Guesthouse vacation rentals in Kissimmee

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Top-rated guesthouse rentals in Kissimmee

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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.

Guest favorite

Guesthouse in Orlando

4.96 out of 5 average rating, 257 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 favorite

Guesthouse in Orlando

4.94 out of 5 average rating, 216 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 favorite

Guesthouse in Orlando

4.88 out of 5 average rating, 223 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.

Superhost

Guesthouse in Davenport

4.96 out of 5 average rating, 224 reviews

Contemporary Guesthouse/private pool near Disney!

Come relax just minutes from Disney in our contemporary studio guesthouse with private entrance and secluded pool. We only host and operate this single listing - taking you back to the days when Airbnb was new and was known for high hosting experiences. We are very close to the theme parks with a convenient back-road connection via Old Lake Wilson road. Our guesthouse is a private stand alone suite across the entry from our main house where my wife and I live.

Guest favorite

Guesthouse in Orlando

4.98 out of 5 average rating, 152 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

4.98 out of 5 average rating, 356 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.

Superhost

Guesthouse in Orlando

4.79 out of 5 average rating, 202 reviews

Luxury 5 star home 3 min Universal/ Orlando City

Enjoy this beautiful cozy and modern guesthouse. Recently built, our place has private entrance, private porch and private free parking located just 2 minutes from Universal Studios. The bathroom suite has a rain shower just like you would expect in a 5 star Hotel, new kitchen, appliances and 2 TVs one in the bedroom another in the living room Need to check-in early or check-out later? Please read Guest Access below.

Guest favorite

Guesthouse in Four Corners

4.98 out of 5 average rating, 428 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 favorite

Guesthouse in Orlando

5.0 out of 5 average rating, 206 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 Orlando

4.93 out of 5 average rating, 163 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.)

Guest favorite

Guesthouse in Orlando

4.96 out of 5 average rating, 491 reviews

Private Luxurious Apt. - Historic Downtown Orlando

Cozy apartment in downtown, off brick-lined streets with private entrance. Full kitchen, living, separate bedroom & bathroom plus space for working. Pullout ottoman in living room. Large outdoor living space. Amenities: fridge, microwave, stove/oven, dishwasher, washer/dryer, TV, WiFi & more. Featured in Orlando Date Night's Guide for locals!

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Popular amenities for Kissimmee guesthouse rentals

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Free parking on premises

4.83 out of 5 average rating, 18 reviews

Lakefront Guest House by downtown :Boat, Fishing…

Guesthouse in Orlando

4.96 out of 5 average rating, 82 reviews

Bungalow Guesthouse Downtown Orlando

4.95 out of 5 average rating, 42 reviews

Palm Suite at Bliss House

5.0 out of 5 average rating, 25 reviews

Modern Private Studio

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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, Wifi, and Pool
Wifi availability
20 properties include access to wifi
Total number of reviews
770 reviews
Nightly prices starting at
$30 before taxes and fees

Guesthouse vacation rentals in Kissimmee

Top-rated guesthouse rentals in Kissimmee

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Guesthouse in Orlando

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Guesthouse in Orlando

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Guest house rentals with a patio

Guesthouse in Orlando

Guesthouse in Orlando

Guesthouse in Orlando

Guesthouse in Orlando

Guesthouse in Orlando

Guesthouse in Orlando

Guesthouse in Orlando

Guesthouse in Orlando

Guest house rentals with a washer and dryer

Guesthouse in Orlando

Guesthouse in Orlando

Guesthouse in Orlando

Guesthouse in Davenport

Guesthouse in Orlando

Guesthouse in Orlando

Guesthouse in Davenport

Guesthouse in Orlando

Quick stats about guesthouse rentals in Kissimmee

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Wifi availability

Total number of reviews

Nightly prices starting at

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