
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.

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.

Resort Style Sunshine Oasis near Theme Parks
Discover Orlando's charm at our resort-style oasis in a gated community with lots of amenities! Nestled near Disney, this modern haven features 2 stunning pools for ultimate relaxation. Delight in nearby restaurants, perfect for foodies. Families will love the kid-friendly atmosphere, and fitness enthusiasts can stay active in the on-site gym. Our clean, contemporary design ensures a comfortable stay, making it an ideal choice for your Orlando getaway. Conveniently located on the first floor.

WATERFRONTWntrGdnPoolHSE VIEWS Dock Wildl Nr Disny
Experience the stunning sunrise views over Lake Apopka from our newly refurbished, elegantly appointed 4-bedroom, 2.5-bath vacation home in Winter Garden, FL. This haven is close to Orlando's Universal Studios 20 min, Disney World 25 min) & shopping (Mall of Millenia, premium outlets 17 min) Modern amenities, spacious layout that promises relaxation and convenience making the perfect home for exploring all local attractions and enjoying Florida's natural beauty. Minutes from City Swimming Pool

St. Augustine suite
Luxurious space with PRIVATE ENTRANCE, PRIVATE BATHROOM and breakfast kitchenette. Located on a large lake front property with amenities that include private dock, pool, large manicured lawns and much more. Ideal for canoeing, watching the sun rise or doing nothing at all. Close to theme parks and beaches. Spring Valley is a peaceful community with age old oak tree , Ample shopping and award winning restaurants very nearby. Come play or rejuvenate your soul in this picturesque setting

"Winnie's Place" A Peaceful Guesthouse with Pool.
Share the quiet backyard and pool with your hosts. Half was between Disney & the beaches. 12 years & older only. Sofa extends to a single bed. Minutes from Interstate-4. 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 29"-standard cabinets. We are not Handicap Certified but most wheelchair guests have not had issues. Grab bars are in the bathroom.

Tranquil Townhome near Disney/Resort Amenities2715
Platform fee 18.5% is paid by host. One of the closest resorts to Disney World (5 miles), 3-bedroom, 2.5-bath townhome overlooks a serene conservation area, There are heated outdoor pools and spas, sauna, gym, game room, mini golf, volleyball, tennis courts and kids' play areas. 1295 sqft of comfort and value—perfect for guests seeking relaxation and convenience, not hotel-style luxury or perfection **Primary guest registration with ID required through guest portal.

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!

Downtown private pool house. Two blocks from ORMC
Recharge in this private one bedroom, one bath pool house. Relax in the pool after a long day and enjoy a restful night in a very comfortable queen size bed. Walking distance to downtown, ORMC, and the Dr. Phillips Performing Arts Center. Two miles to Kia (Amway) Center for concerts and the Orlando Magic. Two miles to the Orlando City and Pride Soccer stadium. Three miles to Camping World Stadium. Nine miles to Universal Studios. 14 miles to SeaWorld. 15 miles to Disney.

A-Frame Cottage near Disney, Universal, & Lakes
Come enjoy a relaxing stay at the Dragonfly Cottage and explore all that Central Florida has to offer. With Disney World just 23 miles (37 km) and Universal Studios 26 miles (42km) away, you will find plenty of entertainment. Beautiful Lake Louisa State Park is less than 3 miles (5 km) and the Downtown Clermont Lakes only 6 miles (9 km) away. With amenities like an Olympic-size pool just steps away, you'll be able to cool off and unwind after long days of sun and fun.

5 mins Universal 10 mins Epic park | Rustic LOFT
Take it easy at this unique oasis and tranquil getaway that is located in the heart of Orlando!! Want to have fun?! Literally walking distance from Universal Studios, Want to go shopping?! 5 mins from Millenia Mall and Premium Outlets. Want to experience Orlandos hottest nightlife or stroll through the city it’s 15 mins from Downtown , Do you want to meet Mickey Mouse or shamu?! 15 mins from Disney and sea-world. Even take a dip in the complex pool or play tennis!!

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!

It's too much like a elegant mini-hotel (5)
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. All of my houses have hosted countless friendly and courteous guests from Brazil. We will always welcome you!
Popular amenities for Winter Garden rentals with a pool
House rentals with a pool

Private 3-bedroom pool & waterfront home

Modern home, w Pool, 5 min from Universal Studios

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

10 Min to Disney • Cozy Townhome + Jacuzzi + BBQ

Pool + Heated spa Family friendly King suite Oasis

Spacious Getaway ~ Heated LED Pool & Ping Pong

2-bedroom home with pool near Kings Landings!

BBQ Grill | Wi-Fi | Pool Access | 20 Min Disney
Condo rentals with a pool

Luxury Condo On I-Drive & One Mile from Universal

Stylish Condo 20 mins to Disney/King Bed

Golf Front Luxury Penthouse: Views, Marvel, 2Pools

Spacious Apartment Near Disney

Stunning view, near Disney.

Luxurious Spot 10 Mins Away to Most Attractions!!!

Luxury Studio, Near to Universal-Epic ,And Disney!

Orlando Fun: Minutes to Disney and Margaritaville
Other vacation rentals with a pool

3BR Family Home near Orlando!

Disney Luxury 5bedroom 4bath Resort WaterPark Free

Cozy Apartment Close to Disney

Magic Spring

Beautiful cozy private studio !!

Luxury Lake Front Orlando Oasis in College Park!

Boutique Suite in Orlando

1,000 sqft Apartment on 3 Acres w/ Pool & Balcony
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 $55 CAD per night before taxes and fees

Verified guest reviews
Over 150 verified reviews to help you choose

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

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




