Vacation rentals with a pool in Winter Garden

4.97 out of 5 average rating, 121 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 Orlando

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

4.88 out of 5 average rating, 562 reviews

A private pool features a natural rock waterfall, surrounded by a paved patio. Lush greenery and trees provide shade, while a secure black fence encloses the area. Large windows of an adjacent building suggest inviting indoor spaces nearby, contributing to a tranquil outdoor setting.

Bungalow in Maitland

Maitland-Orlando Area, FL. Pool House Bungalow

Large open space adjacent to a beautiful pool, waterfall, and fantastic lake view. 27 miles to Disney World, close to Park Avenue, local hospitals, Universities, and less than an hour to local beaches. Only 18 miles to MCO-Orlando International Airport. Great shopping within 3 miles. Location is secluded with large trees, lakeside, and adjacent to the commuter train track. The train runs by on regular basis. Please note in the pictures the pool creates the ambiance to make your stay complete.

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, 69 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.

4.91 out of 5 average rating, 181 reviews

The pool area features a screened lanai with two lounging chairs and conversational seating. A soaking pool with jets is visible, offering a relaxing space. The backdrop includes a serene view of nature through the screens, enhancing the atmosphere of tranquility.

Townhouse in Clermont

Close to Disney! Modern home w/ soaking pool.

Located in a quiet eco-friendly community surrounded by nature, this two-floor end row townhouse offers close proximity to Disney Animal Kingdom (10 miles) and Walmart Supercenter (2 miles) as well as a huge number of dining options. After long days at theme parks or sight seeing, this home will help you take the stress away with its cozy soaking pool and relaxing nature view. Each bedroom has own bathroom! Please see the pictures and captions as well as continue reading below to learn more!

4.92 out of 5 average rating, 99 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

4.9 out of 5 average rating, 112 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

5 out of 5 average rating, 249 reviews

A private pool area reveals clear water surrounded by lounge chairs and tropical landscaping. An umbrella provides shade over the seating area, while a grill and bar are positioned nearby under string lights, creating a relaxing outdoor environment.

Guesthouse in Orlando

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!

Apartment in Winter Garden

The resort-style pool area features a large swimming pool with tanning ledges, surrounded by lounge chairs and tropical palm trees. The building's modern architecture is visible in the background, with multiple floors of well-lit balconies creating a welcoming atmosphere.

4.95 out of 5 average rating, 44 reviews

Pet-Friendly, King Bed, 15 Min to Parks, Amenities

Welcome to our Modern 1-Bedroom, 1-Bathroom Apartment in Winter Garden, FL! This stylish and cozy apartment is the perfect home base for your Florida getaway, offering a relaxing atmosphere and convenient access to nearby theme parks, shopping, and dining. Enjoy resort-style amenities and a comfortable stay in the charming Winter Garden area. Please reach out for any potential multi-day discounts available.

4.93 out of 5 average rating, 214 reviews

A vibrant flower pot sits on a patio table, showcasing colorful blooms. The background features a blue swimming pool surrounded by lush palm trees and greenery. Sunlight brightens the outdoor space, inviting relaxation by the water.

Guest suite in Orlando

Flor de María beautiful and relaxing GUEST ROOM ☘️☘️

Nice and relaxed Guest room with King side bed!! Our beautiful studio is attached to our house. With entrance and bathroom private. Parking included. You can enjoy areas like pool, grill and fireplace (These areas are shared) Our Space is only for 2 adults. Sorry!!! We not accepting kid’s, baby’s or pest. We are sure!!! You will love our place!!! We offer faster WiFi and Nexflix!!!

4.77 out of 5 average rating, 126 reviews

Condo in Kissimmee

1-101 Legacy Dunes, Gym, Tennis, Close To Disney!

One Bedroom Apartment 1 King Sized Bed 1 Queen Sized Sleeper Sofa Bed Sleeps up to 4 Guests One Full Bathroom Ground Floor, No Stairs Fully Equipped Kitchen Living Room with Dining Area Close to Shopping and Restaurants Screened Patio Free Washer and Dryer Free Wi-Fi Free Parking Roku TV's Heated Outdoor Swimming Pool Lighted Tennis Court Children's Playground Game Room Gym

4.96 out of 5 average rating, 136 reviews

A gold keypad lock is mounted on a white door frame, with the blurred outline of a spacious sleeping area behind it. Soft lighting from a nearby table lamp casts a warm glow, while green curtains hang in the background.

Guest suite in Kissimmee

It's too much like a elegant mini-hotel (3)

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.

4.89 out of 5 average rating, 147 reviews

An outdoor screened area surrounds a private pool and jacuzzi, creating a serene atmosphere. The pool features a curved shape and is complemented by a paved border. Surrounding greenery is visible through the screens, offering a natural backdrop.

Home in Delaney Park

3,000 Sqft Historic Home With Pool Near Everything

Welcome to Delaney Park, where the city life meets history! This Spanish Mission, 1920’s home is sure to provide you with a unique experience. Our quiet neighborhood is surrounded by ancient oak trees, lakes and walk-able parks. Make yourself at home here, where you’ll be surrounded by a variety of plants and the use of biophilic design.

Vacation rentals for every style

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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

4.81 out of 5 average rating, 97 reviews

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

Private 3-bedroom pool & waterfront home

4.93 out of 5 average rating, 15 reviews

Home in Clermont

Gorgeous Island Estate- 10 BR in 2 Guest Houses

4.92 out of 5 average rating, 113 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

4.86 out of 5 average rating, 123 reviews

A sparkling pool is surrounded by lush greenery and palm trees, with a peaceful lounging area featuring a double canopy bed nearby. Soft blue waters reflect the clear sky, and a patio area with seating offers a comfortable space for relaxation.

Home in Maitland

Bonheur Ala Maison

4.98 out of 5 average rating, 130 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, 130 reviews

Home in Four Corners

*Luxurious Paradise Mansion: Pool, Spa & Cinema

5 out of 5 average rating, 86 reviews

The recreation area is designed with vibrant blue lighting and themed decor. It features a pool table, arcade games, and a commercial air hockey table. The walls are adorned with popular character themes, including Super Mario and Avengers, creating an engaging and playful atmosphere.

Home in Kissimmee

Dream Vacation w/Avengers, Star Wars, & Mario Kart

4.96 out of 5 average rating, 114 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 Ocoee

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

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Condo rentals with a pool

4.98 out of 5 average rating, 180 reviews

A family-friendly living area is presented with a large, comfortable sectional sofa facing a flat-screen TV. Adjacent, a vibrant children's bedroom features a whimsical Moana theme with a sandy beach mural, complemented by a canopy bed adorned with tropical accents. The ceiling displays playful elements, enhancing the kid-friendly atmosphere.

Condo in Kissimmee

303_To Infinity & the Ocean Breeze Apartment

The open living space features a well-equipped kitchen with modern cabinetry and stainless-steel appliances. A dining table with white chairs is positioned near a window, while a sofa bed is located in the living area. Soft lighting is provided by a stylish ceiling fixture.

4.88 out of 5 average rating, 130 reviews

Suites at Lake Buena Vista close Disney Spring

The living area features a spacious gray sectional sofa accompanied by a bright blue chair. A modern wooden TV stand holds a flat-screen television. Natural light filters through large windows adorned with light curtains, complementing the neutral color palette.

4.94 out of 5 average rating, 148 reviews

VCR2-108 Deluxe New Apartment - Convention Center

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, 143 reviews

Disney & Epic Free Shuttle, Kitchen

4.98 out of 5 average rating, 180 reviews

Lakefront Resort Condo near Disney & Universal

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

4.94 out of 5 average rating, 354 reviews

A serene swimming pool area is surrounded by palm trees and lush landscaping. The pool features a rock formation and a gradual entry, with lounge chairs placed along the water's edge, inviting relaxation. The clubhouse is visible in the background, showcasing a Mediterranean-style architecture.

Condo in Kissimmee

Disney World Condo w/ Full Kitchen, Balcony & Pool

4.96 out of 5 average rating, 112 reviews

An inviting outdoor pool is surrounded by palm trees and lounge chairs. The pool features a clear blue surface reflecting the sunlight, while a tall building with balconies stands in the background. A peaceful atmosphere is created by the landscaped surroundings.

Condo in Florida Center

Lovely studio near Universal

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Home rentals with a private pool

A themed bedroom featuring a spacious bed with white bedding, set against a vivid space-themed mural. Two modern nightstands are flanked by unique lamps, and a large window allows natural light to illuminate the room while offering a view of the outdoors.

Villa in Four Corners

4.33 out of 5 average rating, 3 reviews

Disney's Championsgate: Private Pool & Arcade Fun!

4.78 out of 5 average rating, 9 reviews

An open-concept kitchen and dining area features a large island with seating for four, illuminated by pendant lights. Light-colored cabinetry and modern appliances complement the clean design. Arched doorways lead to the entrance, where natural light brightens the space from the large front door.

Home in Haines City

Minniehaha Castle Retreat

A spacious living area is presented, featuring a gray sectional sofa facing a glass coffee table on a soft rug. Large windows provide natural light and views of the outdoor space. The kitchen area, with modern appliances and bar seating for four, is adjacent to a dining table for six.

Home in Davenport

Gorgeous 9bd (sleeps 24) In the Solterra Resort!

4.95 out of 5 average rating, 115 reviews

Home in Davenport

Airy, Stylish Home with Pool Heat Included in Davenport

Villa in Kissimmee

4.79 out of 5 average rating, 252 reviews

Visit Disney World from a Sunny Home with a Pool

4.92 out of 5 average rating, 50 reviews

Villa in Kissimmee

Family Retreat Near Disney with Pool & Hot Tub!