Holiday rentals with a pool in Kissimmee

A private pool and patio area are enclosed by a screened structure, offering protection while enjoying the outdoor space. Two lounge chairs are positioned poolside, reflecting the vibrant colors of the sunset above, with the pool water shimmering under the evening light.

4.89 out of 5 average rating, 158 reviews

Big Disney Home!-Priv Pool/Spa (Heated) Sleeps 12!

This updated pool home is perfect for families and friends for a Florida vacation! Located just 5mi from Disney, 15mi to Universal Studios! Over 2000 sq ft on a quiet cul-de-sac. Arcade room! Chill in your own heated private pool and hot tub or enjoy the club house pool of BellaVida complete with movie theater, sand volleyball, basketball and tot lot! Work out in the fitness center or walk the lake path in the gated neighborhood Enjoy your private game room w/arcade, air hockey and ping pong!

4.81 out of 5 average rating, 150 reviews

The exterior of a single-story home is depicted, featuring a neatly landscaped front yard with green grass and decorative plants. A driveway accommodates a vehicle, while a garage door is visibly closed. The entrance is framed by a small porch and an arching window above the door.

Home in Orlando

Private Home w/ Pool/3 Bd 2 Bath/Close to Disney

The private home is in the Wellington sub-division in Southchase, Orlando, close to the intersection of SR417 (Greeneway)/Orange Blossom Trail and the Florida Turnpike. It is therefore only minutes to the Walt Disney World, Universal Studios and Sea World theme parks plus some of the world’s best golf courses. There are supermarkets and dining (both formal and informal) nearby. We have a Super Target and a Costco within 2 mile radius. Everything you could possibly need really is close at hand.

5 out of 5 average rating, 5 reviews

15 minutes from Disney Luxury Retreat at Reunion

Relax after a magical day at Disney or Universal. Welcome to Reunion Luxury Retreat, experience the perfect blend of luxury comfort, and privacy in this elegant villa, located within the exclusive gate community of Reunion Village, just minutes from Orlando's world-famous theme parks. Our Home offers everything you need for an unforgettable stay. 4 spacious bedrooms, 5 different pools in our resort. Gate community with 24-7 security. Fast wifi , smart TV, fully equipped kitchen.

A refreshing outdoor pool is surrounded by palm trees and lounge chairs. The water is displayed in a light blue shade, with a shallow entry area visible. A poolside cabana with a roof and seating is located nearby, offering shaded relaxation.

4.75 out of 5 average rating, 122 reviews

Destination Sunsation!1 Bedroom Villa 1st Floor!

Runaway Beach Club Resort located 2.5 miles from Disney World. You can choose to be part of the Orlando landscape or unwind and relax on the grounds and enjoy a lazy day at the pool. More amenities have been added as you now have access to Calypso Cay, including Mini Golf, additional pools, basketball & volleyball courts & children's playground and splash pad! We are a gated family friendly community. Less than a mile away there is a super walmart for any last minute needs!

A grand living area showcases a striking stone wall adorned with an extensive collection of framed artwork. Soft seating is arranged around a fireplace, providing a cozy yet elegant atmosphere. A staircase leads to the upper level, while rich drapery frames the large windows, allowing natural light to flow in.

4.95 out of 5 average rating, 198 reviews

Waterfront Wizarding Near Universal's Harry Potter

This spellbound stay, situated in the prestigious Lake Berkley Resort, boasts lake views & private pool. With 6 bedrooms, 3 bathrooms, well equipped kitchen & comfy living spaces, this thematic home is ideal for families & friends seeking an immersive vacation. A 10min drive to Disney, 15min to Sea World & 20min to Universal's Wizarding World of Harry Potter, this magical manor provides a convenient home base for exploring Orlando's famous attractions.

4.86 out of 5 average rating, 101 reviews

Townhouse in Kissimmee

Disney Area| Private Pool| Resort Waterpark 2956

Minutes from Disney, this spacious 4-bedroom townhome is located in the sought-after Storey Lake Resort. Relax in your private screened pool after a day at the parks and enjoy access to amazing resort amenities including water slides, lazy river, clubhouse, fitness center and kayak rentals. Comfortably sleeps up to 12 guests with a full kitchen, fast WiFi and free parking. Perfect for families visiting Disney and Orlando attractions.

4.88 out of 5 average rating, 164 reviews

Villa in Kissimmee

Premium 6BR | Theater, Games & Heated Pool

Welcome to your 3,400 sq ft luxury escape just minutes from Disney World! Perfect for families and friends, our villa sleeps 12 with ensuite bathrooms in every bedroom. Enjoy the home theater, game room, and a fully equipped kitchen—plenty of space to gather or relax. Close to shopping, dining, and all the Orlando magic. Book now for unforgettable memories in your private Disney-area villa.

4.96 out of 5 average rating, 104 reviews

Top Resort Spot, Star Wars Villa

Embrace the Dark Side in this 8-bedroom Star Wars luxury estate! Perfect for large groups, this home features a private pool, hot tub, home theater, and pool table. Located in the Windsor at Westside resort, you're just a 2-minute walk from the lazy river and clubhouse. Experience a cinematic stay just minutes from Disney World, comfortably sleeping your entire galactic crew.

4.73 out of 5 average rating, 108 reviews

A close-up shows Disney-themed plush toys, Mickey and Minnie, placed in a decorative tray on a kitchen counter. The bright colors of the toys contrast with the modern kitchen setting, highlighting a family-friendly atmosphere.

Home in Davenport

Perfect Disney Relaxation! Water Park, Lazy River!

Welcome to Perfect Disney Relaxation at the highly-rated Solterra Resort, with one of the best water parks in the area featuring a Water Slide, a Lazy River, Zero entry pools, and spas. This fully equipped and upgraded private pool home offers everything for a perfect vacation, including poolside dining.

4.71 out of 5 average rating, 175 reviews

5 BD/3BA Single Level Home! Veranda Palms (4458NP)

• Community: Veranda Palms • 5 Bedrooms/ 3 Bathrooms/ Sleeps 14 • Disney World® (5.8 miles) SeaWorld (9.0 miles) • Convention Center (10.1 miles) Legoland (32.2 miles) • Universal Studios (12.8 miles) Epic Universe (11.8 miles) • Location: Nirvana Parkway, Kissimmee FL 34746

4.81 out of 5 average rating, 21 reviews

6 Bd/5 Ba Sleeps 13! Storey Lake (2664 sq ft)

• Community: Storey Lake • 6 Bedrooms/5 Bathrooms/ Sleeps 13 • Disney (7.0 mi) SeaWorld (9.7 mi) Legoland (37.4 mi) • Convention Center (10.8 mi) Universal Studios (14.0 mi) • Location: Scrapbook Street, Kissimmee FL 34746

4.97 out of 5 average rating, 114 reviews

A private pool is framed by a stone patio, with lounge chairs positioned nearby for relaxation. Lush greenery and palm trees surround the area, creating a serene outdoor environment. A spa is positioned next to the pool, providing an inviting space for relaxation.

Villa in Four Corners

The Golden Bear Villa | Private Pool & Theater

Newly Renovated Stunning Vacation Villa in Reunion Resort with Pond Views, Private Pool, Themed Kids Rooms, and Luxury Movie Theater/Games Room - 5 Bed, 4.5 Bath

Popular amenities for Kissimmee rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A tranquil outdoor space features a private pool under a protective screen enclosure, framed by reclining lounge chairs. The setting offers a view of the lake, contrasting with the colorful sunset sky, creating a serene atmosphere for relaxation.

4.96 out of 5 average rating, 114 reviews

Mickey's Lakefront Villa at Sunset Lakes

A spacious two-story villa is surrounded by a manicured lawn and tropical landscaping. A paved driveway leads up to the entrance, framed by palm trees and vibrant greenery. The exterior features a light-colored stucco finish and a welcoming front porch.

4.89 out of 5 average rating, 18 reviews

5BD Formosa Gardens Near Disney (FG 7939)

An aerial view of the expansive resort area showcases a winding lazy river surrounded by palm trees. Multiple pools are visible, along with lounge chairs and shaded areas. The clubhouse, featuring a modern design, sits centrally amid lush landscaping and recreational spaces.

4.9 out of 5 average rating, 63 reviews

Lux Storey Lake Villa/Water Park/Pool/SPA/Themed

5 out of 5 average rating, 59 reviews

An inviting outdoor area showcases a private pool and spa, surrounded by lounge chairs and colorful beach balls. A dining table and large gas grill offer options for outdoor meals. Lush greenery lines the fence, providing privacy and a vibrant backdrop against a sunny sky.

Home in Four Corners

Gorgeous 5BR @ Encore Next to Disney - 305

4.94 out of 5 average rating, 105 reviews

Disney Themes Villa | Pool+Gameroom | Near Parks

4.93 out of 5 average rating, 102 reviews

Lakeside Paradise, 15 min Disney + Saltwater Pool

5 out of 5 average rating, 6 reviews

Great Themed House with Private Heated Pool 221091

5 out of 5 average rating, 4 reviews

2026 NEW Brand NEW 07 Bedrooms At Solara Resort

Apartment rentals with a pool

The aerial view captures the inviting resort-style pool area surrounded by lush landscaping. Colorful canopies and seating areas enhance the outdoor space. Palm trees frame the scene, while the clubhouse is visible in the background, indicating a range of amenities available for guests.

4.9 out of 5 average rating, 104 reviews

Coastal Retreat | 15 min to Disney

4.97 out of 5 average rating, 243 reviews

Perfect for Two Families • Sleeps 8 • Top Location

A bright living space is showcased, featuring a circular dining table set with four plates. A comfortable teal seating area is arranged against the wall, complemented by a nature-inspired wall art piece and greenery. Large glass doors provide a view of the outdoors and invite natural light.

4.86 out of 5 average rating, 135 reviews

Stylish Condo 20 mins to Disney/King Bed

A modern living area features a white sectional sofa and a stylish coffee table with gold accents. A flat-screen television is mounted on the wall, complemented by minimalist shelving. Large windows dressed with sheer curtains allow natural light to fill the space, creating a bright and welcoming environment.

4.92 out of 5 average rating, 108 reviews

Resort Style Sunshine Oasis near Theme Parks

A family room features a neutral-toned sofa and armchair, accompanied by a mounted flat-screen TV. A children's bedroom displays two twin beds, adorned with playful wall murals. A primary bedroom includes a king bed, with bedside lamps enhancing the calm ambiance. A resort pool area showcases a large pool surrounded by lounge seating and loungers in a vibrant outdoor setting.

4.96 out of 5 average rating, 163 reviews

202_Magical and Cozy 2BR minutes from Disney

A large stone sign displays the name 'Windsor Palms' surrounded by lush greenery and colorful flowerbeds. Palm trees are seen flanking the sign, under a clear blue sky, indicating an inviting entrance to the gated resort community.

4.93 out of 5 average rating, 150 reviews

Resort condo minutes from Disney!!!

A patio area is presented under a covered porch, featuring a round table set for two with a white tablecloth and colorful cups. Two comfortable chairs with blue cushions are positioned around the table. A scenic view of a lake with greenery can be seen in the background.

4.84 out of 5 average rating, 147 reviews

Stunning view, near Disney.

A refreshing swimming pool features a large water slide in vibrant green and blue. Palm trees provide shade around the area. Several lounge chairs are positioned beside the pool, inviting relaxation while enjoying the sunny landscape.

4.96 out of 5 average rating, 159 reviews

Luxurious Spot 10 Mins Away to Most Attractions!!!

Other holiday rentals with a pool

5 out of 5 average rating, 15 reviews

Home in Four Corners

7BR Disney Family Oasis | Pool•Spa• Game Room

5 out of 5 average rating, 31 reviews

Fantabulous Disney Vacation House / 10 min Disney

4.95 out of 5 average rating, 55 reviews

Tiny home in Kissimmee

The Cozy Nook

4.81 out of 5 average rating, 27 reviews

Villa in Kissimmee

Luxury Townhouse Near Disney | 3BR

The private pool area features clear blue water surrounded by a spacious deck. A spa is adjacent to the pool, and patio furniture is visible in the background, providing options for relaxation. A screen enclosure protects the area while allowing natural light to fill the space.

4.75 out of 5 average rating, 20 reviews

Getaway w/ Private Pool & SPA + BBQ | 10min Disney

4.85 out of 5 average rating, 20 reviews

Near Disney! 4 BD/3 BA w Pool! Storey Lake (4832)

4.75 out of 5 average rating, 4 reviews

Villa in Kissimmee

Modern Luxury Themed 7 Bed Pool Villa near Disney