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Guesthouse vacation rentals in Winter Park

Find and book unique guesthouse rentals on Airbnb

Top-rated guesthouse rentals in Winter Park

Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

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Top guest favorite

A vibrant fountain illuminated in red and green is captured in the center of a lake, reflecting the dramatic colors of a sunset. Surrounding buildings frame the scene, contributing to the lively urban backdrop.

Guesthouse in Thornton Park

4.99 out of 5 average rating, 249 reviews

Black House- Private Cottage in Thornton Park!

This historic cottage is a unique free-standing detached dwelling in the heart of Thornton Park (Downtown Orlando). This little gem is newly renovated and gives the guest a perfect secluded launching point to hundreds of bars, eateries, parks as well as easy access to highways to visit Universal, Disney World, etc. Charming historic residence that provides private off street parking, yard/green space and a relaxing hammock just steps outside your door. The style is very unique and fun!

Top guest favorite

The welcoming entrance features a red front door framed by white siding. Potted plants and colorful flowers line the pathway, while a small seating area with chairs is positioned beside the door, inviting guests to relax before entering.

Guesthouse in College Park

4.97 out of 5 average rating, 434 reviews

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

Pet-friendly 2 Bedroom/3 Bath House. Designed by renowned architect James Gamble Rogers II, the house is a 25-minute drive ($23 Uber) from the MCO Airport. Nestled in the heart of Orlando's College Park district, it is an oasis just moments away from Downtown Orlando: nightlife, museums, and funky art and music scene. Take a 25-minute drive into Disney, Universal, or The Outlets. Uber/Lyft/Walk to nearby trendy restaurants, museums, theaters, boutique shopping, and our craft beer scene.

Top guest favorite

A charming tiny cottage farmhouse is set amidst a grassy area, featuring a covered porch with a dining table adorned with bright blue chairs. A grill is positioned nearby, while soft outdoor lighting enhances the evening ambiance.

Guesthouse in Apopka

4.97 out of 5 average rating, 106 reviews

Tiny Home in Apopka

Enjoy a cozy and quiet stay at this trendy Cottage Farm House in Apopka. The gateway to Central Fla! 2.5 miles from our beautiful Wekiva Spgs State Park. Spacious at over 540 sqft. Dogs 20lb max. Kitchenette, full bath/shower, 1 bedroom with closet/queen bed. Minutes from shopping and wonderful restaurants. You won't be disappointed. You will have your own privacy and can come and go at your leisure. Ask in advance for Camper/trailer parking. Self check-in. Come enjoy beautiful Apopka.

A neatly designed bathroom area is visible, featuring a dark wood vanity with a light-colored countertop. A wall-mounted mirror and sconces provide illumination. The floor is adorned with neutral tile, and decorative accent tiles add visual interest to the space.

Guesthouse in Orlando

4.89 out of 5 average rating, 210 reviews

Adorable Studio Guest House

Enjoy a quiet peaceful stay just minutes outside of Downtown Orlando. Walk to local restaurants, bars and cafes. The guesthouse has a fully equipped kitchen, full bathroom, built-in closet, wi-fi, queen bed and pull-out murphy bed. The TV has access to Netflix, Hulu and Disney Plus. Owners live on property in the main house, and are available to answer any questions. Distances to Major Attractions: Downtown Orlando--10 Mins Airport--20 Mins Universal Studios--20 Mins Disney--30 Mins

Top guest favorite

A serene view of Lake Mary is framed by a large tree and a white post. The sky transitions into vibrant hues as the sun sets, reflecting softly on the water's surface. A lamp illuminates the foreground, enhancing the peaceful lakeside atmosphere.

Guesthouse in Lake Mary

4.97 out of 5 average rating, 116 reviews

Sunset Cottage in Lake Mary, Florida

Located on beautiful Lake Mary, this completely renovated studio sized guest house offers beautiful sunsets over the lake from a private patio. A comfortable queen bed, stylish sitting area and fully stocked kitchenette make for a wonderful stay in the Lake Mary- Sanford area. Minutes from the Sanford airport, close to the Sunrail station and 45 minutes to either Disney World or the beach. Our guest cottage is a perfect place to visit. Please note: The cottage is lakeview only.

The bedroom features a queen-sized bed with a tufted headboard. Nightstands with lamps are positioned on either side, and a decorative mirror hangs on the wall. A rug adds texture to the floor, while light fixtures provide illumination in the room.

Guesthouse in Orlando

4.92 out of 5 average rating, 221 reviews

Hidden Luxury Gem w/ private porch

DETACHED GUEST HOUSE Enjoy our recently renovated guest house with a charming porch, detached from the main house. The house is beautifully decorated, and it has spacious bedroom w/ a comfort bed (tempur-pedic), a fully stocked kitchen, and a elegant dining/ living room (w/ sofa bed/ futon) Very central locate!! We are close to major highway (408, 417) 15 min from airport, 25 min from Disney/ universal park. This space was create thinking about your comfort. will love our porch.

The exterior of a renovated guesthouse is shown at night, featuring dark blue siding and a warmly lit interior. The entrance is framed by a large window, and a pathway leads to the back patio, illuminated by soft outdoor lighting.

Guesthouse in Orlando

4.84 out of 5 average rating, 251 reviews

Lovely Spacious Guesthouse in Mills 50 District

Renovated guesthouse on the same property behind our 1920's historic home in the Mills 50 District near Downtown Orlando. A large room with a comfortable queen-sized bed, a flat screen TV, two accent chairs, a kitchen corner, a/c, mini-fridge, microwave, WiFi, coffee maker and full bathroom. There is also access to a shared laundry space in the same building. Within walking distance to many bars and restaurants! A very friendly and safe neighborhood with self-check-in.

An open living space features a comfortable green sofa and light-colored armchairs with decorative pillows. A kitchen area with bar stools is visible in the background, alongside a dining table. Natural light streams through the windows, illuminating a tasteful arrangement of plants on the coffee table.

Guesthouse in Davenport

4.89 out of 5 average rating, 184 reviews

Winsome Farm Guest House

*Rest, *Relax, *Refresh, *Renew Here! Business travel? Vacationing? Escape the hectic pace but be nearby to all Central Florida amusements, restaurants, shopping, theater. Mid-way between east and west coast beaches. Large screened back porch overlooks nature conservancy. Farm to table fresh vegetables and fruits in seasonal garden right out your door and daily fresh eggs, should you choose to cook in fully outfitted kitchen or electric grill outside.

Top guest favorite

A charming guesthouse is nestled among lush tropical vegetation, surrounded by diverse greenery and tall trees. Sunlight filters through the leaves, casting dappled light on the exterior and patio area, creating a serene and inviting atmosphere.

Guesthouse in Windermere

4.94 out of 5 average rating, 266 reviews

Paradise nook near Orlando's theme parks

A quick escape to an amazing stay. Immersed in green tropical vegetation, our unique tiny Guesthouse is where we usually host our visiting family and friends from out of town. It is also open to Airbnb guests who are visiting Greater Orlando! Perfect location to escape from the hustle and bustle of a big city, yet close to everything. Take advantage of its availability and join the great experience our guests are always talking about.

Top guest favorite

A private entrance is framed by lush greenery, featuring several large tropical plants. A small, round black table with two chairs is placed on the concrete patio. Soft lighting from the entrance highlights the welcoming atmosphere.

Guesthouse in Maitland

4.97 out of 5 average rating, 155 reviews

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!

A well-lit bedroom features a spacious bed with soft bedding and decorative pillows. A ceiling fan contributes to the airflow. A small bedside table and a closet enhance the room's functionality. The entrance door is visible, adding convenience to the layout.

Guesthouse in Orlando

4.76 out of 5 average rating, 155 reviews

Renovated Guesthouse Next to Universal/Disney/EPIC

Welcome to your ideal getaway! This beautifully appointed 2-bedroom, 1-bathroom vacation guesthouse offers everything you need for a memorable stay. Centrally located, this guesthouse is only 3 minutes away from Universal Studios and 15 min from Disney! This gem features 2 queen beds, private entrance, and free parking.

The open living space features a modern kitchen with stainless steel appliances and white cabinetry. A cozy seating area includes a gray sofa and colorful throw pillows. Three wooden stools are arranged at the kitchen counter, with patterned flooring adding visual interest.

Guesthouse in Winter Park

4.86 out of 5 average rating, 155 reviews

Cozy guest house close to Downtown Orlando

Enjoy this gorgeous guest house in beautiful Winter Park. Only 10 min away from Downtown Orlando and Downtown Winter Park, 15-30 min or less to theme parks, shopping, 1 hour or less to the beach and a short drive from restaurants and supermarkets. Really close to Rollins College (6 min drive).

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Popular amenities for Winter Park guesthouse rentals

Free parking on premises

Air conditioning

Family-friendly guest house rentals

Top guest favorite

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 Orlando

5 out of 5 average rating, 210 reviews

Your Home Away From Home

The bathroom features a dark wooden vanity with a white sink and a large mirror above. A shower with a curtain and a toilet are also visible, along with light-colored tiles on the floor. Nearby, a kitchenette is partially shown, complete with a countertop.

Guesthouse in Winter Park

4.8 out of 5 average rating, 251 reviews

WELCOME HOME IN WINTER PARK

The exterior of a single-story house is showcased, featuring a combination of light peach-colored walls and stone accents. A neatly manicured lawn and small hedges frame the entrance, which is marked by a covered porch. A driveway leads to a garage door on the left.

Guesthouse in Orlando

4.83 out of 5 average rating, 340 reviews

Nice Brand New Studio !!

A covered porch is showcased, adorned with climbing plants and vibrant foliage. Two sets of double doors lead into the cottage. A mix of potted plants and outdoor seating arrangements provides a welcoming atmosphere, inviting guests to enjoy the surrounding natural beauty.

Guesthouse in Mount Dora

4.88 out of 5 average rating, 329 reviews

A Lakeshore Cottage vintage 1926

Top guest favorite

The inviting exterior features a two-story home framed by lush green grass and mature trees. Arched windows and a symmetrical design enhance the charm, while a driveway leads to the front entrance, providing easy access to the peaceful surroundings.

Guesthouse in Leesburg

4.98 out of 5 average rating, 380 reviews

Silver Lake Guest Pool House

A cozy living area features a floral-patterned sofa paired with a matching armchair. A glass-top coffee table sits in the center, surrounded by soft, neutral carpet. A dining table is visible through a large window, framed by sheer curtains that allow natural light to fill the space.

Guesthouse in Maitland

4.88 out of 5 average rating, 396 reviews

Chez Bienvenu

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.

Guesthouse in Orlando

4.94 out of 5 average rating, 411 reviews

Garden House near Orlando's cultural hub

Top guest favorite

A bright living area features a neutral-colored sectional sofa adorned with colorful throw pillows. A small wooden coffee table sits on a patterned area rug, accompanied by two stylish chairs. Natural light filters through sheer curtains and the space is complemented by a wall-mounted TV.

Guesthouse in Orlando

4.93 out of 5 average rating, 180 reviews

Private Backyard Cottage in Mills50

Guest house rentals with a patio

An inviting backyard is illuminated by string lights, creating a warm ambiance in the evening. A brick pathway leads to the entrance of the guest house, while a trampoline and hammock are positioned nearby, surrounded by grass and decorative landscaping.

Guesthouse in Orlando

4.9 out of 5 average rating, 230 reviews

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

A cozy living area is depicted, featuring a blue sofa, light wooden chairs, and a coffee table with decorative items. Natural light filters through two windows adorned with light curtains. A dining table is seen in the background, accompanied by comfortable seating.

Guesthouse in College Park

4.85 out of 5 average rating, 172 reviews

Cozy Escape in the Heart of Orlando w/ Fire Pit

A cozy seating area features a teal velvet sofa and two matching upholstered chairs, positioned near a tall potted plant. A painting of an urban landscape is displayed on the wall, and natural light enters through a window and a glass door leading to the outside.

Guesthouse in Haines City

4.93 out of 5 average rating, 71 reviews

Historic Romance Studio B

Top guest favorite

A shaded outdoor seating area features a comfortable sofa and table, surrounded by tropical plants. Bamboo fencing provides privacy while soft lighting adds warmth, creating an inviting atmosphere for relaxation. The brick patio adds a rustic touch to the garden-like setting.

Guesthouse in College Park

4.99 out of 5 average rating, 122 reviews

Top 1% ABNB Villa Oasis w/ Botanical Courtyard

A charming arched bridge is framed by lush greenery and hanging Spanish moss. The surroundings are filled with trees and plants, creating a serene outdoor space that invites exploration.

Guesthouse in Orlando

4.94 out of 5 average rating, 160 reviews

Jefferson St. Cottage

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.

Guesthouse in Orlando

4.95 out of 5 average rating, 142 reviews

The 𝕆𝕣𝕝𝕒𝕟𝕕𝕠 is the first step in the process.

The outdoor pool area features a refreshing pool surrounded by lush greenery and various tropical plants. Two teak lounges are positioned on a patterned rug near the water, providing a comfortable spot to relax. A large umbrella shades a seating area in the background.

Guesthouse in Orlando

4.87 out of 5 average rating, 121 reviews

Vintage Florida Vibes House

A spacious outdoor area features a wooden dining table surrounded by lush greenery. The seating is complemented by a variety of tropical plants, with a view of a building that offers expansive glass windows. Sunlight filters through the trees, enhancing the natural setting.

Guesthouse in Orlando

4.9 out of 5 average rating, 104 reviews

Palm Suite at Bliss House

Guest house rentals with a washer and dryer

Top guest favorite

Guesthouse in Thornton Park

4.96 out of 5 average rating, 558 reviews

Private Luxurious Apt. - Historic Downtown Orlando

Top guest favorite

Guesthouse in Deer Island

4.95 out of 5 average rating, 114 reviews

Sapphire Cottage - sleeps 6, on 5 acres with canal

Top guest favorite

Guesthouse in Orlando

5 out of 5 average rating, 104 reviews

Modern Private Studio

A circular hot tub is illuminated with blue lighting, featuring tiled edges and water cascading gently over the sides. The smooth, rounded surface showcases swirling water, creating a serene atmosphere within a well-designed outdoor space.

Guesthouse in Orlando

4.92 out of 5 average rating, 257 reviews

Modern Guest Studio (Private) Pool / Spa available

A gravel path leads to a wooden gate, framed by lush greenery. Circular stepping stones guide the way, which is partially lit, providing a welcoming path towards the guesthouse entrance. The nearby shrubs add to the serene ambiance of the outdoor space.

Guesthouse in Orlando

4.84 out of 5 average rating, 95 reviews

1/1 Private Guesthouse in Orlando (South Downtown)

A modern guest home is framed by lush greenery and trees, featuring a wide stone pathway leading to the entrance. The well-maintained lawn surrounds the house, providing a peaceful and spacious outdoor environment.

Guesthouse in Maitland

4.78 out of 5 average rating, 367 reviews

Modern Guesthome in Central FL

Top guest favorite

Guesthouse in Orlando

4.97 out of 5 average rating, 291 reviews

Peculiar One bedroom Studio.

Guesthouse in Lake Mary

4.98 out of 5 average rating, 54 reviews

Guest House w/pool and WiFi

Quick stats about guesthouse rentals in Winter Park

Total rentals
30 properties
Total number of reviews
2.4K reviews
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
30 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool

Destinations to explore