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Holiday rentals in Kissimmee

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Quick stats about holiday rentals in Kissimmee

  • Total holiday rentals

    Explore 7,040 holiday rentals in Kissimmee

  • Nightly prices starting at

    Kissimmee holiday rentals start at €9 per night before taxes and fees

  • Verified guest reviews

    Over 277,640 verified reviews to help you choose

  • Family-friendly holiday rentals

    5,830 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 1,120 rentals that welcome pets

  • Holiday rentals with a pool

    6,330 properties feature pools

  • Rentals with dedicated workspaces

    3,970 properties have a dedicated workspace

  • Wifi availability

    6,950 of Kissimmee holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Self check-in, Beachfront and Lake access across Kissimmee rentals

  • 4.7 Average rating

    Kissimmee stays receive an average rating of 4.7 out of 5 from guests

Top-rated holiday rentals in Kissimmee

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

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Top guest favourite
Flat in Orlando

Epic stay at Vista Cay!

This 2-bedroom, 2-bathroom apartment at Vista Cay Resort, Orlando, offers an exceptional location for enjoying the best of the city. Just minutes from Orlando International Airport and Walt Disney World, it provides unparalleled convenience for both travelers and residents. Additionally, its proximity to the Convention Center, Universal Studios, SeaWorld, and International Drive grants easy access to major attractions, dining, and shopping, offering a complete experience in the heart of Orlando.

4.95 out of 5 average rating, 60 reviews
Top guest favourite
A lush outdoor water complex showcases a winding lazy river surrounded by palm trees and landscaped greenery. Lounge chairs are positioned alongside the water, providing ample space for relaxation. In the background, a clubhouse and scenic waterfront can be seen under a bright blue sky.
Townhouse in Kissimmee

Disney 5BR • Private Pool Free Heat • Pet Friendly

Welcome to this gem near all major attractions: Disney (5 miles), SeaWorld (7 miles), Universal (12 miles), Convention Center (9 miles), and Airport (20 miles). Nearby are outlets, restaurants, and supermarkets. This luxurious home features 5 bedrooms, 4 bathrooms, a private heated pool/spa, fully equipped kitchen, laundry, and free stroller, playpen, and highchair. Resort amenities include a water complex, lazy river, bar, fitness center, mini golf, kayaking, and more! Pets friendly & welcome!

4.96 out of 5 average rating, 176 reviews
Guest favourite
A private pool area is surrounded by a screened enclosure, featuring a well-shaped pool and a jetted hot tub. Lounge chairs are positioned nearby, with a grassy area beyond. The evening sky displays hues of pink, creating a serene atmosphere, enhanced by string lights that illuminate the space.
Home in Kissimmee

*Luxe Disney Home* Priv Pool/Spa- 6BR Sleeps 15

JUST ADDED! (Check out our other reviews) New Construction!!! 3000ft2! Welcome to our luxury 6-BR private pool home near Disney World, Universal Studios, and Sea World! With 8 beds, it sleeps 15 people comfortably. Enjoy the private heated pool, hot tub, and game room with ping pong, cornhole, and arcade. Located in Veranda Palms community, you also have access to a large pool, clubhouse, gym, and splash pad. Perfect for large families or groups seeking a memorable Orlando stay. Book now!

4.92 out of 5 average rating, 215 reviews
Top guest favourite
The exterior of the house showcases a striking blend of wood and stone finishes, featuring large windows that illuminate the interior. An expansive, clear blue pool reflects the sky, with a bridge extending over the water leading to the main entrance.
Villa in Orlando

The Lakeview Oasis - XL Pool & Jacuzzi - Orlando

Welcome to our stunning lakefront resort, where luxury meets tranquility! Dive into our expansive 100,000-gallon pool, enjoying a refreshing swim surrounded by breathtaking views. Inside, our tastefully designed space features midcentury modern amenities ensuring you have everything for a perfect getaway. Each bedroom offers serene views and plush bedding for a restful night’s sleep. Whether you seek adventure or relaxation, this is your ideal getaway. Book now for unforgettable memories!

4.96 out of 5 average rating, 144 reviews
Superhost
Home in Kissimmee

Luxe Family Escape | Pool Oasis Near Disney

Welcome to your Luxe Family Escape near Disney! ✨ Located in one of Kissimmee’s exclusive golf communities, this home offers the perfect mix of relaxation and fun. Enjoy your private screened pool, hammock, ping pong, and charming backyard gazebo. Inside, you’ll find stylish bedrooms, a fully equipped kitchen, and comfortable living spaces. The perfect private oasis for families and groups looking to enjoy Disney, Orlando’s attractions, and a relaxing Florida getaway. 🌴🏊

5.0 out of 5 average rating, 4 reviews
Guest favourite
A vibrant game room is highlighted by colorful Mario-themed wall art, featuring interactive gaming stations equipped with racing chairs. Adjacent, a home theater is presented with luxurious seating and a large screen, surrounded by atmospheric LED lighting. A resort-style pool and relaxing outdoor space are seen, complemented by poolside lounge chairs.
Home in Kissimmee

NEW Modern Villa Near Disney w/ Pool & Spa!

Create unforgettable memories of a lifetime and enjoy a vacation you’ll remember for years to come. This spectacular home is ideally located within the Sonoma Resort and only 8 miles to Disney, and within a short drive to Universal, Disney Springs, and many beaches! With 6000sqft of luxury living space, a private pool/spa, movie theater, and a game room for the kids, your family can enjoy the relaxing and fun atmosphere together! We can't wait to welcome you!

4.98 out of 5 average rating, 42 reviews
Top guest favourite
Home in Kissimmee

4BR Disney & Universal Themed Villa Reunion Resort

Welcome to our newly remodeled 4BR/4BA luxury villa in Reunion, designed for families and groups seeking comfort, style, and a magical Orlando escape. Enjoy brand-new furnishings, modern finishes, Toy Story and Mickey themed bedrooms, a spacious open living area with massage chair, and a fully equipped game room featuring air hockey, arcade basketball, and PlayStation. Relax in your private screened pool with optional heating after unforgettable park days.

5.0 out of 5 average rating, 23 reviews
Top guest favourite
A unique sleeping area features a round bed designed to resemble a giant clam shell. Vibrant murals depicting underwater scenes adorn the walls, complementing the ocean-themed decor. Soft curtains in shades of green flow down from the ceiling, adding color to the tranquil space.
Home in Davenport

Royal Retreat Disney Themed Pool Home, Arcade, Theater

Welcome to The Royal Retreat. Located just 10 miles away from the entrance of WDW, our rental is the perfect place to stay for your Disney vacation. Our 5 star home features 8 themed bedrooms and 5 bathrooms, a fully-equipped kitchen, private heated pool, private arcade, home theater & BBQ! Free Pool heat & the 1st tank of propane for the BBQ are included. Booking with us includes full access to the Champions Gate Clubhouse, Oasis Resort and Retreat Club!

4.96 out of 5 average rating, 119 reviews
Superhost
Flat in Kissimmee

Luxury Reunion Retreat Patio Views Near Disney

Located in the desirable Spectrum Condo at Reunion Resort, this comfortable 5‑bedroom, 4‑bathroom condo offers a relaxing and convenient home base for families and groups looking to explore all that Orlando has to offer. With a well‑designed layout and comfortable furnishings, this condo provides the perfect balance of privacy and togetherness, making it an ideal choice for your next getaway.

5.0 out of 5 average rating, 3 reviews
Guest favourite
Flat in Kissimmee

Brand new luxury near clubhouse / lake view (405)

STOREY LAKE - 6 GUESTS - 2 BEDROOMS - 2 BATHROOMS - LAKE AND CLUB VIEW DON'T MISS OUT! BE ONE OF THE FIRST TO RENT!! Modern Lake View Apartment – Near Disney, Universal , Outlets This beautiful apartment was fully redecorated with all-new furniture by B & Design (By Barbara Costa), featuring a modern, clean, and airy design. Enjoy relaxing moments on the balcony overlooking the lake.

4.9 out of 5 average rating, 21 reviews
Guest favourite
A screened patio showcases a crystal-clear pool and inviting spa, surrounded by comfortable lounge chairs. Sunlight reflects off the water, creating a serene ambiance. The backdrop features the house's exterior, with large windows allowing views of the interior spaces.
Home in Celebration

12BR | 11.5 BA > Sports Game Room!

Be ready for an amazing vacation or your group retreat, when staying in our beautiful home! Located in the exclusive gated community of Bellavida Resort, a brand-new vacation rental resort located next to Walmart, Restaurants, and many attractions. Just 12 minutes from Disney parks, as upscale brand outlets, malls and numerous championship golf courses..

4.82 out of 5 average rating, 90 reviews
Top guest favourite
Townhouse in Kissimmee

Disney Theme Rooms | Private Pool | Storey Lake

Welcome to your dream vacation at Storey Lake, one of the most loved resorts by travelers visiting Orlando. This beautifully designed 4-bedroom, 3-bath townhome was created to bring comfort, fun, and unforgettable memories all in one place, just minutes from Disney and the area’s top attractions.

5.0 out of 5 average rating, 47 reviews

Popular amenities for Kissimmee holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Kissimmee's top sights

Kissimmee Lakefront Park

344 locals recommend

Walmart Supercenter

989 locals recommend

Gatorland

942 locals recommend

Medieval Times Dinner & Tournament

580 locals recommend

Bellavida Resort

16 locals recommend

Terra Verde Resort

6 locals recommend

Other great holiday rentals in Kissimmee

Guest favourite
Home in Kissimmee

Amazing Home Near Parks w/ Pool & Spa

5.0 out of 5 average rating, 9 reviews
Top guest favourite
Flat in Kissimmee

Haunted Mansion-inspired Ghoulish Sanctuary

4.98 out of 5 average rating, 40 reviews
Superhost
Home in Kissimmee

12 Bd/ 11.5 Ba Sleeps 24! Veranda Palms (2444 RD)

4.76 out of 5 average rating, 41 reviews
Guest favourite
Home in Kissimmee

Disney's Pool House

4.82 out of 5 average rating, 60 reviews
Top guest favourite
Apartment in Kissimmee

Renovated Family Condo • Disney • Free Parking

5.0 out of 5 average rating, 62 reviews
Top guest favourite
Home in Kissimmee

*Modern Condo Resort/Pool/Spa/15 Min to Disney*

4.98 out of 5 average rating, 42 reviews
Guest favourite
Home in Kissimmee

Orlando Dream Escape | Private Pool | Disney

4.83 out of 5 average rating, 18 reviews
Top guest favourite
Townhouse in Kissimmee

5BR to Gather, Relax and Make Memories (2640ST)

5.0 out of 5 average rating, 38 reviews

When is the best time to visit Kissimmee?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price€131€136€145€149€127€131€128€113€104€109€123€145
Avg. temp16°C18°C20°C22°C25°C27°C28°C28°C27°C24°C20°C17°C

Frequently Asked Questions

  • What are the best places to stay in Kissimmee?

    Kissimmee has accommodations in resort areas near theme parks, private homes around Reunion and Storey Lake, and family-friendly neighborhoods with easy access to local attractions. Many spaces feature pools, spacious layouts, and outdoor amenities for group stays.

  • What are the best things to do in Kissimmee with kids?

    Families can explore fun attractions like Gatorland, ride thrilling coasters at Old Town, or enjoy large playgrounds and splash pads in city parks. Themed entertainment and interactive experiences are frequently suggested for younger visitors.

  • What are some of the best things to do in Kissimmee?

    Discover live shows and rides at Old Town, visit Gatorland for wildlife encounters, or explore regional history at the Osceola County Historical Society. The area is also known for airboat tours and vibrant outdoor markets.

  • How is the weather in Kissimmee?

    Kissimmee has mild winters around 49–72°F (10–22°C) and hot, humid summers reaching 74–92°F (23–33°C) with frequent rainfall from May through September. Lightweight clothing, sunscreen, and a rain jacket are recommended.

  • What are the best places to visit in Kissimmee?

    Popular places include Old Town for entertainment and shops, Gatorland for reptile encounters, and the Kissimmee Lakefront Park with walking trails and playgrounds. Museum enthusiasts will often find exhibits at local historical centers.

  • What are some hiking trails in Kissimmee?

    Stroll boardwalks and shaded paths at Shingle Creek Regional Park, walk lakeside trails at Kissimmee Lakefront Park, or explore nature preserves nearby. Trails often highlight local wildlife and peaceful scenery.

  • What are some family activities we can do in Kissimmee?

    Explore Gatorland’s exhibits, ride classic attractions at Old Town, or play in the splash pads at Kissimmee Lakefront Park. Family-friendly dining spots and arcades are also popular choices for shared outings.

  • What are some of the best day trip ideas from Kissimmee?

    Explore Orlando’s theme parks, stroll nature reserves around Lake Tohopekaliga, or enjoy coastal beaches for a change of scenery. You can also visit nearby state parks or experience local wildlife tours.

  • Are there any pet friendly accommodations available in Kissimmee?

    Many Kissimmee neighborhoods, including those near Central Kissimmee and the resort communities, have pet-friendly vacation rentals. Parks and outdoor spaces throughout the area make traveling with pets convenient.

  • What are some local tips for visiting Kissimmee?

    Hydrate frequently in warm months, and bring insect repellent for outdoor activities near lakes. Book popular attractions in advance and explore local eateries for regional flavors beyond the main tourist areas.

  • What is Kissimmee known for?

    Kissimmee is known for its proximity to major theme parks, distinctive wildlife experiences like Gatorland, and vibrant entertainment districts such as Old Town. Airboat rides and access to lakes add an outdoor adventure element.

  • What are the best hidden gems to explore in Kissimmee?

    Visit Shingle Creek Regional Park for quiet paddling and wildlife spotting, shop local at farmers markets, or discover history at the Osceola County Historical Society museum. Neighborhood spots often have authentic flavors and art.

  • What are the best foods to try in Kissimmee?

    Enjoy Southern-style barbecue, fresh seafood, and Latin flavors like Cuban sandwiches or empanadas at locally rooted eateries. Homemade ice cream and citrus-inspired desserts are frequently suggested, especially in summer.

  • What should I bring for a trip to Kissimmee?

    Pack lightweight clothing, sunscreen, and a hat for sun protection. A rain jacket, comfortable walking shoes, and insect repellent are useful for exploring parks and outdoor attractions.

  • What is the nightlife in Kissimmee like?

    Kissimmee has lively spots for live music, themed bars, and outdoor events in areas like Old Town. Nighttime entertainment often includes family-friendly shows and locally owned restaurants with late-night menus.

  • What are the most popular events or festivals in Kissimmee?

    Kissimmee hosts car shows, holiday parades, and cultural festivals around Old Town, with seasonal fairs and outdoor concerts often taking place in parks. Late spring and holiday weekends feature many community gatherings.

  • Are there family friendly vacation rentals in Kissimmee?

    Family-friendly vacation rentals are available throughout Kissimmee, particularly in resort-style neighborhoods and private home communities. Many have amenities like pools, recreation rooms, and easy access to parks and attractions.

  • When is the best time to visit Kissimmee?

    Late autumn and early spring are often recommended, with milder temperatures and smaller crowds. Summer brings lively local events and frequent afternoon rain, while winter stays mild and sunny.

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