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Vacation rentals with a pool in Osceola County

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Top-rated rentals with a pool in Osceola County

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Top guest favourite
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, 197 reviews

303_To Infinity & the Ocean Breeze Apartment

Welcome to your ultimate family getaway near Disney! This spacious 3-bedroom apartment is perfectly located just minutes from the magic of Disney. Designed with families in mind, it features two beautifully themed kids’ bedrooms—a Toy Story adventure and a Moana-inspired tropical escape—guaranteed to delight the little ones. Enjoy full access to an amazing waterpark, included free of charge, making every day feel like a vacation. Whether you're unwinding after a day at the parks or splashing th

Top guest favourite
A tranquil outdoor space features a private pool under a protective screen enclosure, framed by reclining lounge chairs. The setting offers a view of the lake, contrasting with the colorful sunset sky, creating a serene atmosphere for relaxation.
Home in Kissimmee
4.98 out of 5 average rating, 106 reviews

Mickey's Lakefront Villa at Sunset Lakes

Updated Pics Dec 2024. We have no gas burning appliances. We abide by the AirBnB enhanced cleaning protocol. We want our guests to be happy, healthy and safe in their home away from home. Please see house rules. Located in beautiful Sunset Lakes – it's hard to find a vacation home closer to Walt Disney World with all that's offered at Mickey’s Lakefront Villa. Be amazed at how quiet and secluded you will feel yet just minutes away from all of the entertainment that you came here to enjoy.

Top guest favourite
The living room features a modern layout with a large television mounted on the wall, complemented by comfortable seating arrangements, including a blue sofa and a pink armchair. Natural light is invited in through sliding glass doors that lead to a balcony with outdoor seating.
Apartment in Kissimmee
4.97 out of 5 average rating, 115 reviews

3161-401 Resort Lake View Disney Universal Orlando

Minutes from Disney World Orlando Florida, Modern & Stylish 2bed/2bath fully equipped apartment for up to 6 guests, located in the family friendly Storey Lake Resort. FREE Clubhouse & WATERPARK amenities: Heated Pool, Hot Tub, Kids Splash Zone, Water Slides, Lazy River, Gym, Tiki Bar, Ice Cream Shop & more. The apt is located: 10 min drive to DISNEY, 25 min to UNIVERSAL STUDIOS, 18 min to SEA WORLD. FREE Parking. FREE Waterpark. No extra FEES. Gated Resort with Security 24/7 & Self check-in!

Top guest favourite
The exterior of the barn showcases a rustic wooden facade beneath a metal roof. A porch with seating options invites relaxation, while the neatly maintained yard features green grass and landscaping. A driveway leads to a side garage, enhancing the property's charm and accessibility.
Barn in St. Cloud
4.97 out of 5 average rating, 167 reviews

Rustic Barn Retreat

Experience the rustic elegance of this beautifully remodeled 1,800 sq. ft. barn nestled on a serene 17-acre property. Unwind in the private heated hot tub and soak up the peaceful surroundings. The prime location offers convenient access to major attractions—just a 35-45 min drive west will take you to Disney, Universal, SeaWorld, and gator parks, while a 45-60 min drive east leads you to the breathtaking Atlantic beaches and the Space Coast. Plus, the property is only 40 min from the airport

Top guest favourite
A private pool features a spacious deck and a whimsical swan float. Adjacent is a covered dining area with views of landscaped grounds. Inside, a kids’ tube slide and superhero-themed decor are seen, along with a game area featuring a billiards table and arcade console.
Villa in Osceola County
4.99 out of 5 average rating, 132 reviews

*Private Resort Oasis: Golf-Front, Pool/Spa/Cinema

The perfect balance of STYLISH DESIGN, LUXURIOUS COMFORT, & ENDLESS ENTERTAINMENT, beautifully situated with stunning views in the sprawling 3.5 square mile Reunion Resort. You will have your own private pool, spillover spa, STAR WARS cinema-game room with pinball, classic arcade games, and karaoke, MARVEL kids room with tube slide and double bunks, the latest Xbox Series S, a sprawling 2000 ft2 pool deck, fire pit, and even a HARRY POTTER cupboard hidden under the stairs, minutes to Disney.

Top guest favourite
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.
Home in Kissimmee
4.98 out of 5 average rating, 120 reviews

Perfect Getaway. Private Pool.Kissimmee/Orlando

This property is accommodated for families looking to vacation with peace of mind, the facilities are perfectly arranged so that you and your family feel at home. It has 3 rooms equipped for adults and children, the patio area is the perfect place to spend time with your family either in the pool or enjoying a barbecue on the grill.( POOL IS NOT HEATED) -No parties allowed in the house. No smoke. Do not park blocking the sidewalk, no park on the grass, nor in front of the neighbors' house.

Top guest favourite
Townhouse in Four Corners
4.96 out of 5 average rating, 170 reviews

Near Disney/Kid-Friendly/Disney-Themed/Water Park

Your magical vacation starts here! Just 15 minutes from Disney World, this beautiful, family-friendly home offers luxury, themed rooms, and fun, perfect for creating unforgettable memories. The home is located in the ChampionsGate area. It has 3 bedrooms, 2.5 bathrooms, modern furniture, and super fast internet. You will have free access to the Enclaves at Festival amenities center which features a large beach-entry pool, kids water park, beach volleyball, mini-golf, restaurant, and gym.

Guest favourite
An aerial view showcases a large pool surrounded by lounge chairs and palm trees. The pool area is defined by well-maintained landscaping, with a hot tub and a nearby shaded structure visible in the background, creating an inviting atmosphere.
Condo in Osceola County
4.89 out of 5 average rating, 110 reviews

Stunning Orlando Condo 3 BR/2 bath, pets OK

This resort community is amazing to drive around in, let alone stay in. Just 20 to 25 minutes away from Disney World and Universal Studios and everything Orlando has to offer. Convenience stores (7-11), Dunkin' Donuts, CVS pharmacy, restaurants and grocery stores within walking distance. Three gorgeous pools and hot tub Jacuzzis, and world-class gym in the resort in this gated community with security. 5 minute drive to Champions Gate and I-4 highway. Up to 2 dogs/cats ($25/day/animal)

Top guest favourite
A private outdoor area features a pool with a spa, surrounded by a spacious deck. A basketball hoop is positioned nearby. A large inflatable swan floats in the water, while a hammock provides a cozy spot for relaxation. Lush greenery frames the scene under a colorful sky.
Home in Kissimmee
4.95 out of 5 average rating, 130 reviews

Luxury Encore Pool Spa Pets Game Rm Theater Gym

Amazing Brand New Modern Luxurious Home at Encore Resort @ Reunion. PET-FRIENDLY & Minutes to all Theme Parks. BRAND NEW HOME. Private Pool & Spa / Game Room / Movie Theater / Gym / Massage Chair / Fireplace / PS5 / Board Games & Much Much More Embrace the extraordinary and book your stay at our home, where luxury, entertainment come together for an unforgettable vacation experience. ** Please review the rules before booking. Waterpark access is not included. **

Top guest favourite
An outdoor view shows a private pool, where a person is enjoying the water with a serene water view beyond. Inside, an illusion room presents colorful decorations and a lively atmosphere. A cozy bedroom showcases a spacious bed adorned with soft linens. A game room is visible, featuring engaging entertainment options.
Home in Kissimmee
4.99 out of 5 average rating, 141 reviews

[20% OFF] Illusion Home •Waterfront Private Pool

❤ Illusion room with character outfits ❤ Private pool with water view ❤ 15 min to Disney ❤ 25 min to Universal, SeaWorld, Convention Center, 2 min to Walmart ❤ Game room with board games & kids toys ❤ 100" movie theater screen ❤ Free Netflix ❤ Fully equipped kitchen ❤ Sleeps 12 ppl ❤ 2 king beds, 2 cribs, 1 Queen memory foam sofa bed, 6 twins ❤ Newly renovated home ❤ Fully stocked home ❤ Alice in Wonderland®-themed home ‼️ No parties, No smoking, 4 dogs max $75/pet

Guest favourite
A grand living area showcases a striking stone wall adorned with an extensive collection of framed artwork. Soft seating is arranged around a fireplace, providing a cozy yet elegant atmosphere. A staircase leads to the upper level, while rich drapery frames the large windows, allowing natural light to flow in.
Home in Kissimmee
4.97 out of 5 average rating, 177 reviews

Waterfront Wizarding Near Universal's Harry Potter

This spellbound stay, situated in the prestigious Lake Berkley Resort, boasts lake views & private pool. With 6 bedrooms, 3 bathrooms, well equipped kitchen & comfy living spaces, this thematic home is ideal for families & friends seeking an immersive vacation. A 10min drive to Disney, 15min to Sea World & 20min to Universal's Wizarding World of Harry Potter, this magical manor provides a convenient home base for exploring Orlando's famous attractions.

Guest favourite
Townhouse in Kissimmee
4.88 out of 5 average rating, 113 reviews

Kid-Approved Stay – Pool, Parks & Themed Rooms!

Give your family a stay they’ll never forget! Kids can rule their own Frozen kingdom or battle in a galaxy far, far away, while adults unwind after action-packed park days. ✔ Themed kids’ rooms – Frozen castle & intergalactic escape ✔ Private splash pool for a refreshing break ✔ Spacious & modern layout for families & groups ✔ Prime location near Disney, dining & top attractions Don’t miss out—book Let It Go Galaxy before it’s gone!

Popular amenities for Osceola County rentals with a pool

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Guest favourite
Home in Kissimmee
4.93 out of 5 average rating, 123 reviews

No Airbnb Fees! Home Pvt Pool/SPA in Resort 244381

Guest favourite
A modern living area features a sleek black wall with a mounted television displaying a beach scene. A plush, light-colored ottoman sits at the center, while a stylish kitchen area with dark cabinetry can be seen in the background, complemented by pendant lighting.
Home in Kissimmee
4.96 out of 5 average rating, 102 reviews

Modern 4bd house/heated pool,Close to Disney

Top guest favourite
The exterior of the home showcases a modern façade with a manicured lawn and a two-car garage. Inside, a spacious living area is furnished with a comfortable sofa and a large TV displaying a streaming service. A bright bedroom features a queen bed against light-colored walls, with natural light illuminating the space. The outdoor pool area is enclosed by a screened patio, highlighting the inviting water and surrounding lounge chairs.
Home in Kissimmee
4.99 out of 5 average rating, 137 reviews

Traveler's Dream - King Bed, BBQ, Pool, Arcade +

Superhost
A screened-in pool area is illuminated by string lights, offering a serene view of the lake at sunrise. The inviting pool features floating noodles, and the surrounding space is bordered by greenery, enhancing the tranquil atmosphere.
Home in Kissimmee
4.88 out of 5 average rating, 208 reviews

Disney & Universal Retreat| Heated Pool | Fire Pit

Top guest favourite
A private heated pool is set within a screened enclosure, surrounded by a patio area. Two blue chairs and a white lounge chair are positioned nearby, with lush greenery visible beyond the pool. The clear water reflects the sky, creating a serene atmosphere.
Home in Kissimmee
4.99 out of 5 average rating, 149 reviews

Heated Pool 15 Minutes to Disney PS5 l Switch

Superhost
The Captain's Lounge features shiplap walls and vintage maritime decor, with luxurious crimson and gold velvet upholstery. An oversized treasure chest serves as a coffee table, while an entertainment center boasts a 65" HDTV. A vibrant view of the adjacent lake is available from the patio.
Home in Osceola County
4.9 out of 5 average rating, 125 reviews

Pirate & Princess: Themed/Disney/Resort

Top guest favourite
A modern kitchen is featured, showcasing white cabinetry and a marble countertop. The central island is equipped with a sink and offers additional workspace. Sleek stainless steel appliances are present, including a refrigerator and an oven, while pendant lights provide illumination.
Home in Four Corners
4.96 out of 5 average rating, 171 reviews

New Gtd community Sleeps 6 - 3B/2 bth near Disney

Superhost
Home in Kissimmee
4.77 out of 5 average rating, 334 reviews

Free Waterpark! Fantasy World - Fun at BnB

Condo rentals with a pool

Top guest favourite
Condo in Kissimmee
4.91 out of 5 average rating, 173 reviews

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

Guest favourite
A private balcony offers seating with a view of the shimmering lake, highlighting the surrounding landscape. Adjacent images reveal family-friendly amenities, including a vibrant water park with slides, an elegant kitchen space, and a welcoming sleeping area featuring playful decor.
Condo in Kissimmee
4.91 out of 5 average rating, 174 reviews

NEW APARTMENT WITH WATER PARK AND NEAR DISNEY

Guest favourite
A modern living area features a white sectional sofa and a stylish coffee table with gold accents. A flat-screen television is mounted on the wall, complemented by minimalist shelving. Large windows dressed with sheer curtains allow natural light to fill the space, creating a bright and welcoming environment.
Condo in Kissimmee
4.94 out of 5 average rating, 98 reviews

Resort Style Sunshine Oasis near Theme Parks

Guest favourite
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.
Condo in Kissimmee
4.77 out of 5 average rating, 272 reviews

King Bed Small Studio Disney World Universal

Guest favourite
A modern living room features a light-toned sofa facing a wall-mounted television displaying tranquil landscape imagery. Soft blue LED lighting enhances the space, while a stylish area rug with geometric patterns adds texture. A glimpse of the kitchen can be seen in the background.
Condo in Kissimmee
4.91 out of 5 average rating, 152 reviews

Chic Disney Resort Condo • Pool Access Near Parks

Top guest favourite
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, 150 reviews

Luxurious Spot 10 Mins Away to Most Attractions!!!

Top guest favourite
A balcony is depicted with four cushioned chairs arranged around a small table. The railing provides a view of a serene landscape with water and greenery in the background. Light fabric drapes softly from the sliding door frame.
Condo in Kissimmee
4.91 out of 5 average rating, 135 reviews

Modern Condo with Lake View Near Disney 3151

Guest favourite
A bright and open living area features modern furnishings including a sleek dining table and comfortable seating. Natural light filters through large windows, and a flat-screen TV is mounted on the wall. The kitchen island with a quartz countertop provides additional workspace.
Condo in Kissimmee
4.9 out of 5 average rating, 153 reviews

SL106 - Modern Condo - Resort Access included

Home rentals with a private pool

The modern home exterior features a combination of light-colored walls and a stone facade. A landscaped front yard includes neatly trimmed grass and a palm tree. A paved walkway leads to a front entrance, and large windows provide ample natural light.
Home in Four Corners

630sst- the Retreat at Championsgate

A two-story home is displayed with a well-maintained façade featuring a stone accent, multiple windows, and a centered front door. The landscaped yard is complemented by neatly trimmed shrubs and a paved driveway leading to an attached two-car garage.
Home in Haines City

Balmoral Resort - 192kb

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!

Villa in Kissimmee
4.78 out of 5 average rating, 256 reviews

Visit Disney World from a Sunny Home with a Pool

An elegant two-story home features a light grey exterior with stone accents. The front entrance is framed by a covered porch and dark double doors. A well-manicured lawn includes small shrubs and decorative plants, complemented by a paved driveway leading to the garage.
Villa in Davenport

Champions Gate

The exterior of the vacation home showcases a two-story structure with a light blue facade and a welcoming entryway. A driveway leads to a two-car garage, surrounded by low-maintenance landscaping and paved paths. The sky is partly cloudy, enhancing the home's inviting appearance.
Home in Haines City

Balmoral Resort-140aa

A well-appointed bedroom features a spacious bed with a light-colored headboard. Two bedside lamps provide soft illumination beside matching nightstands. Wall art consisting of floral designs adds a touch of elegance, while a ceiling fan aids in airflow, contributing to a comfortable ambiance.
Home in Haines City

Balmoral Resort-126sqm

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