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
A contemporary living room features a comfortable sofa and armchairs, accented by colorful cushions. A wooden coffee table sits atop a patterned area rug, complemented by greenery from a nearby plant. Large windows allow for natural light, enhancing the airy ambiance.
Townhouse in Kissimmee
4.94 out of 5 average rating, 253 reviews

Relax into Resort-Style Living at a Bohemian Retreat

While away balmy evenings on the oversized screened patio and rest tired legs in the hot tub after a long day at the parks. This airy, spacious abode combines patterned rugs and cushions with leafy house plants and botanical prints for a calm vibe. We hope you trust us with your vacation. Your vacation is a priority to us! ABOUT THE SPACE: The first floor consists in living room with sofa bed, 1/2 bathroom, full kitchen, and an oversized patio with HOT TUB. The second floor has three bedrooms. One master with a king bed an a private bathroom and two other rooms, one with a queen bed and the other with two twin beds. In this home, every desire has been anticipated so this resort lifestyle will provide perfect memories and experiences that will last a lifetime. ABOUT WHY US: Self check in, fast WIFI, cable, gym, free parking, washer and dryer inside the home, reliable and fast communication with host, BEAUTIFUL home décor, pack and play with soft mattress, high chair, and sofa bed for extra people. Did I mentioned the HOT TUB? and many other included necessities. You will be have access to the whole house and all the amenities in the resort. This is a self check in/check out home. ABOUT THE COMMUNICATION: We are fast responders and we should answer the very same day you may have an inquire. If you have any question, feel free to ask! The Regal Oaks Resort combines an oversized pool, water slides, a convenience store, a gym, and a bar and grill restaurant. Disney is 10 minutes away and Old Town is next door. Columbia Restaurant, Bucca Di Beppo, Pei Wei, and Red Lobster are nearby. We have AVIS and Budget rental car within walking distance from the house as well as PUBLIX, 7-ELEVEN, WALLGREENS, TMOBILE, and many other stares. Hypoallergenic dogs will be considered on a case to case basis. Not to exceed 20 pounds. Only very well groomed pets. (You will be charged large deposit if we encounter flea).

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

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, 202 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

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, 133 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 modern living area is anchored by a comfortable gray sofa facing a television stand with an illuminated blue outline. Two blue accent chairs provide additional seating. Natural light filters through sheer curtains, illuminating the hardwood floor and decorative rug beneath a coffee table.
Townhouse in Kissimmee
4.93 out of 5 average rating, 204 reviews

Amazing, luxe 3BD/2BA home mins to Parks! 5 Stars!

Welcome to our luxurious resort-style townhome in the heart of the Disney World area! Our prime location puts you just minutes away from all the parks, restaurants, and shopping you could want. With TVs in every room and resort amenities like a fitness center, playroom, and volleyball court, there's something for everyone. And when you're ready to unwind, you can soak up the sunshine and natural beauty that surrounds our resort. Book now and experience the ultimate Orlando vacation!

Guest favourite
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.
Townhouse in Kissimmee
4.93 out of 5 average rating, 306 reviews

Comfy 2 Bedroom Townhouse w/ hot tub - Disney Area

Our Modern and Contemporary townhouse is located at Regal Oaks Resort, an exclusive gated resort style condo very close to the main attractions. Fully equipped, comfortable living room with a sofa bed, an amazing dining area, and a private oversized screened patio with hot tub. This beautiful townhouse provides 2 bedrooms, 2 en-suite bathrooms, and a half-bathroom. Also, an incredible open concept kitchen with wood cabinets, granite counter, and a stainless appliances.

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, 266 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!

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, 215 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
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, 308 reviews

Disney/Universal Home Away from Home!

At the Regal Oaks Resort you will find a fantastic pool, water slides, games room, gym, sauna, onsite dining at the clubhouse and much more! We DO NOT have any additional resort fees, the price you pay is final, it includes everything and all free amenities at our resort! Nature's little get away. Our home is located in a very private section of the resort backing onto a large conservation area. Nothing but green life and palm trees!

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, 249 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, 496 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.

Guest favourite
A comfortable living area features a soft blue sofa adorned with patterned pillows. Natural light enters through window treatments, brightening the space. Nearby, a dining area accommodates four with a wooden table, while a well-equipped kitchen is visible in the background.
Tiny homes in Kissimmee
4.84 out of 5 average rating, 266 reviews

Jubilee Cottage 12 miles from Epic Universe

Quaint cottage with high-end appliances, perfect for business travelers or small families. Fully equipped kitchen. Lovely porch. Comfortable loving room with 2 recliners. A/C and 5 fans keep the unit cool! Full use of facilities: pools, gym, reception area, game room, miniature golf. 5 minutes from Disney, walking distance to Old Town. Why stay in a hotel when you can stay in Jubilee Cottage??

Popular amenities for rentals with a pool near Old Town Kissimmee

Quick stats about rentals with a pool near Old Town Kissimmee

  • Total rentals

    630 properties

  • Nightly prices starting at

    $56 CAD 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

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