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Pet-friendly vacation rentals in Osceola County

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Top-rated pet-friendly home rentals in Osceola County

Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favourite
An inviting living area features a comfortable tufted chaise lounge and a cozy recliner. A flat-screen TV is mounted above a classic fireplace, surrounded by soft curtains that frame bright windows. The floor showcases warm wooden tones, contributing to a homely ambiance.
Cottage in Lake Wales

Charming, renovated 1917 Cottage

Charming, renovated 1917 cottage in beautiful neighborhood. One block from large lake with walking/running trail, 3.5 miles to Bok Tower, 12 miles to Legoland, 38 miles to Disney World, 47 miles to Universal Studios, and 63 miles to Busch Gardens. Pet friendly! King size bed in bedroom, double sofa bed in living area. Newly renovated kitchen has full size refrigerator, sink, microwave, stove top and large toaster oven. Big backyard with beautiful landscaping. Separate driveway. Lots of privacy!

4.98 out of 5 average rating, 172 reviews
Top guest favourite
A resort-style water complex is surrounded by lush landscaping and palm trees. The winding pool features clear, inviting water with lounge areas and shaded cabanas. Bright blue skies filled with clouds create a serene backdrop for this recreational oasis.
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!

4.98 out of 5 average rating, 287 reviews
Top guest favourite
A home cinema room features a large flat-screen TV displaying a film scene. The walls are painted blue and red, and plush seating is arranged in front of the screen. Decor includes framed posters and a Mickey Mouse silhouette, creating an engaging entertainment space.
Villa in Kissimmee

OMG! Disney Area, Movie Theater, Game Room & Pool!

"Guest favorite" - This home is in the top 5% of eligible listings based on ratings, reviews, and reliability. Comfort and Space in an Elegant home with a lot of amenities, 4Bed/3Bath. Private Movie Theater, Game Room, Pool and Themed Rooms. A well equipped Kitchen, Laundry, 3 parking spaces, WiFi, Smart TVs. Located at Crystal Cove Resort, a gated community, close to Disney. Few minutes to Walmart, Target, Sams Club, Publix, Outlets, Restaurants, Disney, Sea World, OCCC, EPIC and Universal.

4.87 out of 5 average rating, 457 reviews
Guest favourite
A waterfront property is showcased, featuring a wooden exterior and a covered boat slip. Lush greenery surrounds the home, with a fire pit visible in the yard. The structure appears elevated, with a spacious deck above the boat area, providing picturesque canal views.
Guest suite in Haines City

2 BR 1 BA Lake House , Boat Slip, Pets, (king bed)

Escape to the perfect, peaceful pet friendly retreat with king bed. We are located on one of the 5 canals on Lake Hatchineha, the first of The Kissimmee Chain of Lakes. Connecting us to The Kissimmee River where you can rent a boat at Camp Mac and drive it home or bring your own boat and park it under cover in one of the boat slips.We are 45 minutes from Orlando airport or an hour from Tampa. 45 min to Disney's Magic kingdom/Universal Studios. 30 min to Legoland. Bok Towers free pass for 4.

4.84 out of 5 average rating, 118 reviews
Top guest favourite
A single-story home showcases a well-maintained front lawn with lush green grass. The house features a welcoming entrance with a central door, flanked by large windows. A driveway leads to a two-car garage with decorative doors, while a fenced yard adds privacy.
Home in Davenport

Sunny-All-Day Pool Vacation Home

Welcome to our Sunny 3-Bedroom Retreat! This inviting home features 3 spacious bedrooms, a south-facing pool for all-day sun, and a private fenced yard. Enjoy the bright living space, modern kitchen, and outdoor oasis with comfortable seating. Conveniently located near local attractions, dining, and shopping. Additional amenities include high-speed Wi-Fi, smart TV, air conditioning, washer and dryer, and free parking. Book now for a perfect getaway! **No parties ($500 fine) and no smoking**

4.94 out of 5 average rating, 109 reviews
Guest favourite
Home in Lake Wales

Sunshine on the Lake | Boat Slip+Lakefront Fishing

Welcome to Florida Lakefront Paradise! ⭐️ Breathtaking Sunsets ⭐️ Bass Fishing ⭐️ Reserved Boat Slip ⭐️ Fish Cleaning Station ⭐️ Boat Wash Station ⭐️ Marina with Ice/Gas ⭐️ Large Fire Pit Area ⭐️ Located on Kissimmee Chain of Lakes ⭐️ Smart TV's ⭐️ Screened Lakefront Back Patio ⭐️ High Speed Internet ⭐️ Spacious ⭐️ Balcony Facing the Lake ⭐️ 30 minutes to Lego Land ⭐️ 20 minutes to Bok Tower Gardens ⭐️ 1 hour to Disney World ⭐️ 18 minutes to Spook Hill ⭐️ 18 minutes to Kissimmee State Park

4.93 out of 5 average rating, 139 reviews
Guest favourite
An aerial view showcases a large pool surrounded by lounge chairs and palm trees. The pool area is defined by well-maintained landscaping, with a hot tub and a nearby shaded structure visible in the background, creating an inviting atmosphere.
Condo in Osceola County

Stunning Orlando Condo 3 BR/2 bath, pets OK

This resort community is amazing to drive around in, let alone stay in. Just 20 to 25 minutes away from Disney World and Universal Studios and everything Orlando has to offer. Convenience stores (7-11), Dunkin' Donuts, CVS pharmacy, restaurants and grocery stores within walking distance. Three gorgeous pools and hot tub Jacuzzis, and world-class gym in the resort in this gated community with security. 5 minute drive to Champions Gate and I-4 highway. Up to 2 dogs/cats ($25/day/animal).

4.9 out of 5 average rating, 129 reviews
Guest favourite
A modern movie theater features a large 155-inch screen displaying a Disney logo, surrounded by plush recliners designed for comfort. The room is illuminated with soft blue lighting, creating a cozy atmosphere for movie nights or gaming sessions.
Villa in Kissimmee

8Bd 4K Movie Theater 155 Inch Screen Pool & Spa

A vacation home that takes your entertainment seriously! That’s our 8-bedroom villa in Emerald Island Resort at 3 miles from Disney… Ready to enjoy themed bedrooms, a premium private movie theater with a 155-inch screen, 4K projector, 5.1 surround sound, and a PS5 for gaming? Relive your favorite films in stunning quality, just like in the best movie theaters. Private Pool and Spa will make your vacation unforgettable! We’re ready for families and groups, to offer fun, comfort, and luxury.

4.86 out of 5 average rating, 147 reviews
Top guest favourite
A cozy living area features two leather sofas positioned around a wooden coffee table with a glass top. In the background, a well-equipped kitchen with wooden cabinetry is visible. Natural light fills the space, enhancing the warm tones of the decor.
Cottage in Lake Wales

The "Little ‘Toa" Ideal for short & long stays!

Welcome to the Little TOA, Central Florida's fishing, hunting and winter get away. The house sits just off the Kissimmee River which is part of the Kissimmee chain of lakes, connecting Lake Hatchineha and Kissimmee. This will be a great spot for you and your buddies or family for a short weekend trip or an extended stay. Come see old Florida, the area holds many things to occupy your vacation time. *Your pet is welcome, please let me know ahead of time. There is a one time fee for pets.

4.91 out of 5 average rating, 138 reviews
Superhost
A modern bedroom features a spacious bed with a light gray patterned comforter. Natural light filters through large windows adorned with soft curtains, illuminating the neutral decor. A nightstand with a lamp adds a touch of warmth.
Townhouse in Kissimmee

5 BR 6 BA Villa 5min to Disney!

Summerville Resort is a new and prestigious collection of town-home villas just 5 miles from the entrance to Walt Disney World! Be among the first to stay in this contemporary vacation rental with pristine finishes & amenities. No need to wait in line to shower here; each of the 5 bedrooms has its own attached bath. After a day exploring the parks, come home to indulgence at the Resort, which features a community hot tub, heated pool, fitness center, playground, and a sleek Clubhouse.

4.84 out of 5 average rating, 102 reviews
Top guest favourite
Home in Kissimmee

Cozy House with Pool. Kissimmee/Orlando

Welcome to Your Kissimmee Getaway! 🏠 Enjoy a relaxing stay in beautiful Kissimmee, conveniently located near Orlando’s world-famous theme parks, restaurants, shopping, and entertainment -Pet friendly home🐾( pet fees may apply) Please make sure to include your pet(s) when making your reservation so any applicable fees can be reflected in your booking. -No parties or events of any kind -No smoking inside the property Please respect the home, neighbors, and community during the stay

4.91 out of 5 average rating, 286 reviews
Guest favourite
The outdoor pool area features a spacious turquoise pool, surrounded by a screened enclosure for comfort. Lounge chairs with bright cushions are positioned nearby, while a basketball hoop stands at one end of the pool, offering fun recreational options.
Home in Kissimmee

Stunning 6BR Lakeview at Storey Lake Disney - 2929

Modern luxury home with lake view, recently built, best location in town, at world-known Storey Lake Resort. Almost 4,000sf of a/c area, featuring 6 bedrooms, 6 full baths, game room, private pool, and spa. 3 Minutes away from Super Target, Publix Supermarket and Walmart 15 Minutes away from Disney Parks 15 Minutes away from Premium Outlets 20 Minutes away from Universal Studios 20 Minutes away from International Dr attractions *PLEASE MAKE SURE TO READ THE HOUSE RULES*

4.91 out of 5 average rating, 279 reviews

Popular amenities for Osceola County pet-friendly home rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Pet-friendly house rentals

Top guest favourite
A private outdoor area features a pool with a spa, surrounded by a spacious deck. A basketball hoop is positioned nearby. A large inflatable swan floats in the water, while a hammock provides a cozy spot for relaxation. Lush greenery frames the scene under a colorful sky.
Home in Kissimmee

Luxury Encore Pool Spa Pets Game Rm Theater Gym

4.94 out of 5 average rating, 169 reviews
Guest favourite
Home in Lake Wales

Lake Retreat w/Pool & Hot Tub near Bok tower

4.86 out of 5 average rating, 101 reviews
Top guest favourite
Home in Kissimmee

Private Pool + Spa Game Room •4m Disney •Pinball

4.93 out of 5 average rating, 166 reviews
Guest favourite
A spacious living area features a comfortable sofa with decorative pillows, a dining area with seating for six, and a fully equipped kitchen. Natural light floods the room through large windows, offering views of the exterior. Subtle decor elements enhance the welcoming environment.
Home in Kissimmee

Happy Place/ 18 Min to Disney/ Lakeview/ Pool/Park

4.96 out of 5 average rating, 139 reviews
Guest favourite
Home in Kissimmee

Luxury Disney Vacation Home on Reunion Golf Resort

4.89 out of 5 average rating, 180 reviews
Top guest favourite
The house exterior displays a blend of white wooden siding and warm wooden accents. Two white, vintage-style chairs are positioned on the porch, leading to a central door with decorative glass. A small set of stairs provides access to the entrance.
Home in Lake Wales

Linda Casita de Lake Wales

4.98 out of 5 average rating, 212 reviews
Top guest favourite
The exterior of the house is presented, showcasing a spacious driveway leading to a two-car garage. Lush green grass frames the driveway, while palm trees add a tropical touch. The house features a modern design with a prominent entrance and neatly arranged landscaping.
Home in Kissimmee

5 Stars Vacation Home with Private Pool/Jacuzzi

4.86 out of 5 average rating, 125 reviews
Top guest favourite
A single-story home is showcased with a light gray exterior and a dark garage door. Lush green grass surrounds the front, complemented by palm trees and shrubs. The driveway leads to the entrance, under a clear blue sky with a few clouds.
Home in Kissimmee

Peaceful Waterfront Retreat, Close to Everything!

4.9 out of 5 average rating, 175 reviews

Pet-friendly home rentals with a pool

Top guest favourite
A bright living area features two white slipcovered sofas accented with patterned cushions. A coffee table rests in the center, surrounded by potted plants. Natural light enters through glass doors leading to the outside, complemented by a ceiling fan and wall decorations.
Townhouse in Kissimmee

Adventure Awaits—Gorgeous Townhouse Close to Disney Parks

4.95 out of 5 average rating, 389 reviews
Guest favourite
Townhouse in Kissimmee

6 miles from Disney ! Private pool

4.86 out of 5 average rating, 325 reviews
Top guest favourite
A clear view of a pool surrounded by lounge chairs and palm trees, reflecting the sunlight. Umbrellas provide shade, and green lawns are visible in the background. The calm water enhances the serene environment, creating a relaxing outdoor space.
Condo in Kissimmee

Disney Dream Condo · Resort Pool · 20 Min to Parks

4.85 out of 5 average rating, 286 reviews
Top guest favourite
A game room features striking themed decor, with large flat-screen TVs and seating. The private pool area showcases a serene swimming pool surrounded by a screen enclosure, highlighted by comfortable lounge furniture. A cozy outdoor seating area is visible, offering a relaxing view.
Villa in Kissimmee

"Disney Serenity": Luxe 8BR Villa/ Privacy/ Pool

4.96 out of 5 average rating, 204 reviews
Top guest favourite
A serene lakeside seating area is highlighted by sandy ground and palm trees. Sturdy wooden posts are anchored with rope, creating a relaxed atmosphere. In the background, a tranquil lake reflects the sky, enhancing the peaceful outdoor setting.
Townhouse in Kissimmee

Disney 5BR • Private Pool Free Heat • Pet Friendly

4.98 out of 5 average rating, 152 reviews
Top guest favourite
A hot tub is situated on a patio with a view of a lake at sunset. The vibrant sky features hues of orange, pink, and purple, while a railing surrounds the space, enhancing the scenic atmosphere. The tranquil water reflects the colors of the sky.
Cottage in Kissimmee

3 Bed Pool/Spa w/ Sunset Water in Margaritaville

4.99 out of 5 average rating, 103 reviews
Superhost
A spacious living area is featured, highlighted by a large sectional sofa and a glass coffee table at the center. Natural light fills the room through multiple windows, illuminating the neutral-colored walls and decorative accents. A dining area is visible in the background, complete with stylish seating.
Townhouse in Kissimmee

Fully Equipped nr Parks, USTA & Lake Nona

4.88 out of 5 average rating, 144 reviews
Top guest favourite
Home in Kissimmee

Lakeview 15 Min to Disney Pool Home 4BR/3BA

5.0 out of 5 average rating, 5 reviews

Private, pet-friendly home rentals

Guest favourite
Guest suite in Kissimmee

temple & A/C glamping under a 120 y/o oak tree

4.93 out of 5 average rating, 289 reviews
Top guest favourite
A wooden dock extends into the calm waters of Lake Rosalie, featuring a small viewing platform at the end. Lush green grass surrounds the water's edge, complemented by reeds along the shore. Clear blue skies reflect off the tranquil lake surface.
Home in Lake Wales

Lake Rosalie Getaway

4.98 out of 5 average rating, 57 reviews
Guest favourite
A serene view of a dock extending into a calm lake at sunrise. The sun rises above the horizon, casting warm hues across the sky and reflecting on the water's surface. Reeds frame the scene, enhancing the natural surroundings.
Home in Lake Wales

Lakefront 2br w/pier & dock 4,500-ac Lake Rosalie

4.9 out of 5 average rating, 41 reviews
Top guest favourite
Condo in Kissimmee

Renovated Family Condo • Disney • Free Parking

5.0 out of 5 average rating, 65 reviews
Top guest favourite
Home in Kissimmee

Fully renovated. 15Mi - Disney. 10Min - Airport.

4.96 out of 5 average rating, 50 reviews
Guest favourite
Home in Polk County

Shady Ln Hideaway Fisherman's Dream Lake Wales, Fl

5.0 out of 5 average rating, 13 reviews
Superhost
A swimming pool is framed by a landscaped area featuring a beige umbrella and two loungers positioned nearby. Bright floral accents can be seen above the fence, creating a relaxed outdoor ambiance.
Home in Kissimmee

contemporary home w/ private pool, near parks

4.74 out of 5 average rating, 100 reviews
Top guest favourite
The entrance of the townhouse is framed by manicured greenery, including shrubs and palm trees. A clean, concrete walkway leads to a black front door, which is complemented by a spacious porch. Bright blue skies and soft clouds provide a cheerful backdrop.
Townhouse in Kissimmee

Relaxing , cozy townhouse w/ pool near Disney

4.98 out of 5 average rating, 42 reviews

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