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.

Jul 3 – 10

$102 per night

Guest favorite

Guesthouse in Orlando

4.89 out of 5 average rating, 609 reviews

Thornton Park's Historic Guest House - private

Please, read my reviews so you know what to expect when staying at the Thornton Park Guest House! One of the things I've personally love is finding new experiences in each city I travel to. Orlando has some amazing neighborhoods that most people don't know about because they stay near the Convention Center or the theme Park hotels... Here's a great spot that's close to the parks/convention center but also only a few blocks to Lake Eola, located in one of the most beautiful neighborhoods in FL

Dec 4 – 11

$81 per night

Guest favorite

Guesthouse in Orlando

5.0 out of 5 average rating, 152 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 7 – 14

$97 per night

Guest favorite

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.

Jan 24 – 31

$60 per night

Guest favorite

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.

Jan 29 – Feb 5

$94 per night

Guest favorite

Guesthouse in Orlando

4.88 out of 5 average rating, 217 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.

Aug 22 – 29

$109 per night

Guest favorite

Guesthouse in Orlando

4.98 out of 5 average rating, 346 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.

Jan 26 – Feb 2

$184 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.

Oct 1 – 8

$93 per night

Guest favorite

Guesthouse in Four Corners

4.98 out of 5 average rating, 425 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.

Nov 23 – 30

$82 per night

Guest favorite

Guesthouse in Orlando

4.95 out of 5 average rating, 131 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.

Oct 18 – 25

$84 per night

Guest favorite

Guesthouse in Orlando

4.93 out of 5 average rating, 257 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.

Aug 31 – Sep 7

$112 per night

Guest favorite

Guesthouse in Orlando

4.96 out of 5 average rating, 488 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!

Oct 1 – 8

$103 per night

Vacation rentals for every style

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Popular amenities for Kissimmee guesthouse rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly guest house rentals

Guest favorite

Guesthouse in Windermere

4.94 out of 5 average rating, 239 reviews

Small Guesthouse near Orlando's Theme Parks

Oct 20 – 27

$118 per night

Guest favorite

Guesthouse in Orlando

4.84 out of 5 average rating, 318 reviews

Nice Brand New Studio !!

Sep 9 – 16

$70 per night

Superhost

Guesthouse in Orlando

4.83 out of 5 average rating, 18 reviews

Lakefront Guest House by downtown :Boat, Fishing…

May 20 – 27

$112 per night

Guesthouse in Kissimmee

4.92 out of 5 average rating, 51 reviews

Bird Watchers Delight - home close to Disney WIFI

Aug 4 – 11

$52 per night

Guesthouse in Orlando

4.96 out of 5 average rating, 82 reviews

Bungalow Guesthouse Downtown Orlando

Nov 1 – 8

$134 per night

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Guest house rentals with a patio

Guest favorite

Guesthouse in Orlando

4.95 out of 5 average rating, 132 reviews

Stylish Private Guest Suite in Downtown Orlando

Jun 26 – Jul 3

$111 per night

Guest favorite

Guesthouse in Orlando

4.93 out of 5 average rating, 138 reviews

Hidden Luxury Gem w/ private porch

May 5 – 12

$83 per night

Guest favorite

Guesthouse in Orlando

4.8 out of 5 average rating, 56 reviews

Vintage Florida Vibes House

Oct 17 – 24

$82 per night

Guest favorite

Guesthouse in Orlando

4.91 out of 5 average rating, 57 reviews

The Cottage

Dec 31 – Jan 7

$74 per night

Guest favorite

Guesthouse in Orlando

4.92 out of 5 average rating, 37 reviews

Cozy new guesthouse to yourself.

Oct 19 – 26

$62 per night

Guest favorite

Guesthouse in Orlando

4.95 out of 5 average rating, 60 reviews

Glamorous guesthouse City Center! 10 min Downtown

Sep 26 – Oct 3

$92 per night

Guest favorite

Guesthouse in Orlando

4.97 out of 5 average rating, 32 reviews

Downtown Cozy/Modern Studio

Aug 29 – Sep 5

$87 per night

Guest favorite

Guesthouse in Orlando

4.99 out of 5 average rating, 78 reviews

King Bed 👑 Fire Pit 🔥 Private ⭐️ Grill 🍗 Location

Sep 27 – Oct 4

$94 per night

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Guest house rentals with a washer and dryer

Guest favorite

Guesthouse in Orlando

4.9 out of 5 average rating, 381 reviews

Bungalow Close to Attractions and Downtown Orlando

Mar 6 – 13

$84 per night

Guest favorite

Guesthouse in Davenport

4.93 out of 5 average rating, 150 reviews

Winsome Farm Guest House

Mar 24 – 31

$99 per night

Guest favorite

Guesthouse in Orlando

4.99 out of 5 average rating, 239 reviews

Black House- Private Cottage in Thornton Park!

Jun 29 – Jul 6

$166 per night

Superhost

Guesthouse in Orlando

4.85 out of 5 average rating, 132 reviews

☼BohoBungalow ☼ Close to EVERYTHING! Work frm home

Mar 1 – 8

$136 per night

Guest favorite

Guesthouse in Orlando

4.89 out of 5 average rating, 47 reviews

Kyle's Place - No Cleaning Fee + Laundry Room

Nov 1 – 8

$73 per night

Guest favorite

Guesthouse in Orlando

5.0 out of 5 average rating, 18 reviews

Modern Private Studio

Jul 14 – 21

$98 per night

Guest favorite

Guesthouse in Kissimmee

4.9 out of 5 average rating, 90 reviews

Cozy 1BR apt-Pool/Tennis/Gym/Near attractions

Nov 27 – Dec 4

$133 per night

Guest favorite

Guesthouse in Orlando

4.97 out of 5 average rating, 65 reviews

The Cottage

Jun 23 – 30

$106 per night

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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

Vacation rentals for every style

Cabins

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Popular amenities for Kissimmee guesthouse rentals

Family-friendly guest house rentals

Guesthouse in Windermere

Guesthouse in Orlando

Guesthouse in Orlando

Guesthouse in Kissimmee

Guesthouse in Orlando

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 Davenport

Guesthouse in Orlando

Guesthouse in Orlando

Guesthouse in Orlando

Guesthouse in Orlando

Guesthouse in Kissimmee

Guesthouse in Orlando

Quick stats about guesthouse rentals in Kissimmee

Total rentals

Local attractions

Popular amenities

Wifi availability

Total number of reviews

Nightly prices starting at

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