Guesthouse vacation rentals in Winter Park

Guesthouse in Thornton Park

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.

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!

Guesthouse in College Park

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.

4.97 out of 5 average rating, 432 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.

4.97 out of 5 average rating, 105 reviews

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

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.

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

4.97 out of 5 average rating, 115 reviews

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

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.

4.92 out of 5 average rating, 220 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.

4.84 out of 5 average rating, 249 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.

4.91 out of 5 average rating, 181 reviews

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

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.

4.94 out of 5 average rating, 266 reviews

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

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.

4.98 out of 5 average rating, 154 reviews

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

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!

Superhost

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.