Holiday rentals with a pool in Kissimmee

The villa features a modern exterior with a sloped roof and a two-car garage. Palm trees are landscaped around the front yard, which is bordered by well-maintained grass. A clear blue sky provides a bright backdrop to the welcoming entrance.

4.87 out of 5 average rating, 263 reviews

3 bedroom Villa in Kissimmee

The villa is in a residential area within a 5-min drive to local amenities including, a pharmacy, 3 supermarkets and 2 gas stations. The property is between 15 - 40 mins drive from Disney, Epic Universe, SeaWorld, Gatorland & Universal Studios. Orlando International Airport is only about 17 mins drive away. Osceola Heritage Park, the home of the world’s largest collector car auction is only 4 mins drive from the villa. The Florida Turnpike that runs through Miami is 6 mins from the property.

A panoramic view captures the lush Arnold Palmer PGA golf course along with the resort pool area featuring a hot tub. The vibrant Star Wars themed bedroom includes wall decorations and arcade features. Inside, a cozy living area is showcased with a large TV and French doors leading outside.

4.96 out of 5 average rating, 173 reviews

Fireworks Penthouse: Top Floor, Star Wars, 2 Pools

This modern 3-bedroom TOP FLOOR (with an ELEVATOR right to the door) luxury condo has one of the most PICTURESQUE VIEWS in the Reunion Resort of the Arnold Palmer PGA golf course. Combining STYLISH DESIGN and LUXURIOUS COMFORT, there are 2 KING bedrooms and a playful STAR WARS themed bedroom with a classic Arcade machine & Xbox. 4 TVs with DirecTV, free high-speed wifi, your own washer & dryer, access to 6 resort pools, 2 of which are only a 3 minute walk away, and only a short drive to Disney.

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, 133 reviews

Stylish Condo 20 mins to Disney/King Bed

Escape to our lovely vacation villa, nestled in the vibrant heart of Orlando's premier golfing destination. Just a 7-mile drive from Disney attractions and 30 minutes from Orlando International Airport. Discover the awe-inspiring Reunion Resort, offering an array of delights. Indulge in delectable dining experiences, take a dip in sparkling pools, savor refreshing drinks at poolside bars and grill. Embark on an extraordinary getaway that exceeds all expectations. Book your stay with us today!

Apartment in Champions Gate

The exterior of a modern two-story building is shown, featuring a combination of light grey and white siding. Lush palm trees frame the front, with a paved driveway visible. A parked vehicle is positioned in front of the entrance, and a sunny blue sky is above.

4.95 out of 5 average rating, 150 reviews

Spacious Condo for 8 Golf Waterpark 15 min Disney

Welcome to your Orlando family getaway! This 3-BR condo at Champions Gate offers a direct Golf Course view and sleeps up to 4 adults and four kids. Two rooms feature King beds, and one has two Full beds. Just 15 mins from Disney Parks! Enjoy complimentary access to the fabulous Oasis Club (3 pools, gym, Tiki Bar) and the Retreat Club. Full kitchen access saves you money. Champions Gate also boasts a 36-hole Greg Norman championship golf course! Location & luxury for all ages.

4.95 out of 5 average rating, 175 reviews

A modern digital door lock is mounted on a light-colored door, featuring a keypad for secure access. A blurred plant with lush green leaves is visible in the background, adding a touch of nature to the entryway.

Guest suite in Kissimmee

It's too much like a elegant mini-hotel (5)

It's too much like a elegant mini hotel with rich artistic atmosphere！ All the pictures on this page are a reflection of the real condition of the house. All the furniture has been carefully selected, and comfortable mattress and pillows will quickly accompany you into sweet dreams. The biggest feature of this house are comfort, economy and convenience. All of my houses have hosted countless guests from South America, including Brazil and Argentina. You will always be welcome here!

4.9 out of 5 average rating, 157 reviews

A bright and open living area features modern furnishings, including a sectional sofa and stylish yellow accent chairs. A large flat-screen TV is mounted on the wall, while decorative elements and a vibrant area rug contribute to the space's contemporary aesthetic.

Home in Davenport

Awesome Vacation Home w/ Private Heated Pool/Spa

Sunshine living at its best! The Abbey at West Haven is an enclave of exclusive vacation homes. This gem has been totally redesigned and upgraded for your vacationing pleasure and is the IDEAL choice for your next family vacation or getaway in Central Florida. Stores, restaurants and golf courses are all within 5 mins and Disney just 15 mins away. After a long day at the Theme Parks or a round of golf, relax at the private, pool and spa or enjoy a BBQ on the enormous covered patio.

An open living area features a comfortable seating arrangement with two armchairs and a sectional sofa. A modern coffee table sits atop a soft rug. Large sliding glass doors lead to a balcony, offering a view of the tranquil lake.

4.86 out of 5 average rating, 163 reviews

3171-107 Resort Lake View Disney Universal Orlando

Relax in our Stylish & Modern 2Bed/2bath fully equipped apartment for up to 7 guests, located in the family friendly Storey Lake Resort. Minutes from DISNEY World Theme Parks in Orlando Florida. Close to UNIVERSAL STUDIOS & SEAWORLD. Enjoy our lake view from the balcony. Close to restaurants, supermarkets, outlet malls & retail stores. Great amenities: Heated Pools, Kids Splash Zone, Water Slides, Lazy River, Gym, Mini Golf, Kayak, Tiki Bar & Ice Cream Shop, security guard!

4.99 out of 5 average rating, 138 reviews

The living area features a comfortable gray sofa adorned with accent pillows, complemented by a wooden coffee table. A large TV is mounted on the wall, with a stylish chair placed nearby. Natural light enters through glass doors, which lead to a balcony.

Flat in Kissimmee

Chic Vibes Comfy King Bed Next to Parks/Food/shops

Welcome to our stylish oasis in Kissimmee, which seamlessly blends sophistication with a laid-back vibe. Your stay begins in a professionally cleaned apartment for your full enjoyment. Discover resort-style amenities – a sparkling pool, a fitness center, and hammocks, offering the luxuries of a five-star retreat. Conveniently located with in walking distance of theme parks, restaurants, and shopping. Book now. We can't wait to host you in our little slice of paradise!

4.83 out of 5 average rating, 143 reviews

The image presents a four-part collage, featuring a bright bedroom with two spacious beds adorned with decorative pillows, a private hot tub surrounded by nature, a resort pool with loungers and a water slide, and a clubhouse area with expansive outdoor seating and vibrant landscaping.

Townhouse in Kissimmee

♥Disney-3 Miles from ♥Private HotTub ♥to Top♥ Resort

Our gated-community townhouse offers a resort feeling with all the comforts of home, peaceful & quiet, yet central to Disney, Old Town, and all major attractions. After an exciting family day, relax in your private patio hot tub and enjoy the nature, or soak up some sun poolside at the resort. Fun for adults and kids of all ages! Also enjoy the resort tennis courts, pool table, gym, restaurant, and poolside snack bar! NO RESORT FEES! FREE PARKING!

A private balcony offers seating with a view of the shimmering lake, highlighting the surrounding landscape. Adjacent images reveal family-friendly amenities, including a vibrant water park with slides, an elegant kitchen space, and a welcoming sleeping area featuring playful decor.

4.9 out of 5 average rating, 184 reviews

NEW APARTMENT WITH WATER PARK AND NEAR DISNEY

Enjoy a carefree vacation at Storey Lake Resort. Located minutes from Disney, Falcon's Fire Golf Club, Universal, Epic Universal, SeaWorld, Orange County Convention, Premium Outlets. Less than 1 mile from Walmart, Target, and restaurants, your family will have everything they need. Water Park, gym, and all amenities FREE. Free parking, 24/7 security in this gated resort and with an automatic check-in with direct access code and elevator available

Apartment in Four Corners

The open living area features a round dining table with four chairs, a wall-mounted TV, and a comfortable sofa. Natural light enters through sliding glass doors leading to a scenic outdoor view. A rustic wood accent wall adds texture to the space.

4.88 out of 5 average rating, 175 reviews

"Ocean's Gate" - 2BD/2BA condo near Disney

Welcome to our beautiful ground-level condo! With the prime location at ChampionsGate Resort near Disney World and major parks, this 2BD/2BA condo unit is designed for your best accommodation. Spread out in 1,558 Sq. Ft., the unit offers a fully equipped kitchen, a cozy living room, a working station, and comfortable bedrooms. With access to the Clubhouse and resort amenities, you’ll spend amazing days in our home!

4.92 out of 5 average rating, 131 reviews

Entire Modern Home near Disney • Pool & Game Room

Make memories at our beautifully renovated home in Kissimmee — close to Disney, Universal, and everything Orlando has to offer. Relax in your private pool, enjoy 3 comfortable bedrooms and 2 full baths, and check in easily with keyless entry. Nestled in the safe, gated community of Cumbrian Lakes, it’s the perfect spot for families and friends to unwind together.

Popular amenities for Kissimmee rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A two-story home with a light brown exterior is set within a lush green landscape. A spacious driveway leads to a white garage with a large door. The property is enclosed by a white privacy fence, creating a secluded outdoor environment.

4.93 out of 5 average rating, 171 reviews

South Facing Pool Home! 5 Miles from Disney

The spacious living area features a light-filled environment with comfortable seating arrangements, including a sofa and armchair. A coffee table sits in the center, accompanied by a decorative bowl of sunflowers. A large television is positioned against a wall, complemented by neutral-toned decor.

4.9 out of 5 average rating, 107 reviews

4BD 2BA Kissimmee Pool House near Disney

A modern living area features a comfortable sofa in neutral tones alongside two vibrant orange chairs. A round glass coffee table is positioned in front of the sofa, while a large television is mounted on a wooden accent wall. Floor-to-ceiling windows allow natural light to fill the space.

4.97 out of 5 average rating, 105 reviews

Modern 4bdr Storey Lake w/themed rooms near disney

4.86 out of 5 average rating, 199 reviews

Amazing 3 BD home w/ Elevator & BBQ - near Disney!

An enclosed in-ground swimming pool is featured, surrounded by a screened lanai. Various lounge chairs and umbrellas provide seating options. The pool is clear and inviting, with a decking area that offers space for relaxation.

4.92 out of 5 average rating, 160 reviews

Disney New Neighbor

The exterior of the home showcases a single-story structure with a combination of pastel hues and stone accents. Lush green grass surrounds the building, accompanied by a variety of tropical plants and a palm tree. A well-maintained driveway leads to a two-car garage.

4.88 out of 5 average rating, 134 reviews

Relaxing Orlando 4 BR home, pool & water view

4.93 out of 5 average rating, 161 reviews

A private, screened-in pool area features a sparkling blue pool with a built-in hot tub on one side. Sunlight reflects off the water, creating a serene environment, while surrounding greenery provides a sense of privacy.

Home in Clermont

Stylish Villa Private Pool-SPA Near Parks Disney!

4.94 out of 5 average rating, 114 reviews

The outdoor pool area features a screened enclosure with views of the golf course beyond. A circular table is set with blue napkins and dinnerware, surrounded by blue chairs. Six lounge chairs are positioned alongside the shimmering pool, providing a comfortable space to relax.

Home in Davenport

"Cozy Retreat with something for everyone"

Apartment rentals with a pool

4.91 out of 5 average rating, 182 reviews

P-Gated Resort-5 miles to Disney-2 FREE Water Park

A spacious living area is designed with light grey sofas and a glass coffee table, surrounded by greenery. Large windows with wooden blinds allow natural light to fill the room, while a ceiling fan enhances airflow. Soft, neutral tones create a relaxing atmosphere.

4.88 out of 5 average rating, 163 reviews

Near Disney/Universal Lovely 2bedroom/2bath Condo

4.98 out of 5 average rating, 133 reviews

Private Rooftop Suite! No resort fees!

A private balcony offers serene views of Lake Bryan and a swimming pool area. A small round table with two chairs invites relaxation, while warm colors from the sunset enhance the tranquil setting. Lush trees frame the scene, creating a peaceful atmosphere.

4.97 out of 5 average rating, 424 reviews

Waterfront Condo minutes to Disney & Universal

A sparkling pool is framed by lush palm trees and lounge chairs, inviting guests to relax. The cheerful two-story building in the background features vibrant blue-green accents and large windows, complementing the clear sky above.

4.93 out of 5 average rating, 122 reviews

Modern, spacious, and relaxing!

A bright living area features a cozy gray sofa paired with two stylish yellow chairs. A wooden coffee table sits atop a textured area rug, while large glass doors lead to a balcony that offers views of Lake Bryan.

4.94 out of 5 average rating, 124 reviews

Modern Lake view Condo 1 mile from 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, 158 reviews

Luxurious Spot 10 Mins Away to Most Attractions!!!

The living area features a spacious gray sectional sofa and a wooden coffee table atop a round, textured rug. A large TV is mounted on a media console, and natural light flows through the floor-to-ceiling sliding doors leading to a balcony with lake views.

4.88 out of 5 average rating, 177 reviews

[Lake View, Modern Decor, 1 Mile to Disney!]

Other holiday rentals with a pool

5 out of 5 average rating, 60 reviews

Flat in Orlando

Pet-Friendly | King Bed | Gym & Pool | Near Parks

A single-story home is presented with a light tan exterior and a welcoming front yard. Lush greenery surrounds the property, featuring neatly trimmed shrubs and palm trees. A paved driveway leads to a two-car garage with solar panels on the roof, providing an energy-efficient touch.

5 out of 5 average rating, 58 reviews

Family Vacay with Pool near WDW!

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 out of 5 average rating, 59 reviews

Luxury Home w/ Pool & 6 Beds near Disney

A spacious living area showcases large windows that invite natural light, complemented by comfortable seating. A private pool is visible outdoors, surrounded by a screened enclosure. The bedroom features a king bed and calming decor, while another area displays two twin beds in bright, inviting colors.

5 out of 5 average rating, 39 reviews

Fun in Paradise: Pool Villa near Attractions!

4.96 out of 5 average rating, 28 reviews

Guest house in Orlando

Boutique Suite in Orlando

Apartment in Four Corners

A large resort-style pool is viewed in the foreground, surrounded by a spacious deck featuring lounge chairs. A clubhouse sits in the background, with palm trees lining the perimeter under a clear blue sky scattered with clouds.

4.93 out of 5 average rating, 40 reviews

2BD Champions Gate Magical Near Disney (CG 1177)

4.8 out of 5 average rating, 30 reviews

A stunning water park showcases multiple pools and attractions surrounded by palm trees. The lazy river winds through the landscape, while vibrant water slides stand ready for enjoyment. Ample lounging space is offered for relaxation, highlighting the inviting atmosphere of this recreational area.

Apartment in Davenport

Stunning 3BR Condo Near Disney