Guesthouse holiday rentals in Kissimmee

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Top-rated Guesthouses in Kissimmee

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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.

Guest favourite

Guesthouse in Orlando

4.96 out of 5 average rating, 140 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!

Guest favourite

Guesthouse in Clermont

4.98 out of 5 average rating, 104 reviews

Downtown Apartment - Walk to Lake, Shops & Dining

This stylish apartment, in Downtown Clermont is @ the center of the coast-to-coast bike trail. Enjoy the quaint lake town experience to the fullest without having to drive anywhere. Lakefront, breweries, retail, dining- all within a 3 min walk! Best features indoors include comfy beds, a double shower, smart TV, & cozy aesthetics. The space is well stocked w/ all the essentials. Small appliances for cooking include an air fryer, crockpot & skillet. Garage storage available 4 recreational gear.

Guest favourite

Guesthouse in Orlando

4.96 out of 5 average rating, 255 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.

Guest favourite

Guesthouse in Orlando

4.94 out of 5 average rating, 214 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.

Guest favourite

Guesthouse in Orlando

4.88 out of 5 average rating, 221 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.

Guest favourite

Guesthouse in Orlando

4.98 out of 5 average rating, 352 reviews

Lakefront Seclusion modern guesthouse+Pool+Hot tub

An oasis in the city is what you will be surprised to find here at your guest house, located on a peaceful estate on the shore of Lake Hourglass. Secluded from the noises of the city, but still just minutes from everything, it's the perfect base to explore Orlando from, or perhaps to enjoy a staycation at if you're a local! For check out, please just enjoy your stay with us, you don’t need do any tidy or clean steps for us.

Guest favourite

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.

Guest favourite

Guesthouse in Four Corners

4.98 out of 5 average rating, 427 reviews

Quiet Room Close to Disney and Attractions

Quaint and quiet retreat just minutes from attractions. Private in-law suite and bathroom, detached from main house. Features all the basic amenities of a hotel room with the feeling of home. Room is perfect for up to three persons. Queen bed and additional sleeper sofa. Located in Reunion Resort. There is a pool, gym, and spa located within the resort but not on the property and is for Reunion club members only.

Guest favourite

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!

Guest favourite

Guesthouse in Orlando

4.95 out of 5 average rating, 133 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.

Guest favourite

Guesthouse in Orlando

4.93 out of 5 average rating, 162 reviews

Private Backyard Cottage in Mills50

Airy one-bedroom garden cottage in Orlando's hippest historic neighborhood. Walk or bike to great restaurants, parks, and bars. Located 5 to 10 min to Downtown Orlando, Florida Hospital, and Winter Park; 20 to 30 min to Universal, Disney, and UCF. Recently upgraded with queen bed, stove, and access to brand-new washer/dryer. (City of Orlando Short-Term Rental registered.)

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4.96 out of 5 average rating, 370 reviews

The Coach House- 2 bedroom/3 bath Orlando Getaway!

Guesthouse in Orlando

4.96 out of 5 average rating, 82 reviews

Bungalow Guesthouse Downtown Orlando

4.95 out of 5 average rating, 37 reviews

Palm Suite at Bliss House

4.9 out of 5 average rating, 51 reviews

Kyle's Place - No Cleaning Fee + Laundry Room

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Quick stats about guesthouse rentals in Kissimmee

Total rentals
20 properties
Local attractions
Star Island Resort & Club, Silver Spurs Arena and FantasyWorld Resort
Popular amenities
Kitchen, Wi-Fi and Pool
Wi-Fi availability
20 properties include access to Wi-Fi
Total number of reviews
770 reviews
Nightly prices starting at
$50 NZD before taxes and fees

Guesthouse holiday rentals in Kissimmee

Top-rated Guesthouses in Kissimmee

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Guesthouse in Kissimmee

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Guesthouse in Orlando

Quick stats about guesthouse rentals in Kissimmee

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