Holiday rentals with a pool in Winter Garden

4.99 out of 5 average rating, 124 reviews

Apartment in Orlando

Private Rooftop Suite! No resort fees!

Enjoy a stylish experience at this centrally-located rooftop terrace. Located at the Enclave Suites, this unit features a rooftop terrace with views overlooking Sandy Lake. Recently remodeled, it boasts practical functionality with beautiful design. This unit is everything you need to enjoy a vacation in Orlando. It is centrally located off of International Drive and minutes from Universal Studios, Volcano Bay, SeaWorld, Disney World and much more. Enjoy a luxurious stay without the hefty price.

4.86 out of 5 average rating, 333 reviews

The living room features a grey sofa adorned with decorative pillows, paired with a glass coffee table and a vibrant area rug. The open space leads to a dining area and modern kitchen, highlighted by yellow bar stools at the countertop under soft lighting.

Condo in Orlando

BreathtakingView-1BR/2BA-1 Mile to Disney-Sleeps 5

Located 1 mile to Disney Springs in a Gated-Community A NEWLY REFURBISHED Spacious 1-bedroom, 2-bath Condo in Lakefront luxury @ Blue Heron Beach Resort nestled on shores of 400+ acre Lake Bryan, 2 blocks off I4 @ Lake Buena Vista exit. This luxurious condo overlooks the Pool & Lake Bryan. Sleeps 4 It’s all here! The ultimate Walt Disney World vacation right here at your fingertips! From the best of Disney or Work Travel this property offers the perfect environment to spend a lifelong memory

4.89 out of 5 average rating, 352 reviews

A spacious studio is furnished with a large bed and a blue couch. Elegant decor is highlighted by a chandelier above, while a backdrop of a city skyline adorns one wall. Natural light filters through large windows, creating an open and bright atmosphere.

Apartment in Orlando

Carmen Romantic Studio W/Private Beautiful Terrace

Beautiful Studio!! Amazing private TERRACE!! King side bed. Enjoy the Jacuzzi bathtub!! Our Studio It is located one block from the International Dr. in Orlando city. In the center of everything!!! Universal Studios area. Washing the video on YouTube: https://youtu.be/tJ1QXsomuY8 The resort has 2 open swimming pools and 1 swimming pool with a closed roof with tempered water. Pool hours may change due to COVID Enjoy the Gym and movies in Netflix! This property is not recommended for children’s

4.98 out of 5 average rating, 151 reviews

Home in Minneola

Pool + Heated spa Family friendly King suite Oasis

Welcome to your perfect Florida getaway! This beautifully updated 3-bedroom, 2-bath home in Minneola offers everything you need for a relaxing and fun-filled stay. Whether you're traveling with family, friends, or pets, this home is designed to make you feel right at home. Step outside to your private backyard oasis featuring a sparkling pool, hot tub, and serene views overlooking a peaceful pond. Fire up the grill, unwind under the market lights, or soak up the sun with your favorite drink.

Guesthouse 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.

4.92 out of 5 average rating, 224 reviews

The private splash pool area is enclosed with a safety fence, featuring a paved deck. Lounge chairs provide seating options, while a covered grill area is visible in the corner. Surrounding greenery adds a natural element to the space.

Townhouse in Clermont

2021 construction, Modern home w/ private pool

Your modern oasis awaits! This newly built home features a private splash pool, perfect for relaxing after a thrilling day at the parks, just 20 minutes from Magic Kingdom. Unwind with smart TVs and high-speed Wi-Fi or cook a family meal in the fully equipped kitchen. This space is thoughtfully designed for comfort and style, creating the perfect, sleek retreat for your entire group's Disney adventure. (Note: Pool heat is included! For guest safety, the heater deactivates below 60°F).

4.99 out of 5 average rating, 128 reviews

The living area features a comfortable gray sofa adorned with accent pillows, complemented by a wooden coffee table. A large TV is mounted on the wall, with a stylish chair placed nearby. Natural light enters through glass doors, which lead to a balcony.

Apartment in Kissimmee

Chic Vibes Comfy King Bed Next to Parks/Food/shops

Welcome to our stylish oasis in Kissimmee, which seamlessly blends sophistication with a laid-back vibe. Your stay begins in a professionally cleaned apartment for your full enjoyment. Discover resort-style amenities – a sparkling pool, a fitness center, and hammocks, offering the luxuries of a five-star retreat. Conveniently located with in walking distance of theme parks, restaurants, and shopping. Book now. We can't wait to host you in our little slice of paradise!

4.93 out of 5 average rating, 134 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

Whether you seek relaxation or adventure, this house offers the best of both worlds! Relax in this spacious bungalow with a private courtyard, pool, hot tub, and fire pit! Take a short walk to downtown Clermont and discover the charming shops, restaurants, and breweries! Explore the sights and attractions that Central Florida has to offer! Whether you crave the vibrancy of downtown or the tranquility of your own oasis, this property offers the best of both worlds!

4.9 out of 5 average rating, 118 reviews

The living room features a modern sofa bed with colorful accent pillows, complemented by a stylish geometric accent wall. Natural light streams through the windows, illuminating a cozy area with a patterned rug and a compact coffee table, creating a relaxing space for guests.

Apartment in Kissimmee

Sleek Modern Gateway 10 Min to Parks Pets Allowed

Welcome to Your Magical Gateway – Just 10 Minutes from Orlando's Magical Parks! Location: Perfectly located for Disney and Universal, our apartment offers a peaceful retreat with all the comforts of home. Whether you’re here to explore the magic unwind, or even stay for longer terms, you’ll love every moment of our cozy space. The property sleeps 4 people! PLEASE CONTACT US TO INQUIRY ABOUT ADDITIONAL POTENTIAL DISCOUNTS FOR MULTIPLE DAYS STAY

4.88 out of 5 average rating, 168 reviews

The open living area features a round dining table with four chairs, a wall-mounted TV, and a comfortable sofa. Natural light enters through sliding glass doors leading to a scenic outdoor view. A rustic wood accent wall adds texture to the space.

Condo in Four Corners

"Ocean's Gate" - 2BD/2BA condo near Disney

Welcome to our beautiful ground-level condo! With the prime location at ChampionsGate Resort near Disney World and major parks, this 2BD/2BA condo unit is designed for your best accommodation. Spread out in 1,558 Sq. Ft., the unit offers a fully equipped kitchen, a cozy living room, a working station, and comfortable bedrooms. With access to the Clubhouse and resort amenities, you’ll spend amazing days in our home!

Guesthouse 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!

4.94 out of 5 average rating, 159 reviews

A door with a keypad entry system is shown, leading into the living space. Framed artwork adorns the wall in soft colors, while green curtains frame a nearby window. A glimpse of a bed is visible, covered with a textured blue bedspread.

Guest suite in Kissimmee

It's too much like a elegant mini-hotel (6)

It's too much like a elegant mini hotel with rich artistic atmosphere！ All the pictures on this page are a reflection of the real condition of the house. All the furniture has been carefully selected, and comfortable mattress and pillows will quickly accompany you into sweet dreams. The biggest feature of this house are comfort, economy and convenience.

Popular amenities for Winter Garden rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.82 out of 5 average rating, 107 reviews

A single-story home is viewed from the street, featuring a covered front entrance and a large driveway. Lush green grass surrounds the property, with palm trees and other foliage enhancing the front yard. The home is enclosed by a privacy fence.

Home in Montverde

Private 3-bedroom pool & waterfront home

4.84 out of 5 average rating, 283 reviews

A modern living area features sleek white furniture and a polished tile floor. A coffee table sits atop the floor, and large windows offer views of the pool area. The space is well-lit, showcasing a wall adorned with textured stone.

Home in Orlando

Modern home, w Pool, 5 min from Universal Studios

4.95 out of 5 average rating, 117 reviews

Home in Davenport

Stylish Villa with Free Pool Heat

4.87 out of 5 average rating, 258 reviews

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

3 bedroom Villa in Kissimmee

4.88 out of 5 average rating, 101 reviews

An inviting pool area is visible within a screened enclosure, featuring turquoise water and tile accents. Lounge chairs are arranged nearby, immersed in greenery. Adjacent is a view of a spacious backyard showcasing a custom mini golf course and landscaped areas, all designed for enjoyment.

Home in Orlando

Mini golf course, 1 mile to Universal, Pool

4.86 out of 5 average rating, 142 reviews

An open-concept living area features a modern kitchen with a central island and stainless steel appliances. A comfortable sectional sofa is paired with wooden armchairs, and a round coffee table sits in the center. Large windows bring natural light into the space, enhancing the clean, neutral decor.

Home in Apopka

2-bedroom home with pool near Kings Landings!

4.88 out of 5 average rating, 233 reviews

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.

Home in Orlando

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

4.97 out of 5 average rating, 171 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.

Condo rentals with a pool

4.84 out of 5 average rating, 113 reviews

A modern kitchen is seen, featuring white cabinetry and a speckled granite countertop. Stainless steel appliances, including a microwave and toaster, are positioned conveniently. A small potted plant adds a touch of greenery, while natural light filters in through the window above the sink.

Condo in Winter Park

Lovely Winter Park Home close to Hospitals !

4.89 out of 5 average rating, 125 reviews

A spacious outdoor area features several palm trees and seating arrangements with turquoise cushions. The backdrop includes a modern multi-story building. A barbecue area is visible, and lounge chairs are positioned around a sparkling pool, creating an inviting environment for relaxation.

Condo in Orlando

Luxury Condo On I-Drive & One Mile from Universal

A spacious living room features a modern design with comfortable seating arrangements, including two dark chairs and an accent table. A large smart TV is mounted on the wall, accompanied by decorative plants. Glass doors open to a patio with a view of the outdoors.

4.95 out of 5 average rating, 131 reviews

3150-106 Resort Pool View Disney Universal Orlando

4.87 out of 5 average rating, 112 reviews

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.

Condo in Orlando

5 mins Universal 10 mins Epic park | Rustic LOFT

A spacious living area is designed with light grey sofas and a glass coffee table, surrounded by greenery. Large windows with wooden blinds allow natural light to fill the room, while a ceiling fan enhances airflow. Soft, neutral tones create a relaxing atmosphere.

4.88 out of 5 average rating, 156 reviews

Near Disney/Universal Lovely 2bedroom/2bath Condo

A spacious living area features large windows framed by bright curtains, providing natural light. A cozy bed is adorned with themed decor, and a comfortable sofa complements the surrounding furnishings. An aerial view showcases the resort's heated pool, surrounded by lush landscaping.

4.9 out of 5 average rating, 250 reviews

Disney Oasis by the lake

A patio area is presented under a covered porch, featuring a round table set for two with a white tablecloth and colorful cups. Two comfortable chairs with blue cushions are positioned around the table. A scenic view of a lake with greenery can be seen in the background.

4.83 out of 5 average rating, 144 reviews

Stunning view, near Disney.

Superhost

A resort-style pool area is surrounded by palm trees and lush landscaping, with inviting lounge chairs arranged nearby. The clear water reflects a bright sky, and a separate lounge area with a decorative façade is partially visible in the background.

Condo in Davenport

4.83 out of 5 average rating, 149 reviews

Orlando Spacious 2-Suites & Resort-Style Pool

Other holiday rentals with a pool

4.96 out of 5 average rating, 27 reviews

Apartment in Orlando

*NEW* Villa Amalfi Boho• FreeParksShuttle•PoolView

4.93 out of 5 average rating, 61 reviews

Apartment in Kissimmee

King Bed Apartment, Close to Disney

4.72 out of 5 average rating, 154 reviews

A modern kitchen features stainless steel appliances, including a refrigerator and microwave. A spacious island with bar seating offers two stools, while a dining table is set with blue dishes. Bright, neutral cabinetry provides a fresh atmosphere, complemented by decorative wall art.

Cottage in Clermont

Gorgeous Cottage near Lake Louisa & mins 2 Disney.

Guest suite in College Park

A serene pool area is surrounded by lush greenery and palm trees, providing a private retreat. The pool features clear, sparkling water, with gentle water features creating a calming atmosphere. The adjacent home is showcased with large windows, enhancing the spacious outdoor experience.

5 out of 5 average rating, 49 reviews

Luxury Lake Front Orlando Oasis in College Park!

Superhost

A contemporary living room is showcased, featuring a comfortable sofa and two green chairs. A round dining table with four chairs is positioned nearby. A flat-screen TV is mounted on the wall, displaying a serene outdoor scene. Natural light filters through large glass doors, enhancing the space.

Townhouse in Four Corners

4.94 out of 5 average rating, 50 reviews

Luxury Villa Near Disney and Universal

5 out of 5 average rating, 8 reviews

The exterior of the home is showcased, highlighting a modern facade with light stone accents. Lush palms frame the entrance, while well-maintained greenery lines the walkway leading to the inviting front doors. Windows offer natural light and create a welcoming atmosphere.

Home in Clermont

Magical Orlando Getaway Awaits!

5 out of 5 average rating, 44 reviews

A spacious studio apartment is displayed, featuring a comfortable seating area with a sectional sofa and a glass coffee table. A large television and workspace are visible on opposing walls. The sleeping area, with a large bed, is partially obscured by a line of natural light from the windows.

Guest suite in Apopka

1,000 sqft Apartment on 3 Acres w/ Pool & Balcony