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Vacation rentals with a pool in Winter Garden

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Top-rated rentals with a pool in Winter Garden

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Guest favorite
Guest suite in Apopka
Wekiva Springs/Orlando Area Poolside Apartment
This is a small, poolside apartment attached to our home. It has a living room, bedroom, bathroom and kitchenette area with fridge, microwave, kurig and toaster. (No sink/range.) Independent ac/thermostat. Located one mile from the entrance to Wekiva Springs State Park and a few minutes to Kelly Park. We are centrally located within an hour to most Central FL attractions and Beaches. (Disney World, Universal, Sea World, Daytona Beach, International Drive.) Less than 30 min. to downtown Orlando.
May 1 – 8
$94 per night
Guest favorite
Home in Minneola
Spacious Home ~ Heated LED Pool & Ping Pong
Welcome to your Spacious Getaway! With over 70 amenities offered, our goal is to provide an unforgettable experience for our guests! Exterior Features: ★ Heated Pool up to 95 Degrees - ($25 a Day to Heat the Pool) ★ LED Lights on pool cage ★ Fenced-in yard & Fire-pit ★ Doorbell & Driveway Camera for safety Interior Features: ★ White/Clean Linens ★ TV with Netflix ★ Ping Pong Table ★ Shower Panel in Guest Bathroom ★Large Shower in Master Bathroom {Willing to Negotiate Monthly Prices}
Nov 2 – 9
$169 per night
Guest favorite
Guest suite in Orlando
Location, Location, Location near all attractions
This is a poolside in-law apartment with a full kitchen, bedroom, full bath and a living room located in a quiet, residential neighborhood in an upper scale part of town. It has a king size bed & will accommodate 2 adults comfortably. This in-law apartment is an addition that was built onto the back of our home. It is completely closed off from the our main house and has it's own main entrance so it is private. So, you will have the apartment all to yourselves.
Jan 4 – 11
$127 per night

Popular amenities for Winter Garden rentals with a pool

House rentals with a pool

Guest favorite
Home in Clermont
Stylish Villa Private Pool-SPA Near Parks Disney!
Nov 11 – 18
$135 per night
Superhost
Home in Orlando
Pool-Jacuzzi & Palm Trees/ 8 Universal/ 15 Disney
Jun 5 – 12
$158 per night
Guest favorite
Home in Kissimmee
Windsor Orlando Private Arcades,Theater,Pool-Spa
Dec 16 – 23
$422 per night
Guest favorite
Home in Kissimmee
"Vista Lago"Hotel Amenities/lake view,private pool
Jan 13 – 20
$372 per night
Guest favorite
Home in Clermont
Our Poolhome by the Mouse house with Game Room.
Aug 20 – 27
$145 per night
Superhost
Home in Davenport
Orlando Disney area home
Jun 23 – 30
$95 per night
Guest favorite
Home in Orlando
*HALF HOME* (read desc) Pool/Disney/Universal
Sep 16 – 23
$95 per night
Superhost
Home in Orlando
Modern, Clean Home, 5 min from Universal Studios
Apr 6 – 13
$174 per night
Guest favorite
Home in Orlando
Lakefront presidential suite / resort pool
Apr 6 – 13
$141 per night
Guest favorite
Home in Kissimmee
3 bedroom Villa in Kissimmee
Feb 7 – 14
$103 per night
Guest favorite
Home in Kissimmee
*Style & Luxury: Reunion Villa, Pool, Spa & Cinema
May 8 – 15
$333 per night
Guest favorite
Home in Davenport
Disney Area Luxury Villa with Private Pool
Sep 9 – 16
$126 per night

Condo rentals with a pool

Guest favorite
Condo in Kissimmee
Minutes To Disney World - Sparkling Clean Condo
Sep 28 – Oct 5
$97 per night
Guest favorite
Condo in Kissimmee
Mickey's Retreat
May 9 – 16
$83 per night
Superhost
Condo in Orlando
☆ Completely renovated + amazing location
Apr 15 – 22
$98 per night
Guest favorite
Condo in Kissimmee
Perfect place for your Disney getaway
Feb 8 – 15
$100 per night
Guest favorite
Condo in Orlando
Spacious 1King/2Bath w/stunning lake view
Apr 12 – 19
$144 per night
Guest favorite
Condo in Kissimmee
3 miles from Disney and Golf affordable condo!
Jul 17 – 24
$100 per night
Guest favorite
Condo in Kissimmee
The Pixie Nest - Fun & Relaxation
Apr 9 – 16
$105 per night
Superhost
Condo in Clermont
Tours to Disney 5003
Jan 31 – Feb 7
$117 per night
Guest favorite
Condo in Orlando
Luxurious Waterfront Resort near Disney &Universal
Feb 2 – 9
$162 per night
Superhost
Condo in Orlando
ORLANDO SUITE@ UNIVERSAL/DISNEY/CONVENTION CENTER
Aug 16 – 23
$91 per night
Superhost
Condo in Orlando
Amaranta/Studio beautiful balcony LAKE VIEW 🫶❤️
Sep 27 – Oct 4
$87 per night
Guest favorite
Condo in Orlando
VCR4-404 Reserve Deluxe Condos - Beautifully Decor
May 21 – 28
$162 per night

Home rentals with a private pool

Guest favorite
Townhouse in Kissimmee
Beach House with Private Pool and Clubhouse near Disney
Apr 24 – May 1
$186 per night
Guest favorite
Townhouse in Kissimmee
Stellar Five Bedroom Townhome Under Ten Minutes to Disney
Jul 6 – 13
$296 per night
Guest favorite
Home in Davenport
Airy, Stylish Home with Pool Heat Included in Davenport
Aug 10 – 17
$183 per night
Villa in Kissimmee
Visit Disney World from a Sunny Home with a Pool
Jan 20 – 27
$149 per night
Guest favorite
Villa in Kissimmee
Family Retreat Near Disney with Pool & Hot Tub!
Feb 7 – 14
$220 per night
Home in Davenport
Luxurious 8br Palms Villa Pool Home-Champions Gate
Oct 3 – 10
$332 per night
Villa in Davenport
Amazing Dream Solterra Villa -Disney/club/pool/spa
Nov 8 – 15
$755 per night
Home in Davenport
Zoe & Zach's Golf Villa at Ella Mae
Sep 29 – Oct 6
$147 per night
Home in Kissimmee
6 Bedroom Home in Solara Resort
Apr 7 – 14
$119 per night
Home in Davenport
Luxe Home @westridge W/private Pool& Yard Wr001or
Nov 6 – 13
$136 per night
Home in Osceola County
Luxe Golf View 4br Reunion Resortvilla Near Disney
Oct 16 – 23
$529 per night
Home in Kissimmee
Vacation Resort Home Right Outside of Disney World
Sep 10 – 17
$174 per night

Quick stats about vacation rentals with a pool in Winter Garden

Total rentals

20 properties

Local attractions

Winter Garden Downtown Pavilion and Farmers Market, Best Buy, and Miller's Ale House - Winter Garden

Popular amenities

Kitchen, Wifi, and Pool

Wifi availability

20 properties include access to wifi

Family-friendly rentals

10 properties are a good fit for families

Total number of reviews

160 reviews

Destinations to explore