Home rentals with a pool near Old Town

A bright living area features a light blue color scheme with ample natural light from large sliding doors. A comfortable light gray sofa is complemented by patterned cushions. The open floor plan shows a kitchen and dining area in the background, with colorful chairs adding a vibrant touch.

4.88 out of 5 average rating, 124 reviews

Luxury Remodeled Townhome minutes from Disney!

Our listing is set up under Airbnb's Simplified Pricing. The price you see is the price you pay, with no unexpected guest service fees added at checkout. NEW CARPET in this recently remodeled luxury townhouse located in gated community of Regal Oaks. Enjoy all the amenities of home plus the resort pool, pool bar, water slides, games for children by the pool, gym, & pickle ball ct. Located directly behind Old Town! Enjoy the screened in lanai equipped with private hot tub, gas grill & more!

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, 247 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 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.

4.98 out of 5 average rating, 141 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).

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, 129 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.

Aerial view of the resort displaying a large, inviting swimming pool surrounded by palm trees and lounge chairs. Water slides are visible next to the pool area. The clubhouse is nearby, with additional greenery and a water feature enhancing the landscape.

4.97 out of 5 average rating, 284 reviews

4M Disney! Private spa, Wi-Fi, Coffee/Tea

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

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, 333 reviews

*Private spa!* 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, 146 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.

4.98 out of 5 average rating, 111 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!!

4.76 out of 5 average rating, 103 reviews

Family-Friendly Home Near Disney with Hot Tub

Welcome to your perfect family getaway near Disney! Our modern, family-friendly home is located in the beautiful Regal Oaks Resort, just minutes from Disney, Universal Studios, and SeaWorld. Enjoy the convenience of nearby restaurants, shopping, and top Orlando attractions, along with easy access to major highways. Whether you’re here for theme parks or relaxation, our home offers comfort, space, and a prime location—only 25 minutes from Orlando International Airport.

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, 272 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 jacuzzi is highlighted, nestled on a spacious patio with a serene view of greenery. The jacuzzi is surrounded by a screened enclosure, ensuring a tranquil outdoor experience. A dining set can be seen nearby, providing a comfortable space for relaxation.

4.81 out of 5 average rating, 358 reviews

Home-like 4 bd w/ jacuzzi 5 min from 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.

This townhouse features a charming exterior with a terracotta tiled roof. The warm orange facade is complemented by white shutters and lush greenery. Nearby, a designated parking area is visible, providing convenient access to the entrance.

4.91 out of 5 average rating, 360 reviews

Stylish Villa Near Disney | Pool & Resort

Welcome to Casa del Sol! Experience the perfect blend of modern comfort and convenience in our 2-bedroom vacation home, just minutes from Disney World and top theme parks. Designed for families and groups, this home features contemporary décor, a fully equipped kitchen, and a private screened patio for ultimate relaxation. Take a refreshing dip in the resort pool or unwind with a cocktail at the Tiki Bar

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.

4.9 out of 5 average rating, 135 reviews

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

The outdoor pool area is surrounded by lush palm trees and lounge chairs, providing a spacious environment for relaxation. Warm lighting illuminates the pool, complemented by a fountain visible in the distance and a backdrop of well-maintained landscaping.

4.73 out of 5 average rating, 105 reviews

Home, Hot Tub, Slide and Pool

An open-concept living area is highlighted by large windows, allowing natural light to illuminate the space. The kitchen features a granite countertop with a dual sink, while a dining area with wooden chairs is visible nearby. A comfortable seating area is situated in the corner.

4.88 out of 5 average rating, 117 reviews

Orlando Oasis<5 Miles from Parks

A large, inviting pool area is surrounded by palm trees and lounge chairs, offering a relaxed atmosphere. A two-story building with a terracotta roof is visible in the background, featuring several windows that reflect the bright blue sky.

4.96 out of 5 average rating, 104 reviews

Resort themed home near Disney with spa

4.9 out of 5 average rating, 216 reviews

*Free Early Check ins / Late Check outs*

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.

4.88 out of 5 average rating, 137 reviews

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

The image displays the Summerville Resort sign, highlighting its proximity to Disney. A comfortable bedroom is shown, featuring two spacious beds and colorful wall art. An inviting patio area with outdoor seating is visible, alongside a community pool surrounded by lounge chairs and palm trees.

4.86 out of 5 average rating, 122 reviews

Comfy Family Villa|5min->Disney!

4.9 out of 5 average rating, 209 reviews

Cozy family home w/ heated pool 15 min. to Disney

Condo rentals with a pool

A spacious pool area is surrounded by palm trees and lounge chairs. A large building with multiple windows and outdoor seating overlooks the pool, which is illuminated under a vibrant sunset sky. Nearby, a water slide can be seen, adding to the resort atmosphere.

4.76 out of 5 average rating, 128 reviews

Beautiful 4BR/4B (2King Ensuite), Pool/Slides/WiFi

The living area features a dark sofa with colorful striped cushions, a modern black television mounted on the wall, and a spacious dining table surrounded by four chairs. A patterned area rug complements the neutral tiled flooring, leading to an open kitchen area visible in the background.

4.98 out of 5 average rating, 101 reviews

Angela's Place @ Lucaya Village

4.85 out of 5 average rating, 116 reviews

A dining area features a round table set with white plates and glasses, complemented by woven placemats. A cozy seating area with a brown leather couch and decorative pillows is visible, alongside a large window offering natural light and views of the outdoor space.

Condo in Celebration

Private balcony, Disney under 10 mins, Roku+Cable

4.92 out of 5 average rating, 203 reviews

Condo in Orlando

Recently Updated: 3b2b, Lake, Pool, Shuttle, Gym!

4.93 out of 5 average rating, 144 reviews

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 Celebration

Pet friendly Orlando area near ESPN Center

The spacious living and dining area features contemporary furnishings with a large grey sofa accented by colorful cushions. A dining table for six is set nearby, with sunlight pouring through multiple windows, illuminating the open layout that extends to a private balcony.

4.8 out of 5 average rating, 273 reviews

Stunning Sunny Central Condo w/ Pool & Balcony

A modern living area is presented with a dining table and four chairs positioned beside a kitchenette. A green sofa adds a pop of color, while large windows provide ample natural light. The space opens to a bedroom area, creating an inviting atmosphere.

4.87 out of 5 average rating, 447 reviews

Family Apartment Near to Disney Orlando Universal

The image showcases a colorful resort with pastel-colored buildings reflecting on a calm lake. Lush greenery surrounds the area, enhancing the tranquil setting. A clear blue sky is visible, with a playful Mickey Mouse graphic indicating proximity to Disney World.

4.98 out of 5 average rating, 323 reviews

Amazing ❤️ Water View Condo near Disney & Universal

Other holiday rentals with a pool

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.

4.95 out of 5 average rating, 342 reviews

Disney/Universal Home Away from Home!

4.84 out of 5 average rating, 147 reviews

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

Near Disney and all Parks- Tiny Cottage

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, 229 reviews

AMAZING vacation house .Mins to Disney Regal oasks

The dining area features a wooden table set for six, adorned with colorful placemats and plates. The bright space flows into a living area with a comfortable sectional sofa and a flat-screen television. Natural light streams through sliding doors leading to a patio.

4.91 out of 5 average rating, 150 reviews

Amazing Location in Regal Oaks close to Disney

4.95 out of 5 average rating, 541 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

4.87 out of 5 average rating, 118 reviews

Mickey and Star Wars Fun, Resort Pool & Slide

4.79 out of 5 average rating, 122 reviews

A charming cottage exterior is depicted, featuring a light green facade and white railings. A single turquoise chair is positioned on the porch. Lush greenery and ornamental plants line the walkway, complemented by a landscaped area with mulch and natural textures.

Bungalow in Kissimmee

Sandcastle Cottage#51 Tropical Palms Kissimmee, FL

An aerial view of the resort showcases a large pool area surrounded by palm trees and lounge chairs. A vibrant water slide is positioned next to the pool, with patio seating visible near the clubhouse. The blue water reflects the landscape in a calm setting.