Home rentals with a pool near Old Town

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!

The open living area features a contemporary design with a curved sofa in neutral tones, two blue accent chairs, and a glass coffee table. A textured area rug complements the decor. Large windows allow natural light to illuminate the space, enhancing the connection to the outdoors.

4.88 out of 5 average rating, 241 reviews

Adorable 2 bdr lakefront w/jacuzzi 5 min *Disney*

This townhouse provides an 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. After a long day at the parks with a beautiful lakefront view, relax in your private spa. Clubhouse with a gym, amazing heated pool, pool bar, a restaurant, and only 5 min from Disney and golfing area Free Parking Close to lakes, camping, beach, vineyards, farms

4.91 out of 5 average rating, 205 reviews

An open living space showcases a comfortable sofa and a TV facing the kitchen area, which features modern appliances. Bright yellow curtains complement the neutral decor. A dining table with chairs and a small vase of flowers is visible, enhancing the inviting atmosphere.

Cottage in Kissimmee

Modern Cottage Near Disney World | Top Rated

Our cozy, modern vacation cottage is tucked away in a quiet, private community just 4 miles from Walt Disney World and close to everything Orlando has to offer. Highly rated by past guests, (nearly 200 five star reviews) it’s known for its cleanliness, comfort, and thoughtful details. The cottage features a queen bedroom, comfortable living area, full bath, and a fully stocked kitchen with new appliances—an inviting, reliable home base to enjoy the magic and sunshine of Central Florida.

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.

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

Visit Regal Oaks Resort, with an onsite waterpark and private hot tub. We're close to everything in Orlando and a 10 min drive to Disney! Our Resort-Style Villa Includes: ❤Onsite Waterpark and Heated Pools ❤Walkable to Old Town Restaurants and Shops ✔No Hidden Fees ✔Onsite Fitness Center ❤24/7 Security ✔Onsite Concierge, Restaurant and Bars Our Home Offers: ❤Private Hot Tub ✔Comfy King and 2 Full-Size Beds ❤Fast WiFi ✔Cable TVs ✔Private Patio ✔Washer/Dryer ✔Stocked Kitchen

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!!

4.99 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 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, 262 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!

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!

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!

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 and 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

A modern two-story house is showcased, featuring a bright exterior and a spacious driveway. Lush green grass surrounds the property, while palm trees add a tropical touch. Large windows on the upper level allow for ample natural light, highlighting the clean lines of the architecture.

4.9 out of 5 average rating, 163 reviews

Villa Resort Club

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, 133 reviews

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

4.97 out of 5 average rating, 181 reviews

Near Disney | Heated Pool, King Bed, Arcade

4.9 out of 5 average rating, 216 reviews

*Free Early Check ins / Late Check outs*

4.9 out of 5 average rating, 208 reviews

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

4.98 out of 5 average rating, 129 reviews

Disney Villa w/ Priv Pool & Lake View-12 Mi parks

4.83 out of 5 average rating, 133 reviews

Home in Davenport

5 Bedrooms/ 4.5 Bathrooms/ Solterra (7291 Ol)

A brightly colored game room features an Avengers-themed mural above a pool table. The space offers a foosball table and is designed for entertainment. A modern home exterior is showcased in the corner, highlighting the property's appealing architecture.

4.82 out of 5 average rating, 113 reviews

Stunning Modern Home!

Condo rentals with a pool

4.85 out of 5 average rating, 105 reviews

Andris Luxury Homes Modern 1BR/1ba

4.96 out of 5 average rating, 160 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.

Condo in Orlando

Marriott Sabal Palms 2BD Villa

4.95 out of 5 average rating, 195 reviews

A1 POOL VIEW-By Disney/Universal/Balcony view

4.97 out of 5 average rating, 446 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.

Condo in Orlando

Waterfront Condo minutes to Disney & Universal

4.95 out of 5 average rating, 138 reviews

Condo in Orlando

Modern Lake view Condo 1 mile from Disney

A bright bedroom features a spacious bed with a tufted headboard, adorned with a light blue and white patterned comforter. Natural light enters through two windows beside stylish wall decor, while bedside tables with lamps create a serene ambiance.

4.8 out of 5 average rating, 272 reviews

Stunning Sunny Central Condo w/ Pool & Balcony

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

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

Other vacation rentals with a pool

4.85 out of 5 average rating, 146 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

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, 277 reviews

BOOK your Disney inspired Lakefront retreat NOW!

5 out of 5 average rating, 12 reviews

Montego Bay Retreat | 15 Min to Disney

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, 239 reviews

2 BR Harmony House at Regal Oaks Resort

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, 295 reviews

Luxurious Dream 4/3 Bedroom Home w/private Pool

4.93 out of 5 average rating, 119 reviews

Villa in Kissimmee

Luxury Villa! /Game Room/ Pool Heater

4.95 out of 5 average rating, 123 reviews

4mi to Disney, Summer Oasis w/ Pool & Water Slides

A spacious outdoor patio is highlighted by a private Jacuzzi, surrounded by a screened enclosure. Comfortable seating is provided by wicker chairs, and a large umbrella offers shade. The home’s large windows enhance the inviting atmosphere of the outdoor space that backs onto a wooded area.