Vacation rentals with a pool in Meadow Woods

5 out of 5 average rating, 115 reviews

A private pool area is showcased with a screened enclosure, featuring a clear, inviting pool surrounded by a stone deck. Comfortable outdoor furniture is set under a red umbrella, offering shade. The villa's exterior walls are visible, alongside large glass doors leading into the interior.

Villa in Kissimmee

Villa Sol Peaceful 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

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.

4.87 out of 5 average rating, 250 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.

4.86 out of 5 average rating, 140 reviews

A back patio area features a refreshing pool surrounded by paved stones. Two lounge chairs sit beside the water, and a swing is positioned nearby under a shaded structure. Lush greenery and potted plants are visible, creating a relaxed outdoor environment.

Guest suite in Orlando

✨️Modern Suite with POOL- Close to All Parks!🎡

This brand new beautiful studio with a POOL! is located in Skylake Orlando, a safe and fun neighborhood surrounded by a variety of great restaurants, shops, malls, but most of all close to ALL the parks. 9 min to Sea World, 7 min to Aquatica, 13 min to Disney World, 13 min to Universal Studios and many more fun places to visit. The studio is perfect for 2, it has a laundry, a spacious bathroom & a fully equipped kitchenette. You will also have access to a gorgeous pool and grill in the backyard

An inviting pool area is framed by a screened enclosure, revealing beautiful water views at sunset. Soft lighting enhances the relaxing atmosphere, with lounge seating positioned nearby for comfort. The tranquil setting is ideal for unwinding and enjoying outdoor moments by the pool.

4.96 out of 5 average rating, 321 reviews

Upscale Renovated HeatedPool Waterfront Piano Home

Welcome to one-of-a-kind upscale contemporary waterfront oasis, where luxury meets comfort in a serene setting. This stunning house is nestled in a tranquil neighborhood, just moments away from the airport and all the attractions you desire. Step inside to find a beautifully renovated space: fully equipped open kitchen, grand piano and more! Outside: private screened in heated pool($20/night heating fee)with breathtaking waterviews, patio equipped with grill, dining table, ping pong and more!

4.97 out of 5 average rating, 107 reviews

Modern House with Private Pool Getaway Kissimmee

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.

Guesthouse in Lake Cherokee

A refreshing pool area is framed by lush tropical plants and features patterned tiles around the edges. Two striped lounge chairs are positioned poolside, facing the water. The charming yellow residence stands in the background, topped with a warm terracotta roof.

4.97 out of 5 average rating, 108 reviews

1926 Spanish Carriage House Lower

Enjoy a shared but private compound resort in the heart of downtown Orlando! Centrally located and within walking distance to major events at the Kia Center, Dr. Phillips Performing Arts Center, restaurants, and downtown nightlife. Park on site, relax and enjoy all that this historic home has to share! Besides a fresh and clean private lodging, you'll enjoy use of the tropical pool, hot tub, gas grill, covered seating and dining area. A washer and dryer are just steps away for your use.

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.

4.88 out of 5 average rating, 104 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

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.

4.9 out of 5 average rating, 133 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!

4.79 out of 5 average rating, 225 reviews

Townhouse in Orlando

12min from Airport and 20min from Parks

🏡 Location, Location, Location! 🏡 All pictures updates as of Mar 2025 Nestled in a safe and vibrant neighborhood, this townhome is just minutes away from top attractions, shopping centers, dining hotspots, and major highways. Whether you’re here for work or leisure, you’ll be close to everything! We pride ourselves on prompt response times and we’re dedicated to making your stay as enjoyable as possible! Unfortunately, we can’t allow parties, smoking, or pets on the premises.

Superhost

A spacious pool area features a crystal-clear pool surrounded by lounge chairs and umbrellas. Lush palm trees provide shade, and a small fence enhances privacy. A gentle slope leads to a shallow section with jets, blending seamlessly into the inviting water.

Home in Orlando

4.86 out of 5 average rating, 207 reviews

Year around Heated Pool 7 min from Airport!

Welcome to Casa Linda Pool! This stylish 3BR, 2.5BA home sleeps 8 and features a private heated pool, fully equipped kitchen, open living space, and an amazing outdoor kitchen with BBQ grill, cooktop, and cooler for your drinks. Just minutes from Orlando Airport, Disney, and Universal. Perfect for families or groups looking to relax and enjoy Florida in comfort. Fast Wi-Fi, A/C, washer/dryer, and free parking included. Book now and enjoy your Orlando getaway!

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.

4.95 out of 5 average rating, 101 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.