Guesthouse vacation rentals in Winter Park

4.99 out of 5 average rating, 163 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 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, 103 reviews

Livingston Hideaway • Walk To Lake Eola • Hot Tub

Welcome to Livingston Hideaway, a charming historic duplex in downtown Orlando, just two blocks from Lake Eola. This private space offers a quiet, residential feel while being steps from dining, nightlife, and events. Perfect for couples or business travelers, it features a private entrance, fenced outdoor area with hot tub and putting green, free parking, and fast Wi-Fi. Thoughtfully updated with modern comforts, Livingston Hideaway blends historic character with walkable downtown convenience.

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, 261 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 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.

4.98 out of 5 average rating, 135 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.

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, 381 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!

4.98 out of 5 average rating, 136 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 yard and pool with hosts. 1 hr. from Disney & the beaches. 12 yr & older only. Single Sofa bed for 3rd guest. NOT a heated pool. Not Handicap Certified, but most wheelchair guests have not had issues. Narrowest opening 32" Ramp into unit by pool. Shower no steps. Queen bed height 29"-standard cabinets. Grab bars in bathroom. Airbnb's Accessibility Policy has exempted this listing from accepting Service & Emotional Support Animals due to owner's severe health condition.

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, 195 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 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, 125 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 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.

4.95 out of 5 average rating, 281 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

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, 104 reviews

20 | Excellent | Above Average

Newly built ! Entire private garage apartment! Step into the comfort of this unique garage apartment nestled in the tranquil and picturesque Mills 50 District . This home promises a relaxing retreat close to the All Major Theme parks and biking trails Downtown Orlando , restaurants, shops, and attractions. ✔ Comfortable Queen bed sleeps "2" ✔ Full Kitchen ✔ Free designated parking spot and free street parking ✔ Smart TV ✔ Washer/Dryer "FREE" ✔ Workspace ✔ High-Speed Wi-Fi

A cozy living space is shown, featuring a teal sofa and a yellow armchair beside a round coffee table. Two windows with bamboo shades allow natural light to enter, while a small desk and chair are visible in the corner, enhancing the usability of the room.

5 out of 5 average rating, 131 reviews

Detached suite in Mills 50 food paradise

Our cozy urban-jungle retreat puts you in the heart of an impressive food district and is centrally located. You’ll be a short drive/walk from dozens of diverse restaurants and several concert venues. Our detached suite is great for both business travel (5 min from downtown) and pleasure (30 min from the theme parks). The main room of the suite has space for lounging, a wet bar, and a small desk. It connects to a room with a queen bed and ensuite bathroom.

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.

4.99 out of 5 average rating, 287 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 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.

4.96 out of 5 average rating, 119 reviews

The Studio

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, 102 reviews

The Green Room Orlando

4.93 out of 5 average rating, 341 reviews

Charming Thornton Park Guesthouse

Guesthouse in Deer Island

4.96 out of 5 average rating, 139 reviews

Sapphire Cottage - sleeps 6, on 5 acres with canal

A cozy sleeping area features a spacious bed with dark bedding. A wall-mounted television displays a calming fire effect. The room's dark walls create an intimate atmosphere, complemented by a side table holding neatly arranged towels. Soft lighting enhances the room’s tranquil feel.

4.97 out of 5 average rating, 125 reviews

Lou’s Garden Hideout

5 out of 5 average rating, 132 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

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.

4.95 out of 5 average rating, 372 reviews

Cozy Guest Suite in heart of Downtown Orlando

A cozy sleeping area is presented with a neatly made bed, featuring layers of soft bedding in neutral tones. A small wooden sign with the word 'XOXO' is placed on a bedside table, adding a touch of character to the room.

4.92 out of 5 average rating, 131 reviews

Peaceful Guest-house in heart of Orlando

Guest house rentals with a patio

4.98 out of 5 average rating, 324 reviews

Guesthouse in Kissimmee

"Little Blue House" Getaway Near the Disney Parks

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.

4.92 out of 5 average rating, 195 reviews

Jefferson St. Cottage

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.

4.9 out of 5 average rating, 194 reviews

The Little House

4.9 out of 5 average rating, 139 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

4.93 out of 5 average rating, 184 reviews

Private Guesthouse | Yard & W/D | Downtown Orlando

4.94 out of 5 average rating, 143 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

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.

4.95 out of 5 average rating, 133 reviews

Modern & Cozy Retreat - Orlando City Center Epic

Guesthouse in Azalea Park

4.99 out of 5 average rating, 109 reviews

Charming Studio for two, 13 min from MCO Airport

Guest house rentals with a washer and dryer

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, 610 reviews

Orlando Birdcage Private Apt, Walkable Downtown

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, 151 reviews

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

Guesthouse in Winter Garden

4.9 out of 5 average rating, 102 reviews

A place with a view

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.

Guesthouse in Bay Hill

4.9 out of 5 average rating, 286 reviews

Modern Guest Studio with pool access

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, 256 reviews

Black House- Private Cottage in Thornton Park!

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.

4.86 out of 5 average rating, 112 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, 111 reviews

Beautiful garage suite w/washer and dryer

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.