Home rentals with a pool near Old Town

A shaded lounging area features comfortable seating and a glass-top table, set with refreshments. In the background, a large pool glistens under the sun, surrounded by palm trees and various seating options, including cabanas and sun loungers.

4.84 out of 5 average rating, 214 reviews

Orlando Disney ºoº 3BD in Resort | Kissimmee

Modern Townhouse in Resort w/ preserve area and Amazing Clubhouse. (NO resort fees!) | 1 min | Old Town Kissimmee | 3 min | Publix®, McDonald's®, Wendy's®, Miller's Ale House® and more | 6 min | Walmart® & Target® | 7 min | Celebration | 9 min | DISNEY® AREA (All Theme Parks) | 9 min | Premium Outlet® | 11 min | Disney Springs | 11 min | ESPN® Sports | 13 min | Convention Center | 15 min | UNIVERSAL® STUDIOS | 26 min | Orlando Airport | 70 min | Bush Garden's® | 95 min | Sarasota & Clearwater

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.

4.98 out of 5 average rating, 208 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!

The living room features a modern design with a comfortable gray sofa adorned with orange accent pillows. A glass table is center stage, accompanied by two plush yellow armchairs. The space is brightened by natural light through large windows, complemented by decorative plants and artwork on the walls.

4.87 out of 5 average rating, 348 reviews

Roomy 2br w/ jacuzzi close to Disney

This townhouse provides a 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. Relax in your own private spa after a long day at the parks. Clubhouse with a gym, amazing heated pool, pool bar, a restaurant and only 5 min from Disney and golfing area. Parking, wifi ,resort’s amenities are free Close to lakes, camping, beach, vineyards, farms

Superhost

An open living space is presented, featuring a gray sofa and a patterned chair. A small television is placed on a stand. A kitchen area is visible, showcasing modern appliances. Light enters through large windows, illuminating the area and enhancing the plush area rug.

4.79 out of 5 average rating, 247 reviews

**LOCATION**Clean/sanitized 1BR apt next to Disney

Your perfect Disney getaway starts here. Safety is our #1 priority and the unit is cleaned & sanitized before your arrival. Newly renovated and 2 miles from Disney. The suite is equipped with all kitchen essentials, located within a condo complex with many amenities including free Wifi, heated pool and Jacuzzi, kids pool, hot tub, basketball court, gym, coin laundry, BBQ area, computers for printing. Free parking! Enjoy a walking trail to many local shops, restaurants and grocery stores.***

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, 234 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.

4.97 out of 5 average rating, 142 reviews

A living area features a light-colored sofa with accent pillows, complemented by a circular coffee table. A patterned rug in shades of red and beige adds warmth. Natural light enters through two windows with yellow curtains, and a front door is prominently displayed.

Cottage in Kissimmee

Cozy Orlando Area Cottage - 4 Miles to Disney

With Disney, popular attractions, restaurants, shops, and famous southern sunshine just minutes from your doorstep, we welcome guests to our cozy cottage for your vacation getaway. Our 1 bedroom, 1 bath cottage boasts modern amenities and entertainment options to help you relax during your stay. The cottage is located in a quiet, gated, resort community. Community amenities include an outdoor pool, hot tub, mini golf, game room, fitness center, planned activities, and tennis court.

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.

4.88 out of 5 average rating, 136 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.

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!

A spacious outdoor pool area is surrounded by lounge chairs and palm trees, with a large building in the background. A waterslide can be seen to the left, and the setting sun casts a warm glow over the entire scene.

4.96 out of 5 average rating, 247 reviews

Resort-style home close to Disney with jacuzzi

This beautifully decorated vacation home sits in the quiet and well located resort of Regal Oaks. The place offers all resort style amenities with the comfort of a home away from home to enjoy and relax. Enjoy your vacation at the outdoor private spa, have a nice homemade meal in the outdoor terrace, or let others take care of you in the resort restaurant in front of the pool, while kids enjoy the slides and resort activities. The Disney parks are 10 min away!

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.

4.85 out of 5 average rating, 258 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!

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.

4.95 out of 5 average rating, 226 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.

4.95 out of 5 average rating, 513 reviews

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

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

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A private heated pool is surrounded by a screened enclosure, featuring a brightly colored tiled edge. Sun loungers are positioned nearby, offering a relaxing space to unwind. A covered BBQ grill is accessible on the patio, creating an inviting setting for outdoor gatherings.

4.93 out of 5 average rating, 109 reviews

3BR / 2BR Heated Pool Home 7 Min to Disney |

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

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.

4.87 out of 5 average rating, 127 reviews

Resort TH 2b/2.5b With Private Hot Tub 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

4.92 out of 5 average rating, 131 reviews

Entire Modern Home near Disney • Pool & Game Room

Superhost

A screened-in pool area is illuminated by string lights, offering a serene view of the lake at sunrise. The inviting pool features floating noodles, and the surrounding space is bordered by greenery, enhancing the tranquil atmosphere.

4.85 out of 5 average rating, 216 reviews

Disney & Universal Retreat| Heated Pool | Fire Pit

A bright and spacious living area showcases a modern design, featuring a welcoming sign displaying 'VACATION MODE ON.' A wine bottle and glasses are positioned on the counter, while natural light floods in through large windows, highlighting the dining area and outdoor views.

4.9 out of 5 average rating, 154 reviews

LARNE LODGE House with Hot Tub 3 miles to Disney!

4.78 out of 5 average rating, 343 reviews

Free Waterpark! Fantasy World - Fun at BnB

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 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

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.

4.92 out of 5 average rating, 128 reviews

Pet friendly Orlando area near ESPN Center

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!

4.94 out of 5 average rating, 124 reviews

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.

Apartment in Orlando

Modern Lake view Condo 1 mile from Disney

A spacious living area features large windows allowing natural light and views of green trees outside. A sectional sofa in a neutral tone is complemented by decorative blue cushions. A glass coffee table rests on a textured area rug, and a television is positioned on a low media console.

4.9 out of 5 average rating, 130 reviews

Home away from home for the Parks!

4.88 out of 5 average rating, 177 reviews

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.

Apartment in Orlando

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

4.98 out of 5 average rating, 236 reviews

A balcony view captures a vibrant sunset over Lake Bryan, with hues of pink and orange reflected on the water. Outdoor seating includes two chairs and a small round table, inviting relaxation while enjoying the scenic surroundings.

Apartment in Orlando

Lakefront Resort Condo near Disney and Universal

Other holiday rentals with a pool

4.87 out of 5 average rating, 326 reviews

The exterior of the cottage is highlighted by a welcoming front porch featuring two teal chairs. A white railing surrounds the steps, leading to the entrance. Natural light pours in through large windows, illuminating the inviting facade.

Tiny home in Kissimmee

Great reviews! Tiny home in quiet & safe area

4.78 out of 5 average rating, 324 reviews

A modern living area features a light gray sofa with decorative yellow and gray pillows. A glass coffee table sits on a striped area rug. A dining table for four is positioned in the background against a yellow wall, complemented by ambient lighting from a floor lamp.

Flat in Kissimmee

Contemporary Villa next to Disney!

4.96 out of 5 average rating, 196 reviews

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

PentHouse Suite with 2X View

A clear blue swimming pool features gentle curves and shimmering water, surrounded by lounge chairs and palm trees. A waterslide is visible in the background, offering a fun attraction for guests. The inviting pool area is framed by a modern building with large windows.

4.84 out of 5 average rating, 318 reviews

Resort Living 4 Bed 3.5 Bath Townhome

Holiday home in Kissimmee

4.91 out of 5 average rating, 120 reviews

12 minutes from Disney+King bed+Free parking

A private hot tub is situated on an outdoor patio, enclosed by a screened area. Surrounding greenery and a tranquil water view are visible beyond the patio, providing a serene setting for relaxation.

4.96 out of 5 average rating, 52 reviews

Waterfront Resort 2BR next to Disney

A modern kitchen is showcased with light green cabinetry and stainless steel appliances. A large island with seating for four sits at the center. Soft lighting illuminates the space, while large glass doors offer views of the outdoor area.

4.96 out of 5 average rating, 150 reviews

Gerard’s Green View Lagoon Disney Getaway