Home rentals with a pool near Old Town

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.

4.97 out of 5 average rating, 290 reviews

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

Welcome to our personal vacation home, Old Town Oasis! 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 & tiki bar with food & drinks, arcade games in Clubhouse and more. If you're up for more fun, walk to Old Town next door! Our place is BABY and KID FRIENDLY!

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, 225 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!

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.

4.91 out of 5 average rating, 222 reviews

AMAZING vacation house .Mins to Disney Regal oasks

Beautiful luxury Resort style Vacation house! Big screened patio with private jacuzzi . Excellent Location! 3miles from Disney resort, just 10 minutes form Disney, universal, sea world , 0.1 mile walking distance to Old Town fun. numerous restaurants ,tourist attractions and easy access to major highways such as SR 417 and 14 .Uber /Lyft stop ,lynx bus to Disney . Guests also have full access to all resort amenities and activities ! *FREE- WiFi and 3 Cable TV for each rooms 52” living room

4.96 out of 5 average rating, 129 reviews

4mi Disney, 3BR w/Private Spa - Pool, Waterslides

✨ Close to Disney, Universal, SeaWorld ✨ Fully stocked kitchen, Free parking, Free WiFi ✨ Access to all resort’s amenities: Heated Pool, Dual Water Slides, Clubhouse, Restaurant, Bar, Gym, Arcades, & more ✨ No Resort Fee ✨ Private hot tub ✨ Steps to Old Town for dining, shopping, live music, & entertainment, and to Fun Spot America Family Rides for rollercoasters, arcades & more! ✨ Perfect for you to relax after a day of magic at Disney or explore Orlando’s best attractions ✨ Gated community

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.

4.9 out of 5 average rating, 126 reviews

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

Welcome to our new resort-style house with a private Jacuzzi and BBQ. Very quiet neighborhood with free parking, free WIFI, swimming pool, a gym, tennis courts, and other amenities. Very centric location with short distances to the best places: - Walt Disney World: Magic Kingdom, Animal Kingdom, Disney Springs, and Epcot are all approx. 10 min drive - Universal Studios: approx. 30 min drive - There is a mini market inside the resort, and all types of supermarkets within a 5-10min drive.

An aerial view of a uniquely shaped swimming pool is seen, surrounded by lush palm trees and blue umbrellas. The pool is designed with a gradual slope and steps, providing a relaxing environment for guests.

4.85 out of 5 average rating, 319 reviews

*Private jacuzzi!* Spacious home! Next to parks!

Soak in a hot tub under the stars at this comfortable home! This 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. Disney parks are 10 min away!

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, 143 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.

4.84 out of 5 average rating, 350 reviews

Comfy 3 bdrs w/private jacuzzi 5 min *Disney*

This spacious and recently upgraded decor townhouse is located in the beautiful Regal Oaks Resort. Regal Oaks is a private, gated Vacation Home Community and Resort. Located just a few minutes away from the traditional Old Town parks,shops and dinning and only 20 minutes away from Disney,this house will bring much fun to families, friends and groups looking for a weekend of fun or enjoy the great theme parks around. ** NO CARPETS **free parking, wifi and all resort’s amenities

4.98 out of 5 average rating, 105 reviews

Clean, stylish retreat • Resort pool • Near Disney

Welcome to Villa Marquesa (private mgmt), a revamped 4-bed, 3.5-bath townhome made for families. After a fun-filled day at the parks, come home to a clean, comfy space where everyone can relax—watch a movie, cook a meal, or unwind by the resort-style pool (no resort fee). Sleeps 6 adults & 4 kids, with lake views from the screened lanai. Just 3 miles to Disney, 20 mins to Universal, steps from Old Town. Includes WiFi, Disney+, Netflix. Your family retreat starts here!!

Serviced apartment in Kissimmee

4.81 out of 5 average rating, 495 reviews

Spacious 2BR Apt in Resort 10 min from Disney

Featuring comfortable, family-friendly amenities, this property provides relaxation in a peaceful, wooded setting while being close to all the major area theme parks. Enjoy the outdoor swimming pool or stay active at the fitness center and tennis courts. Families will appreciate the playground and children's pool. Additional conveniences such as a bar, free Wi-Fi, and free parking ensure this property is your home away from home near Orlando's famous theme parks.

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, 266 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, 232 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.

Popular amenities for rentals with a pool near Old Town

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

Aerial view captures the vibrant resort with multiple pools and water features, surrounded by lush greenery. The lower right features a cozy bedroom with Disney-themed decor and colorful beds. A private patio area is shown with a dining set and outdoor kitchen, along with water slides in a nearby pool.

4.92 out of 5 average rating, 124 reviews

#2666 Resort Home by Disney |Themed |Jacuzzi |Pool

A modern dining area features a wooden table set for six, surrounded by stylish orange chairs. Light fixtures hang above, illuminating the space. The kitchen is visible in the background, showcasing ample cabinetry and stainless steel appliances in a well-coordinated layout.

4.77 out of 5 average rating, 105 reviews

Fancy Family Home 10min-Disney Private Pool |108

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, 210 reviews

Waterfront Wizarding Near Universal's Harry Potter

4.71 out of 5 average rating, 31 reviews

Entire house 15min to Disney with Hot Tub

5 out of 5 average rating, 15 reviews

Spacious Fun, Near Disney, Coffee, Wi-Fi, Pool

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, 132 reviews

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

The resort features a sprawling pool area surrounded by lush palm trees and landscaped gardens. Clear blue waters meander through the space, creating a serene atmosphere. Sun loungers are spaced around the pool, inviting relaxation under the expansive sky.

4.91 out of 5 average rating, 172 reviews

5 Bdrm (sleeps 13), free water park,closeto Disney

4.91 out of 5 average rating, 208 reviews

Free Early Check ins / Late Check outs*

Apartment rentals with a pool

4.97 out of 5 average rating, 253 reviews

Perfect for Two Families • Sleeps 8 • Top Location

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.

4.89 out of 5 average rating, 192 reviews

NEW APARTMENT WITH WATER PARK AND NEAR DISNEY

4.97 out of 5 average rating, 153 reviews

An aerial view of the resort reveals a beautifully landscaped area with palm trees and pathways. The inviting outdoor pool is surrounded by lounge chairs, while nearby, a serene waterway meanders through the lush green landscape. The villas are nestled harmoniously among the greenery.

Apartment in Orlando

Marriott Sabal Palms 2BD Villa

A view from the balcony showcases a large, inviting pool surrounded by palm trees and lounge chairs. The pool area is highlighted by decorative landscaping and is set against a backdrop of a multi-story building, reflecting the vibrant atmosphere of the resort.

4.95 out of 5 average rating, 184 reviews

A1 POOL VIEW-By Disney/Universal/Balcony view

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.

4.78 out of 5 average rating, 305 reviews

King Bed Small Studio Disney World Universal

4.97 out of 5 average rating, 437 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

4.95 out of 5 average rating, 132 reviews

Apartment in Orlando

Modern Lake view Condo 1 mile from Disney

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.

4.78 out of 5 average rating, 257 reviews

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

Other holiday rentals with a pool

A bright bedroom contains two spacious beds dressed in light blue bedding. Floral accent pillows add color, while a large mural of a castle and lush greenery serves as a captivating backdrop. Natural light filters through pink curtains, enhancing the cheerful ambiance.

4.9 out of 5 average rating, 126 reviews

Pets Welcome, Close to Parks, Stocked Kitchen

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.

4.83 out of 5 average rating, 155 reviews

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

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.

4.83 out of 5 average rating, 323 reviews

Resort Living 4 Bed 3.5 Bath Townhome

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.

5 out of 5 average rating, 270 reviews

BOOK your Disney inspired Lakefront retreat NOW!

The spacious living area features a comfortable gray couch adorned with vibrant cushions, complemented by two small tables. A large window provides natural light and a view of the outdoor area with a barbecue and pool, while a wall-mounted TV offers entertainment options.

4.89 out of 5 average rating, 280 reviews

Luxurious Dream 4/3 Bedroom Home w/private Pool

An aerial view of the resort showcases multiple swimming pools surrounded by palm trees, with lounge chairs arranged around the poolside. The property features a water slide and is situated next to a serene lake, providing a picturesque setting for relaxation.

4.82 out of 5 average rating, 179 reviews

Vacation Home at Regal Oaks, 5 Minutes to Old Town

A spacious Master Bedroom features a large bed dressed in white linens, complemented by neutral furnishings. A flat-screen TV is mounted on the wall opposite the bed, while soft natural light filters through the window adorned with light curtains.

4.92 out of 5 average rating, 347 reviews

Stylish Villa Near Disney | Pool & Resort

A comfortable living room features a sofa with plush cushions, alongside a pair of accent chairs. A wooden coffee table rests on a patterned area rug, while two large framed artworks are displayed on the wall. Natural light enters through glass doors, complemented by soft drapes.