Home rentals with a pool near Old Town Kissimmee

A resort-style swimming pool is framed by palm trees and lounge chairs. The image shows a screened patio with a private jacuzzi and outdoor dining space, along with a colorful water slide visible nearby. The themed bedroom features bright decor and ample bedding, appealing to families.

4.92 out of 5 average rating, 104 reviews

#2609 Resort Home near Disney Themed Jacuzzi Pool

Relax in this LARGE FULLY RENOVATED LUXURY DESIGNER HOME in the famous REGAL OAKS RESORT w/ THEMED BR near DISNEY WORLD in ORLANDO FLORIDA! Enjoy the STUNNING LAKE FRONT VIEW, PRIVATE JACUZZI, NEW STYLISH FURNITURE, HEATED POOL, Waterslides, Poolside Bar, GAME ROOM, BILLIARD TABLES, Ping Pong, Restaurant, GYM, Tennis Court, and 24/7 Security Guard! - Walk 5 min to Old Town Amusement Park and World Food Trucks. - Drive 8 min to DISNEY, 20 min UNIVERSAL STUDIO, 15 min SEAWORLD and DISNEY SPRINGS

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, 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

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, 186 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, 210 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

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, 134 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).

4.97 out of 5 average rating, 401 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 Resort Condo near Disney and Universal

Just minutes from Disney World and Universal Studios, this condo places you in the heart of Orlando’s top attractions, including Disney Springs, Islands of Adventure, SeaWorld, Magic Kingdom, Epcot, two outlet malls, and more. Relax on your private balcony with breathtaking views of Lake Bryan, or enjoy the resort-style pool with a full Tiki bar and dining menu. Additional perks include free parking, 24-hour security, and complimentary HBO & Netflix. No deposit required and no extra fees.

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.

4.87 out of 5 average rating, 126 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.

4.99 out of 5 average rating, 113 reviews

The living area features a comfortable gray sofa adorned with accent pillows, complemented by a wooden coffee table. A large TV is mounted on the wall, with a stylish chair placed nearby. Natural light enters through glass doors, which lead to a balcony.

Apartment in Kissimmee

Chic Vibes Comfy King Bed Next to Parks/Food/shops

Welcome to our stylish oasis in Kissimmee, which seamlessly blends sophistication with a laid-back vibe. Your stay begins in a professionally cleaned apartment for your full enjoyment. Discover resort-style amenities – a sparkling pool, a fitness center, and hammocks, offering the luxuries of a five-star retreat. Conveniently located with in walking distance of theme parks, restaurants, and shopping. Book now. We can't wait to host you in our little slice of paradise!

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.

4.93 out of 5 average rating, 308 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.

4.89 out of 5 average rating, 268 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!

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, 310 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!

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.

4.96 out of 5 average rating, 252 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!

Popular amenities for rentals with a pool near Old Town Kissimmee

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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, 112 reviews

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

Superhost

4.8 out of 5 average rating, 534 reviews

Free Waterpark! Fantasy World 2br Universal Studio

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, 121 reviews

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

An enclosed in-ground swimming pool is featured, surrounded by a screened lanai. Various lounge chairs and umbrellas provide seating options. The pool is clear and inviting, with a decking area that offers space for relaxation.

4.93 out of 5 average rating, 149 reviews

Disney New Neighbor

4.8 out of 5 average rating, 176 reviews

#2718 Stunning LakeFront Priv Spa Pool Disney Epic

The exterior features a multi-level blue and beige building set among lush greenery. Large windows and balconies are visible, framed by trees and shrubs. The building's entrance includes archways and brick details, contributing to its inviting appearance.

4.95 out of 5 average rating, 126 reviews

New 3BR/2BA, 15 min. to Disney, close to parks

A living area features a modern television displaying a virtual fireplace, paired with elegant wall art and a decorative plant. Below, a pool area is illuminated with soft purple lighting against a backdrop of warm string lights, creating a relaxed atmosphere.

4.97 out of 5 average rating, 116 reviews

Perfect Getaway. Private Pool.Kissimmee/Orlando

4.99 out of 5 average rating, 141 reviews

Epcot-Themed Home Near Disney | Pool • Game Room

Condo rentals with a pool

A picturesque view of the resort-style pool area is presented, featuring several palm trees and lounge chairs around the sparkling water. Colorful slides and a splash park are visible, with pathways leading to different activities amidst landscaped greenery.

4.91 out of 5 average rating, 173 reviews

P-Gated Resort-5 miles to Disney-2 FREE Water Park

A modern kitchen area is visible, featuring white cabinetry and stainless steel appliances. Four metal stools are arranged around a dark countertop, illuminated by woven pendant lights. A small indoor plant adds a touch of greenery to the wooden coffee table in the foreground.

4.97 out of 5 average rating, 227 reviews

Prime Location for Parks & Family Fun

A family-friendly living area is presented with a large, comfortable sectional sofa facing a flat-screen TV. Adjacent, a vibrant children's bedroom features a whimsical Moana theme with a sandy beach mural, complemented by a canopy bed adorned with tropical accents. The ceiling displays playful elements, enhancing the kid-friendly atmosphere.

4.97 out of 5 average rating, 196 reviews

303_To Infinity & the Ocean Breeze Apartment

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.

4.94 out of 5 average rating, 160 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.

4.77 out of 5 average rating, 270 reviews

King Bed Small Studio Disney World Universal

A patio area is presented under a covered porch, featuring a round table set for two with a white tablecloth and colorful cups. Two comfortable chairs with blue cushions are positioned around the table. A scenic view of a lake with greenery can be seen in the background.

4.83 out of 5 average rating, 141 reviews

Stunning view, near Disney.

4.95 out of 5 average rating, 109 reviews

A bright living area features a cozy gray sofa paired with two stylish yellow chairs. A wooden coffee table sits atop a textured area rug, while large glass doors lead to a balcony that offers views of Lake Bryan.

Condo in Orlando

Modern Lake view Condo 1 mile from Disney

4.91 out of 5 average rating, 122 reviews

A resort-style area is depicted, featuring a circular pool surrounded by lush palm trees and vibrant landscaping. The building is visible in the background, with a clear blue sky above. A purple text overlay states 'No Resort Fees' across the image.

Condo in Celebration

Pet Friendly in Orlando Area near Disney.

Home rentals with a private pool

An open living space features a comfortable beige sectional sofa with colorful accent pillows. A dining table is visible beside a modern kitchen with stainless steel appliances. Large sliding glass doors provide a view of the pool area, enhancing the connection to the outdoors.

Home in Davenport

Wr001or (1stfororlando)

A spacious living area is highlighted by a large wall-mounted TV above a modern electric fireplace. The white sectional sofa, accented with colorful pillows, faces a sleek coffee table on a patterned rug. Natural light floods in through large windows draped with light curtains.

Villa in Four Corners

4.14 out of 5 average rating, 7 reviews

Disney's Championsgate: Private Pool & Arcade Fun!

4.95 out of 5 average rating, 116 reviews

Home in Davenport

Airy, Stylish Home with Pool Heat Included in Davenport

Villa in Kissimmee

4.78 out of 5 average rating, 256 reviews

Visit Disney World from a Sunny Home with a Pool

The image displays four distinct areas of the villa. A games room features a foosball table and a billiard table with a laundry area in the background. A cozy bedroom showcases a queen bed with nightstands. A private screened pool invites relaxation. A kitchen area includes modern appliances and seating at the bar.

Home in Davenport

The Manors at Westridge Home W/ Private Pool

Four themed bedrooms are displayed, featuring vibrant colors and unique decor. Two bedrooms contain spacious beds with playful beddings, while a game room is visible, showcasing air hockey and colorful wall art, adding to the immersive atmosphere for all guests.

4323sl-Storey Lake Resort

The villa's exterior showcases a well-maintained façade with a large front porch. Lush green lawns and neatly trimmed shrubs line the walkway. A two-car garage is situated on the left, while palm trees flank the entrance, enhancing the inviting appearance of the home.

Villa in Davenport

732bd 4 Bedroom Villa

A bright hallway features tiled floors and light blue walls. A modern painting adds a splash of color to the wall beside a console table adorned with decorative plants. The stairway is seen leading to an upper level while a spacious living area is visible in the distance.

Home in Four Corners

601dsd-The Retreat at Championsgate

Other holiday rentals with a pool

The resort pool area is surrounded by palm trees and features a large, curvy swimming pool with a separate children's slide. Lounge chairs and umbrellas are arranged neatly along the poolside, providing ample seating. The clubhouse is visible in the background, with warm lighting under a vibrant sunset sky.

4.93 out of 5 average rating, 55 reviews

Travel Theme Private Home@Disney

4.84 out of 5 average rating, 131 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 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.

4.94 out of 5 average rating, 217 reviews

2 BR Harmony House at Regal Oaks Resort

A private hot tub is situated on an outdoor patio, enclosed by a screened area. Surrounding greenery and a tranquil water view are visible beyond the patio, providing a serene setting for relaxation.

4.98 out of 5 average rating, 44 reviews

Waterfront 2BR, Family resort in Disney area

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.

4.9 out of 5 average rating, 205 reviews

AMAZING vacation house .Mins to Disney Regal oasks

4.97 out of 5 average rating, 34 reviews

A cozy studio is shown, featuring a king-sized bed with an accent wall in warm colors. A seating area with a couch and smart TV is visible. The kitchen area includes a table for two. The outdoor pool reflects sunlight, surrounded by loungers and palm trees.

Apartment in Kissimmee

6min to Disney - Retro Studio - Resort Pool

An outdoor patio area features a hot tub, accompanied by colorful chairs and a small table. The scene is set against a scenic lakeside view, framed by a protective screen enclosure, with gentle evening light illuminating the space.

4.94 out of 5 average rating, 54 reviews

Once Upon A DreamStay: *Luxury *Lakeview *Disney

Superhost

A shaded lounging area features comfortable seating and a glass-top table, set with refreshments. In the background, a large pool glistens under the sun, surrounded by palm trees and various seating options, including cabanas and sun loungers.