Holiday rentals with a pool in Kissimmee

4.95 out of 5 average rating, 191 reviews

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!

4.99 out of 5 average rating, 138 reviews

A themed game room showcases a Batman-inspired design with a bright yellow slide leading to a two-level play area. An air hockey table is positioned prominently, surrounded by stylized dark walls, creating an immersive gaming environment.

Villa in Kissimmee

Sleeps 21|Free Pool Heat|15 min to Disney|Hot Tub

Make memories to last a lifetime in our luxurious seven-bedroom home (sleeps 21) at Orlando's premier vacation community. Enjoy your own Batman cave game room, private pool (heated at no extra charge*), and hot tub. Our 100% Five-Star rating from previous guests and our generous cancellation policy means you can book with confidence. Only 15 minutes to Disney and a short walk to a fabulous resort clubhouse with free access to a lavish pool, kids waterpark, restaurant, playground, gym, and more!

The kitchen showcases modern grey cabinetry and sleek stainless steel appliances. A bright white countertop offers seating for four on padded bar stools. Coffee and tea-making supplies are visible on the counter, with accent decor displayed on the shelves. A pantry door stands closed nearby.

4.95 out of 5 average rating, 123 reviews

Private Gated Community 8 mins away from Disney!

Gorgeous brand NEW luxury condo gated w 24 hr security guard. 8 mins from Disney & all parks!! 2 bedrooms, 2 bathrooms (rain shower & tub) Therapeutic beds in every room, including full size pull out. Smart TVs in every room w/cable, Netflix, Wifi. Extra steps to clean & sanitize. 2 min walk to Super Walmart. Walking distance to food, shopping, gas, Starbucks & more. washer dryer, coffee, tea, toiletries Clubhouse Resort with pool, jacuzzi, playground, gym, tennis & volley ball court, lake.

The open living area features a contemporary design with a curved sofa in neutral tones, two blue accent chairs, and a glass coffee table. A textured area rug complements the decor. Large windows allow natural light to illuminate the space, enhancing the connection to the outdoors.

4.88 out of 5 average rating, 214 reviews

Adorable 2 bdr lakefront w/jacuzzi 5 min *Disney*

This townhouse provides an open main living space that allows you to connect the dining and a fully equipped kitchen. The house can accommodate up to 6 guests, divided into one luxe king en-suite, and a design theme two full en-suite. After a long day at the parks with a beautiful lakefront view, relax in your private spa. Clubhouse with a gym, amazing heated pool, pool bar, a restaurant, and only 5 min from Disney and golfing area Free Parking Close to lakes, camping, beach, vineyards, farms

4.97 out of 5 average rating, 414 reviews

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.

Apartment in Orlando

Waterfront Condo minutes to Disney & Universal

Just minutes from Disney World and Universal Studios, this condo places you in the heart of Orlando’s top attractions, including Disney Springs, Islands of Adventure, SeaWorld, Magic Kingdom, Epcot, two outlet malls, and more. Relax on your private balcony with breathtaking views of Lake Bryan, or enjoy the resort-style pool with a full Tiki bar and dining menu. Additional perks include free parking, 24-hour security, and complimentary HBO & Netflix. No deposit required and no extra fees.

A private pool area is enclosed by a screened lanai, featuring a spacious pool with clear water. A small seating arrangement with two wicker chairs and a table is visible, alongside a vibrant wall decoration. Lush greenery is seen beyond the pool area.

4.9 out of 5 average rating, 169 reviews

Home near Disney with Heated Pool

Our space has been prepped to be modern, spacious, and vibrant! It has 3 Bedrooms and 2 1/2 bathrooms. Includes pool that is regularly maintained as well as other important amenities like washer and dryer. All linens have been replaced along with towels and rugs. Club house is also a great place to spend time as it includes hot tubs, pools, a bar, pool table, & gym! Resort is gated and well maintained by staff. SE HABLA ESPAÑOL *Maintenance may access property only upon approval by guest*

A private hot tub is situated on a patio surrounded by a screen enclosure, offering views of a tranquil lake. A fountain can be seen in the distance, enhancing the serene atmosphere. Steps lead up to the hot tub, providing easy access.

4.95 out of 5 average rating, 226 reviews

4.95 Rated Pool Home 10 Min to Disney

Trusted by over 400 guests with a 4.95 rating. Quiet pool home designed for easy, stress free stays. Spotless, clutter free, and exactly as described. Fast WiFi and simple self check in. 10 minutes to Disney and major attractions. “Spotless, easy check in, and perfect location.” “Exactly as described. Would stay again.” 2-bedroom townhouse in the gated Regal Oaks Resort Private hot tub overlooking a peaceful lake, ll Resort-style amenities like pools, water slides, a fitness center.

A spacious living area is furnished with a light-colored sectional sofa and brown leather chairs. A round coffee table sits at the center, complemented by a decorative bowl. The adjacent kitchen is equipped with modern appliances and a breakfast bar, creating an open and inviting layout.

4.93 out of 5 average rating, 152 reviews

Luxury condo near Walt Disney Parks - Kissimmee FL

Entire family will enjoy this luxury condominium located in Kissimmee Florida. Minutes away from all Walt Disney parks, quick drive to Disney Springs and close to major highways. Many attractions within walking distance such as water parks, Studio Grille movie theater, grocery stores, pharmacies, gift shops and plenty restaurants. The condominium includes two primary bedroom suites with en-suite fully remodeled bathrooms. Entire condo is beautifully remodeled to make you feel at home.

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.

4.99 out of 5 average rating, 123 reviews

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!

A game room is presented with a red and neutral color scheme, featuring a billiard table with a set of colorful pool balls arranged on it. A television is mounted on the wall, and a dartboard is visible. The space is accented with vibrant wall art and seating areas.

4.9 out of 5 average rating, 128 reviews

No Airbnb Fee | Newly Renovated 4BR w/ Pool!

**We offer EV Charger for FREE!!! The magic of Orlando starts at home! This incredible house has much more than you need; it has everything you WANT! We offer guests comfort, convenience and an amazing experience!! Transparency and communication is very important to us! We want to make it clear, that we are here at your disposal for any doubts or suggestions. We can't wait to have you here enjoying peace and quiet and having lots of fun!

4.98 out of 5 average rating, 177 reviews

*Private Modern Oasis: Pool, Spa, Cinema, Arcades

Experience the perfect blend of STYLISH DESIGN, LUXURIOUS COMFORT & ENDLESS ENTERTAINMENT in this stunning home at Reunion Resort. Enjoy a sprawling 2400 ft² southwest-facing pool deck with outdoor kitchen, private pool & overflow spa, plus no rear neighbors. Inside, find a movie room, billiards game room, STAR WARS & FROZEN II kids’ theme rooms with tube slide, and both Xbox & PlayStation for nonstop fun.

4.91 out of 5 average rating, 125 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

4.95 out of 5 average rating, 91 reviews

A game room is featured with a cozy sectional sofa and neon lighting. A virtual golf putting area is visible, with several balls positioned near a hole. A flat-screen TV displays a gaming interface, while a glass table with a gaming console adds to the entertainment setup.

Home in Davenport

Luxuria Homes - Pool | Game Room | Themed Rooms

A stylish seating area features a sleek lounge chair with wooden accents beside a small side table. A textured mural of flowing lines adorns the wall, complementing the modern aesthetic. A dining area is visible in the background, with a wooden table and chairs.

4.96 out of 5 average rating, 102 reviews

Modern 4bd house/heated pool,Close to Disney

A large community pool is set amidst lush greenery, featuring sun loungers around its perimeter. A cozy living area showcases a modern sofa and a television, creating a welcoming space. A scenic view of a lake is complemented by a fountain in the background. A private hot tub invites relaxation, shaded by a colorful umbrella.

4.89 out of 5 average rating, 117 reviews

10 Min to Disney • Cozy Townhome + Jacuzzi + BBQ

A private screened-in pool is surrounded by a clear enclosure, offering unobstructed views of a serene lake and lush greenery. Sunlight reflects off the water, enhancing the tranquil atmosphere. Comfortable lounge chairs are positioned nearby for relaxation.

4.96 out of 5 average rating, 48 reviews

Serene 4BR Pool Home Near Disney

Superhost

5 out of 5 average rating, 4 reviews

New! Epic Dream House with Pool

Home in Championsgate Village

The vibrant Mickey-themed bedroom features a spacious bed adorned with yellow and white bedding, accented by playful green pillows. Wall murals showcase iconic Mickey Mouse imagery, while a colorful area rug adds warmth to the hardwood floor. Two nightstands with lamps provide illumination.

5 out of 5 average rating, 26 reviews

Disney 6 bedroom Luxury Villa Arcade Pool Heat bbq

A spacious living area features a modern white sectional sofa arranged around a circular coffee table. A large flat-screen TV is mounted on the wall, and natural light enters through multiple windows. A textured accent wall adds depth, complementing the neutral color scheme.

4.95 out of 5 average rating, 124 reviews

5BD Windsor Westside Private Pool (WW 8920)

A screened lanai features a large swimming pool, surrounded by a paved deck and four patio loungers. The tranquil water view is visible through the mesh enclosure, with colorful skies reflecting at sunset.

5 out of 5 average rating, 29 reviews

Ohana Lakeside Retreat

Apartment rentals with a pool

An inviting living space features a modern gray sofa centered around a round coffee table, set on a plush area rug adorned with a playful pattern. A wall-mounted fan circulates air beneath a vibrant Mickey Mouse artwork, while a dining table for four is positioned nearby.

4.94 out of 5 average rating, 169 reviews

🏖 Resort Condo | 🎢 2mi -> Disney | 💦 Waterpark Fun

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.

4.94 out of 5 average rating, 101 reviews

Resort Style Sunshine Oasis near Theme Parks

A cozy sleeping area features a spacious bed dressed in crisp linens, accompanied by two bedside tables topped with lamps. A wall-mounted television offers access to various streaming services. Light-colored walls and a vibrant orange accent wall enhance the inviting atmosphere.

4.77 out of 5 average rating, 274 reviews

King Bed Small Studio Disney World Universal

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, 140 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.

4.83 out of 5 average rating, 144 reviews

Stunning view, near Disney.

4.97 out of 5 average rating, 131 reviews

Sol y Mar Resort Style Condo - NO RESORT FEES

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, 151 reviews

Luxurious Spot 10 Mins Away to Most Attractions!!!

The master bedroom features a spacious bed with a tufted headboard, complemented by a decorative mirror and framed artwork. Natural light streams in through a large window, revealing views of greenery. A warm color palette and wood accents create a relaxing atmosphere.

4.94 out of 5 average rating, 135 reviews

*NEW* Adventureland Stay / Sleeps 6 / Near Disney

Other holiday rentals with a pool

An inviting pool area glows in soft blue light against the evening sky. The expansive pool features a raised hot tub, surrounded by lounge chairs and palm trees. Lush greenery enhances the serene atmosphere, creating a perfect retreat for relaxation.

4.97 out of 5 average rating, 32 reviews

Blissful Pool Villa • Bears Den • 6mi to Disney

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.

4.95 out of 5 average rating, 79 reviews

Paradise Suite

4.95 out of 5 average rating, 96 reviews

A game room features various entertainment options, including a treadmill, exercise bike, and classic arcade machines. The decor showcases a 'Star Wars' theme with vibrant blue lighting and dark walls, creating an inviting atmosphere for guests to enjoy recreational activities.

Villa in Kissimmee

Luxury Villa! /Game Room/ Pool Heater

A modern living room is depicted with a full sofa, coffee table, and a smart TV. Natural light enters through the sliding glass door leading to the balcony. Three framed botanical prints decorate the wall, while a floor lamp adds soft illumination.

5 out of 5 average rating, 48 reviews

Modern Condo: 10 Min to Disney + Fireworks Views!

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, 51 reviews

Luxury Home w/ Pool & 6 Beds near Disney

A spacious living area is featured, with a light-colored sofa set against a large window that provides natural light. Two dark chairs and a stylish white coffee table are present. A simple rug covers the floor, and wall art is displayed above the couch.

4.97 out of 5 average rating, 33 reviews

Comfy Reunion Apto /Vista Golf • Piscina y Disney

Townhouse in Four Corners

A bright and open living space features comfortable seating arranged around a large flat-screen TV. A dining area with a round wooden table is surrounded by woven chairs, while the kitchen showcases modern cabinetry and stainless steel appliances, illuminated by pendant lighting.

5 out of 5 average rating, 78 reviews

New Modern Home near Disney in Orlando

The living area features a spacious gray sectional sofa arranged around a white coffee table, with decorative items adding style. A large window provides natural light, complemented by modern shelving and a lamp. The open kitchen is visible in the background, emphasizing a comfortable layout.