Guesthouse vacation rentals in Orlando

Guesthouse in College Park

4.99 out of 5 average rating, 140 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!!!

Guesthouse in Thornton Park

A charming exterior of a cottage-style house is framed by lush greenery and well-kept landscaping. A friendly Golden Retriever stands on the front lawn, which features a mix of plants and decorative elements. A welcoming porch with seating is visible, inviting relaxation.

4.9 out of 5 average rating, 781 reviews

Thornton Park's Historic Guest House - private

Please, read my reviews so you know what to expect when staying at the Thornton Park Guest House! Jackson, our Golden Retriever, is the real Super Host! Come join us for a weekend getaway, work trip or just so you don’t have to drive home after a fun night! We welcome all to stay with us! Orlando has some amazing historic neighborhoods that most people don't know about! Here's a great spot that's only a few blocks to Lake Eola, located in one of the most beautiful neighborhoods in FL!

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, 226 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, 117 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.

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, 157 reviews

Vintage Florida Vibes House

Enjoy a peaceful & stylish getaway in this detached Guesthouse with private entrance, gardens, kitchen & pool. Sip coffee in the shade of our Oak trees. Grill out while you watch TV and cool off in the pool after a day at the parks. Sit under the stars and string lights and nestle into your cozy beds, with your own dedicated central AC unit and ceiling fans to keep you comfortable. Only 2 miles from downtown Orlando and directly off the I4 highway that takes you to every park & attraction.

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, 353 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!

4.99 out of 5 average rating, 140 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

Guesthouse in Delaney Park

A bedroom features a spacious bed dressed in white linens, positioned against a striking black wall adorned with abstract patterns. Natural light is allowed in through an adjacent door, while decorative elements, including wall art and a plant, add a touch of character.

4.96 out of 5 average rating, 320 reviews

Cozy Guest Suite in heart of Downtown Orlando

Private, artistically inspired detached guest suite with private entrance & easy parking. Only 20-30 minutes from the theme parks. Less than 2.5 miles from the Kia Center, Camping World Stadium, Inter&Co Soccer Stadium, and Dr. Phillips Center 1 mile The suite is near the major highways and toll roads making travel a breeze! Safe, quiet, beautiful historic neighborhood including many of the the lakes downtown Orlando is known for. You'll LOVE your stay, check out our reviews!

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, 262 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.

4.76 out of 5 average rating, 525 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, 118 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.

Guesthouse in Lake Eola Heights

A serene pool area features a vibrant red pool float resting in the clear water, surrounded by lush greenery. Comfortable outdoor seating is arranged near the pool, with large umbrellas providing shade. The backdrop showcases a charming pool house with multiple glass doors, inviting natural light.

5 out of 5 average rating, 265 reviews

Livingston Pool House- In The Heart of Downtown

Welcome to the Pool House! Our newly renovated detached pool house is located in the heart of downtown Orlando, in the Lake Eola Heights Historic District. We are two blocks to beautiful Lake Eola and all the dining and entertainment that Orlando has to offer. The Pool House has everything you need for a relaxing time at home, yet all the entertainment at your finger tips! Downtown living with a tropical escape!

Popular amenities for Orlando guesthouses

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly guesthouses

A cozy living area features a dark gray sofa with bright yellow accent pillows and a matching ottoman. There are two wooden side tables with potted plants placed on them, and a wall art piece displaying the word 'FAMILY' hangs above.

4.82 out of 5 average rating, 591 reviews

Spacious getaway close to Universal and Outlets!

A two-story building is set in a green yard with shade from large trees. The exterior features a staircase leading to an upstairs unit, complemented by various plants and shrubs along the base. Clear blue skies provide a bright backdrop.

4.88 out of 5 average rating, 8 reviews

Upstairs cottage room by airport

Guesthouse in Winter Park

The guest house is framed by lush greenery and vibrant papaya trees. French doors open wide, revealing the interior space that includes a queen bed and seating area, creating a seamless connection with the outdoors. A paved walkway guides guests towards the entrance.

4.81 out of 5 average rating, 265 reviews

WELCOME HOME IN WINTER PARK

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.

4.95 out of 5 average rating, 22 reviews

Sunny Side Stay

4.95 out of 5 average rating, 197 reviews

A well-equipped kitchen is visible, featuring modern cabinetry and stainless steel appliances. A small dining table is positioned in the foreground, adorned with a vase of fresh flowers. The backsplash adds a touch of elegance, complementing the overall clean and bright design.

Guesthouse in Clermont

Modern efficiency ~ Great location

Superhost

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.

4.93 out of 5 average rating, 29 reviews

Love Nest Studio nearby highways and Airport

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

4.79 out of 5 average rating, 107 reviews

Unit B Apt Relax House

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

Guesthouses with a patio

A spacious deck features wooden steps leading to a cozy house. Lush greenery surrounds the area, with vibrant plants visible on the deck. Large glass doors provide a view into the interior space, inviting light and natural elements into the setting.

5 out of 5 average rating, 20 reviews

Charming Lakeside small House

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.

4.9 out of 5 average rating, 284 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 modern living area features a black sofa adorned with a soft white throw blanket and decorative pillows. A pair of round coffee tables, one with greenery, rests on a light-colored floor. Art hangs on the wall above, complemented by a window covered with shades.

5 out of 5 average rating, 24 reviews

Cozy Lake View Stay

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, 81 reviews

Livingston Hideaway - 2 Blocks From Lake Eola

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, 157 reviews

The 𝕆𝕣𝕝𝕒𝕟𝕕𝕠 is the first step in the process.

4.97 out of 5 average rating, 176 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

A heated saltwater pool is set within a landscaped backyard, featuring paver stones and surrounded by a white privacy fence. Colorful pool floats rest on the water's surface. Multiple lounge chairs and shade umbrellas are positioned around the pool, enhancing the relaxing outdoor space.

4.98 out of 5 average rating, 42 reviews

~Elegant Suite • Luxe Pool • Prime Orlando Stay

Guesthouse 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, 579 reviews

Private Luxurious Apt. - Historic Downtown Orlando

Guesthouse in College Park

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, 185 reviews

8th Green Cottage - A relaxing oasis in the city

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.

4.93 out of 5 average rating, 179 reviews

Jefferson St. Cottage

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, 135 reviews

Modern 1950s Studio • Near Downtown & Theme Parks

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.

4.92 out of 5 average rating, 130 reviews

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

Guesthouse in Winter Park

A bright living area features a gray sofa adorned with cushions, positioned near a light area rug. A small table and two wooden stools are located by the kitchen counter, with a decorative wall hanging and a potted plant enhancing the space's inviting atmosphere.

4.87 out of 5 average rating, 171 reviews

Cozy guest house close to Downtown Orlando

Guesthouse in College 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.

4.96 out of 5 average rating, 458 reviews

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

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.