Guesthouse vacation rentals in Orange County

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Top-rated guesthouse rentals in Orange County

Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

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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

R2,262 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.

Jan 15 – 22

R2,131 ZAR per night

Guest favorite

Guesthouse in Orlando

4.96 out of 5 average rating, 252 reviews

Peculiar 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.

Feb 21 – 28

R1,322 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!

Oct 7 – 14

R2,051 ZAR per night

Guest favorite

Guesthouse in Orlando

4.88 out of 5 average rating, 219 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 $10 every extra day.

Oct 1 – 8

R2,373 ZAR per night

Guest favorite

Guesthouse in Orlando

4.92 out of 5 average rating, 172 reviews

"Modern Suite with Kitchenette"

"Completly private cozy one-bedroom/bathroom suite with a romantic kitchen & dining area. Centrally located 20 minutes drive from Universal Studios. , 15 minutes to Downtown Orlando, 30 minutes to Disneyworld. Walking distance to Central Florida Fairgrounds, and Chinatown. Book your stay today!" INCLUDED - 1 Full Bed - 1 Full Bathroom - 1 Smart ROKU TV - Wi-Fi 60 Mbps - Kitchen - Refrigerator - Dining table & chairs - 1 Parking Space - AC/Heater -Temperature Range 70°F-79°F

Sep 6 – 13

R1,098 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 25 – Aug 1

R1,863 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!

Sep 19 – 26

R1,644 ZAR per night

Guest favorite

Guesthouse in Orlando

4.99 out of 5 average rating, 143 reviews

Quaint Guesthouse Near the Attractions

This picturesque hideaway suite is recently remodeled with granite and tile throughout. Ideal for couples, but can comfortably accommodate up to a family of four with a separate king size bedroom plus a king size sleeper sofa in living room. You may choose to prepare meals in the kitchenette, use the BBQ grill, dine in one of the hundreds of nearby restaurants, or order Uber Eats if you prefer to stay home and relax.

Sep 15 – 22

R2,026 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 4 – 11

R1,828 ZAR per night

Guest favorite

Guesthouse in Maitland

4.98 out of 5 average rating, 117 reviews

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!

Oct 12 – 19

R1,869 ZAR per night

Guest favorite

Guesthouse in Orlando

4.9 out of 5 average rating, 383 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.

Jan 8 – 15

R1,758 ZAR per night