Guesthouse vacation rentals in Winter Park

4.99 out of 5 average rating, 160 reviews

College Park 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, 253 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.

5 out of 5 average rating, 125 reviews

An exterior view of the guesthouse displays a quaint two-story structure with a black garage and a welcoming front porch. Surrounding greenery provides a natural setting, enhancing the privacy of the location. The two upper windows are adorned with large curtains.

Guesthouse in Ocoee

NEW 1BRM Guesthouse | King Bed | Central Florida

Nestled in a private and central location, this newly constructed space offers everything needed for a relaxing stay. The space is perfect for up to four guests, featuring a king size bed, full kitchen, and smart TVs in every room. Enjoy the convenience of high-speed Wi-Fi, a spacious shower, washer / dryer, and a private driveway. Located close to Downtown, Theme Parks, the Stadiums, I-Drive, Wekiva Springs, Shopping, Dining, and More! Everything needed for your short term or long term stay.

4.98 out of 5 average rating, 130 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, 374 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!

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, 257 reviews

Bungalow Near Epic, Disney and Downtown Orlando

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

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, 194 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.

Guesthouse in Orwin Manor

A stylish kitchen is equipped with modern stainless steel appliances, including a refrigerator and microwave. A central island features two metallic stools, and the cabinetry is finished in a soft gray. A small potted plant adds a touch of greenery to the space.

4.99 out of 5 average rating, 118 reviews

Location, Location, Location!

Enjoy a stylish experience at this centrally-located Guest House. It is located in an excellent area close to the downtown Orlando, excellent restaurants, and much more. It is fully furnished and equipped with new appliances (washer and dryer included) and furniture. It is located minutes from Winter Park, Downtown Orlando and theme parks. Downtown Orlando 3 miles (6 min) Advent Health Hospital 0.6 miles (2 min) Walt Disney World 20 miles (23 min) Universal Studios 11 miles (18 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.

4.76 out of 5 average rating, 561 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, 188 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.

4.88 out of 5 average rating, 431 reviews

Guesthouse in Maitland

Chez Bienvenu

Close proximity to Park Avenue in Winter Park! Sunny and Adorable Vintage Guest House ...entire spacious guest house; with private entrance and driveway* Just a couple of blocks off Park Avenue to enjoy Shopping! Cafes! Museums! Nestled in quiet family community* •Smart TV •Stackable washer and dryer included in the unit. •Grill, Beach Chairs, Fishing Poles available •750 square feet of living space

4.96 out of 5 average rating, 191 reviews

A mid-century modern home is illuminated at dusk, showcasing its distinctive architectural features. Large glass windows reflect the evening light, while the warm glow from interior lighting enhances the inviting exterior. Lush landscaping surrounds the house, providing a serene atmosphere.

Guesthouse in Maitland

Private 1-bd Mid-Century Guesthouse

Welcome to our tranquil & private 1-bd Mid-Century Modern Guesthouse. The space has a separate entrance and keyless access. Full kitchen, living room, bedroom and bathroom. Centrally located in Florida, our guesthouse offers easy access to the surrounding areas. Lots of museums, nature walks, parks & fantastic places to eat. Book now & experience the love & care we have put into our property!

Popular amenities for Winter Park guesthouse rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly guest house rentals

A charming exterior view of the studio garage apartment is shown, featuring a dark door adorned with a floral decoration. Stone steps lead up to the entry, surrounded by lush greenery and plants. The garage door is white with double panels, complementing the neutral wall color.

4.99 out of 5 average rating, 118 reviews

The Studio

Guesthouse in Thornton Park

A welcoming sign for The Green Room is displayed on the exterior wall. The sign features the name 'Green Room' in a stylish font, surrounded by a decorative circular border. The year 'EST 2022' is included, emphasizing a modern touch to the entryway.

4.92 out of 5 average rating, 99 reviews

The Green Room Orlando

Guesthouse in Deer Island

A screened patio area is shown, featuring a private pool surrounded by an expansive deck. Comfortable seating arrangements are visible, along with lush plants and natural light streaming in from large windows overlooking the wooded landscape.

4.96 out of 5 average rating, 138 reviews

Sapphire Cottage - sleeps 6, on 5 acres with canal

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, 104 reviews

Guesthouse Close to Downtown Orlando/UCF/Airport

4.95 out of 5 average rating, 205 reviews

Guesthouse in Sanford

Little Hidden Cottage- Near Sanford Airport

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.

4.85 out of 5 average rating, 119 reviews

Historic lakefront guesthouse

Guesthouse in Park Lake/Highland

The living area features a comfortable brown sofa and a wooden coffee table, positioned on a patterned rug. Natural light filters in through two windows, complementing the neutral wall color. A smart TV is mounted on the wall above a stylish wooden console.

4.94 out of 5 average rating, 102 reviews

20 | Excellent | Above Average

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, 121 reviews

Private full kitchen near Disney & Epic Universe!

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, 305 reviews

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

A cozy bedroom is featured with a spacious bed covered in a yellow blanket. Artwork accents the walls, and a ceiling fan is visible above. A sliding barn door leads to the bathroom area, while a mirror and small closet add functionality to the space.

4.92 out of 5 average rating, 168 reviews

Tiny House | Airport & Downtown Orlando 15 Min

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.

4.89 out of 5 average rating, 175 reviews

King-size Studio 4 min to Universal

4.98 out of 5 average rating, 320 reviews

Guesthouse in Kissimmee

"Little Blue House" Getaway Near the Disney Parks

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.

4.94 out of 5 average rating, 178 reviews

The 𝕆𝕣𝕝𝕒𝕟𝕕𝕠 is the first step in the process.

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.

4.89 out of 5 average rating, 187 reviews

The Little House

4.9 out of 5 average rating, 130 reviews

A well-manicured pathway leads to the studio, surrounded by lush greenery and colorful plants. Visible are large windows framed by white curtains, providing a view of the scenic lake. A patio with a red umbrella and a picnic table is accessible for outdoor relaxation.

Guesthouse in Lake Mary

Nature Unique lake view Tiny Guest studio

4.96 out of 5 average rating, 123 reviews

A brightly painted tiny home is showcased against a serene backdrop. The exterior features red and yellow hues with a blue door and window. Two blue chairs are positioned beside a small table, creating an outdoor seating area surrounded by lush greenery.

Guesthouse in Kissimmee

Orlando Private Tiny Guest House

Guest house rentals with a washer and dryer

4.95 out of 5 average rating, 245 reviews

The exterior of the Carriage House presents a craftsman-style design with warm coral siding. A spacious deck with a railing is visible above the garage doors, which are dark wood with glass panels. A scooter is parked beside the entrance, complemented by potted greenery.

Guesthouse in Mount Dora

Walk to Downtown! - The Carriage House

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, 145 reviews

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

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, 255 reviews

Black House- Private Cottage in Thornton Park!

Superhost

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.

4.9 out of 5 average rating, 285 reviews

Modern Guest Studio with pool access

A comfortable living area is furnished with a dark sofa and an armchair. A light-colored throw blanket is draped over the sofa, and a patterned area rug adds warmth to the tiled floor. Natural light streams through the windows, illuminating the dining area in the background.

4.85 out of 5 average rating, 110 reviews

1/1 Private Guesthouse in Orlando (South Downtown)

A comfortable sleeping area features a spacious bed covered with a floral-patterned blanket. Two bedside lamps provide soft lighting. A small dining table with four chairs is positioned nearby, and a kitchenette is seen in the background with modern appliances and cabinetry.

4.99 out of 5 average rating, 105 reviews

Beautiful garage suite w/washer and dryer

Superhost

A spacious living area features two comfortable blue sofas adorned with decorative pillows. A sleek black coffee table is positioned in the center, holding a small plant. Abstract art pieces hang on the walls, and natural light enters through glass sliding doors.

Guesthouse in Maitland

4.78 out of 5 average rating, 371 reviews

Modern Guesthome in Central FL

A living area features a flat-screen TV mounted on the wall, showcasing a beverage advertisement. A wooden tray holds a remote control, a pair of glasses, and a phone. Light wood paneling adds warmth to the space, complemented by a clock and decorative items on the shelf.