Guesthouse vacation rentals in Winter Park

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Top-rated guesthouse rentals in Winter Park

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Guest favorite

Guesthouse in Thornton Park

4.89 out of 5 average rating, 684 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!

Guest favorite

Guesthouse in College Park

4.93 out of 5 average rating, 240 reviews

Bungalow Near Downtown Orlando - No Cleaning Fee!

Discover this newly renovated gem behind our charming 1950s bungalow in Downtown Orlando's College Park. Enjoy urban living with a small-town vibe, biking along tree-lined streets to restaurants, shops, breweries, and farmers markets. Please message us and ask about our early check-in/out options! Conveniently access Winter Park (10 mins), Downtown Orlando (10 mins), I4 (2 mins), Disney and Universal (20-30 mins), and a nearby hospital (5 mins). Experience the best of Orlando moments away!

Guest favorite

Guesthouse in College Park

4.94 out of 5 average rating, 108 reviews

Beautiful 1 Bed/1 Bath in College Park Orlando

College Park is a great residential neighborhood of Orlando close to all the action, but also far enough away if you are looking for peace and quiet. There are several bars, breweries, and restaurants within minutes by car and you can also Uber downtown within 5-10 minutes. The Advent Health Hospital is within walking distance just 3 blocks away. Everything from Disney and Theme Parks to nightlife and nature are about a 30 minute drive away. If you need any help deciding what to do, just ask.

Guest favorite

Guesthouse in Orlando

4.97 out of 5 average rating, 306 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!

Guest favorite

Guesthouse in College Park

4.91 out of 5 average rating, 163 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.

Guest favorite

Guesthouse in College Park

4.97 out of 5 average rating, 119 reviews

New Mid Century-Modern Studio

Enjoy your stay in this beautifully decorated studio with all the conveniences of home. We are located in College Park of Orlando. The main road here is Edgwater Drive which offers restaurants, bars, and boutique shops. This location is 15 min. from downtown, 30 min. from all the attractions, and 5 min. from one of the city’s largest hospitals in central Florida. Also, you are within walking distance from the historic Dubsdread Golf Club and restaurant. Perfect home away from home.

Guest favorite

Guesthouse in College Park

4.99 out of 5 average rating, 102 reviews

The Studio

Nestled off of a quiet brick street behind a 1922 bungalow, this studio garage apartment is a blend of cozy charm and convenience. Ideal for a solo traveler, but can accommodate two. The Studio has a private entry encompassing 3 rooms (bed/kitchen/bath). WiFi(200mbps); Roku TV, Netflix) provided. Quality grocery stores, restaurants, bars and lakes are a short walk away. Access to major highways are minutes away, making this location perfect for the business or leisure travel.

Guest favorite

Guesthouse in Orlando

4.84 out of 5 average rating, 229 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.

Guest favorite

Guesthouse in Orlando

4.94 out of 5 average rating, 147 reviews

Jefferson St. Cottage

This cottage is a unique free-standing detached dwelling in the heart of Lawsona Park in the Historic District in downtown Orlando. It sits behind the owner's main house in the back of the lot; privacy is not an issue. The cottage is loaded with all the amenities needed to enjoy your stay. We are close to highways to visit Universal, Disney World, Sea World any more attractions in central Florida. In addition, Uber is a very good option for transportation.

Guest favorite

Guesthouse in College Park

4.98 out of 5 average rating, 188 reviews

The Loft in College Park

The Loft is a private guesthouse located above our garage near Downtown Orlando and Ivanhoe Village. It is walking distance to multiple restaurants, bars and shops. Also close to I-4 and easy access to the attractions. The studio space offers a queen size bed as well as a queen size sleeper sofa in the living room area. Luxurious full size bathroom with walk in shower and rain shower head. Perfect get away for those looking to enjoy Orlando!

Guest favorite

Guesthouse in Orlando

5 out of 5 average rating, 226 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!

Guest favorite

Guesthouse in College Park

4.91 out of 5 average rating, 143 reviews

Cozy Escape in the Heart of Orlando w/ Fire Pit

Enjoy a peaceful getaway in this private, pet friendly guest suite. Awake refreshed and ready for a day of exploring Florida. Head out and wander east to beautiful beaches, west to the best theme parks, or stay close in the heart of Orlando and enjoy restaurants, shops, and parks (all in walking distance). After a day of fun, come back and roast some hot dogs or s’mores under the stars in our paver fire pit.