
Vacation rentals with a pool in Winter Garden
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Winter Garden
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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

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.

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.

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.

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.

Close to Disney and Retail Therapy
Our condo is located at Resort-Style community (with No Resort FEES and FREE Parking) with a beautiful clubhouse featuring a game room, gathering rooms, fitness center and outside, a tranquil free-form heated pool with plenty of deck chairs for all the vacationers. This resort features a second pool, golf cage, tennis, basketball and volleyball courts, a playground, car wash area, picnic pavilions and grills, and scenic walking trails around landscaped wooded areas, fountains and ponds.

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!

Modern Retreat close to Disney - King Beds, Pool
Description "A Beautiful Modern Townhome with its own Pool A Spectacular High End Interior about 25 minutes from Magic Kingdom." Our home offers some absolutely stunning accommodation that include the added advantage of a mini private pool. - 3 Bedrooms, 3 Full Bathrooms. - Free WiFi - Fully Equipped Kitchen - Smart TVs in each Bedroom - Towels, Soap and Shampoo available - Free Parking - Community Pool - Community Gym - Community Game Room

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!

Spacious Apartment near Disney
Welcome to our cozy and inviting apartment in the heart of The Loop, Kissimmee! Ideally located for both convenience and comfort, this charming space is perfect for couples, solo travelers, business professionals, and those looking for extended stays. Whether you're here for a magical Disney vacation, a work trip, or a romantic escape, our apartment offers the perfect home away from home for all your adventures.

Luxury 3 bdr townhome 12 miles to Disney
Relax and enjoy a peaceful vacation with family and friends at our beautiful Contact Free Check In townhome . This exceptional 3 bedroom, 3 bathroom with private pool, townhome is splendid for families or groups up to 8 guests. Located in Clermont FL, with just short drive away from Magic Kingdom, Epcot, Animal Kingdom, Hollywood Studios, Disney Springs, Universal Studios, Sea World, and more.

Lakeside Boho Bliss: The BohoBay
✨ Welcome to Bohobay ✨ Your cozy little hideaway just minutes from the magic of Disney and all the excitement Orlando has to offer. Tucked right by a peaceful lake, mornings here start with coffee and glittering water views, and evenings are made for a glass of wine with sunset vibes. 🌅 It’s the perfect blend of fun-filled days out and calm, soul-soothing nights in.
Popular amenities for Winter Garden rentals with a pool
House rentals with a pool

Hook's Cabin- Lake & Pool near Disney A-frame

Mickey's Lakefront Villa at Sunset Lakes

3 bedroom Villa in Kissimmee

Shadow Bay Luxe / Private Pool Near Universal

3,000 Sqft Historic Home With Pool Near Everything

LARNE LODGE House with Hot Tub 3 miles to Disney!

Epcot Themed Home: Private Sunset Near Disney

Luxury Encore Pool Spa Pets Game Rm Theater Gym
Condo rentals with a pool

Beautiful Beach Style Condo minutes from Disney

3161-305 Resort Lake View Disney Universal Orlando

Luxury 3 Bedroom Home at ChampionsGate Golf Resort

Chic Disney Condo w/ Resort, Pool & Near Parks

Modern Lake view Condo 1 mile from Disney

207_ Sparkle Apartment Close to Disney Free Waterp

Lakefront Studio •Private Terrace• near Universal

Fireworks Penthouse: Top Floor, Star Wars, 2 Pools
Home rentals with a private pool

Wr001or (1stfororlando)

Disney's Championsgate: Private Pool & Arcade Fun!

7547oml-Solterra Resort

1116chd-The Retreat at Championsgate

115ep- West Haven

Airy, Stylish Home with Pool Heat Included in Davenport

Visit Disney World from a Sunny Home with a Pool

Champions Gate
Quick stats about vacation rentals with a pool in Winter Garden
Total vacation rentals
Explore 20 vacation rentals in Winter Garden
Verified guest reviews
Over 130 verified reviews to help you choose
Family-friendly vacation rentals
10 properties offer extra space and kid-friendly amenities
Wifi availability
20 of Winter Garden vacation rentals include wifi access
Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Winter Garden rentals
4.9 Average rating
Winter Garden stays are highly rated by guests—averaging 4.9 out of 5!
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- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Universal's Volcano Bay
- SeaWorld Orlando
- Disney Springs
- Discovery Cove
- Old Town Kissimmee
- Disney's Animal Kingdom Theme Park
- Magic Kingdom Park
- Epcot
- ESPN Wide World of Sports
- Amway Center
- Reunion Resort Golf Courses - Palmer & Watson
- Walt Disney World Resort Golf
- Aquatica
- Island H2O Water Park
- Disney's Hollywood Studios
- ICON Park
- Southern Dunes Golf and Country Club
- ChampionsGate Golf Club
- Kissimmee Lakefront Park
- Universal's Islands of Adventure
- Ventura Country Club