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 Orlando

5.0 out of 5 average rating, 162 reviews

Treehouse Inn Downtown Orlando, 2 bedrooms 2 bath

Treehouse in Downtown Orlando is surrounded by majestic heritage Oaks. Two Bed Two Bath with a Mini-Master & full Kitchen. Very private deck near Bamboo Hedge. Two blocks from a small neighborhood Deli serving breakfast, lunch and dinner with Great coffee & Craft beers. We are walking distance from popular Thornton Park pubs and restaurants. Lake Greenwood and Lake Davis are close by for a leisurely walk or brisk jog. Enhanced cleaning in use. Jakob and Marty are happy to help with your stay.

Jul 2 – 9

R2,221 ZAR per night

Guest favorite

Guesthouse in Orlando

5.0 out of 5 average rating, 155 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.

Aug 15 – 22

R1,959 ZAR per night

Guest favorite

Guesthouse in Orlando

4.97 out of 5 average rating, 288 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!

Aug 22 – 29

R1,815 ZAR per night

Guest favorite

Guesthouse in Orlando

4.91 out of 5 average rating, 145 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.

Jul 6 – 13

R2,444 ZAR per night

Superhost

Guesthouse in Winter Park

4.92 out of 5 average rating, 266 reviews

Tiny Cottage - 3 MI to Downtwn w/ Grill & Hammocks

Renovated guest suite using original reclaimed materials to create a modern vintage farmhouse vibe. Centrally located in highly desirable Winter Park - less than 10-mins to downtown Orlando. 5-mins to grocery & convenience stores, 8-mins to restaurants & shopping, 20-mins to Disney & Universal Studios. Includes comfortable queen-size bed, work station / dining area, fridge, microwave, access to free parking & Wi-Fi, friendly neighborhood, self check-in, and sanitized for your safety.

Jul 13 – 20

R1,956 ZAR per night

Guest favorite

Guesthouse in Orlando

4.93 out of 5 average rating, 227 reviews

Bungalow Near Downtown Orlando - No Cleaning Fee!

🌟 Newly Renovated Gem! 🏡 Nestled behind our 1950’s bungalow in Downtown Orlando's charming College Park district. Explore urban living with a small-town vibe! 🚲 Bike along brick tree-lined streets to award-winning restaurants, boutique shops, local breweries, and vibrant farmers markets! Nearby: 🌳 Winter Park: 10 mins 🏙️ Downtown Orlando: 10 mins 🛣️ I4: 2 mins 🏰 Disney and Universal: 20-30 mins 🏥 Hospital: 5 mins Experience the best of Orlando just moments away! ✨

May 11 – 18

R2,188 ZAR per night

Guest favorite

Guesthouse in Orlando

4.84 out of 5 average rating, 201 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.

Aug 10 – 17

R1,309 ZAR per night

Guest favorite

Guesthouse in Winter Park

4.98 out of 5 average rating, 250 reviews

Private and Peaceful with Full Kitchen

Welcome to our spacious, secure getaway tucked in a quiet Winter Park neighborhood. Enjoy full kitchen, hardwood floors, high ceilings, superfast WiFi and lots of TV steaming options, walk-in closets and walk-in shower. The hosts live in a separate space attached to the house. Your suite and patio are completely private. Please register all guests when making your reservation. For everyone’s safety, we ask that there be no visitors besides registered guests.

Jul 21 – 28

R1,827 ZAR per night

Guest favorite

Guesthouse in Orlando

4.98 out of 5 average rating, 149 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!

Oct 24 – 31

R1,633 ZAR per night

Guest favorite

Guesthouse in Orlando

4.95 out of 5 average rating, 132 reviews

Jefferson St. Cottage

This cottage is a unique free-standing detached dwelling in the heart of Lawsona Park (Historic Downtown Orlando). It sits behind the owner's main house in the back of the lot. The cottage is newly updated with all the amenities to give guests a perfect secluded area near bars, eateries, parks as well as easy access to highways to visit Universal, Disney World, Sea World any more attractions in central Florida.

Feb 5 – 12

R1,793 ZAR per night

Guest favorite

Guesthouse in Orlando

5.0 out of 5 average rating, 201 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!

Jan 6 – 13

R4,016 ZAR per night

Guest favorite

Guesthouse in Maitland

4.87 out of 5 average rating, 381 reviews

Chez Bienvenu

Close proximity to Park Avenue in Winter Park! Sunny and Adorable Vintage Guest House ...entire spacious guest house; with private entrance and driveway* Just a couple of blocks off Park Avenue to enjoy Shopping! Cafes! Museums! Nestled in quiet family community* •Smart TV •Stackable washer and dryer included in the unit. •Grill, Beach Chairs, Fishing Poles available •750 square feet of living space

Mar 30 – Apr 6

R2,146 ZAR per night