Places to stay near Old Town

The resort-style pool is surrounded by palm trees and lounge chairs with blue umbrellas. A spacious deck features seating areas overlooking the water. The expansive pool area is designed with different sections for relaxation and recreation, enhancing the appeal of the outdoor environment.

4.93 out of 5 average rating, 183 reviews

Resort Style Vacation Townhouse, 10 Mins to Disney

Located only 10 minutes from DISNEY, this RESORT STYLE townhouse provides the perfect home for your vacation! Luxury 2 bedroom, 2.5 bathroom with 1 King-sized bed, and 2 double beds. Charming conservation view with screened patio featuring private Jacuzzi. Regal Oaks at Old Town community has world class Clubhouse: large pool, water slide, indoor gym, tennis court, restaurant, bar, convenience store, and 24HR security with gates. Walking distance to Old Town and Fun Spot, restaurants and stores.

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, 244 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!

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, 282 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, 331 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, 110 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!!

4.88 out of 5 average rating, 241 reviews

Disney Area Lakefront Townhome + Private Jacuzzi

Relax by the lake after a full day at Disney! This family-friendly 2-bedroom townhome features a private jacuzzi on a screened lakefront patio, two ensuite bedrooms, a fully equipped kitchen, and space for up to 6 guests. You'll also enjoy complimentary access to resort amenities including a heated pool, waterslides, fitness center, tennis court, tiki bar and restaurant—all inside a 24-hour gated resort. Disney parks, Disney Springs and Old Town are just minutes away.

4.99 out of 5 average rating, 100 reviews

A hot tub is situated on a patio with a view of a lake at sunset. The vibrant sky features hues of orange, pink, and purple, while a railing surrounds the space, enhancing the scenic atmosphere. The tranquil water reflects the colors of the sky.

Cottage in Kissimmee

3 Bed Pool/Spa w/ Sunset Water in Margaritaville

Welcome to Sol Oasis Cove! This amazing pool / spa cottage has one bedroom on the first floor and 2 bedrooms upstairs with a balcony positioned perfect for the sunset over the lake! This property comes with all the comforts from home but worlds away. Conveniently located minutes from the Disney parks, a state-of-the art water park and newly opened 196,000 square foot shopping and dining district with multiple dining food and beverage options & brand-new movie theater.

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, 271 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 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.

4.91 out of 5 average rating, 358 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.

4.85 out of 5 average rating, 286 reviews

Tiny home in Kissimmee

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??