Guesthouse vacation rentals in Winter Park

A welcoming arrangement is presented on a woven tray, featuring a bottle of wine and two glasses alongside a decorative pumpkin and a small sign. The background displays a cozy bedroom with a quilted bedspread and decorative pillows.

4.99 out of 5 average rating, 139 reviews

Top 1% ABNB Villa Oasis w/ Botanical Courtyard

TOP 1% ABNB PRIVATE-SAFE-QUIET Villa Oasis central to DT ORL/Eola/Winter Park. Tranquil bamboo lined Cottage provides relaxed setting in much desired COLLEGE PARK neighborhood. Former recording studio @ 2X the living space of most College Park listings. Newly renovated bathroom, kitchen, outdoor space. Guest's own separate residence, bath/laundry room, garden patio and parking. I-4 EZ access to downtown ORL, Winter Park, THEME PARKS, central Fla activities! PLEASE MESSAGE with ANY QUESTIONS!!!

A charming entrance showcases a white door adorned with a circular floral wreath reading 'welcome.' Flanking the door are two planters with lush greenery, and the address '114 GH' is displayed above the door under an awning.

5 out of 5 average rating, 222 reviews

The Sacred Space Downtown Orlando Milk District

This delightful hideaway embodies brightness, cleanliness, and a fragrance-free environment. Enjoy a tranquil stay with hypoallergenic bedding and experience unmatched comfort on a luxurious purple mattress for rejuvenating sleep. Conveniently located near Lake Eola, lively bars, and an abundance of dining options, this private sanctuary provides the perfect balance of convenience and serenity. Amidst the bustling surroundings, our tranquil retreat remains tucked away, offering a peaceful stay.

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, 113 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.

4.97 out of 5 average rating, 119 reviews

A refreshing pool with stone borders is surrounded by lush greenery and shaded by a blue canopy. Comfortable seating for two is visible, along with a hammock, creating a serene outdoor space ideal for relaxation.

Guesthouse in Longwood

"Winnie's Place" A Peaceful Guesthouse with Pool.

Share the quiet backyard and pool with your hosts. Half was between Disney & the beaches. 12 years & older only. Sofa extends to a single bed. Minutes from Interstate-4. NOT a heated pool. Wheelchairs are fine. Driveway Entry gate 39"- Breezeway to Ramp entrance 32"- Slider Entrance 33"-Bedroom door 35"-Shower (no step) 35"-Laundry 32"-Closet 35"-Queen bed 29"-standard cabinets. We are not Handicap Certified but most wheelchair guests have not had issues. Grab bars are in the bathroom.

The front porch features two wicker chairs with bright orange cushions, inviting relaxation. Potted plants and hanging baskets add greenery, while a gentle overhang provides shade. A pathway leads to the entrance and a nearby guest house, framed by well-maintained shrubs.

4.97 out of 5 average rating, 348 reviews

Oasis Garden Cottage -cozy, chic, near everything!

Our cozy cottage is located within minutes of some of the best areas, restaurants, bars, and attractions Orlando has to offer. Winter Park and College Park are 3-5 minute drives, Disney and Universal only 20 minutes, etc. The interior is chic and inviting, with a homey feel. Enjoy the fireplace, play some board games, soak in bath salts in the claw foot tub, curl up on the porch with a coffee and read one of our provided books— it’s so peaceful you’ll have a hard time leaving for the day!

The exterior of the two-story cottage is captured, showcasing a red and white color scheme with black shutters. Lush green landscaping and a well-maintained lawn surround the home, while a concrete driveway leads to a detached garage nearby. A white picket fence adds charm to the property.

4.91 out of 5 average rating, 183 reviews

8th Green Cottage - A relaxing oasis in the city

The 8th Green Cottage is a relaxing oasis in the heart of Orlando. Located 5 minutes from downtown. Sitting on the historic 1924 Dubsdread golf course. Enjoy the great views, pleasant and quiet neighborhood all with easy access to everything Orlando has to offer. Location is key when traveling and the 8th Green Cottage delivers! Disney, Universal, and Sea World all within a straight shot down I4. Free play Arcade with 3500 games included in spare bedroom Pets are welcome and stay Free.

4.99 out of 5 average rating, 138 reviews

Baldwin Park Guest House

Welcome to Beautiful Baldwin Park, This Brand New Private sanctuary with modern day decorations, amenities and large screen television is the perfect place for a couple or single to experience the beautiful Orlando area. Conveniently located near the Orlando International Airport, Winter Park and downtown area Enjoy your morning coffee on the private patio . This entire property is very clean and well maintained, we look forward to being your host for your next central Florida visit

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, 134 reviews

Modern 1950s Studio • Near Downtown & Theme Parks

Fully renovated 1950s studio (2024) in a safe, quiet Orlando neighborhood! Enjoy a plush queen bed, walk-in shower, Roku TV, and full kitchen with Keurig. Includes a private driveway, separate entrance, and cozy living area with stylish modern décor. In-unit washer and dryer for your convenience. Just 3 mi to downtown, 10 mi to Universal, 8 mi to the airport, and 18 mi to Disney—perfect for couples or solo travelers seeking comfort, privacy, and modern style in a peaceful setting.

A cozy studio suite is shown with warm wood accents. A small kitchenette is equipped with a microwave and refrigerator. A workspace with a blue desk and two chairs is visible. Bright green plants add a touch of nature, complemented by a vibrant area rug.

4.76 out of 5 average rating, 519 reviews

Private Cozy Cottage in heart of Orlando

Come stay at our Cozy quaint suite located in the historic downtown Lake Davis neighborhood with a 5 minute walk to a quiet neighborhood market, 1 mile walk to downtown Orlando with entertainment and the Downtown Farmers Market. Less than 30 minutes to the worlds greatest attractions Disney, Universal Studios, Sea World etc. The beach is a 1 hour drive. One car parking. The room is connected to a family home you’re able to hear guest next door. Not for parties . Please NO pets.

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, 115 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.

A spacious living area is highlighted by a sleek, modern design featuring polished floors. A green couch and two accent chairs are arranged around a wooden coffee table. A dining table with ample seating is situated nearby, complemented by decorative wall art and soft lighting.

4.99 out of 5 average rating, 166 reviews

Luxe Guesthouse w/Pool/Hot tub-Near Rollins/UCF

This luxury guesthouse (on the same property as our main house but they are completely separate) is a hidden oasis conveniently located in the middle of downtown Winter Park (Rollins College/Full Sail) and UCF. It's roughly 10 minutes to each. Close to 417 expressway (toll road) so you can easily get around to the other areas of Orlando. Note: The guesthouse is 35 minutes to Disney, 25 minutes to Universal Studios and 20 minutes to Orlando International Airport.

A light blue elevated guesthouse features a spacious deck with white railings overlooking a landscaped yard. A set of stairs leads up to the entrance, surrounded by greenery and large trees. The ground area includes outdoor seating, complementing the serene environment.

4.98 out of 5 average rating, 240 reviews

The Loft in College Park

The Loft is a private guesthouse located above our garage near Downtown Orlando and Ivanhoe Village. It is walking distance to multiple restaurants, bars and shops. Also close to I-4 and easy access to the attractions. The studio space offers a queen size bed as well as a queen size sleeper sofa in the living room area. Luxurious full size bathroom with walk in shower and rain shower head. Perfect get away for those looking to enjoy Orlando!

Popular amenities for Winter Park guesthouse rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly guest house rentals

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.

4.93 out of 5 average rating, 128 reviews

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

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.

4.88 out of 5 average rating, 156 reviews

The Little House

4.95 out of 5 average rating, 172 reviews

Guesthouse in Sanford

Little Hidden Cottage- Near Sanford Airport

A cozy bedroom is showcased with warm wood paneling and soft lighting. A spacious bed is adorned with neutral tones and decorative pillows. A flat-screen TV is mounted on the wall, and large windows, covered by modern shades, allow filtered light to enter the room.

4.78 out of 5 average rating, 548 reviews

Private Studio Near Universal, Disney & Shopping!

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

4.89 out of 5 average rating, 229 reviews

A spacious sleeping area features a queen bed with a patterned white and navy bedspread. A wooden nightstand is positioned beside the bed. A ceiling fan provides airflow. The kitchenette and dining area are visible in the background, showcasing modern appliances.

Guesthouse in Lake Como

Adorable Studio Guest House

A sleeping area features a full bed with a floral-patterned blanket, complemented by a decorative 'COZY' pillow. A wall-mounted shelf displays a plant and decorative items, while a ceiling fan provides air circulation. Soft lighting creates a calm ambiance.

4.76 out of 5 average rating, 111 reviews

Private full kitchen near Disney & Epic Universe!

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.

4.97 out of 5 average rating, 307 reviews

Peculiar One bedroom Studio.

Guest house rentals with a patio

Guesthouse in Park Lake/Highland

A cozy living area is adorned with deep green walls, featuring a spacious bed with decorative pillows and a textured blanket. A television is mounted against the wall, accompanied by a wooden console. A light-colored sofa adds to the inviting atmosphere, complemented by woven wall art.

4.91 out of 5 average rating, 276 reviews

“The Clementine” Boho Home in Orlando’s Food Scene

Guesthouse in Winter Garden

A welcoming outdoor space is presented with two patterned armchairs and a wicker chair arranged around a glass-topped table. A decorative wall feature adds texture, while potted plants and a decorative heron enhance the tranquil atmosphere. Warm light filters through the area.

4.93 out of 5 average rating, 100 reviews

Blue Heron Bungalow

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, 137 reviews

King-size Studio 4 min to Universal

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, 154 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.

4.94 out of 5 average rating, 109 reviews

Modern & Cozy Retreat - Orlando City Center Epic

Superhost

A spacious bed is presented with deep blue bedding and decorative pillows, creating a comfortable sleeping area. Soft lighting is provided by modern floor lamps, and natural light enters through a partially open window with blinds.

4.76 out of 5 average rating, 133 reviews

Cozy Vacation Guesthouse Near Universal

Superhost

A pathway made of concrete stepping stones is lined with white gravel, leading to a charming entrance of a small building. The surrounding area features minimal landscaping with green plants and trees visible, and a wooden fence encloses the space.

Guesthouse in Kissimmee

4.8 out of 5 average rating, 104 reviews

Unit B Apt Relax House

4.94 out of 5 average rating, 108 reviews

The living area features a comfortable blue chair and a gray sofa, with a flat-screen TV mounted on the wall. A standing lamp provides soft lighting. Natural light enters through the window, complemented by light curtains and green walls.

Guesthouse in Oviedo

Cozy Knight Stay

Guest house rentals with a washer and dryer

5 out of 5 average rating, 210 reviews

A master bedroom features a queen bed dressed with light bedding and decorative pillows. Soft green walls enhance the space, while natural light filters in through window shutters. A small nightstand is placed beside the bed, accompanied by a cozy chair positioned by a glass door.

Guesthouse in Clarcona

Your Home Away From Home

A cozy seating area features a patterned armchair and a sleek gray sofa. A TV mounted on the wall displays a tranquil beach scene. Light streams in through a window with blinds, illuminating the natural wood floor and woven area rug.

4.93 out of 5 average rating, 250 reviews

Bungalow Near Epic, Disney and Downtown Orlando

Superhost

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.

Guesthouse in Wadeview Park

4.85 out of 5 average rating, 107 reviews

Relaxing Private Studio in the Trees!

Guesthouse in Lake Eola Heights

A bright living space features a comfortable sectional sofa adorned with decorative pillows, paired with a light-colored armchair. A wooden coffee table sits on a textured area rug, while a ceiling fan and pendant lighting add modern touches. The kitchen bar is equipped with high stools, enhancing the open layout.

5 out of 5 average rating, 77 reviews

Livingston Hideaway - 2 Blocks From Lake Eola

A modern pool house is featured, with large glass doors opening to a swimming pool. The exterior includes a tree emblem and a small seating area with a chair. Sun loungers are positioned near the pool, surrounded by lush grass and a wooden fence.

4.98 out of 5 average rating, 92 reviews

Amazing New Pool House!

Guesthouse in Thornton Park

A cozy sleeping area is featured with a spacious bed dressed in a textured blanket. A small kitchenette area is visible in the background, accompanied by a wall-mounted shelf adorned with greenery. Natural light filters in through a nearby window, illuminating the warm wooden floor.

4.99 out of 5 average rating, 250 reviews

Black House- Private Cottage in Thornton Park!

Guesthouse in Orwin Manor

A studio space features a four-poster bed adorned with colorful linens, complemented by decorative pillows. Nearby, two comfortable chairs provide additional seating. Light filters through a window, illuminating the room, while neutral walls enhance the cozy atmosphere. Storage options are available with double closet doors.

4.98 out of 5 average rating, 58 reviews

tinyhouse on the edge of orlando + winter park

A comfortable living area features a dark leather sofa, a wooden coffee table, and a dining table with chairs. Bright light filters in from the outdoor patio, revealing lush greenery and a seating area beyond the sliding glass doors adorned with a vibrant red umbrella.