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Home rentals with a pool near Old Town Kissimmee

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool near Old Town Kissimmee

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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 favorite

The expansive lake is showcased during sunset, reflecting vibrant colors in the sky. Surrounding greenery adds a natural touch, while a dock extends into the water, offering a serene view of the landscape. Soft light illuminates the pathway along the lake's edge.

Hotel room in Orlando

4.96 out of 5 average rating, 188 reviews

PentHouse Suite with 2X View

Located at the gates of Walt Disney World, this Awesome PentHouse Suite offers easy access to area theme parks, and entertainment venues in the surrounding area, including Walt Disney World, Universal Studios, Sea-world, Legoland + Amazing Restaurants, Shopping and many more. Best of all wonderful views with 2 Large Balcony's, 1 for Sunrise @ East Side and 1 for Sunset @ West side overlooking Disney World with amazing fireworks every night, Enjoy! **Security camera for safety @ Entry door only!

Top guest favorite

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, 253 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

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.

Townhouse in Kissimmee

4.88 out of 5 average rating, 208 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 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, 201 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 favorite

A cozy living area showcases a rattan sofa adorned with patterned cushions. The walls are decorated with unique artwork, native artifacts, and framed pictures. Lush tropical accents and colorful lighting fixtures create a vibrant yet tranquil atmosphere. Natural light filters through decorative window panes.

Cottage in Kissimmee

4.99 out of 5 average rating, 173 reviews

Tahiti Gil’s Mananui: Disney Poly & Tiki Inspired!

Aloha Adventurers! Welcome to Faré Mananui. Your passport to a far away tropical hideaway awaits, so get ready to grab your favorite Aloha shirt! Mananui was made for the Disney/Tiki ADULT in mind! Imagined by artist @TahitiGil & designed by @TyphoonTommy (Former Disney/Universal creative team & designer of the Suffering Bastard Tiki Bar in Sanford, Fl. Experience your next Adventureland/ Enchanted Tiki Room “story dwelling” adventure from the moment you step thru the door! - Kungaloosh!!

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.

4.84 out of 5 average rating, 289 reviews

*Private jacuzzi!* 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 bright and spacious living area showcases a modern design, featuring a welcoming sign displaying 'VACATION MODE ON.' A wine bottle and glasses are positioned on the counter, while natural light floods in through large windows, highlighting the dining area and outdoor views.

Home in Kissimmee

4.9 out of 5 average rating, 125 reviews

LARNE LODGE House with Hot Tub 3 miles to Disney!

Experienced superhosts - check out our other listing for reviews! Larne Lodge has just gone through a full modern renovation! Located just 3 miles from Disney and 11 miles from Universal Studios, Larne Lodge is the perfect vacation spot for families and friends to make lasting memories! This spacious townhouse is located in a beautiful private and gated resort, which offers guests a shared pool with a pool bar, gym, bar, restaurant, games room, and a convenience store.

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, 305 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.

The image presents a four-part collage, featuring a bright bedroom with two spacious beds adorned with decorative pillows, a private hot tub surrounded by nature, a resort pool with loungers and a water slide, and a clubhouse area with expansive outdoor seating and vibrant landscaping.

Townhouse in Kissimmee

4.84 out of 5 average rating, 128 reviews

♥︎ Disney-3 miles ♥︎ Private HotTub ♥︎Top Resort♥︎

Our gated-community townhouse offers a resort feeling with all the comforts of home, peaceful & quiet, yet central to Disney, Old Town, and all major attractions. After an exciting family day, relax in your private patio hot tub and enjoy the nature, or soak up some sun poolside at the resort. Fun for adults and kids of all ages! Also enjoy the resort tennis courts, pool table, gym, restaurant, and poolside snack bar! NO RESORT FEES! FREE PARKING!

Top guest favorite

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

4.95 out of 5 average rating, 213 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.

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!

Popular amenities for rentals with a pool near Old Town Kissimmee

Free parking on premises

Air conditioning

House rentals with a pool

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.

Home in Kissimmee

4.91 out of 5 average rating, 115 reviews

Pet friendly Orlando area near ESPN Center

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.

Home in Kissimmee

4.86 out of 5 average rating, 118 reviews

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

Top guest favorite

The exterior of the home is showcased, featuring a well-maintained landscape with neatly trimmed grass and flower beds. A light-colored façade is complemented by a blue front door. The driveway leads to a two-car garage, enhancing the welcoming curb appeal.

Home in Kissimmee

4.94 out of 5 average rating, 111 reviews

3Bed/2Ba House w Pool NEAR Disney and Theme Parks!

Top guest favorite

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.

Home in Kissimmee

4.92 out of 5 average rating, 145 reviews

Disney New Neighbor

Top guest favorite

Home in Kissimmee

4.86 out of 5 average rating, 129 reviews

6BD/ 6 BA Sleeps 18! Storey Lake (2851 BD)

Top guest favorite

Home in Kissimmee

4.85 out of 5 average rating, 163 reviews

#2750 Cosy Resort Masters 4/3.5 Disney Universal

Top guest favorite

Home in Kissimmee

4.97 out of 5 average rating, 112 reviews

Modern House with Private Pool Getaway Kissimmee

A spacious water park area is showcased, featuring a pair of large water slides in green and blue spiraling down into a clear pool. Palm trees are visible in the background, with seating areas and safety features surrounding the pool.

Home in Kissimmee

4.95 out of 5 average rating, 112 reviews

Private Pool/Grill-Free Water Park-15Min to Disney

Condo rentals with a pool

The living room features a Mickey Mouse mural, complemented by a yellow sofa adorned with a blue star-patterned blanket. A glass coffee table sits in the center, while a small blue chair and a television are positioned against a light gray wall. Decorative items include a plush Mickey Mouse.

Condo in Kissimmee

4.77 out of 5 average rating, 186 reviews

Mickey's House vacation/kissimmee4

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.

Condo in Kissimmee

4.97 out of 5 average rating, 192 reviews

303_To Infinity & the Ocean Breeze Apartment

Top guest favorite

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

4.97 out of 5 average rating, 396 reviews

Waterfront Resort Condo near Disney &Universal

Top guest favorite

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.

Condo in Kissimmee

4.83 out of 5 average rating, 139 reviews

Stunning view, near Disney.

Top guest favorite

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

4.96 out of 5 average rating, 106 reviews

Modern Lake view Condo 1 mile from Disney

Top guest favorite

The modern living area features a spacious gray sectional sofa accented by colorful cushions. A minimalist coffee table is positioned centrally, and large sliding glass doors provide a view of the outdoor space, allowing natural light to fill the room. Light-colored cabinetry and appliances are visible in the kitchen area.

Condo in Kissimmee

4.93 out of 5 average rating, 209 reviews

3150-303 Resort Pool View Disney Universal Orlando

Top guest favorite

A refreshing swimming pool features a large water slide in vibrant green and blue. Palm trees provide shade around the area. Several lounge chairs are positioned beside the pool, inviting relaxation while enjoying the sunny landscape.

Condo in Kissimmee

4.96 out of 5 average rating, 148 reviews

Luxurious Spot 10 Mins Away to Most Attractions!!!

A modern kitchen space is highlighted, featuring stainless steel appliances, white cabinetry, and a large island with seating for three. A dining area with a round table accommodates four, illuminated by soft overhead lighting. Neutral tones and textured tiles create a clean and open atmosphere.

Condo in Kissimmee

4.95 out of 5 average rating, 222 reviews

BRAND NEW CONDO- 2 BR 2 Bath-Great location!

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!

The exterior of the home features a two-story structure with a light beige facade and a tiled roof. Lush landscaping, including palm trees and shrubs, enhances the entrance, while a spacious driveway leads to a two-car garage.

Home in Davenport

Beautiful 9 Br Pool Home In the Solterra Resort!

The exterior of the townhouse is presented, featuring a modern design with a combination of smooth white walls and textured stone accents. Lush greenery and landscaped shrubs frame the entrance, which is adorned with double red doors under a covered porch.

Townhouse in Kissimmee

1116chd-The Retreat at Championsgate

Home in Davenport

4.95 out of 5 average rating, 116 reviews

Airy, Stylish Home with Pool Heat Included in Davenport

Villa in Kissimmee

4.78 out of 5 average rating, 255 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

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

Other vacation rentals with a pool

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

4.84 out of 5 average rating, 129 reviews

Near Disney and all Parks- Tiny Cottage

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.

Townhouse in Kissimmee

4.85 out of 5 average rating, 241 reviews

Resort Style 12 min Disney, Jacuzzi, Sleeps 8

Top guest favorite

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.

Townhouse in Kissimmee

4.98 out of 5 average rating, 42 reviews

Waterfront 2BR next to Disney, private hottub

Top guest favorite

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.

Townhouse in Kissimmee

4.91 out of 5 average rating, 321 reviews

Stylish Villa Near Disney | Hot Tub & Resort

Top guest favorite

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.

Townhouse in Kissimmee

4.98 out of 5 average rating, 186 reviews

Townhouse - 5 miles to Disney!

Top guest favorite

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

Top guest favorite

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.

Home in Kissimmee

4.98 out of 5 average rating, 48 reviews

Once Upon A DreamStay: *Luxury *Lakeview *Disney

Top guest favorite

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

5 out of 5 average rating, 27 reviews

6min to Disney - Retro Studio - Resort Pool

Quick stats about rentals with a pool near Old Town Kissimmee

Total rentals
630 properties
Nightly prices starting at
€ 34 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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