Guesthouse holiday rentals in Orange County

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Top-rated Guesthouses in Orange County

Guests agree: These guesthouses are highly rated for location, cleanliness and more.

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Guest favourite

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.

3–10 Jul

$234 NZD per night

Guest favourite

Guesthouse in Orlando

5.0 out of 5 average rating, 154 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.

29 Jan – 5 Feb

$246 NZD per night

Guest favourite

Guesthouse in Orlando

4.95 out of 5 average rating, 133 reviews

Stylish Private Guest Suite in Downtown Orlando

Enjoy an artistic experience at this centrally-located detached guest suite in Downtown Orlando. This recently renovated home away from home is your perfect spring board for all things Orlando & the surrounding areas. The suite is 15-20 minutes from Universal Studios and about 25-30 minutes to Disney parks. Our historic neighborhood also provides some of the best scenic walks around the lakes downtown Orlando is known for. You'll LOVE the Delaney Park Casita! We hope to host you soon!

13–20 Jun

$232 NZD per night

Guest favourite

Guesthouse in Orlando

4.97 out of 5 average rating, 251 reviews

Peculiar newly built one bedroom Studio.

"(Non Smoker and No Pets)". This is an amazing and comfortable in law-suite to stay in. It is a separate portion of my home with its own private entrance. In the kitchen there is a large mini-fridge/freezer, microwave and a coffee maker. There is also an under counter washer and dryer. The sitting area includes a small couch with a twin mattress. This place is close to Walmart and Publix (5 minutes away). All attractions including Disney, Sea World and Universal are within 20-30minutes.

21–28 Sep

$147 NZD per night

Guest favourite

Guesthouse in Orlando

4.94 out of 5 average rating, 212 reviews

Modern Guest Studio (Private) Pool / Spa available

Private Guest Studio (Not Shared ) in a Perfect Orlando location, 5 minutes from I-Drive, Universal Studios, Disney World & Premium Shopping Outlets. Very Quiet lovely neighborhood with Biking distance to "Restaurant Row" where all your favorite restaurants are located. Pool & Spa available (Not Shared) All major highways at your finger tips / ride 15 min to Disney! This space has an industrial modern look with high ceilings, Stay and cook with all the amenities including a Washer and Dryer.

26 Dec – 2 Jan

$241 NZD per night

Guest favourite

Guesthouse in Orlando

4.92 out of 5 average rating, 218 reviews

Tropical Village

Private entrance to a quite and cozy one-bedroom/bathroom suite with a romantic kitchen & dining area. Centrally located less than 10 minutes from the Orlando International Airport. Great convenient shopping areas, 10 minute Lee Vista Promenade Shopping Center 15 minute drive to Waterford Lakes Town Center. Great Variety of Dining Restaurants around this area. Near UCF, Valencia, Full Sail, and Rollins College. Easy access to the mayor expressway of the beautiful city. Book your stay today!

13–20 Nov

$162 NZD per night

Guest favourite

Guesthouse in Orlando

4.97 out of 5 average rating, 287 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!

5–12 Sep

$225 NZD per night

Guest favourite

Guesthouse in Orlando

4.88 out of 5 average rating, 218 reviews

Couples Oasis *Heated Pool* and Lake View

Have a romantic getaway in this SODO Couples Oasis Retreat with private pool or come work alone in this peaceful oasis. Perfect for couples or the busy profesional who want privacy and quiet with lake view while relaxing by the pool. Centrally located in SODO by downtown Orlando. Close to everything. Walk to great nearby eating places. Love ice cream Kelly’s Hand Made ice cream is a 5 minute walk from the house. *Heated Pool* available for $20 fee for first day and $5 every extra day.

22–29 Aug

$247 NZD per night

Guest favourite

Guesthouse in Winter Park

4.98 out of 5 average rating, 249 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.

18–25 Jul

$204 NZD per night

Guest favourite

Guesthouse in Orlando

4.98 out of 5 average rating, 147 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!

3–10 Oct

$162 NZD per night

Guest favourite

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.

28 Jan – 4 Feb

$198 NZD per night

Guest favourite

Guesthouse in Orlando

4.9 out of 5 average rating, 381 reviews

Bungalow Close to Attractions and Downtown Orlando

This bungalow is the perfect mix of beauty and function. Close to downtown Orlando, Disney, Universal, and SeaWorld. Only 20 minutes from Orlando International Airport and less than one hour to Florida’s world renowned beaches. Adjacent to the SoDo area of Orlando, the space is within walking distance to restaurants, shops, parks, a Super Target, Orlando Regional Medical Center and much more.

8–15 Mar

$192 NZD per night