Pet-friendly vacation rentals in Osceola County

4.92 out of 5 average rating, 134 reviews

A spacious pool area features a large swimming pool surrounded by comfortable lounge chairs and a hot tub. The hot tub bubbles gently, and the area is enclosed by a screened patio, providing privacy and protection from insects.

Home in Kissimmee

Disney Playhouse, Private Pool & Spa, Near Disney

Disney Playhouse – Your Dream Vacation Awaits! Indulge in elegance and comfort at this newly upgraded, pet-friendly retreat. Relax in your private pool & spa within a fully fenced backyard. Unwind in the plush master suite, enjoy Roku TVs in every room, and stay connected with blazing fast 1GB WiFi. The Diner Themed game room features a Marvel electronic pinball machine, pool table, and Wii. Pool heat is optional, hot tub always free! Pets welcome. King Master. Book your luxury getaway today!

4.97 out of 5 average rating, 133 reviews

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!

4.94 out of 5 average rating, 118 reviews

A spacious bedroom is presented, featuring a king-size bed adorned with crisp white linens and a soft navy blanket. A large flat-screen TV is mounted on the wall, with natural light filtering in through bright windows. A small table holds a vase of fresh flowers, and neatly folded towels are placed on the bed.

Apartment in Kissimmee

*KingSizeBed*NrDisney* 100%private*PetsOK

Relax in this 5-star studio, just 15 minutes from Disney, MCO Airport, Downtown, and Universal! Enjoy your private patio, dining under the stars or swaying in the hammock! Take in serene lake views and beautiful sunsets just steps away. With nearby shopping, dining, and local parks, this studio offers the perfect blend of tranquility and easy access to top attractions. Whether you’re here for a Disney vacation or a business trip, this is the ideal retreat for relaxation, comfort, and convenience

4.94 out of 5 average rating, 16 reviews

An aerial view showcases the community pool and tennis courts surrounded by lush trees. The large pool area features lounge chairs, while the brightly colored tennis courts are located nearby, highlighting the resort's amenities within a green landscape.

Apartment in Kissimmee

3 br Disney area condo with a view & FREE resort!

Hands down the Best value and location for a visit to the parks! This super clean and cozy 3 bedroom, 2 bath condo with a private porch and views of the conservation is just what you were looking for in that perfect vacation in the Orlando/Kissimmee areas! Situated inside beautiful Windsor Palms resort and it's FREE resort amenities and mere minutes from all of the main area attractions, the nice furnishings and linens, private views and attention to detail will get your entire family smiling.

4.79 out of 5 average rating, 102 reviews

The exterior of the home features a spacious driveway, paved in light-colored bricks, leading up to an attached garage with an ornate door. A well-maintained lawn with green grass and palm trees is visible, complemented by a clear blue sky filled with clouds.

Home in Kissimmee

View the Disney fireworks from your pool!

Our home is close to Walt Disney World - Shopping - Restaurants . You’ll love the fully stocked granite kitchen, ALL SMART TVs in EVERY room, the views (fireworks), the location, the high ceilings & ceiling fans. Our home is great for couples, families (with kids), and furry friends (pets). Laundry room is INSIDE. The garage is full of games (air hockey, pool & foosball) The pool has a covered lanai with table & chairs for outdoor eating while overlooking our lake with a lighted fountain.

4.99 out of 5 average rating, 101 reviews

A large swimming pool is set within a landscaped area, featuring a gentle curve and surrounded by lounge chairs and umbrellas. A clubhouse with a tiled roof is visible in the background, contributing to the inviting atmosphere of the gated community.

Townhouse in Kissimmee

Family friendly/Pet friendly Orlando paradise

*PET AND CHILD FRIENDLY* *Long term renters welcome* 2 bedroom 2.5 bath Townhome in gated community! 10 mins to Disney, 20 to seaworld, and 30 to universal studios. Community includes large beautiful heated pool and playground/bbq area. Professional cleaning services after each guest stay. Fully stocked kitchen with Keurig coffee, all dishes, utensils, seasonings etc. All bathrooms fully stocked with toiletries and plenty of extra towels. Patio includes chairs, gas grill, and sitting area.

4.79 out of 5 average rating, 214 reviews

The living area is furnished with a black sofa featuring yellow accent pillows. A dining table with four chairs is positioned nearby. The kitchenette is equipped with modern appliances. A bedroom with a blue and white striped bedspread is visible through an open doorway, allowing natural light to flow in.

Condo in Kissimmee

Comfortable Universal Disney Orlando Family Condo

Welcome🌞! This unit is on the second floor! Your much deserved fun vacation away from home starts here 😎! Llocated in the heart 💗 of Walt Disney World and all Kissimmee and Orlando best fun spots 🎢! Includes 2 full size bed. and 1 Full size sofa bed. Just added BIG SMART TVs with Disney+, Netflix, Amazon Video perfect for relaxing after a fun-filled day.✨ 🚗 NEED A CAR? Ask us about our 8-passenger minivan. You can plan your stay and car rental all in one go. Ask us for the link!

4.72 out of 5 average rating, 96 reviews

An outdoor seating area features a dining table surrounded by teal chairs, inviting relaxation. String lights illuminate the space, which overlooks a swimming pool and lush greenery. A cozy double hammock is positioned nearby, contributing to a peaceful ambiance during sunset.

Home in Kissimmee

Southwest facing pool! 5 Miles from Disney.

Enjoy the sunset by your SOUTHWEST facing pool, just 5 miles from Disney. The huge pool area has a conservation & lake view. Enjoy outdoor games or shoot some hoops with the family! Bedroom theming includes 101 Dalmatians (popular with pups AND kids), Harry Potter, Little Mermaid, and Mickey rooms. After a day spent in the parks, wind down with a game of pool or watch a movie in the theatre/game room. Bring your fur baby and the whole family to this spacious and open pet-friendly home!

4.81 out of 5 average rating, 134 reviews

A screened-in private splash pool is surrounded by comfortable seating, featuring playful Minion characters on the walls of the adjoining rooms. The layout includes vibrant décor and modern furnishings, creating a family-friendly space with direct access to outdoor relaxation.

Townhouse in Kissimmee

T7674O/Windsor Hills Resort/3Bedrm/2miles Disney

Highlights: -2 miles to Disney main gate & conveniently located to restaurants & shopping -Amazing theme rooms kids will LOVE -Free Wifi and fast internet for your Zoom meetings -0.3 miles to Clubhouse -Prestigious Windsor Hills Resort (No resort fee) with amazing amenities -New Kids Water Park -Private splash pool is fully screened-in -Free parking -24 hour security / gated - Have a pet? $150 pet fee on 1st; $75 each additional pet (One time fee) -Check out our 5 Star Reviews!

4.94 out of 5 average rating, 108 reviews

A spacious living room features a large, plush sectional sofa in earthy tones, inviting relaxation. A coffee table with a marble finish sits centrally, surrounded by tiled flooring. Soft lighting from a ceiling fixture complements the light cream-colored walls, creating a warm atmosphere.

Home in Davenport

Spacious Family Retreat Near Disney Just~ 8 Miles!

Experience a splendid stay at this 3BR family-friendly home, located at a prime location of Davenport. Explore the exciting world of central Florida where Disney World, Universal Studios Orlando, multiple golf courses, shopping malls & restaurants are super close to your doorstep. Equipped with high-end luxuries, this modern haven is perfect for families to enjoy a relaxing getaway. Book with us for an extraordinary Davenport stay, we await you at your next holiday trip!!!!!

4.93 out of 5 average rating, 99 reviews

A spacious bedroom features a king bed with a gray comforter and decorative pillows. Two bedside lamps provide soft lighting next to the bed. A ceiling fan is above, and a television is positioned on a dresser. Natural light enters through a window with light curtains.

Townhouse in Kissimmee

Private Pool-StoreyLakesResort-Near Disney!

This gated community is perfect for your family &friends to create amazing memories! The home has a first floor bedroom (king) &a very PRIVATE LAKEFRONT pool (that can be heated at a reasonable fee). The resort is very lively.... has TONS AND TONS of amenities including a micky shaped pool, lazy river, tiki bar, slides, &kayaking. You are sure to enjoy your ultimate dream vacation! 5miles-Disney, 14 miles-Universal Studios. We provide all basic essentials, too!