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Home rentals with a pool near Old Town Kissimmee

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Top-rated rentals with a pool near Old Town Kissimmee

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Top Guest favourite
The master bedroom features a king-size bed adorned with plush pillows and a cozy blanket. Large sliding doors open to a private balcony with serene views. Stylish lamps illuminate the room, complemented by rich maroon and neutral tones on the walls.
Townhouse in Kissimmee
5 out of 5 average rating, 254 reviews

BOOK your Disney inspired Lakefront retreat NOW!

Begin and end your dream vacation in a place where modern comfort meets magical wonder! This one-of-a-kind retreat is sure to please the family looking for adventure in Orlando as well as couples in search of a relaxing, romantic getaway. Great location just minutes from Disney, Universal, SeaWorld, numerous restaurants, tourist attractions and easy access to major highways such as SR417 and I4. *FREE WIFI, Netflix & Disney+ included! *STROLLER, BABY GATE, HIGH CHAIR, PACKNPLAY, TODDLER BED

Top Guest favourite
An outdoor patio area is enclosed with a protective screen, featuring a dining table with an umbrella. Comfortable seating is arranged nearby. A hot tub is positioned to the side, surrounded by lush greenery and a wall for privacy.
Townhouse in Kissimmee
4.98 out of 5 average rating, 187 reviews

Townhouse - 5 miles to Disney!

Dip in the heated community pool, enjoy the many amenities at this amazing resort, unwind in this vacation rental’s private hot tub with Bluetooth and night lights when you book in this exciting stay in Kissimmee! Going out? Gather family and friends & experience the magic of Disney World, Harry Potter rides at Universal Studios, Sea World, etc. At less than a mile to Old Town where you can go on rides, shop, and dine! Return to the 3-bd, 2.5-bths townhome and lounge in the sunny lanai & ENJOY!

Guest favourite
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.
Townhouse in Kissimmee
4.88 out of 5 average rating, 209 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

Top Guest favourite
A collage showcasing the townhome's features. The Mickey-themed guest room displays a bright mural, while the master suite is elegantly arranged. The kitchen is equipped with stainless steel appliances, and the living area offers a serene pond view through large sliding glass doors. A resort-style pool area is depicted from above.
Townhouse in Kissimmee
4.98 out of 5 average rating, 134 reviews

Regal Oaks Resort Lake View 2BR near Disney Parks

Our gorgeous 2 bed 2.5 bath DELUXE townhome is located in the pristine Regal Oaks Resort located just behind Old Town theme park and minutes from Disney, shopping, restaurants & more. Inside our home you will find a living/dining room combo and a kitchen boasting stainless steel appliances and granite countertops. Upstairs an in suite beautiful Mickey decor guest room and one master suite with private balcony overlooking a beautiful pound view and huge conservation area (all rooms no carpet).

Top Guest favourite
A luxurious cabana overlooks a sparkling pool, surrounded by palm trees and lounge chairs. A tray with drinks and snacks rests on a soft seating area, while the vibrant clubhouse is visible in the background, creating an inviting atmosphere for relaxation.
Townhouse in Kissimmee
4.89 out of 5 average rating, 142 reviews

Orlando Disney Premium Home in Resort & Lake View!

Renewed house in Resort with fantastic lake view and an Amazing Clubhouse. (NO resort fees) | 1 min | Old Town Kissimmee | 3 min | Publix® | 3 min | McDonald's®, Wendy's®, Miller's Ale House® and much more | 6 min | Walmart® & Target® | 7 min | Celebration | 9 min | Premium Outlet® I-4 | 9 min | DISNEY® AREA (All Parks) | 10 min | ESPN Sports | 10 min | Convention Center | 14 min | UNIVERSAL® STUDIOS | 26 min | Orlando Airport | 60 min | Bush Garden's® | 95 min | Sarasota & Clearwater

Guest favourite
A resort pool area is surrounded by palm trees and sunshine, featuring lounge chairs under white umbrellas. A paved deck encircles the pool, creating a relaxing atmosphere for guests. A blue slide can be seen in the background, enhancing the recreational space.
Townhouse in Kissimmee
4.87 out of 5 average rating, 125 reviews

Entire townhouse, Resort style, 5 miles to Disney!

Feel right at home in our outstanding location JUST 5 MILES FROM DISNEY! Exceptional 2 bed/2.5 bath townhome features premium one King bed, 2 twin beds and a queen size sofa bed with fully equipped kitchen, washing machine, smart TVs, a private patio, Jacuzzi and lake view. Contemporary furnishings, luxury feel. Located in gated resort with clubhouse, beautiful pool, water slide, gym, tennis court and more. Within 10 minutes drive to a variety of restaurants, shops, Fun Spot and more.

Superhost
The dining area features a large wooden table set for dinner, with stylish chairs surrounding it. A cozy seating space is visible in the background, accompanied by a large window allowing natural light to enhance the warm tones of the decor.
Townhouse in Kissimmee
4.89 out of 5 average rating, 267 reviews

RUSTY'S DEN House with Hot Tub 3 miles from Disney

This spacious and recently updated townhouse is located in a beautiful private and gated resort, which offers guests their own private hot tub, a shared pool with pool bar, gym, and a convenience store. No resort or parking fees! Guests have a private hot tub and enjoy neutral colors in the interior design that lend a gentle aesthetic, while modern industrial accents add a charm and character. Located just 3 miles from Disney & 11 miles to Universal Studios!

Guest favourite
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
4.85 out of 5 average rating, 131 reviews

♥︎ Disney-3 miles ♥︎ Private HotTub ♥︎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!

Top Guest favourite
A private patio features a bubbling hot tub alongside a dining area with a table and chairs, shaded by a vibrant orange umbrella. The space is enclosed by screens, offering a bright atmosphere with clear blue skies in the background.
Townhouse in Kissimmee
4.85 out of 5 average rating, 247 reviews

Resort Style 12 min Disney, Jacuzzi, Sleeps 8

Escape the crowds and enjoy your private oasis in our family-friendly townhouse, just 12 min from Disney! Located in the gated Regal Oaks Resort, you’ll enjoy resort perks—heated pool, gym, tennis & kids-eat-free restaurant—plus the comfort of home. Professional cleaning, fresh linens, free highchair & Pack ’n Play, sofa bed sheets on request, stroller rentals, starter kit & discounted park tickets. Comfort, savings & fun for up to 8 guests!

Top Guest favourite
A private screened hot tub is featured in the foreground, surrounded by an inviting outdoor seating area with a table and chairs. Lush tropical plants enhance the atmosphere, while a large mirror reflects the vibrant orange wall and soft natural light from the spacious windows.
Townhouse in Kissimmee
4.94 out of 5 average rating, 216 reviews

2 BR Harmony House at Regal Oaks Resort

Come get away to our modern, super-clean, self-contained garden oasis town house in the Regal Oaks Resort - close to grocery stores and take out food - minutes walk from Old Town Kissimmee and a short drive from Disney's ESPN - World of Sports and Town Center Celebration. We are 15 minutes drive from Epic - Universal and Disney parks. Our private screened in hot tub is the perfect place to relax in the Florida sun or under our sun shade.

Top Guest favourite
An aerial view of the resort reveals a scenic layout surrounding a sparkling blue pool and vibrant water slides. Palm trees line the poolside area, where lounge chairs are arranged around the water's edge. The lush greenery and nearby lake add a natural touch to the inviting ambiance.
Townhouse in Kissimmee
4.96 out of 5 average rating, 251 reviews

*LAKEVIEW* Resort 4m Disney! Private Spa Wi-Fi

Beautiful LAKEVIEW property in Regal Oaks Resort! Coffee, Nespresso, tea, free Wi-Fi! It's close to the theme parks and everything that Orlando has to offer! Come relax in your own private spa after a long day at the parks, or enjoy the resort water slides, heated pool, pool side games and food and beverage stand. If you're up for more fun, walk to Old Town next door! Our place is BABY and KID FRIENDLY! Welcome to our Old Town Oasis!

Top Guest favourite
A yellow cottage is featured, with a welcoming entrance that includes a set of wooden steps leading to a covered porch. White railings frame the porch, while a ceiling fan hangs above. Lush greenery and flowering plants are positioned near the entrance, enhancing the overall charm.
Cottage in Kissimmee
4.95 out of 5 average rating, 498 reviews

Bright & Cozy Cottage Near Disney

My place located within 10 miles of: Disney World, Celebration, Universal, Water Parks, Old Town & Fun Spot USA's More than 70 Restaurants and Dining, Gifts Shop. My place is good for couples, solo adventurers, business travelers, and families (with kids). You’ll love my place because of In Our Cozy and Comfortable Sand Castle Cottage You'll discover that perfect Mix of High-Energy Fun and Laid Back Florida Lifestyle Right Here.

Popular amenities for rentals with a pool near Old Town Kissimmee

Kitchen
Wi-Fi
Pool
Free parking on premises
Air conditioning

House rentals with a pool

Guest favourite
The image displays a variety of spaces within the resort-style house. A comfortable living area is observed with two gray sofas and decor accents, while a cozy sleeping area features a large bed and artwork. A private hot tub and a sparkling pool surrounded by palm trees add to the appeal.
Home in Kissimmee
4.9 out of 5 average rating, 112 reviews

Resort Style 3Br/2.5Ba w/ Private Jacuzzi, and BBQ

Top Guest favourite
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.
Home in Kissimmee
4.98 out of 5 average rating, 171 reviews

Waterfront Wizarding Near Universal's Harry Potter

Guest favourite
The outdoor pool area features a heated pool and a jetted spa, surrounded by a screened-in patio. Two chaise lounge chairs are positioned nearby for relaxation, while a dining table offers additional seating. Natural light filters through the overhead structure, enhancing the inviting space.
Home in Kissimmee
4.94 out of 5 average rating, 122 reviews

Blue Door Escape - Private Pool - Close to Disney

Guest favourite
A resort area is depicted with a large swimming pool surrounded by palm trees. The two-story building features numerous windows and outdoor seating, creating an inviting space. Soft evening light reflects on the water's surface, enhancing the tranquil atmosphere.
Home in Kissimmee
4.87 out of 5 average rating, 119 reviews

Resort TH 2b/2.5b With Private Hot Tub near Disney

Top Guest favourite
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.
Home in Kissimmee
4.93 out of 5 average rating, 148 reviews

Disney New Neighbor

Top Guest favourite
A living area features a modern television displaying a virtual fireplace, paired with elegant wall art and a decorative plant. Below, a pool area is illuminated with soft purple lighting against a backdrop of warm string lights, creating a relaxed atmosphere.
Home in Kissimmee
4.97 out of 5 average rating, 113 reviews

Perfect Getaway. Private Pool.Kissimmee/Orlando

Guest favourite
Two lounge chairs are positioned beside a heated pool, overlooking a serene lake. A pink flamingo pool float rests nearby. The outdoor area includes a large umbrella for shade, creating a peaceful space for relaxation.
Home in Kissimmee
4.89 out of 5 average rating, 100 reviews

Dreamy Waterside Villa | Heated Pool & Near Disney

Top Guest favourite
The image features a collage of vibrant themed bedrooms and a modern kitchen area. One room showcases a playful bunk bed against a backdrop reminiscent of a train station, while another has colorful Disney-themed décor. A spacious living area boasts light-colored furniture and a contemporary kitchen with stainless steel appliances.
Home in Kissimmee
4.97 out of 5 average rating, 106 reviews

3BD/3BA Themed House Near Disney

Condo rentals with a pool

Top Guest favourite
A modern kitchen area is visible, featuring white cabinetry and stainless steel appliances. Four metal stools are arranged around a dark countertop, illuminated by woven pendant lights. A small indoor plant adds a touch of greenery to the wooden coffee table in the foreground.
Condo in Kissimmee
4.97 out of 5 average rating, 224 reviews

Prime Location for Parks & Family Fun

Top Guest favourite
Condo in Kissimmee
4.95 out of 5 average rating, 185 reviews

3161-305 Resort Lake View Disney Universal Orlando

Guest favourite
The image captures a vibrant pool area surrounded by lush palm trees and comfortable lounge chairs. An inviting infinity pool is centrally located, accompanied by cabanas and umbrellas. Multiple water slides are visible in one corner, enhancing the family-friendly atmosphere of the space.
Condo in Kissimmee
4.92 out of 5 average rating, 118 reviews

Pet friendly Orlando area near ESPN Center

Top Guest favourite
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.
Condo in Kissimmee
4.97 out of 5 average rating, 155 reviews

202_Magical and Cozy 2BR minutes from Disney

Guest favourite
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.
Condo in Kissimmee
4.77 out of 5 average rating, 269 reviews

King Bed Small Studio Disney World Universal

Top Guest favourite
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.
Condo in Orlando
4.97 out of 5 average rating, 399 reviews

Waterfront Resort Condo near Disney &Universal

Guest favourite
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.
Condo in Orlando
4.95 out of 5 average rating, 109 reviews

Modern Lake view Condo 1 mile from Disney

Top Guest favourite
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.
Condo in Kissimmee
4.96 out of 5 average rating, 150 reviews

Luxurious Spot 10 Mins Away to Most Attractions!!!

Home rentals with a private pool

An open living space features a comfortable beige sectional sofa with colorful accent pillows. A dining table is visible beside a modern kitchen with stainless steel appliances. Large sliding glass doors provide a view of the pool area, enhancing the connection to the outdoors.
Home in Davenport

Wr001or (1stfororlando)

A spacious living area is highlighted by a large wall-mounted TV above a modern electric fireplace. The white sectional sofa, accented with colorful pillows, faces a sleek coffee table on a patterned rug. Natural light floods in through large windows draped with light curtains.
Villa in Four Corners
4.14 out of 5 average rating, 7 reviews

Disney's Championsgate: Private Pool & Arcade Fun!

The exterior of the home features a two-story structure with a light beige facade and a tiled roof. Lush landscaping, including palm trees and shrubs, enhances the entrance, while a spacious driveway leads to a two-car garage.
Home in Davenport

Beautiful 9 Br Pool Home In the Solterra Resort!

Guest favourite
Home in Davenport
4.95 out of 5 average rating, 116 reviews

Airy, Stylish Home with Pool Heat Included in Davenport

Villa in Kissimmee
4.78 out of 5 average rating, 255 reviews

Visit Disney World from a Sunny Home with a Pool

The image displays four distinct areas of the villa. A games room features a foosball table and a billiard table with a laundry area in the background. A cozy bedroom showcases a queen bed with nightstands. A private screened pool invites relaxation. A kitchen area includes modern appliances and seating at the bar.
Home in Davenport

The Manors at Westridge Home W/ Private Pool

A themed bedroom features two twin beds adorned with space-themed bedding. Soft lighting casts a blue glow across the room, creating a cozy environment. Creative pillows shaped like space characters are placed on each bed, enhancing the playful atmosphere.
Villa in Davenport

801dsd-The Retreat at Championsgate

The villa's exterior showcases a well-maintained façade with a large front porch. Lush green lawns and neatly trimmed shrubs line the walkway. A two-car garage is situated on the left, while palm trees flank the entrance, enhancing the inviting appearance of the home.
Villa in Davenport

732bd 4 Bedroom Villa

Other holiday rentals with a pool

Guest favourite
A charming blue cottage is depicted, showcasing a combination of large windows and decorative greenery. The entrance is framed by a small garden, with a stone border and a variety of plants, creating an inviting outdoor space. A covered porch area is also visible.
Cottage in Kissimmee
4.91 out of 5 average rating, 216 reviews

Cozy Private Cottage 5 miles from Disney!

Top Guest favourite
The expansive lake is showcased during sunset, reflecting vibrant colors in the sky. Surrounding greenery adds a natural touch, while a dock extends into the water, offering a serene view of the landscape. Soft light illuminates the pathway along the lake's edge.
Hotel room in Orlando
4.96 out of 5 average rating, 190 reviews

PentHouse Suite with 2X View

Guest favourite
A charming pink tiny house is positioned at the end of a tree-lined street. The house features a front porch with white railings and steps leading to a bright entry. Lush greenery and colorful shrubs enhance the front yard, creating a welcoming outdoor space.
Cottage in Kissimmee
4.84 out of 5 average rating, 131 reviews

Near Disney and all Parks- Tiny Cottage

Guest favourite
A private screened patio features a jacuzzi with colorful lights, creating a calm ambiance. Two outdoor chairs are positioned nearby, providing a comfortable spot to relax. Soft lighting illuminates the area against a backdrop of lush greenery and a clear evening sky.
Townhouse in Kissimmee
4.9 out of 5 average rating, 204 reviews

AMAZING vacation house .Mins to Disney Regal oasks

Top Guest favourite
A vibrant dining area is shown, featuring a large table set for six. Below, a private hot tub is visible on a patio, surrounded by lush greenery. A spacious bedroom with elegant decor is highlighted, showcasing a comfy bed and large windows letting in natural light.
Townhouse in Kissimmee
4.98 out of 5 average rating, 61 reviews

Disney Getaway, Hot Tub, 10 min to Parks, 6 people

Top Guest favourite
The image showcases the vibrant swimming pool area of the resort, featuring a water slide and surrounded by palm trees. The kitchen area displays modern appliances, including a stove and granite countertops. A dining table is set for six, and a comfortable living space is visible with seating for relaxation.
Townhouse in Kissimmee
4.94 out of 5 average rating, 309 reviews

Disney/Universal Home Away from Home!

Guest favourite
A screened patio features a hot tub surrounded by lounge chairs and a dining area. An umbrella provides shade over the table, and potted yellow flowers add a touch of color. The backdrop includes the exterior of the house and a glimpse of the landscape.
Townhouse in Kissimmee
5 out of 5 average rating, 10 reviews

Waterfront Views/Private hot tub/3 miles to Disney

Top Guest favourite
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.
Townhouse in Kissimmee
4.95 out of 5 average rating, 219 reviews

Relaxing Resort Stay Hot Tub Lake View Near Disney

Quick stats about rentals with a pool near Old Town Kissimmee

  • Total rentals

    630 properties

  • Nightly prices starting at

    $61 AUD before taxes and fees

  • Total number of reviews

    37K reviews

  • Family-friendly rentals

    350 properties are a good fit for families

  • Pet-friendly rentals

    320 properties allow pets

  • Rentals with dedicated workspaces

    320 properties have a dedicated workspace

Destinations to explore