Guesthouse vacation rentals in Kissimmee

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Top-rated guesthouse rentals in Kissimmee

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

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Guest favorite

Guesthouse in Orlando

4.96 out of 5 average rating, 137 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!

Sep 5 – 12

$132 per night

Guest favorite

Guesthouse in Orlando

4.94 out of 5 average rating, 213 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.

Jul 28 – Aug 4

$106 per night

Guest favorite

Guesthouse in Orlando

4.88 out of 5 average rating, 220 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.

Aug 24 – 31

$109 per night

Guest favorite

Guesthouse in Orlando

4.88 out of 5 average rating, 169 reviews

Adorable Studio Guest House

Enjoy a quiet peaceful stay just minutes outside of Downtown Orlando. Walk to local restaurants, bars and cafes. The guesthouse has a fully equipped kitchen, full bathroom, built-in closet, wi-fi, queen bed and pull-out murphy bed. The TV has access to Netflix, Hulu and Disney Plus. Owners live on property in the main house, and are available to answer any questions. Distances to Major Attractions: Downtown Orlando--10 Mins Airport--20 Mins Universal Studios--20 Mins Disney--30 Mins

Oct 6 – 13

$72 per night

Guest favorite

Guesthouse in Orlando

4.94 out of 5 average rating, 140 reviews

Hidden Luxury Gem w/ private porch

DETACHED GUEST HOUSE Enjoy our recently renovated guest house with a charming porch, detached from the main house. The house is beautifully decorated, and it has spacious bedroom w/ a comfort bed (tempur-pedic), a fully stocked kitchen, and a elegant dining/ living room (w/ sofa bed/ futon) Very central locate!! We are close to major highway (408, 417) 15 min from airport, 25 min from Disney/ universal park. This space was create thinking about your comfort. will love our porch.

Jul 21 – 28

$88 per night

Guest favorite

Guesthouse in Orlando

4.82 out of 5 average rating, 450 reviews

Spacious getaway close to Universal and Outlets!

PLEASE READ BEFORE BOOKING Checkin -4pm Checkout-10-am Welcome to our home! The home is a basement apartment with private entrance ,driveway, and one bedroom in your suite with 2 queen size beds, sofa pull out,and kitchen (portable burners no stove) and a large bathroom with double shower head. This is your own space we have zero way to interact with you but we are a family who lives above you similar to neighbors in apartment. 5 min- universal 10 min- outlets 20 min- Disney

Oct 25 – Nov 1

$86 per night

Guest favorite

Guesthouse in Orlando

4.98 out of 5 average rating, 351 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.

Apr 12 – 19

$188 per night

Superhost

Guesthouse in Orlando

4.8 out of 5 average rating, 201 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.

May 20 – 27

$94 per night

Guest favorite

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.

Sep 2 – 9

$81 per night

Guest favorite

Guesthouse in Orlando

4.92 out of 5 average rating, 259 reviews

CLEAN & Modern 2BR w/ sunny yard, close to Disney

Our place is a 2BR, one-bath entire home, with a cozy fire pit and patio furniture space, a fun kids playground area, and a large sunny yard with mature trees for you and guests to explore and enjoy. Excellent location within 15 mins driving distance to the main Disney amusement parks. Free WiFi and HDTV with streaming services available. Please read “Guest Access” for note on other house in the property.

Sep 25 – Oct 2

$118 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.

Jun 26 – Jul 3

$96 per night

Guest favorite

Guesthouse in Orlando

4.9 out of 5 average rating, 107 reviews

Downtown private pool house. Two blocks from ORMC

Recharge in this private one bedroom, one bath pool house. Relax in the pool after a long day and enjoy a restful night in a very comfortable queen size bed. Walking distance to downtown and ORMC. Two miles to Kia (Amway) Center. Three miles to Camping World. Nine miles to Universal Studios. 14 miles to SeaWorld. 15 miles to Disney.

Jul 27 – Aug 3

$78 per night