Guest house holiday rentals in Winter Park

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.

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.

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

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.

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.

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.​

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!

Renovated Guesthouse Next to Universal/Disney

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.

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).