Holiday rentals with a pool in Meadow Woods

5 out of 5 average rating, 121 reviews

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

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

A modern living area features a plush blue sectional sofa complemented by two stylish lounge chairs. A light area rug sits under a chic coffee table, while large sliding glass doors provide a view of the outdoors and allow natural light to enhance the space.

4.92 out of 5 average rating, 199 reviews

3171-206 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!

4.86 out of 5 average rating, 130 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 house in Lake Cherokee

A serene pool area is surrounded by lush tropical greenery, including palm trees and bamboo. A spa is integrated into the pool with a stone wall feature. Chaises with striped cushions are positioned beside the water, and a spacious patio includes various stone pavers.

4.98 out of 5 average rating, 122 reviews

1924 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 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.

4.97 out of 5 average rating, 414 reviews

Waterfront Condo minutes to Disney & 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.

4.98 out of 5 average rating, 464 reviews

Guest suite in Orlando

Sunny Heated Pool Suite • Prime Resort Area

Resort-style vacation with enhanced privacy—you’ve found the perfect place. 🌴 From our family to yours, we welcome you to a modern, stylish, and thoughtfully designed Airbnb guest suite created for comfort and relaxation. Ideally located just minutes from Disney and Universal Studios, this retreat also offers access to a beautiful oasis-style backyard, perfect for unwinding after a day of adventure. We are dedicated to making your stay memorable and look forward to welcoming you back.

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.

4.89 out of 5 average rating, 114 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

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.

4.94 out of 5 average rating, 103 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.

4.8 out of 5 average rating, 232 reviews

A spacious living area features a light blue color scheme with tiled flooring. The room contains various seating options, including patterned cushions and a large wall art piece. A staircase leads to the upper level, while a dining area is visible in the background.

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.

4.95 out of 5 average rating, 363 reviews

A light blue tiny house features a welcoming front porch with white railings and stairs leading to the entrance. The exterior is complemented by a clean driveway and soft landscaping in the surrounding area. Nearby, another tiny house in yellow adds to the charming setting.

Tiny home in Kissimmee

Blue Bungalow Tiny House near all Attractions!!

Our Tiny House in Mill Creek RV Resort is minutes away from Disney, Universal, Sea World & most area attractions. Our cozy cottage has a private bedroom, full kitchen, large island, living room, bathroom, free washer/dryer, and the perfect front porch. There is a private drive and free parking. The resort is peaceful with plenty of amenities! We have four tiny house cottages - please check us out on our profile page — http://airbnb.com/users/132701751/listings

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, 106 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 house in Lake Eola Heights

A serene pool area features a vibrant red pool float resting in the clear water, surrounded by lush greenery. Comfortable outdoor seating is arranged near the pool, with large umbrellas providing shade. The backdrop showcases a charming pool house with multiple glass doors, inviting natural light.

5 out of 5 average rating, 268 reviews

Livingston Pool House- In The Heart of Downtown

Welcome to the Pool House! Our newly renovated detached pool house is located in the heart of downtown Orlando, in the Lake Eola Heights Historic District. We are two blocks to beautiful Lake Eola and all the dining and entertainment that Orlando has to offer. The Pool House has everything you need for a relaxing time at home, yet all the entertainment at your finger tips! Downtown living with a tropical escape!

Popular amenities for Meadow Woods rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A private heated pool is surrounded by a screened enclosure, featuring a brightly colored tiled edge. Sun loungers are positioned nearby, offering a relaxing space to unwind. A covered BBQ grill is accessible on the patio, creating an inviting setting for outdoor gatherings.

4.92 out of 5 average rating, 104 reviews

3BR / 2BR Heated Pool Home 7 Min to Disney |

A serene pool area is surrounded by lush landscaping and tall palm trees, with sunlight glistening on the clear water. The pool features a gentle curve, and a white fence encloses the backyard, providing privacy and a sense of tranquility.

4.87 out of 5 average rating, 155 reviews

3 BR/2BA Home w Private Pool~12 min to Airport!

A modern living area features a comfortable sofa in neutral tones alongside two vibrant orange chairs. A round glass coffee table is positioned in front of the sofa, while a large television is mounted on a wooden accent wall. Floor-to-ceiling windows allow natural light to fill the space.

4.97 out of 5 average rating, 101 reviews

Modern 4bdr Storey Lake w/themed rooms near disney

A screened-in patio features a heated pool surrounded by concrete flooring. Colorful inflatables are present in the water, with a rainbow umbrella positioned nearby. Lush greenery and residential buildings are visible in the background under a clear blue sky.

4.85 out of 5 average rating, 120 reviews

New Listing! Casita Bonita Pool House

A large, inviting pool glistens under the sun, surrounded by a spacious patio and palm trees. A stylish, shaded cabana is positioned nearby, offering a retreat for relaxation. The pool area is enclosed and features a clean white fence, enhancing the tranquil outdoor atmosphere.

4.88 out of 5 average rating, 232 reviews

Pool-Jacuzzi & Palm Trees/ 8 Universal/ 15 Disney

A sparkling pool is surrounded by a paved patio, featuring several lounge chairs with blue cushions. Large umbrellas provide shade for relaxation. Lush greenery is visible in the background, enhancing the outdoor setting.

4.86 out of 5 average rating, 222 reviews

Year around Heated Pool 7 min from Airport!

4.99 out of 5 average rating, 142 reviews

Disney Retreat | BBQ, King Bed, Pool, Game Room +

A spacious pool area is enclosed by a screened gazebo, providing a view of the calm lake at sunset. The water reflects the warm colors of the sky, while tropical plants add greenery to the surroundings.

4.81 out of 5 average rating, 172 reviews

Beautiful private home with pool on the lake

Apartment rentals with a pool

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.

4.91 out of 5 average rating, 178 reviews

NEW APARTMENT WITH WATER PARK AND NEAR DISNEY

An aerial view of the clubhouse area is displayed, featuring a large pool surrounded by lounge chairs. Palm trees provide greenery around the poolside, while guests can be seen enjoying the water. The architecture of the clubhouse complements the inviting outdoor space.

4.92 out of 5 average rating, 131 reviews

Location,Location 3bd 2bth near parks conv.ct/Int.

A warm living space features a dark wooden ceiling and an accent wall with textured concrete. Comfortable seating faces a mounted television, while wooden shelves are adorned with books and decorative plants. Natural light enters through large windows, enhancing the inviting atmosphere.

4.86 out of 5 average rating, 111 reviews

5 mins Universal 10 mins Epic park | Rustic LOFT

A vibrant living area features a Super Mario-themed mural depicting iconic characters against a blue backdrop. Plush seating surrounds a coffee table styled with bright colors, while a playful rug showcases a character from the Mario universe, creating a fun and inviting atmosphere for relaxation and gaming.

4.95 out of 5 average rating, 151 reviews

Super Mario's Sky Suite - Epic Universe 3 BD SUITE

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.

4.95 out of 5 average rating, 115 reviews

Modern Lake view Condo 1 mile from Disney

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.

4.96 out of 5 average rating, 154 reviews

Luxurious Spot 10 Mins Away to Most Attractions!!!

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.

4.91 out of 5 average rating, 136 reviews

Modern Condo with Lake View Near Disney 3151

An aerial view of a community pool area features a curvilinear swimming pool surrounded by lounge chairs and shaded seating areas. A hot tub is located adjacent to the pool, surrounded by lush landscaping and palm trees. The clubhouse is visible, contributing to the inviting atmosphere.

4.89 out of 5 average rating, 280 reviews

Marvelous apartment near Disney first floor

Other holiday rentals with a pool

A modern two-story house is showcased, featuring a bright exterior and a spacious driveway. Lush green grass surrounds the property, while palm trees add a tropical touch. Large windows on the upper level allow for ample natural light, highlighting the clean lines of the architecture.

4.89 out of 5 average rating, 88 reviews

Villa Resort Club

Superhost

5 out of 5 average rating, 3 reviews

Pool Home Getaway Near Airport

4.92 out of 5 average rating, 37 reviews

Flat in Kissimmee

Your Dream Apartment Stay

4.92 out of 5 average rating, 12 reviews

Modern 3BR Home w/ Pool, near Disney & Universal

4.93 out of 5 average rating, 84 reviews

A cozy private home is framed by a well-maintained porch with white railings and steps leading to a concrete pathway. The exterior is clad in light yellow siding, with large windows allowing natural light to enter. Nearby, another residence and a parking area are visible.

Tiny home in Kissimmee

Tiny Home GetAWay, near the Parks!

An open-concept living area features a large sectional sofa in soft gray, arranged around a circular coffee table. A contemporary fireplace is integrated into the wall, providing a focal point. Glass doors lead to the outdoor pool area, enhancing natural light throughout the space.

5 out of 5 average rating, 53 reviews

Luxury Home w/ Pool & 6 Beds near Disney

4.96 out of 5 average rating, 23 reviews

A modern kitchen features dark cabinetry with gold accents. An island offers two bar stools, while a farmhouse sink and stainless steel appliances are prominently displayed. Warm lighting highlights the white backsplash and countertop, contrasting with the wood-tone flooring.

Guest house in Orlando

Boutique Suite in Orlando