A large, historic building with a tower, reflecting on a calm lake with lily pads, surrounded by trees and a sunset sky.

Search Holiday Rentals in Kissimmee

Dates

November 2026

December 2026

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Our top choices for Kissimmee holiday rentals

A dining area with a table set for four, two armchairs, and a sofa.

1. Vacation Village Orlando, Celebration

Kissimmee

Desiree

includes taxes & fees

29 Nov - 30 Nov

A pool area with lounge chairs and umbrellas, surrounded by a fence and buildings.

2. Villas at Fortune Place

Kissimmee

iris

includes taxes & fees

8 Dec - 9 Dec

A two-story house with a porch, surrounded by palm trees and greenery.

3. Barefoot'n Resort Kissimmee Orlando

Kissimmee

James

includes taxes & fees

8 Nov - 9 Nov

An aerial view of a resort with two large swimming pools, a tennis court, and a small playground.

4. Barefoot Suites

Kissimmee

Mary

includes taxes & fees

8 Nov - 9 Nov

A swimming pool with a curved design, surrounded by a paved deck and a fence.

5. Lyrios Vacation Rentals - The Palms

Kissimmee

includes taxes & fees

8 Nov - 9 Nov

An aerial view of a resort with multiple swimming pools, a large central pool, and surrounding greenery.

6. Margaritaville Cottages Orlando by Rentyl with H2O Waterpark

Kissimmee

Ashley

includes taxes & fees

16 Nov - 17 Nov

A resort with a large central pool, multiple guest villas, and a scenic view of the surrounding landscape.

7. Regal Oaks Resort Vacation Townhomes by IDILIQ

Kissimmee

Tina

includes taxes & fees

9 Nov - 10 Nov

A modern living room with a glass dining table, leather sofas, and a flat-screen TV.

8. Grand Lake Resort

Kissimmee

Rose

includes taxes & fees

30 Nov - 1 Dec

A view of a park with a lake, benches, and trees.

9. Lifetime of Vacations Resort

Kissimmee

Alena

includes taxes & fees

29 Nov - 30 Nov

A modern kitchen with a dining area, featuring a large island, grey and beige furniture, and a TV mounted on the wall.

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

Kissimmee

katie

includes taxes & fees

12 Nov - 13 Nov

A hotel room with two beds, a desk, a chair, a TV, and a window with a view of greenery.

11. Hotel-Style Room Pool, Disney Shuttle

Kissimmee

includes taxes & fees

9 Nov - 10 Nov

A decorative stone fountain with a twisted base, surrounded by vibrant red flowers and tropical foliage, set against a backdrop of a pool and palm trees.

12. Maple Leaf Inn & Suites

Kissimmee

Alex

includes taxes & fees

8 Nov - 9 Nov

A spacious lobby with modern furniture, large windows, and a high ceiling.

13. Vacation Townhomes by IDILIQ at Encantada Resort

Kissimmee

Pamela

includes taxes & fees

16 Nov - 17 Nov

A balcony with a table and chairs, overlooking a parking area and a body of water.

14. Sunset Bliss Retreat Condo - Near Disney

Kissimmee

marie c.

includes taxes & fees

9 Nov - 10 Nov

A swimming pool with a football on the edge, surrounded by a covered area with a view of trees and a building in the background.

15. 129 Seneca Point Trl

Indian Point

includes taxes & fees

18 Nov - 19 Nov

A spacious lobby with a grand chandelier, large windows offering a view of a pool, and a second-floor balcony with a railing.

16. The Berkley, Orlando

Kissimmee

Kristyn

includes taxes & fees

7 Dec - 8 Dec

A pool area with a waterfall, palm trees, and a rocky backdrop.

17. Reunion Resort & Golf Club

Reunion

Karen G

includes taxes & fees

8 Dec - 9 Dec

A modern kitchen with a central island, built-in appliances, and a large window providing natural light.

18. Resort Stay~Near Disney~Bright~Gym~Hot Tub

Kissimmee

John

A modern kitchen with dark cabinetry, stainless steel appliances, and a granite countertop.

19. LOVELY LUXURY APARTMENT CLOSE DISNEY

Kissimmee

Yandra

includes taxes & fees

9 Nov - 10 Nov

A modern kitchen with white cabinets, a central island, and pendant lighting. There is a dining area with a bar stool and a TV mounted on the wall.

20. Luxe Condo Double Bed Bliss Getaway near Disney

Kissimmee

Jeremy

includes taxes & fees

11 Nov - 12 Nov

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Find holiday rentals that suit your style

Top Kissimmee Hotel Reviews

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

Kissimmee

10/10 Excellent

James

A two-story house with a porch, surrounded by lush greenery and hanging moss.

Kapp and Kappy B&B

Historic Downtown Kissimmee

10/10 Excellent

Helen

A Hampton Inn hotel with a modern design, featuring a clear entrance, a flag, and a well-lit exterior.

Hampton Inn Kissimmee North

Kissimmee

10/10 Excellent

Angela

A spacious lobby with a high ceiling, two exits, and comfortable seating areas with tables and chairs.

Hilton Vacation Club Polynesian Isles Kissimmee

Kissimmee

10/10 Excellent

Josephine

The Berkley, Orlando

Kissimmee

10/10 Excellent

We really cannot fault the hotel and staff during our two week stay. We went October/November so at then end of the season, therefore the hotel was only at 25% capacity, however the style and standard of the accomodation was excellent, we would definitely reccomend it and would stay there again without reservation. Our only tiny gripe (and this is pedantic) is that it is placed a little out of the main area. However, everything is within 20 to 25 minutes drive. We also felt that the security...

Fiona

A resort with multiple swimming pools, a large central pool, and a lake.

Embassy Suites By Hilton Orlando Sunset Walk

Kissimmee

10/10 Excellent

james

A large, multi-story hotel with a central courtyard, palm trees, and illuminated signage.

Gaylord Palms Resort & Convention Center

Kissimmee

10/10 Excellent

James

Lifetime of Vacations Resort

Kissimmee

10/10 Excellent

Grant

Grand Lake Resort

Kissimmee

10/10 Excellent

Grant

A pool area with people swimming and relaxing.

Universal's Endless Summer Resort - Dockside Inn and Suites

Florida Center

10/10 Excellent

This was our third stay here and it is still a really good hotel with great facilities. Yes the walls are thin and you can literally hear everything going on around you but ear plugs do the trick. The Pier 8 dining is still as good as ever and park shuttles are brilliant. The loungers around the pool need a good clean now and a certain bartender needs to learn some bar etiquette on serving those at the bar first rather than the ones he knows and chats to. Several people walked away from the bar...

Jason

A modern hotel lobby with a reception desk, a round coffee table, a sofa, and a large window with curtains.

Seasons Kissimmee - Orlando - Lake Buena Vista South, Florida Resort

Kissimmee

10/10 Excellent

Ahmed

An aerial view of a swimming pool with lounge chairs and a small waterfall feature.

Galleria Palms Hotel

Kissimmee

10/10 Excellent

Dean

A pool with a waterfall feature, lounge areas, and a building with a green roof in the background.

Hilton Vacation Club Mystic Dunes Orlando

Kissimmee

10/10 Excellent

Wendy

Barefoot Suites

Kissimmee

10/10 Excellent

Me and my Girlfriend had a wonderful 10 nights at the BearFoot Suites. Located close to Old Town and within driving distance from the main theme parks, this was an ideal location for us to book, and they didn't disapoint either. Staff always willing to help, the apartments are massive, and we only had a one bedroom apartment too. They are well maintained and full of everything you would need. Free Wifi too which is good. The pool was heated, so was lovely. The overall experience of staying was...

Ben

Find out more about Kissimmee

Everything you need to know about Kissimmee holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Kissimmee holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Kissimmee holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Kissimmee holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Kissimmee. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Kissimmee holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Kissimmee holiday rentals we have selected for you start as low as £49 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Kissimmee rentals

At Expedia, we put the best Kissimmee holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Kissimmee rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Kissimmee holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Kissimmee. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Can I find holiday rentals in Kissimmee?

Yes, there are holiday rentals in Kissimmee close to Disney's Animal Kingdom® Theme Park, or you can select a more secluded option if you're looking for a relaxing stay. Tourists who visit Kissimmee like the fun-filled theme parks and lively festivals. The array of shops and renowned opera are some other things you might want to check out while you're here.

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

Beautiful 9-bedroom house with AC in serene Kissimmee , Bring the whole Family !: This highly rated holiday home rental in Kissimmee has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Other favourite homes for rent in Kissimmee are Newly Totally Renovated-Video Game Room-Private Pool and Spacious villa with themed bedrooms and private pool.

How many holiday rentals are there in Kissimmee?

Choose from 1618 Expedia holiday rentals in Kissimmee for a memorable holiday.

What can I see and do in Kissimmee?

Disney's Animal Kingdom® Theme Park and Walt Disney World® Resort are a couple of the family-friendly sights, whereas cultural attractions include Medieval Times and Osceola Center for the Arts. Other popular places to visit in the area include Old Town and Disney Springs™.

What are holiday rentals like in Kissimmee?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Kissimmee. Holiday rentals feature amenities like laundry facilities and kitchens so you'll have everything you want. If you're concerned about a sanitised environment, a holiday rental can offer a sense of seclusion away from public hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great choice for a small group gathering.

Search Holiday Rentals in Kissimmee

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Kissimmee holiday rentals

1. Vacation Village Orlando, Celebration

2. Villas at Fortune Place

3. Barefoot'n Resort Kissimmee Orlando

4. Barefoot Suites

5. Lyrios Vacation Rentals - The Palms

6. Margaritaville Cottages Orlando by Rentyl with H2O Waterpark

7. Regal Oaks Resort Vacation Townhomes by IDILIQ

8. Grand Lake Resort

9. Lifetime of Vacations Resort

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

11. Hotel-Style Room Pool, Disney Shuttle

12. Maple Leaf Inn & Suites

13. Vacation Townhomes by IDILIQ at Encantada Resort

14. Sunset Bliss Retreat Condo - Near Disney

15. 129 Seneca Point Trl

16. The Berkley, Orlando

17. Reunion Resort & Golf Club

18. Resort Stay~Near Disney~Bright~Gym~Hot Tub

19. LOVELY LUXURY APARTMENT CLOSE DISNEY

20. Luxe Condo Double Bed Bliss Getaway near Disney

Find holiday rentals that suit your style

Top Kissimmee Hotel Reviews

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

10/10 Excellent

Find out more about Kissimmee

Kissimmee holiday rentals: An excellent choice for every season

How to find incredible deals on Kissimmee rentals

Frequently Asked Questions

Can I find holiday rentals in Kissimmee?

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

How many holiday rentals are there in Kissimmee?

What can I see and do in Kissimmee?

What are holiday rentals like in Kissimmee?

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