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.

4.87 out of 5 average rating, 145 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, 280 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.

Guesthouse in Lake Cherokee

A serene pool area is surrounded by lush tropical greenery, including palm trees and bamboo. A spa is integrated into the pool with a stone wall feature. Chaises with striped cushions are positioned beside the water, and a spacious patio includes various stone pavers.

4.97 out of 5 average rating, 119 reviews

1924 Spanish Carriage House Lower

Enjoy a shared but private compound resort in the heart of downtown Orlando! Centrally located and within walking distance to major events at the Kia Center, Dr. Phillips Performing Arts Center, restaurants, and downtown nightlife. Park on site, relax and enjoy all that this historic home has to share! Besides a fresh and clean private lodging, you'll enjoy use of the tropical pool, hot tub, gas grill, covered seating and dining area. A washer and dryer are just steps away for your use.

The kitchen area features white cabinetry and a granite countertop, accompanied by a mini-fridge, microwave, and a coffee maker. A washer and dryer are integrated into the cabinetry. A dark upholstered bench is positioned nearby, enhancing the functional space.

4.96 out of 5 average rating, 311 reviews

Peculiar One bedroom Studio.

"(Non Smoker and No Pets)". This is an amazing and comfortable studio. It is a separate portion of my home with a reserved parking space on our driveway In the kitchen there is a mini-fridge/freezer, microwave and a coffee maker. There is also an under counter washer and dryer. The sitting area includes a small couch with a twin mattress. This place is close to Walmart and Publix (5 minutes away). All attractions including Disney, Sea World and Universal are within 20-30minutes.

Guesthouse in Wadeview Park

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.

4.86 out of 5 average rating, 322 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 eating places. Love ice cream Kelly’s Hand Made ice cream is a 5 minute walk from the house. *Heated Pool* available for $20 fee for first day and $10 every extra day.

4.91 out of 5 average rating, 146 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, 500 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.

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, 115 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

4.98 out of 5 average rating, 292 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.

4.86 out of 5 average rating, 115 reviews

Great place to stay in Orlando!

Casa particular with exceptional location in the City of Orlando - Florida📍 The house has a smart front door, kitchen and bathrooms, accessories equipped with everything you need! It also has completely free parking. Minutes from Orlando and Universal water parks!

4.95 out of 5 average rating, 199 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 guesthouse rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly guest house rentals

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.

4.91 out of 5 average rating, 44 reviews

Spectacular Relaxing Blue Moon-EPIC,OIA,Fl Mall

A serene mural depicting a lush landscape with arches frames a tranquil scene featuring greenery and a flowing stream. A desk and chair are positioned in one corner, while a neatly made bed with bright red linens occupies the opposite side, complemented by wooden furniture.

4.97 out of 5 average rating, 86 reviews

Cozy private cabin between downtown Orlando & MCO

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 spacious seating area features a dark blue sectional sofa adorned with light throw pillows. A wooden coffee table rests in front, accompanied by a plush area rug. Bright lighting highlights the open layout leading to a well-equipped kitchen in the background.

4.97 out of 5 average rating, 67 reviews

Cozy Suite Located By Main Attractions

A welcoming entrance is framed by a wooden fence and vibrant greenery. The patio features a comfortable hanging chair and a small table, providing a cozy space to relax. The front door, adorned with decorative glass, offers a glimpse into the stylish guesthouse.

4.85 out of 5 average rating, 59 reviews

Elegant and cozy guest house

A cozy sleeping area features a spacious bed with a soft white coverlet and decorative pillows. A flat-screen TV is mounted on the wall. A full-length mirror and a small shelf are positioned nearby, while the floor is adorned with a black-and-white checkered rug.

4.85 out of 5 average rating, 66 reviews

Luxury Nature Escape with Private Patio.

A spacious studio room features a large bed with soft bedding and decorative pillows. A stylish rug runs alongside. A small seating area includes a soft pouf, while a kitchenette and dining table are subtly incorporated. Natural light filters through the window next to dark curtains.

4.56 out of 5 average rating, 9 reviews

Unique Studio Minutes From Disney & Universal

Guest house rentals 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, 21 reviews

Charming Lakeside small House

4.89 out of 5 average rating, 38 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

The exterior of the property is framed by a vibrant tropical garden, featuring lush greenery and colorful plants. A stone pathway leads to the entrance of the house, bordered by well-maintained grass and large trees, creating a welcoming approach.

4.89 out of 5 average rating, 163 reviews

The Little House

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, 66 reviews

Orlando Private Tiny Guest House

Guesthouse in Delaney Park

A bedroom features a spacious bed dressed in white linens, positioned against a striking black wall adorned with abstract patterns. Natural light is allowed in through an adjacent door, while decorative elements, including wall art and a plant, add a touch of character.

4.96 out of 5 average rating, 324 reviews

Cozy Guest Suite in heart of Downtown Orlando

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, 8 reviews

BRAND NEW! 1 Bedroom APT

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

4.84 out of 5 average rating, 62 reviews

A cozy bedroom features a neatly made bed with a soft grey comforter and coordinating pillows. Two bedside tables with lamps are placed on either side, providing gentle light. Natural light enters through a window adorned with simple blinds, enhancing the room's inviting atmosphere.

Guesthouse in Davenport

Charming & Cozy Guest House Minutes from Disney

Guest house rentals with a washer 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, 26 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.

4.84 out of 5 average rating, 109 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, 137 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, 131 reviews

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

4.94 out of 5 average rating, 82 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

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, 159 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, 115 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.