Guesthouse vacation rentals in Winter Park

A private deck area features two red chairs and a small table, accompanied by a decorative pumpkin. The entrance to the interior is framed by a set of French doors, providing a welcoming transition to the living space. Nearby, a plant arrangement adds a natural touch.

5 out of 5 average rating, 189 reviews

Treehouse Inn Downtown Orlando, 2 bedrooms 2 bath

Treehouse in Downtown Orlando is surrounded by majestic heritage Oaks. Two Bed Two Bath with a Mini-Master & full Kitchen. Very private deck near Bamboo Hedge. Two blocks from a small neighborhood Deli serving breakfast, lunch and dinner with Great coffee & Craft beers. We are walking distance from popular Thornton Park pubs and restaurants. Lake Greenwood and Lake Davis are close by for a leisurely walk or brisk jog. Enhanced cleaning in use. Jakob and Marty are happy to help with your stay.

4.97 out of 5 average rating, 114 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 backyard and pool with your hosts. Half was between Disney & the beaches. 12 years & older only. Sofa extends to a single bed. Minutes from I-4 makes commuting easy. 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 have issues. Grab bars in the bathroom.

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, 213 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.

A quaint exterior view of a small house surrounded by lush greenery. The porch is framed by a railing and features a couple of chairs, while string lights add a charming touch. Colorful flowers bloom in the foreground, enhancing the serene atmosphere.

4.94 out of 5 average rating, 429 reviews

Garden House near Orlando's cultural hub

On a quiet cobblestone street, yet close to art and culture, more than 3 dozen restaurants in walking distance, Florida Hospital and family-friendly activities. You’ll love our place because of the location, the large bathroom with jacuzzi, the skylights, window seat, porch swing. It is nestled in our back yard surrounded by trees and has its own private entrance via a rustic walk way of pavers and stones. Couples, families, most anyone will find it charming. STR 1009942 (City registration)

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, 108 reviews

1926 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 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, 344 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, 181 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.

A well-equipped kitchen features white cabinetry and a granite countertop. A red vintage refrigerator adds a pop of color, while star-patterned tiles create visual interest. Two bar stools are positioned at the counter, and a rug runs along the floor, enhancing the space's warmth.

4.99 out of 5 average rating, 132 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

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, 248 reviews

Bungalow Near Epic Universe and Downtown Orlando!

Discover our charming cottage behind our bungalow in Downtown Orlando's College Park - conveniently located near Epic Universe and the Disney parks! Enjoy urban living with a small-town vibe, biking along tree-lined streets to restaurants, shops, breweries, and farmers markets. Private access, yard, and driveway and a beautiful park across the street! Conveniently access Winter Park (10 mins), Downtown Orlando (10 mins), Disney and Universal (15-30 mins). STR Permit # STR-1118212

Guesthouse in Lake Eola Heights

A bright and airy studio space is depicted, featuring a spacious bed with a light-colored blanket. A wooden tray sits on the bed with a drink. A TV is mounted on the wall opposite a casual seating area with a coffee table and a comfortable couch.

4.94 out of 5 average rating, 251 reviews

Bright + Modern Downtown Guesthouse near Lake Eola

Best location in Orlando. No need for a car. This beautiful, historic 1947 garage apartment is a 5-minute walk to Lake Eola, and within walking distance of many lovely cafes, restaurants, and bars. We are very proud of our little guesthouse behind our home. We would love to host you and show off our beautiful city. Driving distances to major attractions: - Dr Phillips Center || 5 min (1.2 miles) - Amway Center || 5 min (1.5 miles) - Universal Studios || 20 min - Disney || 30 min

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.

4.75 out of 5 average rating, 505 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.

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, 162 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.

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Popular amenities for Winter Park guesthouse rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly guest house rentals

Guesthouse in Malibu Groves

A bright sleeping area is highlighted by a spacious bed covered with a white quilt. Dark beams run across the ceiling, complementing the light walls. A small side table is positioned next to the bed, with a lamp on top. An image adorns the wall above the bed, and doors lead to the kitchenette.

4.92 out of 5 average rating, 105 reviews

Tiny Home in Orlando, Florida

A small outdoor seating area features two chairs with tropical-themed cushions and a metal table between them. A green decorative flower hangs on the wall, and the tiled floor reflects a light color. A door is positioned nearby, leading to the interior.

4.77 out of 5 average rating, 617 reviews

Little Studio,Pequeño estudio .

An open space features a cozy sleeping area with a patterned quilt atop a spacious bed. A glass dining table with two modern chairs is positioned in the foreground, accented by a decorative vase. Light-colored tile flooring enhances the room's brightness.

4.96 out of 5 average rating, 205 reviews

Welcome to The Blue House

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, 146 reviews

La Casita

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, 538 reviews

Private Studio Near Universal, Disney & Shopping!

4.81 out of 5 average rating, 188 reviews

Studio apartment, min to UCF with patio & grill

An outdoor pool is centered within a landscaped patio area, surrounded by lush greenery and mature plants. Two teak lounge chairs are positioned in the foreground, facing the calm water, while sun umbrellas and vibrant seating are visible nearby.

4.89 out of 5 average rating, 146 reviews

Vintage Florida Vibes 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.

4.75 out of 5 average rating, 108 reviews

Private full kitchen near Disney & Epic Universe!

Guest house rentals with a patio

A serene nighttime view of a swimming pool is illuminated by soft lighting, highlighting its clear water. The pool is surrounded by a paved area with a potted plant nearby, creating an inviting outdoor space for relaxation.

5 out of 5 average rating, 15 reviews

Sunny Side Stay

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.

4.86 out of 5 average rating, 130 reviews

King-size Studio 4 min to Universal

A private entrance is framed by a wooden fence and presents a clean white door. Potted red flowers are positioned on either side of the entrance, complemented by decorative wall art. The pathway is lined with square stone pavers, surrounded by decorative gravel.

4.85 out of 5 average rating, 75 reviews

Guesthouse Close to Downtown Orlando/UCF/Airport

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, 73 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, 90 reviews

Amazing New Pool House!

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, 107 reviews

Modern & Cozy Retreat - Orlando City Center Epic

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, 131 reviews

Cozy Vacation Guesthouse Near Universal

A cozy bedroom features a spacious bed with a deep green headboard and coordinating bedding. A tufted bench is positioned at the foot of the bed. Natural light enters through a window, illuminating a side table and a small seating area with a fan overhead.

5 out of 5 average rating, 24 reviews

Love Nest Studio nearby highways and Airport

Guest house rentals with a washer and dryer

Guesthouse in Thornton Park

The bedroom features a spacious bed dressed in a dark grey coverlet, accented by light pillows. Natural light enters through a window draped with white blinds. A ceiling fan provides air circulation, while artwork and bedside tables enhance the decor.

4.96 out of 5 average rating, 570 reviews

Private Luxurious Apt. - Historic Downtown Orlando

Guesthouse in Deer Island

An outdoor patio area features a screened enclosure with a private swimming pool. Comfortable seating is arranged around the pool, and lush greenery surrounds the space, providing a serene environment. Potted plants add a touch of color, enhancing the tranquil setting.

4.95 out of 5 average rating, 126 reviews

Sapphire Cottage - sleeps 6, on 5 acres with canal

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, 137 reviews

Top 1% ABNB Villa Oasis w/ Botanical Courtyard

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, 123 reviews

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

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.

4.91 out of 5 average rating, 270 reviews

Modern Guest Studio (Private) Pool / Spa available

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, 111 reviews

The Cottage A Pet Friendly Guesthouse

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.

4.97 out of 5 average rating, 448 reviews

The Coach House -2 bedroom/3 bath Orlando Getaway!