
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.

Unique Spacious Home w/ Pool near Downtown Orlando
Nestled on a quiet street, 15 mins from Downtown Orlando. This home has a massive pool, hot tub, water fountain, real outdoor and indoor fire place, outdoor patio area w/seating. The Kitchen is equipped with everything you need to make delicious meals, and there are two living areas to provide ample space for relaxation. There is also a designated office area to take work calls. ☀ College Park – 10 mins ☀ Downtown Orlando – 15 mins ☀ Universal Studios – 28 mins ☀ Walt Disney World – 34 mins

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.

Private Pool & Free Heat - Close to Disney!
3 bed, 3 bath luxury villa in exclusive gated community 10 mins from Disney. Private pool & hot tub with free heat not overlooked by other homes. Main rooms open onto pool. Kitchen with granite counter tops. Outside bar, loungers, table & chairs. Master bedroom with double sink ensuite and twin with ensuite shower room. Queen is separate to main house providing additional privacy when travelling with friends/family. 32 inch tv's and comfortable beds with pillow top mattresses in all bedrooms

3176-301 Resort 2BR Apt by Disney World Orlando
Just minutes from DISNEY WORLD ORLANDO FLORIDA, fully renovated 2bed/2bath & fully equipped apartment for up to 6 guests, located in the family friendly Secret Lake Resort. Master suite has a KING bed & 65" Smart TV. Second bedroom has 2 Full beds and a 40" Smart TV. The open floor plan blends Kitchen, Dining and Living room with a 70" Smart TV. Close to Parks, Margarita Ville Water Park, Outlet malls & Retail stores. All amenities included: Wi-Fi, Pool, Gym & BBQ area. NO RESORT FEES

Hook's Cabin- Lake & Pool near Disney A-frame
Hook’s Cabin is nestled within the peaceful gated community of Vacation Village it is a beautifully renovated A-Frame home and your perfect place to stay & play! You will enjoy private Lake Louisa access, Heated Olympic-sized community Pool, Pickleball / Basketball courts, play grounds, & FREE parking, Fast WiFi, flat screen smart Tv's w/ cable, full kitchen, & in home laundry. All less than 25 mins from Disney & other Orlando theme parks, and 5 miles from the National Training Center.

Spacious Getaway ~ Heated LED Pool & Ping Pong
Welcome to your Spacious Getaway! Exterior Features: ★ LED Lights in Pool and on Pool Cage ★ Fenced-in yard & Fire-pit ★ Doorbell & Driveway Camera for safety Interior Features: ★ Ping Pong Table ★Large Shower in Master Bathroom ★ROKU on each TV Extras: ★ Heated Pool up to 95 Degrees - $40 per day (Pool Water is normally at 75 degrees without the Pool Heater) ⚠️ Pet-Friendly, but the pet must be added to the reservation ($75 Pet fee)⚠️ {Willing to Negotiate Monthly Prices}

2-bedroom home with pool near Kings Landings!
Private 2-bedroom home with a queen size bed and a separate room with a twin daybed. There are many exciting things to do in the area! My home is about 30 minutes from theme parks such as Universal, SeaWorld, and Disney parks. Extra activities to do are Southern Hill Farms to pick fresh fruits and sunflowers. Want more fun in the sun? There is Wekiwa National park which is 7 miles away for kayaking and water springs. Additionally, Kings Landings is located 10 minutes away.

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!

Stay A While
Welcome to Your Secluded Getaway Enjoy a quiet retreat minutes from supermarkets and Florida’s top attractions. Top Attractions Island H2O: 23m | Epcot: 27m | SeaWorld: 32m Disney Springs: 34m | Universal: 36m Legoland: 1h | Busch Gardens: 1h 27m Shopping & Dining Winter Garden/Clermont: 14m Outlets: 28m | Florida Mall: 35m | I-Drive: 40m Travel MCO Airport: 40m Oversized Parking: Dedicated space for boats, RVs, and moving trucks. storage only

Lush Green Retreat 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

Private Country House | 16 Guests | Gatherings
Bring the whole family to this private 5-acre retreat, situated in one of the few hilly regions of Florida. Enjoy privacy, nature, spectacular sunsets, and starry nights—perfect for relaxing or enjoying outdoor activities. ⚠️ Gatherings require prior approval—please contact us before booking. Note: There is another house on the property that may be rented by other guests. Both are completely private, with no shared areas or parking.

Lakeview Oasis West of Orlando magnificent sunsets
We are proud to provide a No Smoking on property listing. This Sun Kissed Lake house overlooks Starke Lake in Central Florida. Great fishing, magnificent sunsets and Disney fireworks every night . Close to Disney 19 miles & 12 miles to Universal & 14 miles to Downtown Orlando. Other activities include air boating, Cape Cape Canaveral and centrally located just 1 hour from ocean or gulf. Please NO SMOKING on premises.
Popular amenities for Winter Garden rentals with a pool
House rentals with a pool

Elegant 5B & 3B Private Pool Villa near Disney

Private Pool Oasis w/Xbox, Fireplace, Projector

Villa Resort Club

Paradise pool home /5 Min Universal /13 min Disney

Harmony | Heated Pool | 10 min Universal & Epic.

Casa Bella Mediterranean Style near Disney

Pool & Jacuzzi+Cinema+Games+Fire Pit | Near Disney

Waterfront Wizarding Near Universal's Harry Potter
Condo rentals with a pool

Beautiful Beach Style Condo minutes from Disney

Resort Style Sunshine Oasis near Theme Parks

Sunshine & Magic Lakeview

Lakefront Resort Studio -5 min to Universal

Cozy Condo at Secret Lake near Disney

Modern Lake view Condo 1 mile from Disney

Chic Disney Resort Condo • Pool Access Near Parks

Modern Condo with Lake View Near Disney 3151
Other vacation rentals with a pool

Pool & Spa Oasis/Golf Retreat/Near Disney/3BR Home

Family-Friendly Condo with Pool & Sauna

Pet-Friendly Pool Home Near Orlando

Bright & Modern Stay Closest to Disney

Stunning Townhome with Private Pool & Games Room

Luxury home | Lakeside Landing

3 Bed Pool/Spa w/ Sunset Water in Margaritaville

2026 NEW Themed 05 Bedrooms At Windsor Cay
Quick stats about vacation rentals with a pool in Winter Garden

Total vacation rentals
Explore 20 vacation rentals in Winter Garden

Nightly prices starting at
Winter Garden vacation rentals start at R 663 ZAR per night before taxes and fees

Verified guest reviews
Over 330 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Winter Garden vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Winter Garden rentals

4.6 Average rating
Winter Garden stays receive an average rating of 4.6 out of 5 from guests
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- Rentals with pools Orange County
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- Universal Studios Florida
- Walt Disney World Resort
- Universal Orlando Resort
- Orange County Convention Center
- Disney Springs
- SeaWorld Orlando
- Universal's Volcano Bay
- Orlando / Kissimmee KOA
- Magic Kingdom Park
- Discovery Cove
- Epcot
- Disney's Animal Kingdom Theme Park
- Kia Center
- Old Town
- Reunion Resort Golf Courses - Palmer & Watson
- Camping World Stadium
- Aquatica
- Disney's Hollywood Studios
- ICON Park
- University of Central Florida
- Island H2O Live!
- Southern Dunes Golf and Country Club
- ChampionsGate Golf Club
- ESPN Wide World of Sports





