Pet-friendly holiday rentals in Kissimmee

4.95 out of 5 average rating, 101 reviews

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**

PetsWalkabilityCheck-in

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, 171 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

WalkabilityOutdoor spacesLong stay

4.99 out of 5 average rating, 107 reviews

Home in Davenport

Pool & Spa Oasis/Golf Retreat/Near Disney/3BR Home

Escape to paradise at our Davenport home, only 11 miles from Walt Disney World! Relax by the huge pool with spa, and savor BBQ delights. Rest in well-designed bedrooms: Master room with a king bed, second room with a queen bed, and third one with two twin beds. Experience ultimate fun in the game room, indulge your culinary skills in the fully equipped kitchen, and step out onto the greens from our backyard on a golf course. Don't miss out, book now and make the most of your vacation

WalkabilityPetsAccuracy

4.89 out of 5 average rating, 104 reviews

Aerial view of the pool area shows vibrant water slides winding through landscaped surroundings. Multiple swimming pools can be seen, complemented by palm trees and open spaces. Sun loungers are arranged around the pools, offering ample relaxation spots for guests.

Apartment in Kissimmee

Apartment in Four Corners

Escape to this stylish 2-bedroom, 2-bathroom condo, perfect for families or friends seeking a memorable getaway. Enjoy spacious living area, complete with a comfortable sofa bed, and a fully-equipped kitchen. Relax in luxury with a king-size bed and en-suite bathroom. Access at NO ADDITIONAL cost to world-class pools, a lazy river, and a fitness center . Enjoy complimentary Wi-Fi and parking Located in the heart of Champions Gate, Aprox. 15 mins to Disney Parks & 30mins to Universal

PetsOutdoor spacesQuiet

4.99 out of 5 average rating, 100 reviews

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

Welcome to Sol Oasis Cove! This amazing pool / spa cottage has one bedroom on the first floor and 2 bedrooms upstairs with a balcony positioned perfect for the sunset over the lake! This property comes with all the comforts from home but worlds away. Conveniently located minutes from the Disney parks, a state-of-the art water park and newly opened 196,000 square foot shopping and dining district with multiple dining food and beverage options & brand-new movie theater.

WalkabilityPetsComfort

Superhost

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.

Home in Buenaventura Lakes

4.9 out of 5 average rating, 166 reviews

Villa Resort Club

LUXURIOUS VILLA - SUPER BEAUTIFUL NEIGHBORHOOD POOL HEATER HOUSE - Have fun with the whole family in this modern style home, you will love the picnic area in front of the house , the play area and pool with heater , a spacious artificial grass place to play your children and in a very trankila area near the Disney parks and the MCO airport. YOU WILL LOVE THE HOUSE Local utility or county staff may access outdoor areas for maintenance without prior notice.

PetsOutdoor spacesComfort

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.

4.94 out of 5 average rating, 161 reviews

Luxury Encore Pool Spa Pets Game Rm Theater Gym

Amazing Brand New Modern Luxurious Home at Encore Resort Reunion. PET-FRIENDLY & Minutes to all Theme Parks. BRAND NEW HOME. Private Pool & Spa / Game Room / Movie Theater / Gym / Massage Chair / Fireplace / PS5 / Board Games & Much More. Embrace the extraordinary and book your stay at our home, where luxury, entertainment come together for an unforgettable vacation experience. ** Please review the rules before booking. Waterpark access is not included. **

PetsOutdoor spacesLocation

4.77 out of 5 average rating, 13 reviews

Orlando Dream Escape | Private Pool | Disney

Welcome to your perfect Orlando getaway! Enjoy this beautifully renovated home with a private pool, just 20 minutes from Disney, Universal, and SeaWorld. Perfect for families and groups of up to 8 guests. Features 3 bedrooms, 2 full bathrooms, a fully equipped kitchen, fast Wi-Fi, washer & dryer, free parking, and self check-in. Relax, unwind, and create unforgettable memories close to Orlando’s best attractions, shopping, and restaurants. 🏊‍♀️ Private Pool

Outdoor spacesIndoor spacesHospitality

4.91 out of 5 average rating, 149 reviews

A welcoming living area features a dark brown sofa adorned with decorative pillows in warm tones. Greenery decorates the wall behind the sofa, complemented by a modern lamp. A nearby circular table and chair set add to the inviting space, with natural light filtering through a window.

Apartment in Kissimmee

Lush Green Retreat 10 Min to Parks Pets Allowed

Welcome to Your Magical Gateway – Just 10 Minutes from Orlando's Magical Parks! Location: Perfectly located for Disney and Universal, our apartment offers a peaceful retreat with all the comforts of home. Whether you’re here to explore the magic unwind, or even stay for longer terms, you’ll love every moment of our cozy space. The property sleeps 4 people! PLEASE CONTACT US TO INQUIRY ABOUT ADDITIONAL POTENTIAL DISCOUNTS FOR MULTIPLE DAYS STAY

PetsWalkabilitySleep quality

4.87 out of 5 average rating, 138 reviews

Mi Casita Near Disney & Universal

Welcome to your own private oasis in Kissimmee! Our charming 3-bedroom home boasts a beautiful private pool. Unwind in the serene surroundings while still being just moments away from the excitement of world-class theme parks and entertainment. Enjoy a fully-equipped kitchen, comfortable living areas, and spacious bedrooms for a memorable stay that combines the comforts of home with a sun-soaked Florida experience. Book your escape today!

PetsOutdoor spacesAccess

4.9 out of 5 average rating, 155 reviews

Private Heated Pool & BBQ Included Near Disney

Stay close to Orlando’s top attractions in this modern 4-bedroom, 3.5-bath vacation home for up to 10 guests. Enjoy your own private heated pool and built-in BBQ, both included with your stay, plus a bright open living area, full kitchen, fast Wi-Fi, laundry, and family-friendly sleeping spaces. This home is a great fit for families, extended families, and groups who want more space, privacy, and comfort than multiple hotel rooms.

Outdoor spacesWalkabilityComfort

5.0 out of 5 average rating, 12 reviews

Montego Bay Retreat | 15 Min to Disney

Enjoy a stylish stay in this newly renovated 3-bedroom, 2-bath home, perfect for families and groups of up to 9 guests. Located only 15 minutes (8 miles) from Disney and close to Orlando’s top attractions, restaurants, and shopping. Relax in modern, comfortable spaces after a fun day at the parks. Outdoor grill available for $30/day (gas included). The perfect mix of location, comfort, and convenience for your Florida vacation! ✨

PetsSolo travelAccess

Popular amenities for Kissimmee pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

A serene outdoor space features a screen-enclosed private pool, with crystal-clear water reflecting sunlight. A shaded lounge chair is positioned beside the pool, creating a peaceful spot to relax. The surrounding greenery adds a touch of nature to this inviting oasis.

4.86 out of 5 average rating, 213 reviews

3BR Private Pool Oasis Home – 10 Min to Disney

PetsWalkabilityAmenities

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.

4.97 out of 5 average rating, 134 reviews

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

WalkabilityCheck-inValue

A private pool is surrounded by a screened enclosure, offering clear views of the lush greenery beyond. The pool features a gentle curve and is complemented by decorative tiling. The pool deck is painted in a soft pink hue, enhancing the overall serene environment.

4.85 out of 5 average rating, 191 reviews

Private 3BR Pool Home, WiFi, Game Room, AppleTV, ROKU

WalkabilityOutdoor spacesParks

4.95 out of 5 average rating, 112 reviews

Pool | Themes | Game Room

WalkabilityOutdoor spacesDecor

A private back deck features a sparkling swimming pool and a spill-over jacuzzi hot tub, surrounded by a screened enclosure. Pool floats in the shapes of donuts add a playful touch. Seating is arranged around a small dining area, with access to the stone coping and grassy yard.

4.89 out of 5 average rating, 9 reviews

Perfect Disney Holiday! Private Pool, Spa

WalkabilityHot tubHospitality

4.98 out of 5 average rating, 94 reviews

The exterior of a large, two-story home is displayed, featuring a light-colored facade and a covered front porch. Lush landscaping surrounds the driveway, which is paved with stone. A garage door is positioned on the right side, complemented by decorative lanterns and palm trees.

Home in Osceola County

Large Private Home on Golf course by Disney

PetsOutdoor spacesIndoor spaces

Superhost

5.0 out of 5 average rating, 3 reviews

6 miles from Disney ! Private pool ! 4 bedrooms

HospitalityCleanlinessLocation

An open-concept living area features a large sectional sofa in soft gray, arranged around a circular coffee table. A contemporary fireplace is integrated into the wall, providing a focal point. Glass doors lead to the outdoor pool area, enhancing natural light throughout the space.

5.0 out of 5 average rating, 82 reviews

Luxury Home w/ Pool & 6 Beds near Disney

Outdoor spacesPetsAir conditioning

Pet-friendly home rentals with a pool

4.98 out of 5 average rating, 121 reviews

Villa in Davenport

Amazing Villa near DisneyWorld FREE heated-pool

Outdoor spacesPetsBathroom

4.95 out of 5 average rating, 102 reviews

Villa in Davenport

Retreat with Pool, Jacuzzi, Game Room, BBQ, Cinema

Outdoor spacesPetsDecor

4.93 out of 5 average rating, 69 reviews

Condo in Horizon West

2BR Modern Pet-Friendly Condo 6 mins from Disney

PetsOutdoor spacesAir conditioning

4.95 out of 5 average rating, 56 reviews

Apartment in Orlando

Epic stay at Vista Cay!

Outdoor spacesWalkabilityPool

5.0 out of 5 average rating, 6 reviews

Luxury Disney Villa | Game Room | Free Pool Heat

HospitalityPoolAccuracy

4.98 out of 5 average rating, 40 reviews

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

WalkabilityOutdoor spacesDecor

Superhost

Home in Clermont

4.82 out of 5 average rating, 11 reviews

Private Pool Home Near Disney | 4BR Sleeps 10

LaundryComfortCleanliness

4.82 out of 5 average rating, 34 reviews

Gated Family Resort * (10 Min to Disney)

Check-inCheckoutWi-Fi

Private, pet-friendly home rentals

5.0 out of 5 average rating, 53 reviews

Condo in Kissimmee

Renovated Family Condo • Disney • Free Parking

PetsGetting aroundLong stay

The exterior of the home is characterized by a light yellow facade and a landscaped front yard featuring a variety of plants and stones. A well-maintained lawn complements the structure, which includes a two-car garage with a glass door.

5.0 out of 5 average rating, 21 reviews

Sunshine Resort

PetsOutdoor spacesCheckout

The cottage features a vibrant blue exterior with yellow accents on the balcony and windows. Tropical landscaping with palm trees frames the entrance, complemented by a covered porch. The structure is two stories high, showcasing a welcoming atmosphere in a gated community.

4.98 out of 5 average rating, 54 reviews

Margaritaville Cottage, Hot Tub, near Disney

Outdoor spacesWalkabilityIndoor spaces

5.0 out of 5 average rating, 15 reviews

Guesthouse in Orlando

Cozy Guest House Near MCO & Theme Parks

HospitalityLocationCondition

4.85 out of 5 average rating, 40 reviews

Magical Stays Near Disney

Outdoor spacesWalkabilityCheckout

4.98 out of 5 average rating, 81 reviews

The backyard features a private pool and spa surrounded by a paved patio. Comfortable seating areas with plush cushions are visible, inviting relaxation. Chaise chairs are positioned nearby, offering sunny spots to unwind. A basketball hoop is installed at the pool's edge, adding a fun activity option.

Home in Four Corners

Zen luxury 6BR at Encore Resort next to Disney 372

PetsOutdoor spacesValue

Guesthouse in Meadow Woods

4.96 out of 5 average rating, 54 reviews

Guest Home-Orlando Airport and Disney-Free Parking

Outdoor spacesPetsAmenities