Vacation rentals with a pool in Osceola County

4.85 out of 5 average rating, 211 reviews

A private pool is framed by a screened enclosure, featuring a gentle waterfall and bordered by comfortable lounge chairs. The serene lake view is visible beyond the pool, complemented by lush greenery lining the shore.

Villa in Kissimmee

Near Disney Gated LakeView Pvt Heated Pool

LIMITED OFFER! FREE CLEANING FOR BOOKING 10 DAYS OR MORE DAYS! LOWEST CLEANING FEE! Miltary dscnts. New Pool Heatr, Dolby ATMS, 65" LED TV w/ Airplay. Remote office setup. Sunset Lakes a secure gated comnty ~12 min from Disney & other parks. Villa offers Lake View pvt pool, gorgeous sunset, Playroom, Fishing dock. Fully furnished, sparkling clean w/ 5 bds - 1 King, 2 Qns, 2 Twin beds w/ 3 baths, kitchen & Lndry. Come & enjoy your next trip to Disney & leave everything to a fantastic experience!

4.99 out of 5 average rating, 153 reviews

Villa in Osceola County

*Private Golf-Front Oasis with Pool, Spa & Cinema

Escape to one of Reunion Resort's most unforgettable homes, where luxury meets nonstop fun just minutes from Disney. Enjoy your private pool & spillover spa on the sprawling 2,000 sq ft pool deck, then take in golf course views from the separate fire pit terrace & balcony. Inside, discover a Star Wars theater/game room with digital pinball, arcade games & karaoke, a Marvel kids' suite with tube slide, Xbox Series S, and a hidden Harry Potter cupboard. Perfect for unforgettable family vacations.

4.9 out of 5 average rating, 126 reviews

Encanto at Emerald Island-Pool House by Disney

POOL HEATER OPTION!! Make some memories at this unique and family-friendly place. A guarded Resort- neighborhood awaits! As you enter this magical place you will fall in love with the unique landscaping full of palm trees surrounding the neighborhood. This secluded place has everything you need! 5 star location, security, private pool, and also a clubhouse with many activities for the young ones. You will be next to restaurants, shopping and more. Only 3 miles aways from Disney's exit & parks!

4.91 out of 5 average rating, 106 reviews

A private theater is presented with six reclining seats, arranged in rows facing a large 155-inch screen. The room is accented by dark walls and illuminated with blue lighting, enhancing the cinematic atmosphere. Movie posters adorn the walls, contributing to the entertainment theme.

Villa in Kissimmee

Disney Fun Time 8BD 4K Movie Theater Jacuzzi Pool

World! This Disney Resort gem, crafted with 20 years of hosting expertise, boasts a 155-inch 4K theater with PS5, a sparkling pool with Jacuzzi, Patio and Grill, with 8 Bedroom and themed rooms (Star Wars, Mickey, Princess) family fun is guaranteed! Gourmet kitchen, dining room, 9 Smart TVS, living room, and high-speed Wi-Fi await, plus strollers and baby gear. Enjoy resort perks: heated pools, gym, mini golf. Fully renovated, it’s our best-ever creation—book now for an unforgettable vacation!

A private pool area is surrounded by a screened enclosure, featuring a well-shaped pool and a jetted hot tub. Lounge chairs are positioned nearby, with a grassy area beyond. The evening sky displays hues of pink, creating a serene atmosphere, enhanced by string lights that illuminate the space.

4.92 out of 5 average rating, 215 reviews

*Luxe Disney Home* Priv Pool/Spa- 6BR Sleeps 15

JUST ADDED! (Check out our other reviews) New Construction!!! 3000ft2! Welcome to our luxury 6-BR private pool home near Disney World, Universal Studios, and Sea World! With 8 beds, it sleeps 15 people comfortably. Enjoy the private heated pool, hot tub, and game room with ping pong, cornhole, and arcade. Located in Veranda Palms community, you also have access to a large pool, clubhouse, gym, and splash pad. Perfect for large families or groups seeking a memorable Orlando stay. Book now!

A private patio area is presented, featuring a refreshing turquoise rug adorned with floral patterns. Two wicker chairs, accompanied by a small table and a potted plant, offer a cozy seating arrangement beside a sparkling pool, enclosed by a protective mesh screen.

4.93 out of 5 average rating, 116 reviews

Paradise Suite With Private Pool

Relax with the whole family at this peaceful place to stay. The spacious living area features windows that flood the space with natural light, while the kitchen is equipped with stainless steel appliances and granite countertops. The master bedroom offers a peaceful oasis with a spa-like master bath and walk-in closet. Property is located in a gated Golf community with a 3 mile walking trail that offers beautiful lake views. close to major intersections and shopping mall less than 2 miles

4.97 out of 5 average rating, 188 reviews

Near Disney | Heated Pool, King Bed, Arcade

✨ Family-Friendly Retreat Near Disney in a gated, safe & quiet community 🏰 Loved by guests for its cleanliness, comfort, and fast communication. 🏊‍♂️ Unwind after park days in your private HEATED pool 🍔 Enjoy the outdoor BBQ for easy family meals 🎮 Have fun in the upgraded game room with pool table, ping pong, foosball, and a retro arcade ⭐ Hosted by 3 experienced Superhosts known for quick, reliable replies. A perfect balance of fun and relaxation. Book now as dates fill fast!

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

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.

4.91 out of 5 average rating, 278 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*

4.96 out of 5 average rating, 119 reviews

A unique sleeping area features a round bed designed to resemble a giant clam shell. Vibrant murals depicting underwater scenes adorn the walls, complementing the ocean-themed decor. Soft curtains in shades of green flow down from the ceiling, adding color to the tranquil space.

Home in Davenport

Royal Retreat Disney Themed Pool Home, Arcade, Theater

Welcome to The Royal Retreat. Located just 10 miles away from the entrance of WDW, our rental is the perfect place to stay for your Disney vacation. Our 5 star home features 8 themed bedrooms and 5 bathrooms, a fully-equipped kitchen, private heated pool, private arcade, home theater & BBQ! Free Pool heat & the 1st tank of propane for the BBQ are included. Booking with us includes full access to the Champions Gate Clubhouse, Oasis Resort and Retreat Club!

A spacious living area features a large sectional sofa, paired with a round coffee table. Natural light floods in through sliding glass doors that open to the pool area. Decorative accents include coastal-themed artwork and soft lighting fixtures, enhancing the inviting ambiance.

4.84 out of 5 average rating, 150 reviews

Park Place! 7 Min from Disney, Pool, Theater

Elevate your next getaway at this outstanding 5-bedroom, 3-bathroom home! Nestled in an upscale, gated community, Park Place boasts 2500 sq. ft. of beautiful living space and easily accommodates 10 guests. This home is ideal for families or a small group visiting the magical Orlando area’s countless attractions. Ideally located between theme parks, shops, and restaurants, you're perfectly situated to experience all the area has to offer!