Holiday rentals with a pool in Osceola County

4.94 out of 5 average rating, 180 reviews

Condo in Kissimmee

3161-305 Resort Lake View Disney Universal Orlando

Minutes from Disney World Orlando Florida, Modern & Stylish 2bed/2bath fully equipped apartment for up to 7 guests, located in the family friendly Storey Lake Resort. FREE Clubhouse & WATERPARK amenities: Heated Pool, Hot Tub, Kids Splash Zone, Water Slides, Lazy River, Gym, Tiki Bar, Ice Cream Shop & more. The apt is located: 10 min drive to DISNEY, 25 min to UNIVERSAL STUDIOS, 18 min to SEA WORLD. FREE Parking. FREE Waterpark. No extra FEES. Gated Resort with Security 24/7 & Self check-in!

4.97 out of 5 average rating, 162 reviews

Barn in St. Cloud

Rustic Barn Retreat

Experience the rustic elegance of this beautifully remodeled 1,800 sq. ft. barn nestled on a serene 17-acre property. Unwind in the private heated hot tub and soak up the peaceful surroundings. The prime location offers convenient access to major attractions—just a 35-45 min drive west will take you to Disney, Universal, SeaWorld, and gator parks, while a 45-60 min drive east leads you to the breathtaking Atlantic beaches and the Space Coast. Plus, the property is only 40 min from the airport

4.96 out of 5 average rating, 321 reviews

Upscale Renovated HeatedPool Waterfront Piano Home

Welcome to one-of-a-kind upscale contemporary waterfront oasis, where luxury meets comfort in a serene setting. This stunning house is nestled in a tranquil neighborhood, just moments away from the airport and all the attractions you desire. Step inside to find a beautifully renovated space: fully equipped open kitchen, grand piano and more! Outside: private screened in heated pool($20/night heating fee)with breathtaking waterviews, patio equipped with grill, dining table, ping pong and more!

4.99 out of 5 average rating, 128 reviews

Villa in Osceola County

*Private Resort Oasis: Golf-Front, Pool/Spa/Cinema

The perfect balance of STYLISH DESIGN, LUXURIOUS COMFORT, & ENDLESS ENTERTAINMENT, beautifully situated with stunning views in the sprawling 3.5 square mile Reunion Resort. You will have your own private pool, spillover spa, STAR WARS cinema-game room with pinball, classic arcade games, and karaoke, MARVEL kids room with tube slide and double bunks, the latest Xbox Series S, a sprawling 2000 ft2 pool deck, fire pit, and even a HARRY POTTER cupboard hidden under the stairs, minutes to Disney.

4.97 out of 5 average rating, 110 reviews

Modern House with Private Pool Getaway Kissimmee

This property is accommodated for families looking to vacation with peace of mind, the facilities are perfectly arranged so that you and your family feel at home. It has 3 rooms equipped for adults and children, the patio area is the perfect place to spend time with your family either in the pool or enjoying a barbecue on the grill.( POOL IS NOT HEATED) -No parties allowed in the house. No smoke. Do not park blocking the sidewalk, no park on the grass, nor in front of the neighbors' house.

Superhost

Home in Osceola County

4.93 out of 5 average rating, 122 reviews

Pirate & Princess: Themed/Disney/Resort

Wishes come true at The Pirate & Princess 5BR/6BA immersive vacation home, 6 miles from Disney. Seeking enchanted adventure? Sprinkle pixie dust, second star to the right, to… Reunion Resort! Gated golf resort; pools/dining/gym. Treasure Island, Peter Pan, Tinker Bell, Captain’s Lounge, Little Mermaid & Moana; Disney-inspired rooms, professionally designed! Private Pool/Spa/BBQ/Chef’s Kitchen/Office/Laundry/WiFi/In-Law Apt./Sunset Lake Views. Family-friendly gem to delight kids! Sleeps 15.

4.99 out of 5 average rating, 134 reviews

Epcot Themed Home: Private Sunset Near Disney

LOCATION! LOCATION! LOCATION! Hello all my globetrotters! Our fun home features a diverse international culture in each room. Experience Italy in the kitchen, America in the living room, Japan in the game room, and sleep in Paris, China or Morocco bedrooms. In the backyard, Mexico awaits with amazing private pool and a glow party at sunset each night. Depend on traffic, between 10-20 min to Disney, fast WiFi, ample natural light, tons of nearby grocery stores, restaurants, and shopping

4.89 out of 5 average rating, 101 reviews

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)

4.88 out of 5 average rating, 203 reviews

Waterfront retreat,KING Bed,Heated Pool & Fire Pit

Sit back and relax in this stylish home with all the amenities you need for a fun family getaway. This home has a spacious layout with 3 bedrooms and 2 baths. We have thought of everything so you don't have to-toiletries,washer/dryer, and wifi. Enjoy your morning coffee in the screened in pool area with a beautiful sunrise and lake view or sip a glass of wine while floating in the pool. Just minutes to Theme Parks and major highways, this is the dream home you have been waiting for!

4.93 out of 5 average rating, 414 reviews

Cottage in Kissimmee

Bungalow cottage close to Disney Universal, for 4!

A full cottage for 4! The perfect place. Located just 20 minutes from Disney and Universal. Shopping and Restaurants are less than 5 minutes from the cottages. All new furnishings, fresh linens, fresh paint! Privately owned. This cottage is our favorite!!! We also just updated the A/C. Check our unit. We also have three other cottages on property, the Bitty Bungalow, Bitty Bliss, and the Bitty Blossom. All cottages are within 70 yards of each other.

4.96 out of 5 average rating, 99 reviews

Manor on Knottingham Near Disney

Welcome to "Manor on Knottingham," nestled in the heart of Four Corners. The rustic charm, adorned with vintage Disney-inspired decor, transports guests to a bygone era of beloved characters and timeless tales. Outside, enjoy the sparkling blue pool and warm summer weather. A great place for family and friends. "Manor on. Knottingham" promises an extraordinary stay, where the magic of Disney and the comfort of a home merge into an unforgettable experience.