Private suite holiday rentals in Winter Park

Guest suite in College Park

A cozy sleeping area features a spacious bed with a light-patterned coverlet. Adjustable reading lamps are positioned on either side. A simple desk with a chair and a small bookshelf are present, complemented by a light decorative wall piece. Natural light enters through a window with blinds.

4.98 out of 5 average rating, 460 reviews

A SUITE RETREAT with a Garden View in the City

A lovely remodeled in-law suite in a 1920s Mission Styled home in College Park suited for 2 people with a separate entrance, private bath & a little kitchenette.The Suite looks out into a garden to offer a relaxing view. Even though you are in the Downtown area, the suite was designed to offer solitude. We are walking distance to many restaurants & only an easy 5 minute drive to downtown Orlando. I am looking forward to hosting any and all who would like to visit. All are welcome. #STR-1009437

A spacious room showcases a comfortable bed dressed in quality linens, complemented by decorative pillows. Two bedside lamps provide soft illumination. A dining table for two is visible, alongside a mirrored accent wall that reflects the room's minimalist design and elegant decor.

4.94 out of 5 average rating, 273 reviews

Mirror House

Soon as you enter our doors, you'll be enchanted by the blend of modern design with a homely atmosphere. It’s a single-room marvel that offers a comforting sanctuary. Immerse yourself in lines, tasteful furnishings, and a subtle color scheme that sets the stage for a stay. Modern amenities are at your fingertips.Sink into top-quality linens as you bask in the comfort of this space. We guarantee that you wake up feeling refreshed and prepared to embark on a brand new day filled with experiences.

A comfortable sitting area is visible, featuring a blue sofa with yellow accent pillows, a gray armchair, and a dark wood TV stand with a large flat-screen TV. Natural light filters through the large windows adorned with blinds, creating a bright and inviting space.

4.98 out of 5 average rating, 124 reviews

Private Studio King Bed & Massage Chair + Sofa

Quiet, peaceful & centrally-located private studio in Altamonte Springs. 1st floor, 2 private entrances, full kitchen, private AC, strong WiFi, free parking, and total privacy. Walk to Sandlando Park & Seminole Wekiva Trail. Just 2 blocks from I-4, 1.5 mi to Cranes Roost, Uptown & Altamonte Mall. Less than 10 min to Downtown Orlando, Wekiva Springs, hospitals & shopping. Ideal for remote work, extended stays, couples or solo travelers. Enjoy comfort, location & convenience. Book now and enjoy!

A bright bedroom features a spacious bed with a patterned duvet and a comfortable couch. A wall-mounted smart TV is visible, and natural light filters in through vertical blinds on the window. Neutral-colored walls enhance the calming environment.

4.92 out of 5 average rating, 304 reviews

Homey Newly Built Apt w/ WiFi and Private Entrance

This comfortable, 2 story, 1 bedroom, 1 bath suite is perfect for two to three people. It is a separate portion of our home with its own private entrance. The unit includes a full kitchen with a fridge/freezer, countertop stove, coffee maker, toaster, blender, a microwave, and many pots, pans, and utensils. The living area features a queen sofa bed and an adjustable smart tv. The bedroom has a smart tv, as well as a comfortable couch perfect for lounging. **Any stolen items will be charged**

A serene pool area features a clear blue pool surrounded by elegant tile flooring. Comfortable lounge chairs are arranged around the pool, providing ample space for relaxation. Potted plants add a touch of greenery to the setting, contributing to a calming atmosphere.

4.96 out of 5 average rating, 386 reviews

St. Augustine suite

Luxurious space with PRIVATE ENTRANCE, PRIVATE BATHROOM and breakfast kitchenette. Located on a large lake front property with amenities that include private dock, pool, large manicured lawns and much more. Ideal for canoeing, watching the sun rise or doing nothing at all. Close to theme parks and beaches. Spring Valley is a peaceful community with age old oak tree , Ample shopping and award winning restaurants very nearby. Come play or rejuvenate your soul in this picturesque setting

4.94 out of 5 average rating, 139 reviews

The Paradise Bird Cottage

" This cozy Home it’s private with own access located at beautiful Baldwin Park, not far from downtown Orlando and Winter Park. Great and convenient location,few miles from Orlando International Airport easy access to restaurants, shops along with Baldwin Park Lake, beautiful park for your enjoyment, walk, run or biking. This apartment has big tv screen, washer and dryer. It is clean, private newly renovated with a wildlife theme that provides a peaceful atmosphere to relax and enjoy

Guest suite in Thornton Park

4.96 out of 5 average rating, 257 reviews

Orlando Oasis in the heart of Thornton Park

The perfect Oasis located in the beautiful Historic Thornton Park, one of the safest and quietest neighborhoods in Downtown Orlando, this brand new studio apt is perfect for couples, business travelers, and families of 3. Enjoy custom cozy decor, a super-comfy queen bed, full kitchen amenities, and a private view of the pool & downtown skyline. Easily walk to great parks, restaurants, bars, shopping, and Lake Eola. 20 min to Universal. 25 min to Disney. *VIDEO TOUR* available on YouTube.

Guest suite in College Park

A white door with a glass panel leads into the studio, framed by a decorative welcome mat on stone pavers. Lush green plants are positioned beside the door, adding a natural touch to the entrance. Soft shadows from nearby foliage create a calming atmosphere.

4.97 out of 5 average rating, 302 reviews

New Mid Century-Modern Studio

Enjoy your stay in this beautifully decorated studio with all the conveniences of home. The bed is Queen. We are located in College Park of Orlando. On Edgewater Drive there are restaurants, bars, and boutique shops. Close to downtown , 30 min. from all the attractions, and 5 min. from one of the city’s largest hospitals, 23 miles from ORMC airport. Walking distance from the historic Dubsdread Golf Club and restaurant. Pet fee required. Please make sure to add the pet to the reservation.

Guest suite in Casselberry

A spacious living area is highlighted by a brown sofa and a round dining table surrounded by wooden chairs. A ceiling fan circulates air while large windows provide natural light and views of the backyard. A television is mounted on the wall.

4.9 out of 5 average rating, 115 reviews

Orlando, spacious, quiet, centrally located, suite

This suite includes private entrance, living room, kitchen with utensils and cookware, one bedroom with king bed and private bath. Third and fourth persons may be accommodated with recliner that lays flat into a queen-size bed in living room. Also a queen size air mattress and portacrib is available. Excellent location for Disney, Universal, SeaWorld, and beaches. Approx. 35 min. to Disney; 27 min. to Universal; 23 min. to convention center; 45 min. to beach; and 35 min. to Airport.

Guest suite in Lake Underhill

A private outdoor area is showcased, featuring a sparkling pool accompanied by a hot tub. Lush greenery and colorful plants surround the space, while comfortable seating options, including bright blue chairs, invite relaxation. A pergola provides shade, enhancing the tranquil atmosphere.

4.93 out of 5 average rating, 408 reviews

Downtown Orlando Garden Retreat

This space is a mother-in-law suite, completely private from the main house, accessible through a private entrance outside and entering through the garage. THIS IS NOT THE ENTIRE HOUSE! There is a queen size bed... perfect for a couples getaway! It is conveniently located about 15 min. from OIA and 5 min. from downtown Orlando. There is a beautiful pool and hot tub with stunning sunset views of across the lake... so peaceful and you feel like you are in a resort

Guest suite in College Park

A cozy guest suite is displayed, featuring a spacious queen bed with a textured white coverlet. A kitchenette is visible, equipped with a refrigerator, microwave, and wall shelves. Light streams in from the ceiling fan overhead, illuminating the modern and inviting decor.

4.89 out of 5 average rating, 277 reviews

Luxury Suite Near Disney & Downtown Orlando

Come enjoy a cozy & newly-renovated private guest suite centrally located near Downtown Orlando. Features a full kitchen, spacious bathroom, & luxurious queen bed for a peaceful & enjoyable stay. Private entrance, driveway and front porch, and convenient self check-in. Perfectly located walking distance from restaurants, shopping, and parks in a safe and family-friendly neighborhood. Easy access to Downtown Orlando, Theme Parks, and Winter Park/Park Ave.

The exterior of a charming green house is framed by lush landscaping, featuring tropical plants and palm trees. The house is elevated, showcasing a wraparound porch with white railings and decorative details. A tall chimney adds character to the roofline under a clear blue sky.

4.96 out of 5 average rating, 441 reviews

Guest Suite! Key West in Altamonte Springs!

This Beautiful Little Guest Suite on ground floor with courtyard entrance. Completely separate entrance and private from the main house. Beautifully decorated with four post queen shutter style bed, wet bar area with mini fridge, morning coffee bar, full bathroom with shower. Driveway parking. Walking distance to Altamonte Mall. 45 mins from Atlantic Coast. 35 mins to Disney Area Attractions.

Popular amenities for Winter Park Self-Contained Units

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly private suite rentals

4.92 out of 5 average rating, 172 reviews

Private guest studio in the heart of orlando.

A spacious sleeping area is presented, featuring a full-size bed dressed in a patterned blanket and a futon sofa. A round glass coffee table sits in the center, topped with a decorative sign. An artistic wall piece adds a touch of color to the room.

4.86 out of 5 average rating, 109 reviews

Hidden Corner @ River

A comfortable seating area features a soft blue chaise lounge beside a side table with a lamp. A large mirror leans against the wall, reflecting natural light from a nearby window. Framed artwork adorns the walls, enhancing the space's aesthetic.

4.86 out of 5 average rating, 106 reviews

Abe and su villa

4.99 out of 5 average rating, 664 reviews

A serene lake scene is captured at sunset, reflecting hues of orange and blue across the water's surface. A wooden dock extends into the lake, surrounded by lush greenery, providing a tranquil atmosphere.

Guest suite in Chuluota

Enjoy Our Beautiful Sunsets and Peaceful Sunrises

A cozy bedroom features a spacious bed adorned with multiple pillows. Light beige walls are complemented by a stylish chandelier. A round mirror reflects the room, while a subtle artwork adds a touch of decor. A window with curtains allows natural light into the space.

4.88 out of 5 average rating, 602 reviews

Cozy Suite Near Orlando Airport

4.83 out of 5 average rating, 642 reviews

A pool area is enclosed by a screened structure, featuring a sparkling blue pool with a connected hot tub. Tropical palm trees are visible in the background, adding a touch of greenery to the tranquil setting.

Guest suite in Kissimmee

Private 2 bedroom w/bathrm in portion of POOL home

A compact kitchenette features a dining area with two black chairs and a countertop. The bathroom includes a sink and a shower with a colorful curtain. A well-lit sleeping area offers a spacious bed with a grey blanket, complemented by decorative pillows and a nightstand.

4.88 out of 5 average rating, 114 reviews

Studio

4.87 out of 5 average rating, 135 reviews

Cute Guest Suite in Orlando

Self-Contained Unit with a patio

A welcoming entrance is framed by a vibrant green leaf panel, with a cheerful sunflower decoration displaying the word 'WELCOME.' The surrounding area features a red fence and a light-colored door leading into the home.

4.92 out of 5 average rating, 185 reviews

Grey House near Orlando Universal Parks

A small, private room features a comfortable bed with a patterned blanket. A desk is positioned against the wall, accompanied by a chair. Natural light enters through a window, with decorative plants and simple wall décor enhancing the space.

4.9 out of 5 average rating, 136 reviews

Adorable, private studio in College Park

A cozy bedroom features a wooden bed framed by light-colored walls. The bed is covered with a patterned duvet, complemented by decorative pillows. A mounted TV is positioned nearby, alongside windows with dark curtains that allow for light control. A welcoming wall decal adds a charm to the space.

4.84 out of 5 average rating, 114 reviews

Homey Private Entry 1/1 Apt w/ Full Size Kitchen

4.98 out of 5 average rating, 421 reviews

~Chic Oasis • 6-Guest Suite • Pool Heat • Near All

A private studio features a king-size bed with a light patterned coverlet. A wall-mounted television is positioned above a small table with chairs. Natural light filters through a nearby window, while a decorative plant and a textured rug enhance the space.

4.82 out of 5 average rating, 132 reviews

Entire Suite - 17 min from airport

4.93 out of 5 average rating, 228 reviews

The Floridita Tropical

The living area features a stylish black sofa with colorful throw pillows, a queen bed with a tufted headboard, and a vibrant area rug. Natural light fills the space through large windows, complemented by a ceiling fan and modern decor. A dining table for four is also visible.

4.84 out of 5 average rating, 153 reviews

Adorable and private suite in Orlando

4.95 out of 5 average rating, 172 reviews

The exterior of the lodge features rustic cypress wood siding and a modern metal roof. A central cupola adds architectural interest above the entrance. The surrounding landscape includes palm trees and a curved pathway leading to the building, set against a colorful sunset sky.

Guest suite in St. Cloud

Cypress Lodge w/Theater & Pool Access

Private suite rentals with a washing machine and dryer

4.91 out of 5 average rating, 480 reviews

An iron gate stands at the entrance of a private driveway, flanked by brick pillars. Lush greenery surrounds the path, leading to a bright, open area in the distance, suggesting a tranquil and secluded setting.

Guest suite in Sanford

Sanford airport/lakehouse/Boombah/venue1902

Guest suite in Winter Garden

A light-filled living room is depicted, featuring a comfortable white couch with assorted decorative pillows. A wooden coffee table sits in front of the couch, complemented by a patterned area rug. A large television is mounted on a wooden media console, with soft curtains framing the window.

4.84 out of 5 average rating, 401 reviews

Designer Guest Suite Near Disney/Universal/DT

A modern kitchen area is featured with sleek cabinetry and a countertop that includes two wooden bar stools. Blue accent lighting highlights the space. A coffee maker and complimentary water bottles are positioned on the shelving above, with a door leading to an outdoor area visible in the background.

4.93 out of 5 average rating, 169 reviews

Contemporary smart bedroom studio

4.98 out of 5 average rating, 235 reviews

A bright bedroom features a queen-size bed with light bedding, two bedside lamps, and a wooden dresser. A large window provides natural light, offering views of the outdoors. Decorative wall art adds color to the creamy yellow walls, creating a welcoming atmosphere.

Guest suite in Montverde

Green Mountain Getaway (No indoor Smoking or Pets)

A spacious sleeping area features a queen bed with a soft grey blanket. A television is mounted above a brick fireplace. Large windows allow natural light, offering views of the tropical backyard. A bistro table and chair set is positioned nearby.

4.94 out of 5 average rating, 232 reviews

Cozy Orlando Studio • Private Entrance • Queen bed

A spacious living room is featured with light-colored tile flooring. A large flat-screen television is mounted on the wall above a dark media console. One side includes a sleek sofa and a foldable futon, while a round coffee table is situated in the center.

4.94 out of 5 average rating, 199 reviews

Comfortable Guest Suite-Stylish Altamonte Springs!

A well-appointed studio bedroom features a spacious white bed with a decorative yellow throw. A comfortable gray chaise lounge is positioned nearby, and framed artwork is displayed on the wall. Soft curtains frame a window, allowing natural light to brighten the room.

4.91 out of 5 average rating, 247 reviews

Cozy Private Studio Close to Downtown Orlando