
Holiday 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.
Sapphire Cottage - sleeps 6, on 5 acres with canal
Escape to Sapphire Cottage, a 5-acre wooded retreat with a private canal boat dock. Relax by the shared pool, fish from the dock, or enjoy a BBQ at the firepit. Our cozy cottage features a queen master, 2 sofa-beds, a full kitchen, and dining for 6. From meeting our farm animals, biking, kayaking, or reading in the gazebo, there is something for everyone! We live in the main house across the way and are happy to help while ensuring you have a peaceful stay. Come make lasting memories with us!

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.

Farmhouse near the Springs
Enjoy the ducks, chickens, and goats. Wake to the neighbor's rooster crowing. Have fresh eggs for breakfast when the chickens and ducks cooperate. This three bedroom home with a pool sleeps six. It is - 6 minutes to a grocery store, - 12 minutes to Rock Springs or Wekiva Springs, - 15 minutes to the Lake Apopka Wildlife Drive and - 30 to 45 minutes to the major theme parks, depending on traffic. - a 4 minute bike ride to the 22 mile long West Orange Trail. NO PARTIES TWO VEHICLES MAXIMUM

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}

Luxury Villa! /Game Room/ Pool Heater
Luxury Villa on a gated community in Kissimmee (Four Corners). Modern. Situated 10 min. from Disney theme parks. Well decorated and presented. Game Room, Mini Gym, Beautiful, large pool deck which is totally enclosed and secluded. There is a private Pool and Spa. Three Bedrooms and Bedroom one is separate from the main house but still enclosed in the building. This would be ideal for a young couple within the group as it has its own bathroom, small kitchen and also total privacy.

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.

Amazing Pool • Huge Yard • 5 Min Universal
Welcome to your Orlando Family Oasis! Just 5 min to Universal, 15 min to Disney, and 10 min to Epic Universe. Enjoy a heated pool, huge backyard, outdoor grill, and plenty of space to relax after the parks. This comfortable 4BR/3BA home is perfect for families and groups. Modern living, a fully equipped kitchen, and an unbeatable location make this the ideal base for your Orlando getaway! This property offers both excitement and relaxation in one incredible package.

Beautiful country house
Take the whole family to this fantastic place with many areas to have 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 you will witness a beautiful sunset unparalleled, stay and watch the stars, spaces suitable for unique souvenir photos. Ideal area for cycling and hiking. NOTE: if you want an event, check first for our rates

Tranquil Azure Haven 10 Min to Parks Pets Friendly
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

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.

Amazing Villa near DisneyWorld FREE heated-pool
Have fun with the whole family at this stylish place. Our home has everything you will need for you and your guest to have a great experience. This home is a short drive from Walt Disney World and Orlando Attractions!! Don’t wait book with us now and give you and your family the vacation you all deserve. We can’t wait to welcome you . BBQ ( free to use ) Heated pool (free) Dogs friendly! Extra fee $120 per stay
Popular amenities for Winter Garden rentals with a pool
House rentals with a pool

3 BR/2BA Home w Private Pool~12 min to Airport!

Comfy 4BR near Disney/pool and Hottub

Villa Resort Club

Game Room/HeatedPool/Piano Upscale Waterfront Home

4BR Pool Home 4mi to Disney – Perfect for Families

Waterfront Wizarding Near Universal's Harry Potter

8615 Vacation Oasis House Private Pool Grill

Our Poolhome by the Mouse house with Game Room.
Apartment rentals with a pool

Stylish Condo 20 mins to Disney/King Bed

The thrill of luxurious living just 15 min/Disney!

Disney Oasis by the lake

Private Rooftop Suite! No resort fees!

1-104 Legacy Dunes, Pool View, Close to Disney

Cozy Condo at Secret Lake near Disney

Modern Condo with Lake View Near Disney 3151

VISTA CAY RESORT, 2 BEDROOM STANDARD APARTMENT
Other holiday rentals with a pool

Beautifully Renovated, Centrally Located Pool Home

Family-Friendly Condo with Pool & Sauna

Gorgeous Cottage near Lake Louisa & mins 2 Disney.

Hope House- Vacation Village 1 Bedroom with Loft

Swim & Chill Hideaway | Heated Pool + Fire Pit

Key West Themed Lakefront Oasis with Sailboat

NEW 2026 07BR Windsor Cay Resort Home Near Disney

Ohana Lakeside Retreat
Quick stats about holiday rentals with a pool in Winter Garden

Total holiday rentals
Explore 20 holiday rentals in Winter Garden

Nightly prices starting at
Winter Garden holiday rentals start at £30 per night before taxes and fees

Verified guest reviews
Over 330 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Winter Garden holiday 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
Destinations to explore
- Seminole Holiday rentals
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- Rentals with a washing machine and dryer Winter Garden
- Pet-friendly rentals Winter Garden
- Rentals with a fireplace Winter Garden
- Family-friendly rentals Winter Garden
- Flat rentals Winter Garden
- House rentals Winter Garden
- Rentals with outdoor seating Winter Garden
- Fitness-friendly rentals Winter Garden
- Villa rentals Winter Garden
- Rentals with a patio Winter Garden
- Rentals with pools Orange County
- Rentals with pools Florida
- Rentals with pools United States
- Walt Disney World Resort
- Universal Studios Florida
- Universal Orlando Resort
- Orange County Convention Center
- Walt Disney World Resort Golf
- Disney Springs
- Magic Kingdom Park
- SeaWorld Orlando
- Universal's Volcano Bay
- Orlando / Kissimmee KOA
- Discovery Cove
- ESPN Wide World of Sports
- 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
- Island H2O Live!
- Southern Dunes Golf and Country Club
- ChampionsGate Golf Club




