Vacation rentals with a pool in Winter Garden

4.97 out of 5 average rating, 123 reviews

A heated pool surrounded by lush greenery features a stone ledge and a small waterfall. Hammocks are placed for relaxation. The screened patio allows for unobstructed views of the sunset, creating a tranquil setting. Warm lighting highlights the natural textures of the landscape.

Home in Lake Formosa

Spacious Home with Pool & Hot Tub near Downtown

Nestled in one of the most coveted neighborhoods near Downtown Orlando (Ivanhoe Village), you'll be within a 5-min walk to tons of restaurants, bars, breweries, and boutique shops. Boasting a heated pool, hot tub, tiki bar, patio area w/seating & two living areas -you'll have ample room to play, entertain or relax in your Tropical Oasis! ☀ Harry P. Leu Gardens – 4 mins ☀ Orlando Museum of Art – 4 mins ☀ Universal Studios – 19 mins ☀ Walt Disney World – 24 mins ☀ The Mall at Millenia – 16 mins

Apartment in Winter Garden

A resort-style pool is framed by lush palm trees and neatly arranged lounge chairs. The tranquil water features gentle fountains, while a spacious building stands in the background, showcasing balconies with views of the inviting pool area.

5 out of 5 average rating, 75 reviews

Comfy King Bed Serenity Vibes 12 Min to Parks/Golf

Find peace at Boho Serenity Sanctuary! This professionally cleaned retreat, just 7 minutes to the parks, offers a calming escape. Step inside to a curated space blending eclectic boho styles creating a unique and relaxing atmosphere. We've provided everything for your comfort and enjoyment. Dive into the pool, unwind with games, or hit the gym nearby. Our prime location is minutes from theme parks, restaurants, shopping, and golf courses. Come experience serenity with a touch of boho charm.

A well-lit pool area is featured, showcasing a curved swimming pool with clear blue water. Surrounding amenities include several lounge chairs and palm trees. The building in the background contains multiple balconies, reflecting warm light from the interior.

4.88 out of 5 average rating, 233 reviews

Maria Luz Studio-Huge Terrace/Universal area.

We are sure that you will fall in love with our STUDIO!! Beautiful, Romantic and incredible lake view Studio!! King side bed and sofabed. Enjoy a LARGE PRIVATE TERRACE. Enjoy the jacuzzi bathtub inside the bathtub. Our Studio is located one block from the famous International Dr. In Orlando City. In the center of everything!! Universal Studio’s area. FREE PARKING. -Universal Studio 8 minutes by car -Disney park’s 10 to 15 minutes by car. Airport 15 minutes by car. -Seaworld Park’s 8 minutes.

4.97 out of 5 average rating, 110 reviews

A refreshing pool with stone borders is surrounded by lush greenery and shaded by a blue canopy. Comfortable seating for two is visible, along with a hammock, creating a serene outdoor space ideal for relaxation.

Guest suite in Longwood

"Winnie's Place" A Peaceful Guesthouse with Pool.

Share the backyard and NON Heated Pool with your hosts if we are home. Between Disney & the beaches. 12 years & older only. Sofa extends to a single bed. Minutes from I-4 makes commuting easy. NOT a heated pool. Wheelchairs are fine. Driveway Entry gate 39"- Breezeway to Ramp entrance 32"- Slider Entrance 33"-Bedroom door 35"-Shower (no step) 35"-Laundry 32"-Closet 35"-Queen bed 31". We are not Handicap Certified but most wheelchair guests do not have issues. Grab bars in the bathroom.

Apartment in Winter Garden

A stylish living area features a large, gray sectional sofa accompanied by two teal chairs. A coffee table with decorative items is centered on a soft area rug. Natural light enters through two large windows, complemented by flowing curtains. A wall adorned with tropical leaves adds a vibrant touch.

5 out of 5 average rating, 12 reviews

Emerald Grove - Close to Disney

2 Bedroom | 2 Bath | Prime Winter Garden Location | Near Disney & Universal Nestled in the heart of charming Winter Garden, this beautifully designed 2-bedroom, 2-bath apartment offers the perfect blend of modern luxury and small-town charm — just 20 minutes from Walt Disney World and Orlando’s top attractions. Located on the iconic Plant Street, you’ll be steps away from historic downtown Winter Garden, home to popular restaurants, boutiques, coffee shops, and the famous West Orange Trail.

Guesthouse in Deer Island

A screened patio area is shown, featuring a private pool surrounded by an expansive deck. Comfortable seating arrangements are visible, along with lush plants and natural light streaming in from large windows overlooking the wooded landscape.

4.95 out of 5 average rating, 120 reviews

Sapphire Cottage - sleeps 6, on 5 acres with canal

On 5 beautiful wooded acres with a boat dock on the canal. Relax by the shared pool, enjoy a BBQ by the firepit, fish from the boat dock, enjoy nature, or simply read a book in the gazebo. Sapphire Cottage has a Master with a queen size bed, a fully equipped kitchen, 2 full size sofa-beds, dinning area for 6, and a full size bathroom. Whether you are looking to relax, enjoy the farm animals, or a bit of adventure we have the perfect location. We live in the main house across the cottage.

4.96 out of 5 average rating, 346 reviews

A tranquil pool area is surrounded by a screened enclosure, showcasing a crystal-clear saltwater pool. Comfortable lounge chairs are positioned near the water, and lush greenery, including ferns and tropical plants, enhances the serene setting.

Guest suite in Lake Mary

Stylish & spa like Getaway - peaceful garden suite

Relax and unwind from your busy life in this serene and quiet getaway. We are located 5 minutes to shopping and dining in downtown Lake Mary in a beautiful and safe neighborhood. Enjoy the solar heated saltwater pool and the comfy outdoor lounge area, Enjoy the backyard with its mature trees and tropical flowers. The indoors come with a luxury and modern wellness bathroom. Soak in the oversized tub or reenergize in the stylish rainfall shower with inbuilt bench and mood lighting.

The master bedroom suite is spacious and features a king size bed adorned with blue and white accents. Two lamps are positioned on each side of the bed, with artwork displayed above. Natural light enters through the window, and a private bathroom can be seen through the open door.

4.96 out of 5 average rating, 181 reviews

Luxury 2B2B APT Near Convention Center, Universal

*Location: On Universal BLVD, right next to International Dr Driving: 2 Min to Orange County Convention Center 7 Min to Sea World 12 Min to Universal Studio 15 Min to MCO airport 18 Min to Disney World Luxury 2b2b APT: (Designed by Danna) 1800 sqft, 2 King beds free community parking, gated community Access to community swimming pool, gym, sports court Free private wifi + spectrum cable TV We provide all supplies including towels, kitchen ware, cleaning supplies, shower supply

Guest suite in Lake Underhill

A private outdoor area is showcased, featuring a sparkling pool accompanied by a hot tub. Lush greenery and colorful plants surround the space, while comfortable seating options, including bright blue chairs, invite relaxation. A pergola provides shade, enhancing the tranquil atmosphere.

4.92 out of 5 average rating, 377 reviews

Downtown Orlando Garden Retreat

This space is a mother-in-law suite, completely private from the main house, accessible through a private entrance outside and entering through the garage. THIS IS NOT THE ENTIRE HOUSE! There is a queen size bed... perfect for a couples getaway! It is conveniently located about 15 min. from OIA and 5 min. from downtown Orlando. There is a beautiful pool and hot tub with stunning sunset views of across the lake... so peaceful and you feel like you are in a resort

4.92 out of 5 average rating, 103 reviews

The outdoor swimming pool is surrounded by palm trees and lounge chairs, providing a refreshing oasis. Umbrellas are positioned beside the pool, casting shade on the paver stone deck. The clear blue sky enhances the tranquil atmosphere of the resort-like setting.

Condo in Winter Garden

Spacious Condo 15min to Disney with private patio!

Spacious 3 bedrooms condo with outdoor dining and hanging out area located at the Palisades Condominiums in Winter Garden Conveniently located on the luxurious west side of Disney, just a 15-20 mins drive to Disney parks, close to other major theme parks, restaurants and supermarkets. This luxury condo is spacious, modern, and has everything that you'll need for your stay! The kitchen is fully equipped to prepare your meals and enjoy it on your private balcony

5 out of 5 average rating, 461 reviews

A private outdoor area is presented, featuring a clear swimming pool with a jacuzzi and steps leading up to a spacious deck. Vibrant greenery surrounds the space, and a rainbow flag adds a welcoming touch. Large windows reflect natural light, creating an inviting ambiance.

Guest suite in Orlando

LAKEFRONT STUDIO APARTMENT (private entrance)

This studio apartment is located in the lower level of our home and is perfect for one or two people. It has a private entrance, a king bed, overlooks the pool and the lake with views of downtown Orlando. Please note there is no kitchen, but there is a wetbar with microwave and mini fridge. In addition to the indoor shower, there is also a outdoor shower and a dock with canoe. Please also note the inside ceiling height is lower than average at 6'3”.

4.9 out of 5 average rating, 113 reviews

Cottage in Clermont

Beautiful country house

Take the whole family to this fantastic place with many areas for fun. we have 5 acres of land just for you, beautiful country house in the only hills of the state of Florida, you will enjoy the tranquility, privacy, connection with nature and witness a beautiful sunset unparalleled, stay and observe the stars, spaces suitable for unique souvenir photos. Ideal area for cycling and walking. NOTE: if you want an event check our rates first

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Villas

Luxurious estates for the ultimate escape

Popular amenities for Winter Garden rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

Superhost

A screened-in patio area features a private pool surrounded by a spacious deck. Sunlight reflects off the water, and greenery is visible beyond the enclosure. The entrance to the home is easily accessible from this outdoor area.

Home in Montverde

4.82 out of 5 average rating, 100 reviews

Private 3-bedroom pool & waterfront home

4.92 out of 5 average rating, 117 reviews

A circular fire pit area is surrounded by six blue adirondack chairs, set on a stone patio. Lush greenery and colorful plants frame the space, with a view of the house and pool area in the background. Sunlight brightens the inviting outdoor gathering spot.

Home in Clermont

Spacious Bungalow with Private Pool and Courtyard

4.98 out of 5 average rating, 100 reviews

A spacious outdoor area features a private pool, inviting lounge chairs, and a submerged spa with views of the serene lake. The pool area is enclosed with a screened canopy, allowing for an abundance of natural light and protection from insects. Lush greenery surrounds the space.

Home in Kissimmee

Mickey's Lakefront Villa at Sunset Lakes

4.98 out of 5 average rating, 132 reviews

A sparkling pool is surrounded by a screened enclosure, featuring a yellow floating toy. A soothing spa area with bubbling jets is visible, with lush greenery framing the scene. A shaded area with an umbrella is included, providing a relaxing retreat.

Home in Minneola

Pool + Heated spa Family friendly King suite Oasis

4.99 out of 5 average rating, 133 reviews

Home in Four Corners

*Luxurious Paradise Mansion: Pool, Spa & Cinema

4.97 out of 5 average rating, 119 reviews

The private pool is surrounded by lush greenery and features a gentle waterfall cascading into the water. Colorful plants line the edge, offering a tranquil environment for relaxation. The clear blue water is inviting and complements the serene outdoor setting.

Home in Clarcona

BBQ Grill | Wi-Fi | Pool Access | 20 Min Disney

4.88 out of 5 average rating, 153 reviews

A screened patio surrounds a refreshing pool, featuring a slide and a small swimming area. Several blue chairs surround a table, offering a space for outdoor dining. Lush trees provide a natural backdrop, enhancing the tranquil outdoor setting.

Home in Apopka

Country Pool home on 2 acres-30 minutes to Disney

4.93 out of 5 average rating, 112 reviews

A collage of themed rooms showcases distinct styles. The first features a cozy bed surrounded by stacked books, evoking a literary atmosphere. The second room has a celestial mural and plush bedding. The third room offers a whimsical sky design above a bright bed, and the fourth presents elegant decor with soft tones and a chandelier.

Home in Four Corners

Harry Potter Themed | Theater & Resort Perks!

Show all

Condo rentals with a pool

An outdoor pool is set within a landscaped area, surrounded by lounge chairs arranged under palm trees. The clear water reflects the blue sky, and the building features a multi-story design with several balconies visible in the background.

4.9 out of 5 average rating, 226 reviews

Deluxe studio near Epic & Universal, free parking

4.99 out of 5 average rating, 125 reviews

A whimsical bedroom features two beds adorned with white linens and vibrant red throw blankets displaying Mickey Mouse. A large Mickey-shaped decor piece is showcased on the wall, with cheerful lighting and a stuffed Mickey Mouse plush sitting on one bed.

Condo in Four Corners

The Mouse Pad: Luxury Condo near Walt Disney World

A spacious outdoor pool is surrounded by lounge chairs and lush greenery, set against the backdrop of a multi-story building. Clear blue water reflects the sky, creating a calm and inviting setting for relaxation.

4.9 out of 5 average rating, 136 reviews

Studio near Universal & Epic, + Netflix, +parking

4.93 out of 5 average rating, 118 reviews

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

The living area is furnished with a blue couch adorned with patterned pillows. Two matching wooden side tables with lamps provide soft lighting, while a wooden coffee table sits in the center. A decorative wall piece featuring palm trees adds a touch of character to the room.

5 out of 5 average rating, 145 reviews

Disney & Epic Free Shuttle, Kitchen

A circular seating area is featured, surrounded by vibrant turquoise chairs set around a central fire pit. Lush palm trees and colorful landscaping enhance the outdoor space, with a gazebo visible in the background under a partly cloudy sky.

4.93 out of 5 average rating, 496 reviews

Cozy Cay 2BR 4beds *low cleaning fee for May

A modern kitchen and dining area showcase sleek black cabinetry and stainless steel appliances. A wooden dining table is set for six, featuring turquoise accents. Natural light floods the space, illuminating the open layout and inviting atmosphere for meal preparation and enjoyment.

4.91 out of 5 average rating, 161 reviews

VCR4-410 4th Floor Deluxe Condo Convention Center