Holiday rentals with a pool in Winter Garden

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Top-rated rentals with a pool in Winter Garden

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Guest favourite

Guest suite in Orlando

4.99 out of 5 average rating, 124 reviews

Beautiful studio with pool & close to attractions!

An amazing studio space, attached to the main home, with private entrance, King size bed, full bath, and kitchenette. Recently renovated and very comfortable. New Mitsubishi mini-split AC system and a Nespresso Machine for your morning coffee. Access to pool area, gazebo, and washer/dryer outside! Centrally located: under 20 minutes to the airport, 5 minutes to Florida Mall, 10 minutes to Mall at Millenia, under 20 minutes to Universal Studios, 35 minutes to Disney, and 10 minutes to Downtown!

18–25 Sep

$116 SGD per night

Guest favourite

Flat in Orlando

4.93 out of 5 average rating, 102 reviews

Apartment, 7 Min to Orlando Airport/ Lake Nona

Complete private unit . A Private Door inside the room to step out to the pool .1 Bed/1 Bath, 2 TV’s , Netflix Amazon, sitting area, and and a small kitchen, We a Manual Slingshot available for rent, the rent for the Slignshot will be $200 per day. Pool area will be available all the time .We just build a door inside the room that way is easy access. This place is 25 Minutes driving to Disney World and most Parks, Lake Nona is 10 minutes away. We are Close to UCF, lake Nona, MCO, Waterford lakes

14–21 Oct

$161 SGD per night

Guest favourite

Bungalow in Maitland

4.86 out of 5 average rating, 492 reviews

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.

28 Sep – 5 Oct

$127 SGD per night

Guest favourite

Guest house in Orlando

4.94 out of 5 average rating, 213 reviews

Modern Guest Studio (Private) Pool / Spa available

Private Guest Studio (Not Shared ) in a Perfect Orlando location, 5 minutes from I-Drive, Universal Studios, Disney World & Premium Shopping Outlets. Very Quiet lovely neighborhood with Biking distance to "Restaurant Row" where all your favorite restaurants are located. Pool & Spa available (Not Shared) All major highways at your finger tips / ride 15 min to Disney! This space has an industrial modern look with high ceilings, Stay and cook with all the amenities including a Washer and Dryer.

21–28 Sep

$152 SGD per night

Guest favourite

Home in Minneola

4.98 out of 5 average rating, 111 reviews

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}

21–28 Sep

$307 SGD per night

Guest favourite

Guest suite in Orlando

4.99 out of 5 average rating, 244 reviews

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.

11–18 Oct

$205 SGD per night

Guest favourite

Home in Clermont

4.86 out of 5 average rating, 127 reviews

Our Poolhome by the Mouse house with Game Room.

Spacious four-bedroom, two-bathroom residence conveniently located near Disney and Universal Studios. Enjoy the expansive screened-in south-facing pool and fenced backyard for ultimate privacy. Entertain in the fantastic game room, perfect for family fun. Rest assured with 24/7 monitoring of security cameras installed outside the property. Additionally, the pool can be heated upon request for an additional fee—reach out for current rates.

1–8 Oct

$246 SGD per night

Superhost

Flat in Maitland

4.81 out of 5 average rating, 263 reviews

At Mine | Elegant Double Suite in North Orlando

Experience ultimate comfort at our Maitland, FL hotel, ideally located just north of Downtown Orlando. we're the area's largest hotel. Enjoy the convenience and luxury of plush bedding, modern furnishings, and upscale Grohe showers in your room. Relax by our outdoor pool, keep fit in the 24-hour gym, and access the Genesis Health Club. With over 15,000 square feet of event space, secure parking, and free Wi-Fi, we've got you covered.

26 Aug – 2 Sep

$91 SGD per night

Guest favourite

Cottage in Kissimmee

4.96 out of 5 average rating, 421 reviews

Bright & Cozy Cottage Near Disney

My place located within 10 miles of: Disney World, Celebration, Universal, Water Parks, Old Town & Fun Spot USA's More than 70 Restaurants and Dining, Gifts Shop. My place is good for couples, solo adventurers, business travelers, and families (with kids). You’ll love my place because of In Our Cozy and Comfortable Sand Castle Cottage You'll discover that perfect Mix of High-Energy Fun and Laid Back Florida Lifestyle Right Here.

17–24 Sep

$138 SGD per night

Guest favourite

Guest house in Orlando

4.99 out of 5 average rating, 143 reviews

Quaint Guesthouse Near the Attractions

This picturesque hideaway suite is recently remodeled with granite and tile throughout. Ideal for couples, but can comfortably accommodate up to a family of four with a separate king size bedroom plus a king size sleeper sofa in living room. You may choose to prepare meals in the kitchenette, use the BBQ grill, dine in one of the hundreds of nearby restaurants, or order Uber Eats if you prefer to stay home and relax.

3–10 Aug

$158 SGD per night

Guest favourite

Guest suite in Orlando

4.95 out of 5 average rating, 168 reviews

Flor de María beautiful and relaxing GUEST ROOM ☘️☘️

Nice and relaxed Guest room with King side bed!! Our beautiful studio is attached to our house. With entrance and bathroom private. Parking included. You can enjoy areas like pool, grill and fireplace (These areas are shared) Our Space is only for 2 adults. Sorry!!! We not accepting kid’s, baby’s or pest. We are sure!!! You will love our place!!! We offer faster WiFi and Nexflix!!!

7–14 Aug

$123 SGD per night

Guest favourite

Flat in Orlando

4.98 out of 5 average rating, 138 reviews

Entire Lovely & Cozy Centrally Located Place

Enjoy a comfortable experience at this centrally-located place it is Close to Disney, Seaworld, Universal, shopping and Restaurants. Large spacious 1 BR/BA unit 1 Queen size bed and Queen Sofa bed, Access to Entire apartment, Full Kitchen, amenities Swimming Pool and Fitness Center Including free high speed WIFI, cable , Roku, Netflix and Free parking

24–31 Aug

$169 SGD per night

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for Winter Garden rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

Guest favourite

Home in Clermont

4.86 out of 5 average rating, 117 reviews

Cozy Family Home near Disney

19–26 Oct

$193 SGD per night

Guest favourite

Home in Orlando

4.95 out of 5 average rating, 313 reviews

*HALF HOME* (read desc) Pool/Disney/Universal

12–19 Jun

$152 SGD per night

Guest favourite

Home in Mount Dora

4.94 out of 5 average rating, 109 reviews

Modern Farmhouse & Pool in Mount Dora by Lake Ola

22–29 Jun

$238 SGD per night

Guest favourite

Home in Clermont

4.9 out of 5 average rating, 117 reviews

Stylish Villa Private Pool-SPA Near Parks Disney!

24–31 Oct

$217 SGD per night

Guest favourite

Home in Clermont

4.89 out of 5 average rating, 108 reviews

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

4–11 Sep

$200 SGD per night

Guest favourite

Home in Clermont

4.88 out of 5 average rating, 132 reviews

Disney Pool Villa, Cranberry South,

17–24 Sep

$196 SGD per night

Guest favourite

Home in Kissimmee

4.84 out of 5 average rating, 205 reviews

3 bedroom Villa in Kissimmee

21–28 Apr

$167 SGD per night

Superhost

Home in Davenport

4.87 out of 5 average rating, 135 reviews

Insta-worthy getaway near Disney w/ free parking!💎

27 Sep – 4 Oct

$147 SGD per night

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Apartment rentals with a pool

Guest favourite

Apartment in Kissimmee

4.94 out of 5 average rating, 160 reviews

Like Home Family Getaway

5–12 Dec

$128 SGD per night

Guest favourite

Apartment in Four Corners

4.86 out of 5 average rating, 107 reviews

"Ocean's Gate" - 2BD/2BA condo near Disney

4–11 Dec

$180 SGD per night

Guest favourite

Apartment in Kissimmee

4.92 out of 5 average rating, 264 reviews

Beautiful Beach Style Condo minutes from Disney

21–28 Oct

$147 SGD per night

Guest favourite

Apartment in Kissimmee

4.94 out of 5 average rating, 159 reviews

Affordable condo 3 miles from Disney and Golf!

7–14 Jan

$171 SGD per night

Superhost

Apartment in Kissimmee

4.79 out of 5 average rating, 153 reviews

Mickey's Retreat

11–18 Jul

$140 SGD per night

Guest favourite

Apartment in Orlando

4.97 out of 5 average rating, 297 reviews

Luxurious Waterfront Resort near Disney &Universal

29 Aug – 5 Sep

$242 SGD per night

Guest favourite

Apartment in Kissimmee

4.97 out of 5 average rating, 160 reviews

New Lovely 3-bedroom Condo 5 minutes from Disney’s

11–18 Apr

$208 SGD per night

Guest favourite

Apartment in Four Corners

4.99 out of 5 average rating, 148 reviews

Orlando Fun: Minutes to Disney and Margaritaville

29 Oct – 5 Nov

$148 SGD per night

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Home rentals with a private pool

Superhost

Townhouse in Kissimmee

4.83 out of 5 average rating, 191 reviews

Beach House with Private Pool and Clubhouse near Disney

4–11 Sep

$196 SGD per night

Guest favourite

Townhouse in Kissimmee

4.88 out of 5 average rating, 128 reviews

Stellar Five Bedroom Townhome Under Ten Minutes to Disney

30 Jan – 6 Feb

$403 SGD per night

Guest favourite

Home in Davenport

4.97 out of 5 average rating, 97 reviews

Airy, Stylish Home with Pool Heat Included in Davenport

24–31 Aug

$266 SGD per night

Guest favourite

Villa in Kissimmee

5.0 out of 5 average rating, 13 reviews

Family Retreat Near Disney with Pool & Hot Tub!

11–18 Jan

$339 SGD per night

Villa in Kissimmee

4.79 out of 5 average rating, 223 reviews

Visit Disney World from a Sunny Home with a Pool

4–11 Oct

$244 SGD per night

Home in Davenport

4.61 out of 5 average rating, 23 reviews

Solterra Resort 7br Family Home Pool Near Disney

3–10 Dec

$291 SGD per night

Home in Davenport

4.75 out of 5 average rating, 4 reviews

Luxurious 8br Palms Villa Pool Home-Champions Gate

25 Jun – 2 Jul

$536 SGD per night

Villa in Davenport

4.67 out of 5 average rating, 6 reviews

Amazing Dream Solterra Villa -Disney/club/pool/spa

6–13 Dec

$1,052 SGD per night

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Quick stats about holiday 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
180 reviews

Holiday rentals with a pool in Winter Garden

Top-rated rentals with a pool in Winter Garden

Holiday rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Winter Garden rentals with a pool

House rentals with a pool

Home in Clermont

Home in Orlando

Home in Mount Dora

Home in Clermont

Home in Clermont

Home in Clermont

Home in Kissimmee

Home in Davenport

Apartment rentals with a pool

Apartment in Kissimmee

Apartment in Four Corners

Apartment in Kissimmee

Apartment in Kissimmee

Apartment in Kissimmee

Apartment in Orlando

Apartment in Kissimmee

Apartment in Four Corners

Home rentals with a private pool

Townhouse in Kissimmee

Townhouse in Kissimmee

Home in Davenport

Villa in Kissimmee

Villa in Kissimmee

Home in Davenport

Home in Davenport

Villa in Davenport

Quick stats about holiday rentals with a pool in Winter Garden

Total rentals

Local attractions

Popular amenities

Wifi availability

Family-friendly rentals

Total number of reviews

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