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 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

Welcome to Bonsai Home, a unique blend of modern comfort and nature's embrace. Our charming abode, nestled between Orlando and Winter Park, offers a harmonious fusion of stylish interior design and a soothing ambiance. As you settle into your cozy living space, indulge in our thoughtful amenities and captivating details inspired by the tranquility of bonsai. Rest assured that we are at your service whenever you need assistance or have any inquiries. We extend our warmest welcome to Bonsai Home!

Guest suite in Altamonte Springs

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!

Guest suite in Altamonte Springs

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, 378 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, 276 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.

4.91 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.

A spacious guest room features a comfortable bed adorned with a pink throw blanket. Elegant wallpapers and green curtains complement the decor. A seating area includes a cozy couch and a round dining table. Natural light enters through a unique arched window, enhancing the inviting ambiance.

4.92 out of 5 average rating, 285 reviews

Luxurious Bath, Peaceful Stay: Private Guesthouse

This beautifully appointed guesthouse offers a serene retreat with a double sink, a large walk-in shower, and a luxurious bathroom. Enjoy complete privacy from the main house as you enter your secluded space through a private entrance and patio garden. Whether you're seeking a romantic getaway or a peaceful solo retreat, this guesthouse provides the perfect escape. ⁃ Orlando airport: 16 minutes ⁃ Downtown Orlando: 10 minutes ⁃ Disney parks: 25 minutes ⁃ Universal studio: 27 minutes

A comfortable seating area features a dark gray sectional sofa adorned with decorative pillows. A patterned area rug lies underneath, complementing the wooden floor. A dining table with colorful chairs is visible in the background, alongside a TV stand and natural light filtering through sheer curtains.

4.96 out of 5 average rating, 191 reviews

Upscale Urban Chic Apartment

This warm “Carriage House Apartment” offers a cozy relaxed studio suite, it's 500 sq ft in a premiere established neighborhood. Built in 1938, updated for modern fine living with charm. Enjoy scenic views, romantic evening strolls through tree lined streets to nearby parks and lakes. Ample on street parking. Walking distance to shopping, bars, fine dining, the Orlando Regional Medical Center and near major attractions. Live a local’s life in the heart of Orlando, Florida.

Guest suite in Wadeview Park

A compact studio features a double bed with light bedding, alongside a kitchenette equipped with a mini fridge, microwave, and coffee machine. A small dining table is present, and patterned tiles add character to the space. Natural light fills the room through the nearby window.

4.85 out of 5 average rating, 192 reviews

The Golden Sodo Studio!

"This is a small, private studio attached to triplex . It has a private bathroom and kitchenette area with a mini fridge, microwave, coffee machine and kettle for the tea lovers. There is a sink but no (range.) We are located 1.5 miles south downtown Orlando and a 5 minute walk to Wade view Park. We are centrally located within an hour to most Central FL attractions and Beaches. (Disney World, Universal, Sea World, International Drive.) All are within 35 min from the unit.

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, 399 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

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, 280 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

Popular amenities for Winter Park Self-Contained Units

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly private suite rentals

4.96 out of 5 average rating, 135 reviews

A spacious studio features a large bed adorned with a patterned quilt, flanked by two bedside lamps. Dark wooden shelves and a small kitchenette are visible, while warm wooden flooring complements the inviting interior. Natural light fills the room through a nearby door.

Guest suite in Lake Mary

Quiet, Upscale Studio

4.93 out of 5 average rating, 164 reviews

Private guest studio in the heart of orlando.

A well-appointed studio space is depicted, featuring a spacious bed with light bedding. A comfortable leather recliner set faces the bed, while a dining table is positioned against the wall. Modern appliances and decor elements add to the inviting atmosphere.

4.94 out of 5 average rating, 557 reviews

Confortable Studio near Airport Orlando

A backyard oasis is highlighted by a heated spa and pool, illuminated in vibrant blue hues. A multi-level deck features outdoor seating and a colorful pride flag. Lush greenery surrounds the area, creating a secluded and inviting atmosphere.

5 out of 5 average rating, 474 reviews

LAKEFRONT STUDIO APARTMENT (private entrance)

4.97 out of 5 average rating, 255 reviews

A studio-style living space features a spacious bed with neutral bedding, complemented by decorative pillows. A round mirror hangs over a wooden nightstand. The kitchenette area includes a small microwave and cabinetry, while an area rug adds warmth to the wooden floor.

Guest suite in Sanford

The Secret Sanctuary in Sanford, 5min from Airport

A bright, open bedroom features a spacious bed with layered bedding and a light duvet. A smaller bed is positioned next to a modern coffee table. Natural light fills the room through double windows, complemented by stylish drapes. Minimalistic decor and wooden flooring enhance the design.

4.88 out of 5 average rating, 182 reviews

M&M Twins House

4.81 out of 5 average rating, 118 reviews

A vibrant sunset casts shades of orange and pink over a calm lake. Silhouetted trees frame the scene, while a gazebo on a floating dock provides a tranquil spot to enjoy the view.

Guest suite in Apopka

Lake Front Suite -Close to all Attractions

Guest suite in College Park

A spacious room features a wooden bed frame with a patterned comforter and two pillows. A wall-mounted TV is positioned opposite the bed. Natural light enters through a window, complemented by a patterned curtain. A comfortable chair and a desk are situated in the corner.

4.8 out of 5 average rating, 45 reviews

Comfortable Studio

Self-Contained Unit with a patio

Guest suite in Azalea Park

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, 131 reviews

Adorable, private studio in College Park

4.81 out of 5 average rating, 139 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

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

Guest suite in Azalea Park

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

The Floridita Tropical

4.96 out of 5 average rating, 145 reviews

Cozy Private Studio Suite • Near Theme Parks

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

Private suite rentals with a washing machine and dryer

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, 387 reviews

Designer Guest Suite Near Disney/Universal/DT

Guest suite in Azalea Park

4.75 out of 5 average rating, 197 reviews

☀️ Relaxation Station ☀️ Close to DT•HUGE backyard

4.89 out of 5 average rating, 151 reviews

The exterior of a single-story house is depicted, showcasing a brown facade with a pitched roof. A covered porch features two orange chairs. A driveway leads to an attached garage, surrounded by a landscaped yard with mature trees and blue skies above.

Guest suite in Clermont

Private In-Law Suite. House in Hills. BIKE Trail

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 back patio area features a refreshing pool surrounded by paved stones. Two lounge chairs sit beside the water, and a swing is positioned nearby under a shaded structure. Lush greenery and potted plants are visible, creating a relaxed outdoor environment.

4.88 out of 5 average rating, 152 reviews

✨️Modern Suite with POOL- Close to All Parks!🎡

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, 237 reviews

Cozy Private Studio Close to Downtown Orlando

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