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, 450 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 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.

4.97 out of 5 average rating, 115 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, 293 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, 379 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

Guest suite in Thornton Park

A serene pool area is surrounded by a well-maintained patio with paver stones. Lush greenery and tall palm trees are visible in the background, creating a peaceful atmosphere. A staircase leads to an upper level, enhancing the outdoor space's layout.

4.96 out of 5 average rating, 249 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, 277 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.

An open kitchen area features a modern counter with a stainless steel sink and sleek cabinetry. Two pendant lights hang above, illuminating the space. A comfortable gray couch is situated nearby, with a flat-screen TV mounted on the wall. Natural light filters in through the windows.

4.91 out of 5 average rating, 194 reviews

The Oasis Of Orlando!

"This Luxury studio apartment is connected to a single family home, with its own private and secure entrance. In our open floor plan you will find a queen bed , updated bathroom and walkin in closet where you can easily roll in your suitcase to store during your stay. Feel free to pour yourself a hot coffee in the AM and a glass of wine in the PM at our adorable kitchenette in which you will also find a toaster, microwave and mini fridge. Located just 10mins away from the MCO airport."

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.

4.91 out of 5 average rating, 110 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, 400 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 Delaney Park

A charming exterior of a guest suite is framed by lush greenery and colorful plants. A stone walkway leads to the entrance, while a well-maintained lawn adds to the inviting appearance. The sky is painted with soft hues, enhancing the peaceful environment.

4.92 out of 5 average rating, 128 reviews

Historic Delaney House

Stay at the Historic Delaney House, just south of downtown Orlando. Our private guest suite offers quick access to SR 408 & I-4, placing you less than 30 mins from theme parks, beaches, and top attractions. Enjoy nearby venues like Kia Center, Dr. Phillips, and Camping World Stadium all within a 10 min drive. A park with a playground is across the street, plus you’ll have 1 parking spot, shared laundry, and hosts close by to help if needed. IG: dc_getaway

A well-appointed sleeping area features a spacious bed with soft bedding. Two lamps provide gentle illumination on either side. Above the bed, framed artwork adds a touch of color, while a sliding barn door in green adds an interesting architectural detail.

4.85 out of 5 average rating, 281 reviews

Guesthouse, Walk To Baldwin Lake - 1 mi to Dining

Right outside Baldwin Park, this backyard studio retreat offers comfort and convenience with beautiful sunset views and walkable access to Baldwin Lake’s trails, dining, and breweries. Features include: • Oversized bathroom with rain shower and separate vanity countertop • Huge walk-in closet with full-length mirror to get organized • Kitchenette for light cooking and thoughtful touches • Outdoor seating at the front door to watch our beautiful sunsets

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, 431 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, 452 reviews

Two sparkling glasses filled with a bright orange beverage are placed by the edge of a non-heated swimming pool. The pool area is surrounded by lush greenery and light stone walls, offering a serene outdoor retreat.

Guest suite in Oviedo

Oviedo Oasis:2/1 attached Guest Suite;Private Pool

Guest suite in Casselberry

A clean bedroom features a spacious bed with a grid-patterned blanket, accompanied by a wooden nightstand and lamp. A window provides natural light, while a fan is mounted on the ceiling. A decorative mirror and a coat rack add functional elements to the room.

4.94 out of 5 average rating, 77 reviews

2B/2B Close to Orlando/Winter Park/Winter Springs

4.71 out of 5 average rating, 7 reviews

Urban Retreat: 10 min MCO, Near Universal/Epic

Guest suite in Lake Eola Heights

4.63 out of 5 average rating, 19 reviews

Chic Downtown Orlando | Near Lake Eola | Sleeps 2

Guest suite in Belle Isle

The kitchen features wooden cabinetry and a modern backsplash, paired with a compact countertop. A sink, coffee maker, microwave, and refrigerator are present. The floor is adorned with a patterned tile, adding subtle texture to the space.

4.86 out of 5 average rating, 614 reviews

Comfy studio 5 min from Airport.

A spacious bed is featured with a richly textured, light-colored comforter and an assortment of decorative pillows. The wooden headboard adds a classic touch, while natural light filters through nearby blinds, enhancing the cozy atmosphere of the room.

4.92 out of 5 average rating, 48 reviews

Mills Hideaway Retreat|Near Concert Venues+Laundry

A contemporary studio space is presented with a soft grey sofa, adorned with cushions, along with a small wooden side table. Adjacent to the living area is a stylish dining table and chairs, while the kitchenette features modern appliances and light-colored cabinets.

4.88 out of 5 average rating, 129 reviews

Cute Guest Suite in Orlando

A bright bedroom features a spacious bed with crisp white bedding. A relaxing seating area is provided by a small round table with two chairs. Natural light fills the room through a nearby door leading to the patio. A wall-mounted television and decorative shelving add functional style.

4.95 out of 5 average rating, 131 reviews

Cozy cottage in the heart of downtown 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, 176 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.

4.89 out of 5 average rating, 132 reviews

Adorable, private studio in College Park

4.81 out of 5 average rating, 140 reviews

A cozy room features a bed covered with a blue quilt and a wooden nightstand beside it. A ceiling fan hangs above, providing airflow. Light enters through a window dressed with sheer curtains. A flat-screen TV is mounted on the wall opposite the bed.

Guest suite in Oak Ridge

Beautiful and clean suite for you stay

4.98 out of 5 average rating, 407 reviews

Guest suite in Sky Lake

~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.

4.8 out of 5 average rating, 123 reviews

Entire Suite - 17 min from airport

4.93 out of 5 average rating, 216 reviews

Guest suite in Sky Lake

The Floridita Tropical

4.95 out of 5 average rating, 166 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

A bright and airy bedroom is furnished with two spacious beds, each topped with coordinating grey bedding. A comfortable seating area is located in the background, and decorative plants create a calming atmosphere. Elegant wall art adds a touch of sophistication to the space.

4.97 out of 5 average rating, 235 reviews

Bonsai House

Private suite rentals with a washing machine and dryer

4.91 out of 5 average rating, 468 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.

4.83 out of 5 average rating, 388 reviews

Designer Guest Suite Near Disney/Universal/DT

Guest suite in Thornton Park

The exterior of a historic bungalow is presented, featuring a light blue facade with white trim. A welcoming front porch is visible, complemented by a landscaped pathway and vibrant greenery, including flowering shrubs and trees, contributing to the home’s charm.

4.85 out of 5 average rating, 224 reviews

Walk to restaurants & Lake Eola

4.75 out of 5 average rating, 197 reviews

☀️ Relaxation Station ☀️ Close to DT•HUGE backyard

4.98 out of 5 average rating, 230 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.

4.93 out of 5 average rating, 219 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, 193 reviews

Comfortable Guest Suite-Stylish Altamonte Springs!

A spacious bedroom is centered around a comfortable bed covered with a soft, turquoise blanket. A collection of artwork adorns the wall above the bed, while a lamp and a potted plant provide thoughtful accents. An open doorway leads to a kitchenette area in the background.