Restaurants & Shops

A spacious deck features wooden steps leading to a cozy house. Lush greenery surrounds the area, with vibrant plants visible on the deck. Large glass doors provide a view into the interior space, inviting light and natural elements into the setting.

5 out of 5 average rating, 24 reviews

Charming Lakeside small House

A shared private pool area features a clear blue pool surrounded by light-colored paving stones. Palm trees and green foliage are visible in the background, with a serene lake reflecting the sky. Lounge chairs are arranged nearby, providing a relaxing outdoor space.

4.96 out of 5 average rating, 26 reviews

Lakeside Palm Escape

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.

4.92 out of 5 average rating, 25 reviews

Private 2BR Guesthouse + Pool-Heart of Kissimmee!

4.94 out of 5 average rating, 49 reviews

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

Thousand Oaks Peaceful Studio with Private Pool

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.

4.97 out of 5 average rating, 75 reviews

Orlando Private Tiny Guest House

5 out of 5 average rating, 5 reviews

Sage Guest House

4.97 out of 5 average rating, 30 reviews

Guest Home| Orlando Airport & Florida Mall 15 Min

Guest house rentals with a washing machine and dryer

A modern living area features a black sofa adorned with a soft white throw blanket and decorative pillows. A pair of round coffee tables, one with greenery, rests on a light-colored floor. Art hangs on the wall above, complemented by a window covered with shades.

5 out of 5 average rating, 31 reviews

Cozy Lake View Stay

Guesthouse in Wadeview Park

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.

4.85 out of 5 average rating, 112 reviews

Relaxing Private Studio in the Trees!

The studio features a spacious queen size bed with a warm throw blanket, paired with nightstands on either side. A dining area with high chairs is visible near a modern kitchen, which includes stainless steel appliances. A ceiling fan and artwork enhance the stylish decor.

4.96 out of 5 average rating, 142 reviews

Modern 1950s Studio • Near Downtown & Theme Parks

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.

4.92 out of 5 average rating, 132 reviews

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

The living area features a soft mustard-yellow sofa complemented by two green accent chairs. A glass coffee table sits in front of the sofa, and a large flat-screen TV is mounted on the wall, above a decorative piece showcasing soothing colors.

4.95 out of 5 average rating, 161 reviews

The 𝕆𝕣𝕝𝕒𝕟𝕕𝕠 is the first step in the process.

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, 117 reviews

Modern & Cozy Retreat - Orlando City Center Epic

A modern kitchen features dark cabinetry with gold accents. An island offers two bar stools, while a farmhouse sink and stainless steel appliances are prominently displayed. Warm lighting highlights the white backsplash and countertop, contrasting with the wood-tone flooring.

4.96 out of 5 average rating, 23 reviews

Boutique Suite in Orlando

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.