Guesthouse accommodation & 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.

3 – 10 July

$1,489 AUD total

Guest favourite

Guesthouse in Orlando

5.0 out of 5 average rating, 153 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.

29 Jan – 5 Feb

$1,567 AUD total

Guest favourite

Guesthouse in Orlando

4.95 out of 5 average rating, 133 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!

13 – 20 June

$1,477 AUD total

Guest favourite

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.

21 – 28 Sept

$934 AUD total

Guest favourite

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.

26 Dec – 2 Jan

$1,534 AUD total

Guest favourite

Guesthouse in Orlando

4.88 out of 5 average rating, 218 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.

22 – 29 Aug

$1,570 AUD total

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.

5 – 12 Aug

$1,332 AUD total

Guest favourite

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.

8 – 15 Aug

$1,182 AUD total

Guest favourite

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.

28 Jan – 4 Feb

$1,261 AUD total

Guest favourite

Guesthouse in Orlando

4.96 out of 5 average rating, 489 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!

4 – 11 Sept

$1,453 AUD total

Guest favourite

Guesthouse in Orlando

4.91 out of 5 average rating, 106 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.

17 – 24 July

$1,062 AUD total

Guest favourite

Guesthouse in Orlando

4.96 out of 5 average rating, 185 reviews

Charming 1 bedroom Casita with private entrance

Enjoy this private oasis in Orlando 15 minutes from the international airport. The Casita has it's own entrance and patio all your own in a quiet neighborhood. 30 minutes from the theme parks, and minutes from the downtown, we are within driving distance to all that Orlando has to offer. We are looking forward to hosting you!

19 – 26 July

$751 AUD total

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for Kissimmee guesthouses

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-Friendly guesthouses

Guest favourite

Guesthouse in Windermere

4.94 out of 5 average rating, 239 reviews

Small Guesthouse near Orlando's Theme Parks

21 – 28 Mar

$1,760 AUD total

Guest favourite

Guesthouse in Orlando

4.84 out of 5 average rating, 318 reviews

Nice Brand New Studio !!

5 – 12 Sept

$1,028 AUD total

Superhost

Guesthouse in Orlando

4.83 out of 5 average rating, 18 reviews

Lakefront Guest House by downtown :Boat, Fishing…

8 – 15 May

$1,352 AUD total

Guesthouse in Kissimmee

4.92 out of 5 average rating, 51 reviews

Bird Watchers Delight - home close to Disney WIFI

3 – 10 Aug

$758 AUD total

Guesthouse in Orlando

4.96 out of 5 average rating, 82 reviews

Bungalow Guesthouse Downtown Orlando

2 – 9 Nov

$2,542 AUD total

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Guesthouses with a patio

Guest favourite

Guesthouse in Orlando

4.93 out of 5 average rating, 138 reviews

Hidden Luxury Gem w/ private porch

7 – 14 June

$1,160 AUD total

Guest favourite

Guesthouse in Orlando

4.8 out of 5 average rating, 56 reviews

Vintage Florida Vibes House

9 – 16 Oct

$1,363 AUD total

Guest favourite

Guesthouse in Orlando

4.91 out of 5 average rating, 58 reviews

The Cottage

17 – 24 Nov

$1,054 AUD total

Guest favourite

Guesthouse in Orlando

4.92 out of 5 average rating, 37 reviews

Cozy new guesthouse to yourself.

13 – 20 Jan

$903 AUD total

Guest favourite

Guesthouse in Orlando

4.95 out of 5 average rating, 37 reviews

Palm Suite at Bliss House

7 – 14 Jan

$1,902 AUD total

Guest favourite

Guesthouse in Orlando

4.99 out of 5 average rating, 78 reviews

King Bed 👑 Fire Pit 🔥 Private ⭐️ Grill 🍗 Location

6 – 13 Sept

$1,522 AUD total

Guest favourite

Guesthouse in Orlando

4.95 out of 5 average rating, 60 reviews

Glamorous guesthouse City Center! 10 min Downtown

21 – 28 June

$1,429 AUD total

Guest favourite

Guesthouse in Orlando

4.97 out of 5 average rating, 32 reviews

Downtown Cozy/Modern Studio

21 – 28 Feb

$1,301 AUD total

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Guest house rentals with a washing machine and dryer

Guest favourite

Guesthouse in Orlando

4.9 out of 5 average rating, 381 reviews

Bungalow Close to Attractions and Downtown Orlando

8 – 15 Mar

$1,222 AUD total

Guest favourite

Guesthouse in Orlando

4.98 out of 5 average rating, 350 reviews

Lakefront Seclusion modern guesthouse+Pool+Hot tub

17 – 24 Sept

$2,618 AUD total

Guest favourite

Guesthouse in Davenport

4.93 out of 5 average rating, 150 reviews

Winsome Farm Guest House

30 Jan – 6 Feb

$1,338 AUD total

Guest favourite

Guesthouse in Orlando

4.99 out of 5 average rating, 239 reviews

Black House- Private Cottage in Thornton Park!

29 June – 6 July

$2,253 AUD total

Superhost

Guesthouse in Orlando

4.85 out of 5 average rating, 132 reviews

☼BohoBungalow ☼ Close to EVERYTHING! Work frm home

17 – 24 Nov

$1,934 AUD total

Guest favourite

Guesthouse in Orlando

4.89 out of 5 average rating, 47 reviews

Kyle's Place - No Cleaning Fee + Laundry Room

11 – 18 Dec

$997 AUD total

Guest favourite

Guesthouse in Orlando

5.0 out of 5 average rating, 18 reviews

Modern Private Studio

17 – 24 July

$1,421 AUD total

Guest favourite

Guesthouse in Four Corners

4.93 out of 5 average rating, 14 reviews

BeachGuyDave's Reunion Guesthome

1 – 8 Apr

$1,658 AUD total

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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
$46 AUD before taxes and fees

Guesthouse accommodation & holiday rentals in Kissimmee

Top-rated Guesthouses in Kissimmee

Holiday rentals for every style

Cabins

Villas

Houses

Popular amenities for Kissimmee guesthouses

Family-Friendly guesthouses

Guesthouse in Windermere

Guesthouse in Orlando

Guesthouse in Orlando

Guesthouse in Kissimmee

Guesthouse in Orlando

Guesthouses 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 washing machine and dryer

Guesthouse in Orlando

Guesthouse in Orlando

Guesthouse in Davenport

Guesthouse in Orlando

Guesthouse in Orlando

Guesthouse in Orlando

Guesthouse in Orlando

Guesthouse in Four Corners

Quick stats about guesthouse rentals in Kissimmee

Total rentals

Local attractions

Popular amenities

Wi-Fi availability

Total number of reviews

Nightly prices starting at

Destinations to explore