Kissimmee Holiday Rentals, Orlando: Private House Rentals

Our top choices for Kissimmee hotels

Kompose Boutique Resort at Theme Parks

Kissimmee

Olga

฿5,064 total

includes taxes & fees

10 May - 11 May

Hampton Inn Kissimmee North

Kissimmee

Jennifer

฿4,203 total

includes taxes & fees

17 May - 18 May

Vacation Village Orlando, Celebration

Kissimmee

Aiden and Karla

฿3,987 total

includes taxes & fees

10 May - 11 May

Margaritaville Resort Orlando with H2O Waterpark

Kissimmee

Rula

฿6,152 total

includes taxes & fees

17 May - 18 May

Affordable Stays Kissimmee

Kissimmee

฿7,178 total

includes taxes & fees

7 May - 8 May

Embassy Suites by Hilton Orlando Lake Buena Vista South

Kissimmee

Mercedes

฿3,017 total

includes taxes & fees

26 May - 27 May

Quality Inn & Suites Heritage Park

Kissimmee

Ingrid

฿2,977 total

includes taxes & fees

26 May - 27 May

Comfort Suites Maingate East

Kissimmee

Jessica

฿3,215 total

includes taxes & fees

27 May - 28 May

Disney's Animal Kingdom Lodge

Bay Lake

JULIO

Club Sevilla

Kissimmee

Frank

฿2,215 total

includes taxes & fees

10 May - 11 May

Magic Moment Resort & Kids Club, Dazzler Select by Wyndham

Kissimmee

Jose

฿2,620 total

includes taxes & fees

7 May - 8 May

Delta Hotels by Marriott Orlando Celebration

Kissimmee

Doraize

฿3,252 total

includes taxes & fees

26 May - 27 May

Harmony Ensuite Room Shared Home No Car

Kissimmee

฿6,477 total

includes taxes & fees

11 May - 12 May

Super Boho - At Lake Toho Fishing Vintage Vibes

Historic Downtown Kissimmee

฿9,065 total

includes taxes & fees

11 May - 12 May

Embassy Suites By Hilton Orlando Sunset Walk

Kissimmee

Alex

฿6,127 total

includes taxes & fees

12 May - 13 May

Oak Ridge Inn

Kissimmee

Michael

฿2,765 total

includes taxes & fees

9 May - 10 May

Adeline Apartments 15m to Parks, Pet Friendly, Free Parking by Heavenly Homes

Kissimmee

katie

฿7,428 total

includes taxes & fees

7 May - 8 May

Seasons Florida Resort

Kissimmee

Hugo

฿2,220 total

includes taxes & fees

12 May - 13 May

Galleria Palms Hotel

Kissimmee

ERIKA

฿3,248 total

includes taxes & fees

25 May - 26 May

55-inch flat-screen TV with cable channels

Budget Inn

Kissimmee

Taylor

฿2,507 total

includes taxes & fees

15 May - 16 May

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Holiday Rentals in Kissimmee

Condo

Vacation Village Orlando, Celebration

Kissimmee

"Great place to stay at. Very clean and very nice rooms."

Aparthotel

Margaritaville Cottages Orlando by Rentyl with H2O Waterpark

Kissimmee

"Beautiful stay rooms were clean pool was nice as well"

Aparthotel

Club Wyndham Cypress Palms

Kissimmee

"The suite was well stocked and very clean. It was very quiet and peaceful, my family and I had a great time."

Apartment

Adeline Apartments 15m to Parks, Pet Friendly, Free Parking by Heavenly Homes

Kissimmee

"Would stay again and so should you! "

Holiday Home

2 outdoor pools, free pool cabanas, pool umbrellas

Luxurious 2 Bd Close to Disney @ Storey Lake 204 3131

Kissimmee

"The accommodation not only has a good equipment and location, but is also absolutely top and highly recommended. I will be very happy to book here again."

Villa

7 Bedroom Villa, Private Pool, Resort Amenities

Kissimmee

"We were very disappointed with this property. I asked to get hot tub and pool heated and i was willing to pay the $40 fee. I received no response from Expedia or the property manager until 2nd last day. I was trying everyday a few times a day. I finally got a response that the hot tub and pool heater were broken. If i knew this i wouldn't have booked this property. I had grandkids that would've loved to use this everyday. Also many things wrong in the house. Kitchen sink garberaror"

Apartment

Updated Condo, 5 mi to Disney, On-site Water Park!

Kissimmee

"Great spot!"

Aparthotel

Barefoot'n Resort Kissimmee Orlando

Kissimmee

"Very nice clean place to stay"

Villa

< 8 Mi to Disney: Getaway w/ Deck in Kissimmee!

Kissimmee

Holiday Home

Formosa Valley Resort by UNE Homes

Kissimmee

"Excellent house, very confortable, everything was clean.. very very recommendable "

Villa

Magic Village 4br, Spacious and Stylish

Kissimmee

"I absolutely loved the area and the home. Everything was clean and beautiful & communication with the host was excellent! However the pool and other amenities like the gym are not included with the stay and you have to pay a large fee daily to just include them. "

Holiday Home

Amazing 4Bd Screened Pool Close to Disney 4572

Bellavida

" Great for our family, close to activities, parks, attractiins"

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Where to stay in Kissimmee

Find the best Kissimmee areas for the activities you enjoy most. Learn more about Kissimmee

Reunion

Reunion delivers the ultimate resort experience with championship golf courses, luxurious holiday homes, and water parks just minutes from Orlando's famous theme parks. Three legendary courses designed by Palmer, Nicklaus, and Watson provide perfect fairways for golf enthusiasts. The Mediterranean-style community offers pristine pools and upscale amenities throughout. Families appreciate the water park with slides and lazy rivers. Active travellers enjoy tennis facilities and spa treatments between theme park visits. Though limited in local dining and shopping options, the gated community provides a peaceful retreat from Orlando's tourist bustle.

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Historic Downtown Kissimmee

Historic City centre Kissimmee charms visitors with preserved Victorian architecture along Broadway Street. The 1890s Osceola County Courthouse stands proudly with its distinctive red brick and clock tower. Seasonal street festivals and farmers markets bring this cultural hub to life throughout the year. Stroll along the waterfront paths of Lake Tohopekaliga or explore the quirky Monument of States. Local shops offer everything from cowboy memorabilia to Florida-themed crafts. The area's Cuban cafes and Southern comfort food restaurants perfectly complement its small-town atmosphere.

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Southern live oak trees (Quercus virginiana) covered in Spanish moss (Tillandsia usneoides) - Clermont, Florida, USA

Windsor Hills

Windsor Hills offers families a perfect retreat just minutes from Disney's Animal Kingdom and other Orlando attractions. This welcoming area features Mediterranean-style holiday homes with resort amenities like community pools and game rooms. Wide, palm-lined streets create a peaceful atmosphere after busy theme park days. The area primarily serves as a comfortable base for exploring Central Florida's famous destinations. Most homes include private pools and themed decor for extended family stays. While dining and shopping options are limited within the area, everything you need is just a short drive away.

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Sunset at the Twin Oaks Conservation Area near Kissimmee, Florida.

Orange Lake

Orange Lake combines resort luxury with prime access to Orlando's world-famous attractions. This Four Corners area centers around Orange Lake Resort, where championship golf courses and sprawling pool complexes create a holiday paradise. Walt Disney World is just minutes away, making this an ideal home base for theme park adventures. Families love the balance of on-site recreation and nearby entertainment options. Holiday villas with full kitchens offer space to relax after busy days. Resort shuttles make reaching major attractions simple, though rental cars provide the most flexibility for exploring beyond the area.

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Celebration Florida Wide Aerial Panorama. July 3, 2025.

Lake Berkley

While Lake Berkley may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Medieval Times and Give Kids the World Village.

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Stay near popular Kissimmee attractions

Old Town

4.3/5 (14,011 reviews)

This retro-themed district transports you to a nostalgic era with vintage architecture. Stroll the brick-paved streets at dusk when live music and illuminated attractions create a magical atmosphere.

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Learn more about Kissimmee

Just minutes from Orlando's theme parks, this sunny gateway offers airboat tours where gators glide beneath your feet. Spend mornings paddling through natural springs and evenings exploring Old Town's vintage car shows and family-friendly restaurants.

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Top Kissimmee Hotel Reviews

Palazzo Lakeside Hotel

4/10 Poor

"I liked the pool breakfast was basic staff was ok while their other children were staying their with their family’s but only I got a complaint of noisy children when their were plenty other children and for that they didn’t return my deposit and when I called about my deposit front desk told me bout another complaint about children spilling juice on the housekeeping cart but couldn’t prove it was my children so that’s why they were keeping my deposit and kept me on hold for over a hour when I asked to speak to a manager on duty"

Delta Hotels by Marriott Orlando Celebration

6/10 Okay

"Facility is nice, especially the pool area. Love that there is a bar by the pool. However, when we checked in around 9:30pm on the first night of our stay, our room wasn’t ready yet. Extremely frustrating to not be able to check into your room so late in the night when check-in started at 4:30. I totally understand they’re busy, but not having a room ready 5 hours past the start of check-in is unacceptable. Otherwise, the stay was good."

Margaritaville Resort Orlando with H2O Waterpark

6/10 Okay

"We arrived at around 430 and our room was not ready. The girl at the front desk was not friendly and said she would call when the room was ready, but did not. We went to check again around 630 and our room was in fact ready. The view from our room was of the parking lot, however, our room was clean. The restaurant Euphoria on site was just ok. We got bamboozled into going to listen to the vacation club in service which took up 4 hours of our time and stupidly we fell for it. Hours later I came to my senses and revoked immediately, however, the process is stressful. "

More cheap stays in Kissimmee

Clarion Inn & Suites Kissimmee-Lake Buena Vista South

4985 W Irlo Bronson Hwy Kissimmee FL

฿1,512

฿2,106 total

10 May - 11 May

includes taxes & fees

6.4/10 (1,185 reviews)

Frequently asked questions

What's the best place to stay in Kissimmee?

Vacation Village Orlando, Celebration is one of the top choices for your stay based on our traveller data. This condo offers 7 outdoor pools and private balconies. Other good choices for your visit include Kompose Boutique Resort at Theme Parks and Margaritaville Resort Orlando with H2O Waterpark. See all available top hotels, or vacation rentals in Kissimmee.

What are some of the best holiday rentals that Kissimmee has to offer?

The Berkley, Orlando: This highly rated holiday home rental in Kissimmee offers a furnished patio, a terrace and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a microwave and a coffee maker. You can relax into your holiday with an arcade/games room and 1 hot tub. Another good choice for your trip to Kissimmee is Casa con Piscina Privada en Orlando. See all vacation rentals in Kissimmee.

If I need to cancel my hotel reservation in Kissimmee, will I receive a refund?

Yes! Most hotel reservations are fully refundable provided that you cancel before the accommodation's cancellation deadline, which in most cases is within 24 or 48 hours of your check-in date. If you have a non-refundable reservation, you might be able to cancel it and be given a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Kissimmee.

What's the best place to stay on a budget in Kissimmee?

Based on reviews, Seasons Florida Resort is a popular hotel for our travellers who want a more economical choice, and features free Wi-Fi and free parking. Other good choices for your budget-friendly stay include Parkway International Resort and Ramada by Wyndham Kissimmee Gateway. View all budget hotels in Kissimmee.

What's the best family accommodation in Kissimmee?

Kompose Boutique Resort at Theme Parks is a resort with an outdoor pool and a waterslide, and it's a top choice on Expedia for families. Other good choices for your stay with the children include Westgate Town Center Resort and Margaritaville Resort Orlando with H2O Waterpark. Also, attractions such as Disney's Animal Kingdom® Theme Park and Walt Disney World® Resort are fun for children of all ages. Find more child-friendly accommodations in Kissimmee.

What is the favourite LGBTQ-friendly hotel in Kissimmee?

Holiday Inn Club Vacations at Orange Lake Resort by IHG is a top LGBTQ-friendly resort that features 7 outdoor pools and a golf course. Hilton Vacation Club Mystic Dunes Orlando and Legacy Vacation Resorts - Kissimmee/Orlando are two other good options for your trip. See all available hotels listed as LGBTQ-friendly in Kissimmee.

What's the best dog-friendly place to stay in Kissimmee?

Kompose Boutique Resort at Theme Parks is a top resort for people travelling with their pets, and offers 2 hot tubs - and free WiFi for its human guests. Other good choices to stay with your pet include Westgate Town Center Resort and Margaritaville Resort Orlando with H2O Waterpark. See more pet-friendly hotel accommodations in Kissimmee.

What's the best accommodation option to stay near the beach in Kissimmee?

The Vietta Hotel is a top hotel located on the beach . See more stays near the beach in Kissimmee.

What's the best high-end place to stay in Kissimmee?

Encore Resort and Water Park at Reunion by Rentyl is a luxury resort with 2 restaurants and a full-service spa, and it's a popular choice for Expedia travellers looking for an elegant place to stay. Disney's Animal Kingdom Lodge and ette hotel are two other upscale options for your holiday. Find more luxury hotels in Kissimmee.

What's the best golf hotel in Kissimmee?

Holiday Inn Club Vacations at Orange Lake Resort by IHG is a top resort that has a golf course and features free WiFi. Other good options to stay near a golf course include Hilton Vacation Club Mystic Dunes Orlando and Spectrum Resort Villas Orlando and Waterparks. Visit Reunion Resort Golf Course, Mystic Dunes Golf Club or Orange Lake Golf to perfect your golf swing. See more golf hotels in Kissimmee.

What are some accommodation options with pools in Kissimmee?

Margaritaville Resort Orlando with H2O Waterpark is a top resort with 3 outdoor swimming pools, free water park access and a lazy river. A couple of other options that offer an on-site pool include Seasons Florida Resort and Delta Hotels by Marriott Orlando Celebration. View all hotels with pools in Kissimmee.

What is the best spa hotel in Kissimmee?

Margaritaville Resort Orlando with H2O Waterpark is a top spa hotel featuring 3 pools, 3 restaurants, 3 bars and a water slide. Enjoy a facial, body scrub or Swedish massage at St. Somewhere Spa. Other popular spa hotels in Kissimmee include Encore Resort and Water Park at Reunion by Rentyl and Gaylord Palms Resort & Convention Center. See all spa hotels in Kissimmee.

What's the best hotel in Kissimmee with an on-site water park or a water park nearby?

Westgate Town Center Resort is a popular resort, featuring water park access, 14 outdoor pools and a children's club. You'll find Aquatica within 19 minutes by car. Margaritaville Resort Orlando with H2O Waterpark and Westgate Vacation Villas Resort are two other water park hotels you can choose from. Take a look at all hotels with or near waterparks in Kissimmee.

What's it like to stay in Kissimmee?

Families will find child-friendly activities in Kissimmee, and visitors give high marks for the festivals, theme park and shopping. This city also attracts tourists with its entertainment, sporting events and restaurants. Top sights in the city include Walt Disney World® Resort, Disney's Animal Kingdom® Theme Park and Old Town. In Kissimmee, there are 27633 hotels and other accommodation options to choose from. Find out more about Kissimmee.

What should I do while I'm visiting Kissimmee?

Known for its festivals and opera, cultural venues include Medieval Times, Osceola County Welcome Center and History Museum and Capone's Dinner Show. Families come for attractions such as Disney's Animal Kingdom® Theme Park, Walt Disney World® Resort and Old Town. Landmarks like Monument of States and Bataan-Corregidor Memorial might be worth a visit. Take a look at what more there is to see and do in Expedia's Kissimmee guide.

How can I get around Kissimmee?

Local metro stations include Tupperware Station and Poinciana Station. If you want to venture outside the area, take a train from Kissimmee Station. If you want to venture out around the area, you may want a rental car in Kissimmee for your journey.

What's the seasonal weather like in Kissimmee?

The hottest months are usually July and August, with an average temperature of 27°C, while the coldest months are January and February, with an average of 18°C. The rainiest months in Kissimmee are August, July, September and June, with each month seeing an average of 196 mm of rainfall.

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Our top choices for Kissimmee hotels

Kompose Boutique Resort at Theme Parks

Hampton Inn Kissimmee North

Vacation Village Orlando, Celebration

Margaritaville Resort Orlando with H2O Waterpark

Affordable Stays Kissimmee

Embassy Suites by Hilton Orlando Lake Buena Vista South

Quality Inn & Suites Heritage Park

Comfort Suites Maingate East

Disney's Animal Kingdom Lodge

Club Sevilla

Magic Moment Resort & Kids Club, Dazzler Select by Wyndham

Delta Hotels by Marriott Orlando Celebration

Harmony Ensuite Room Shared Home No Car

Super Boho - At Lake Toho Fishing Vintage Vibes

Embassy Suites By Hilton Orlando Sunset Walk

Oak Ridge Inn

Adeline Apartments 15m to Parks, Pet Friendly, Free Parking by Heavenly Homes

Seasons Florida Resort

Galleria Palms Hotel

Budget Inn

Holiday Rentals in Kissimmee

Vacation Village Orlando, Celebration

Where to stay in Kissimmee

Reunion

Historic Downtown Kissimmee

Windsor Hills

Orange Lake

Lake Berkley

Stay near popular Kissimmee attractions

Old Town

Learn more about Kissimmee

Top Kissimmee Hotel Reviews

Palazzo Lakeside Hotel

More cheap stays in Kissimmee

Clarion Inn & Suites Kissimmee-Lake Buena Vista South

Frequently asked questions

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