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, 141 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 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.

4.9 out of 5 average rating, 279 reviews

Modern Guest Studio (Private) Pool / Spa available

Private Guest Studio (Not Shared ) 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. Pool & Spa available (Not Shared) 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.

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, 591 reviews

Spacious getaway close to Universal and Outlets!

PLEASE READ BEFORE BOOKING Checkin -4pm Checkout-10am Welcome to our home! The home is a basement apartment with private entrance ,driveway for one car, and one bedroom in your suite with 2 queen size beds, sofa pull out,and kitchen (portable burners NO STOVE) and a large bathroom with double shower head. This is your own space we have zero way to interact with you but we are a family who lives above you similar to neighbors in apartment. 5 min- universal 10 min- outlets 20 min- Disney

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

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, 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.

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, 325 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.

4.84 out of 5 average rating, 109 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.

4.93 out of 5 average rating, 107 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 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.

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

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, 281 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, 286 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.

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, 113 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

Guesthouse in Four Corners

A light blue exterior of a two-story house is visible, featuring white railings and a staircase leading to the entrance. The landscape includes neatly trimmed shrubs and palm trees, contributing to a welcoming atmosphere. Two garage doors are accessible below the house.

4.82 out of 5 average rating, 73 reviews

Spacious Guesthouse in Reunion Resort w/ Pool

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, 24 reviews

Private 2BR Guesthouse + Pool-Heart of Kissimmee!

4.96 out of 5 average rating, 52 reviews

comfortable stay

An inviting kitchen and dining area are visible, featuring a wooden dining table with four chairs and soft lighting. A cozy sofa adorned with decorative cushions is placed nearby. Natural light filters through the window, while a fan offers a touch of comfort.

4.71 out of 5 average rating, 45 reviews

A house near Disney and Universal - mikeyfl-1

The kitchen space is equipped with essential appliances, including a microwave and coffee maker. A door leads to a patio area featuring outdoor seating. The light-colored cabinetry contrasts with the dark countertops, while colorful cups hang decoratively on the wall.

4.85 out of 5 average rating, 152 reviews

Break.

A cozy futon, adorned with a decorative pillow, is positioned in a well-lit space. It faces a small side table with a lamp and a wooden dresser, reflecting a blend of comfort and functionality. Soft natural light streams through a nearby window.

4.92 out of 5 average rating, 64 reviews

Nature Kissed Casita. Embrace the chill!

5 out of 5 average rating, 6 reviews

Guest Suite at Reunion Golf Resort close to Disney

A well-lit bedroom features a spacious bed with crisp bedding and two bedside lamps on dark nightstands. A ceiling fan provides airflow. A closet is visible in the background, along with a door leading to the bathroom, enhancing the room's functional design.

4.61 out of 5 average rating, 74 reviews

Guest Suite 15 minutes from Disney

Guesthouses with a patio

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, 19 reviews

Charming Lakeside small House

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.

4.91 out of 5 average rating, 35 reviews

Privatepool studio near Disney Restaurants & Shops

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.

4.84 out of 5 average rating, 45 reviews

Inviting 3 br haven: vaca/work

5 out of 5 average rating, 4 reviews

~ Luxe Modern Suite • Heated Pool • 2BR Gem

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.

4.96 out of 5 average rating, 45 reviews

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.

4.98 out of 5 average rating, 55 reviews

Orlando Private Tiny Guest House

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.

4.9 out of 5 average rating, 30 reviews

Convenient Getaway Near Orlando Hotspots

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, 6 reviews

BRAND NEW! 1 Bedroom APT

Guest house rentals with a washing machine and dryer

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, 25 reviews

Lakeside Palm Escape

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, 24 reviews

Cozy Lake View Stay

A kayak glides through calm waters surrounded by lush greenery, with a wooden dock visible in the background. Tall trees frame the scene, providing a serene atmosphere. This image highlights the tranquility and natural beauty of the area, reflective of the unit's peaceful surroundings.

4.5 out of 5 average rating, 12 reviews

Waterfront/KayakFishing/nearDisney&LakeTohoa/Pets

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.

4.94 out of 5 average rating, 78 reviews

Beauty & Beast Guest House, Near Disney, Sleeps 4

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.

4.78 out of 5 average rating, 9 reviews

Beautiful room for couples

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.

4.95 out of 5 average rating, 19 reviews

Boutique Suite in Orlando

Guesthouse in Four Corners

5 out of 5 average rating, 11 reviews

MR 2 - Comfort and Privacy

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.