Pet-friendly holiday rentals in Kissimmee

A vibrant collage showcases themed children's bedrooms featuring Disney characters, including Cars and Frozen. A cozy loft area highlights seating for relaxation. The central image promotes amenities such as pool heat and BBQ access, emphasizing an inviting and playful atmosphere perfect for families.

4.89 out of 5 average rating, 148 reviews

Stunning Disney Home w/Pool & Free Resort Access

Our property was featured in Travel Guide USA - 2025 Orlando Edition!! Welcome to our beautiful spacious home, featuring 3 king-sized bedrooms, 2 themed bedrooms, an entertainment loft and 4.5 bathrooms, which will comfortably accommodate three families. We are located in the upscale gated resort of Windsor at Westside with a 10,000 sq. ft. of state-of-the-art club house with a large pool, lazy river, water park, hot tub, gym, beach volleyball and basketball courts, restaurant & bar, arcade.

4.79 out of 5 average rating, 243 reviews

Thematic, New Townhouse, Private Pool, Clubhouse

Welcome home! Just 15 minutes from Disney World, this modern townhouse comfortably accommodates up to 12 people, perfect for your family vacation or a friends getaway! Ask me about theme park discounts after you book! 3 cars max, free parking Pet-friendly, $50 per pet (for cleaning) 5 Bedrooms/ 4.5 Bathrooms/ Sleeps 12 + 1 full size crib Private pool Charcoal grill Frozen and Monsters Inc themed bedrooms TV in every room! Gated community Resort-style clubhouse (at no additional charge!)

4.86 out of 5 average rating, 115 reviews

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.

A modern two-story house is showcased, featuring a bright exterior and a spacious driveway. Lush green grass surrounds the property, while palm trees add a tropical touch. Large windows on the upper level allow for ample natural light, highlighting the clean lines of the architecture.

4.93 out of 5 average rating, 136 reviews

Villa Resort Club

VILLA LUJOSA - BARRIO SÚPER HERMOSO POOL HEATER HOUSE - Diviértete con toda la familia en este alojamiento con estilo moderno , te encantará el área de picnic frente de la casa , el área de juegos y piscina con calentador , un espacioso lugar de hierba artificial para jugar tus niños y en una zona muy trankila cerca de los parques de Disney y del aereopuerto MCO . TE ENCANTARÁ LA CASA Local utility or county personnel may access exterior areas for maintenance without prior notice.

4.97 out of 5 average rating, 435 reviews

A private balcony offers serene views of Lake Bryan and a swimming pool area. A small round table with two chairs invites relaxation, while warm colors from the sunset enhance the tranquil setting. Lush trees frame the scene, creating a peaceful atmosphere.

Condo in Orlando

Waterfront Condo minutes to Disney & Universal

Just minutes from Disney World and Universal Studios, this condo places you in the heart of Orlando’s top attractions, including Disney Springs, Islands of Adventure, SeaWorld, Magic Kingdom, Epcot, two outlet malls, and more. Relax on your private balcony with breathtaking views of Lake Bryan, or enjoy the resort-style pool with a full Tiki bar and dining menu. Additional perks include free parking, 24-hour security, and complimentary HBO & Netflix. No deposit required and no extra fees.

A vibrant outdoor area features a sparkling saltwater pool with fountain jets and colorful LED lighting. A large screen displays a movie, surrounded by lounge chairs. The area is enhanced by string lights and a cozy seating arrangement, creating an inviting space for relaxation and entertainment.

4.87 out of 5 average rating, 245 reviews

Mad Men Magic Kingdom House*FAB POOL*OutdoorMOVIE

AMAZING Pool Deck Extension cira 2023! Its the BIGGEST pool deck at the resort! Plus JAW DROPPING, Fancy, Fun, Fountain Jets w/ LED lighting, high-end glass tile & a Mickey Mosaic giving you an ULTIMATE luxury pool experience. This SALT WATER POOL/SPA will leave your skin feeling soft w/ no eye-sting & it has botanical qualities for your muscles after long days at the parks! Enjoy all this plus our unique OUTDOOR MOVIE EXPERIENCE & FIRE-PIT for the BEST vacay ever only 6 miles to Disney!

A dining area featuring a wooden table set for six, complemented by blue-patterned placemats and white dishware. In the background, a comfortable living space is visible, offering a sectional sofa and a ceiling fan. Large windows provide a view of the private pool.

4.85 out of 5 average rating, 296 reviews

6 miles from Disney ! Private pool

This Beautiful newly renovated 3 bedroom 2.5 bathroom luxury townhouse has a private pool with complimentary resort facilities. The house is close to the Resort and Clubhouse, which has a lobby/reception, snack bar, all-year heated pools, training facilities, and a game room. It is 15 minutes from all Disney parks and close to Orlando attractions. Orlando International Airport is just 40 minutes from the home. Very relaxing and cozy. Newly renovated with new appliances and furniture.

An outdoor view shows a private pool, where a person is enjoying the water with a serene water view beyond. Inside, an illusion room presents colorful decorations and a lively atmosphere. A cozy bedroom showcases a spacious bed adorned with soft linens. A game room is visible, featuring engaging entertainment options.

4.99 out of 5 average rating, 158 reviews

Themed Illusion House •Waterfront •Private Pool

Alice in Wonderland®-themed home with a uniquely designed Illusion room with character outfits. ❤ Private pool with water view ❤ 15 min to Disney ❤ 25 min to Universal, SeaWorld, Convention Center, 2 min to Walmart ❤ Game room with board games & kids toys ❤ 100" movie theater screen ❤ Sleeps 12 ppl ❤ 2 king beds, 1 Queen memory foam sofa bed, 6 twins, 1 crib, 1 pack & play ❤ Fully stocked home ❤❤❤ Message us for seasonal discounts! ❤❤❤ ‼️ No parties, No smoking, 4 dogs max $75/pet

4.97 out of 5 average rating, 191 reviews

A spacious bedroom features a four-poster bed with a soft white comforter and decorative pillows. A plush sofa provides additional seating, while a workspace with a desk and chair is positioned nearby. Natural light streams through an arched window draped with elegant black curtains.

Home in Davenport

Luxury Villa•FREE Pool Heat•Hot Tub•Arcade•Fenced•

Escape to Sprocket Palms, a beautifully renovated 3,000 sq ft retreat just 20 minutes from Disney. The home blends style, comfort, and fun with a heated pool and spa, retro ’90s arcade, plush bedrooms and a relaxed outdoor lounge with TV for easy evenings together after long days at the parks. Designed for memorable stays, it’s the perfect spot for families and groups of all age, a place to unwind, spend time together and make the kind of memories that last long after the trip ends.

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.

4.92 out of 5 average rating, 265 reviews

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*

4.93 out of 5 average rating, 176 reviews

4BR/Close to Disney/Free BBQ&Storey Lake WaterPark

This stunningly designed townhouse is the perfect family escape, located just 4 miles from Walt Disney World 🎢. Relax in spacious king-size rooms, splash in your private screened-in pool, and enjoy top-notch resort amenities. Bring the whole family – furry friends included – and create magical memories at nearby theme parks! 🐬 16 miles to SeaWorld 🎢 19 miles to Universal Studios ✈️ 27 miles to Orlando International Airport Your dream vacation starts here! Book now!

4.87 out of 5 average rating, 104 reviews

4m Disney Sun, Free Snacks, Golf, Pool• Spa• Games

SUN SUN SUN. All day sun with our Private LARGE sun deck. Newly added golf putt putt. Also Cornhole 🎉 Complimentary welcome snack basket with sweet & salty treats included with every stay. Hot Tub, Private pool , fully fenced large yard . A game room with pool table, darts, arcade game and just added , an electronic pinball machine , there’s also a retro record player. 4 miles to Disney. Disney themed, king bed, queen bed and twins, large fenced yard for dogs

Popular amenities for Kissimmee pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

A stylish seating area features a sleek lounge chair with wooden accents beside a small side table. A textured mural of flowing lines adorns the wall, complementing the modern aesthetic. A dining area is visible in the background, with a wooden table and chairs.

4.96 out of 5 average rating, 115 reviews

Modern 4bd house/heated pool,Close to Disney

4.95 out of 5 average rating, 110 reviews

A cozy in-home movie theatre is showcased, featuring plush reclining chairs arranged in front of a large 150-inch projector screen. Warm lighting reflects off the walls, while elegant curtains frame the screen, creating a comfortable viewing experience.

Home in Four Corners

Luxury Villa near Disney: Arcade, Theater, & more!

An outdoor dining area features a large, custom-built farmhouse table surrounded by benches. Refreshments and fruit are displayed on the table, with a private pool visible in the background, enclosed by a screened lanai. Lush green grass complements the serene atmosphere.

4.96 out of 5 average rating, 231 reviews

★Completely Renovated★ 3 mi to Disney+Free Resort!

4.96 out of 5 average rating, 28 reviews

Modern 3BR Home w/ Pool, near Disney & Universal

4.88 out of 5 average rating, 164 reviews

4BD Deluxe nxt to Mickey

4.84 out of 5 average rating, 219 reviews

The kitchen features a large, centrally located island with green counter stools arranged around it. Dark cabinetry complements the light countertops, with a stainless steel stove and microwave. Natural light illuminates the space from overhead fixtures and nearby windows.

Home in Four Corners

Resort acess - Themed rooms

4.94 out of 5 average rating, 31 reviews

Magical Villa Near Disney World

The exterior of the pool house reveals a welcoming facade with a well-maintained lawn. A screened-in pool area showcases a spacious pool surrounded by tile flooring. The interior features a game room with a billiards table and air hockey, highlighted by modern entertainment options.

4.84 out of 5 average rating, 142 reviews

Pool House in Kissimmee

Pet-friendly home rentals with a pool

4.93 out of 5 average rating, 89 reviews

Home in Davenport

Disney Villa, Heated Pool, Spa and Game Room

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.

4.85 out of 5 average rating, 86 reviews

contemporary home w/ private pool, near parks

A contemporary living area is displayed, featuring teal sofas and a wooden coffee table. A television is mounted on the wall, displaying a scenic mountain view. Large glass doors provide natural light and views of the outdoor seating area and community space beyond.

5 out of 5 average rating, 36 reviews

New listing near Disney 2BR/2BA - Pool, Golf, Etc!

5 out of 5 average rating, 90 reviews

Home in Orlando

Harmony | Heated Pool | 10 min Universal & Epic.

4.81 out of 5 average rating, 36 reviews

Luxury Townhouse Near Disney | 3BR

4.97 out of 5 average rating, 60 reviews

A modern living room is depicted with a full sofa, coffee table, and a smart TV. Natural light enters through the sliding glass door leading to the balcony. Three framed botanical prints decorate the wall, while a floor lamp adds soft illumination.

Apartment in Kissimmee

Modern Condo: 10 Min to Disney + Fireworks Views!

4.92 out of 5 average rating, 51 reviews

WaterView 4 miles to Disney 3Br 2Ba Pool Home

4.71 out of 5 average rating, 24 reviews

15 Mins Disneyworld | Private Pool & Game Room

Private, pet-friendly home rentals

4.88 out of 5 average rating, 32 reviews

The Disney House • Immersive Rooms • Gaming Lounge

4.92 out of 5 average rating, 39 reviews

Apartment in Orlando

Epic stay at Vista Cay!

An outdoor space features a screened pool area, softly lit with string lights. White lounge chairs and dark wicker seating provide ample relaxation options. Lush green artificial grass surrounds the pool deck, with a serene backdrop of a low-maintenance garden and the evening sky.

4.94 out of 5 average rating, 33 reviews

House 3 miles from Disney

The outdoor area features a screened-in heated pool and hot tub, surrounded by a spacious deck. Lounge chairs are positioned nearby, while colorful inflatable floats are seen in the water. Natural light filters through the mesh cover, creating a bright atmosphere.

4.93 out of 5 average rating, 44 reviews

Resort Villa! Pool, Hot Tub & Game Room by Disney!

4.93 out of 5 average rating, 30 reviews

Cozy 4BR Pool Home Near Disney

5 out of 5 average rating, 8 reviews

Disney-themed Pool home (4BR) in Kissimmee

A spacious living room features a light grey sectional couch adorned with decorative pillows. A glass coffee table sits atop a plush area rug. Large windows allow natural light to fill the space, with a view of the lush backyard garden. An adjacent dining area is visible.

4.9 out of 5 average rating, 39 reviews

Workspace ~ Movie Room~ Luxurious Gem near Disney

A private pool area features a crystal-clear pool, complemented by a spa and surrounded by paving stones. Lush palm trees are visible on the sides, and views of the golf course stretch in the background, creating a serene atmosphere for relaxation.