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Vacation rentals with a pool in Meadow Woods

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Meadow Woods

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

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Top guest favourite
The villa features a distinct architectural style with a terracotta roof and a landscaped front yard. Lush palm trees are positioned around the entrance, while a spacious driveway leads to a three-car garage, all set against a tranquil evening sky.
Villa in Kissimmee
5 out of 5 average rating, 127 reviews

Villa Sol Quite Family Pool/Hot tub Home

Close to all major attractions, and airport sits this private villa. It has a little something for all ages! Your family can play in the pool or relax in the hot tub. Enjoy fun game nights with a cabinet full of games, or play a game of basketball, pickleball, or tennis right outside our pool. Fun on the playground or enjoy the clubhouse gym. All of your needs for the beach trips or the ball games. All of your baby's needs are covered as well. Ask about Stroller and cart rentals. We have it all

Superhost
Cottage in Kissimmee
4.93 out of 5 average rating, 341 reviews

Entire Cottage for 4 Near Disney - Bitty Bliss

Welcome to Bitty Bliss, your cozy Tiny Cottage escape! Located just 20 minutes from Disney and Universal, with shopping and restaurants only 5 minutes away, it's perfect for relaxation and adventure. Enjoy fantastic amenities like pickleball, mini golf, a new gym, and a rec room—all smoke-free pet-free, and hassle-free with no resort or parking fees! Sleep comfy in the one-bedroom queen bed or the super cozy sleeper sofa, accommodating up to four guests. Charm, comfort, and fun all in one place

Guest favourite
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.
Townhouse in Kissimmee
4.84 out of 5 average rating, 214 reviews

Orlando Disney ºoº 3BD in Resort | Kissimmee

Modern Townhouse in Resort w/ preserve area and Amazing Clubhouse. (NO resort fees!) | 1 min | Old Town Kissimmee | 3 min | Publix®, McDonald's®, Wendy's®, Miller's Ale House® and more | 6 min | Walmart® & Target® | 7 min | Celebration | 9 min | DISNEY® AREA (All Theme Parks) | 9 min | Premium Outlet® | 11 min | Disney Springs | 11 min | ESPN® Sports | 13 min | Convention Center | 15 min | UNIVERSAL® STUDIOS | 26 min | Orlando Airport | 70 min | Bush Garden's® | 95 min | Sarasota & Clearwater

Top guest favourite
The villa features a modern exterior with a sloped roof and a two-car garage. Palm trees are landscaped around the front yard, which is bordered by well-maintained grass. A clear blue sky provides a bright backdrop to the welcoming entrance.
Home in Kissimmee
4.87 out of 5 average rating, 263 reviews

3 bedroom Villa in Kissimmee

The villa is in a residential area within a 5-min drive to local amenities including, a pharmacy, 3 supermarkets and 2 gas stations. The property is between 15 - 40 mins drive from Disney, Epic Universe, SeaWorld, Gatorland & Universal Studios. Orlando International Airport is only about 17 mins drive away. Osceola Heritage Park, the home of the world’s largest collector car auction is only 4 mins drive from the villa. The Florida Turnpike that runs through Miami is 6 mins from the property.

Guest favourite
Condo in Orlando
4.86 out of 5 average rating, 133 reviews

Orlando-Lake view apartment

Stylish second floor apartment overlooking a lake (community with gated entry and swimming pool). Total area: 1,013 SqFt with central AC. Two bedrooms and two bathrooms. Dedicated workspace. Screened porch overlooking natural forest, full of wild animals. Living room open to the dinning area. Natural wood look flooring. Kitchen with closet pantry and service bar. Parking area in front . Minutes to major roadways making easy access to all area attractions, and Orlando International Airport.

Guest favourite
A single-story home is showcased with a light gray exterior and a dark garage door. Lush green grass surrounds the front, complemented by palm trees and shrubs. The driveway leads to the entrance, under a clear blue sky with a few clouds.
Home in Kissimmee
4.9 out of 5 average rating, 150 reviews

Peaceful Waterfront Retreat, Close to Everything!

Beautiful 4br peaceful lakefront home in safe, quiet community. Close to major shopping and restaurants! Just a short drive to the Turnpike and 417 highway, close to Disney, Seaworld, Medical City, Lake Nona and the VA Hospital. Comfortable space with smart TVs and central AC. Fully equipped kitchen. Split floor plan perfect for families and friends. The master bedroom faces the rear of the home, large windows allowing natural light to enter the home all while enjoying your waterview!

Guest favourite
A shaded outdoor deck features a rectangular wooden table surrounded by four dark wicker chairs. A ceiling fan hangs above, providing airflow. The view beyond includes lush greenery and the presence of trees, creating a serene and private setting.
Home in Kissimmee
4.89 out of 5 average rating, 121 reviews

Kissimmee cottage *15mi to WDW*

Brand new private home in Mill Creek RV park. 1 bedroom home with queen bed and additional pull out sofa. Play yard/crib available for 5th guest. Full kitchen, washer/dryer in home. Enjoy a central location backing onto a green space with pond for peaceful privacy on the back deck. Full access to all Mill creek amenities ( pool, gym, playground, corn hole, pickle ball, putting green) 2 smart TV’s in unit 1 mile to Walmart 15 mile to Disney World & Universal 13 mile to Orlando airport

Top guest favourite
A cozy hanging egg chair provides a relaxing spot next to the heated saltwater pool. A blue lounge chair and a shaded umbrella offer additional seating options. Lush greenery adds a refreshing touch to the outdoor area.
Home in Kissimmee
4.97 out of 5 average rating, 98 reviews

Modern Villa with Saltwater Pool & Themed Rooms

Find your bliss in our Kissimmee haven, where the modern villa boasts saltwater pool, airy living spaces, and enchanting themed rooms that promise magical dreams. The master suite caters to comfort with direct pool access and a luxurious ensuite bathroom, ensuring a private sanctuary for relaxation. The villa is complemented by access to a well-equipped gym and a communal pool. Perfectly situated, our home is a gateway to exploring the best of Orlando, from theme parks to the shores.

Guest favourite
The exterior of the house is displayed, featuring a well-maintained lawn with manicured shrubs and a palm tree. The light-colored structure is complemented by large windows, and decorative stones are arranged artistically in the landscape. A clear blue sky enhances the inviting appearance.
Home in Kissimmee
4.94 out of 5 average rating, 105 reviews

Your All in One Home, 17 mins from Disney World

Welcome to JeremyAnthonyHouse, a place that was created with so much love and care thinking of you. The house has everything you might need during your stay, it does not matter if it is for one night or an entire month; from bathroom amenities, free Netflix, Wifi, YouTube, in house laundry and dryer to kids' toys, security system. In addition, it has a private pool, easy access to expressways and theme parks. Very close to Disney springs and The Medieval Times Castle is a must see.

Top guest favourite
A screened patio area features a sparkling saltwater pool with a gentle waterfall. Comfortable loungers and dining furniture are arranged around the pool, providing ample space for relaxation. Lush plants add natural touches, while the surrounding view includes nearby homes and green lawn areas.
Home in Kissimmee
4.95 out of 5 average rating, 111 reviews

Home w/ Heated Pool, Near Disney & Universal

Relax in this peaceful lakeview home just 15–20 minutes from the Orlando International Airport and top attractions like Disney, Universal, and SeaWorld. Perfect for families, this fully equipped 3-bedroom home features a private heated pool, outdoor living space, full kitchen, washer/dryer, and more. Enjoy nearby shopping centers, outlet malls, and a variety of restaurants. No smoking or parties allowed—just comfort, convenience, and fun for the whole family.

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
4.9 out of 5 average rating, 184 reviews

NEW APARTMENT WITH WATER PARK AND NEAR DISNEY

Enjoy a carefree vacation at Storey Lake Resort. Located minutes from Disney, Falcon's Fire Golf Club, Universal, Epic Universal, SeaWorld, Orange County Convention, Premium Outlets. Less than 1 mile from Walmart, Target, and restaurants, your family will have everything they need. Water Park, gym, and all amenities FREE. Free parking, 24/7 security in this gated resort and with an automatic check-in with direct access code and elevator available

Guest favourite
A spacious living area is featured, highlighted by a large sectional sofa and a glass coffee table at the center. Natural light fills the room through multiple windows, illuminating the neutral-colored walls and decorative accents. A dining area is visible in the background, complete with stylish seating.
Townhouse in Kissimmee
4.89 out of 5 average rating, 130 reviews

Fully equipped house 5 beds, 7 people, near parks

New house, is a family home decorated with the best furnitures, to be a great experience to spend a family time. You can park your car on the street in front of the main door. The garage is closed whit my cars inside. Beautiful common spaces, whith pool, GYM, basketball and tennis courts, Kids playgroud. Beautiful common spaces, with pool, basketball and tennis courts. Kids playground Security access gate to visitors and residents

Popular amenities for Meadow Woods rentals with a pool

When is the best time to visit Meadow Woods?

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Quick stats about vacation rentals with a pool in Meadow Woods

  • Total vacation rentals

    Explore 110 vacation rentals in Meadow Woods

  • Nightly prices starting at

    Meadow Woods vacation rentals start at $41 CAD per night before taxes and fees

  • Verified guest reviews

    Over 3,940 verified reviews to help you choose

  • Family-friendly vacation rentals

    50 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wifi availability

    110 of Meadow Woods vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Meadow Woods rentals

  • 4.7 Average rating

    Meadow Woods stays receive an average rating of 4.7 out of 5 from guests