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!

12–19 Oct

$177 NZD per night

Guest favourite

Condo in Orlando

4.89 out of 5 average rating, 327 reviews

FantasticView, 1 BR/2BA, 1 MILE TO DISNEY-Sleeps 6

Located 1 mile to Disney Springs in a Gated-Community A NEWLY REFURBISHED Spacious 1-bedroom, 2-bath Condo in Lakefront luxury @ Blue Heron Beach Resort nestled on shores of 400+ acre Lake Bryan, 2 blocks off I4 @ Lake Buena Vista exit. This luxurious condo overlooks the Pool & Lake Bryan. Sleeps 6 It’s all here! The ultimate Walt Disney World vacation right here at your fingertips! From the best of Disney or Work Travel this property offers the perfect environment to spend a lifelong memory

23–30 Nov

$260 NZD per night

Guest favourite

Apartment in Orlando

4.93 out of 5 average rating, 101 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

20–27 Dec

$231 NZD per night

Guest favourite

Guest suite in Altamonte Springs

4.97 out of 5 average rating, 300 reviews

St. Hemingway Suite

Very tranquil Romantic room with views and access to large lake. PRIVATE ENTRANCE and private bathroom. Amenities include, private dock, pool, large manicured lawns, private parking, breakfast kitchenette and much more. Close to theme parks and beaches. Ample shopping and award winning restaurants very nearby. Peaceful setting to read, do Yoga, enjoy quiet moments by the lake, watch the boats sail by or watch the sun rise. Peace and tranquility at its best. We welcome you to Spring Valley

18–25 Sep

$182 NZD per night

Guest favourite

Bungalow in Maitland

4.86 out of 5 average rating, 490 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.

9–16 Oct

$177 NZD per night

Guest favourite

Guesthouse in Orlando

4.94 out of 5 average rating, 212 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.

26 Dec – 2 Jan

$241 NZD 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}

12–19 Jan

$460 NZD per night

Guest favourite

Home in Orlando

4.95 out of 5 average rating, 313 reviews

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

We LOVE hosting! Think of us as friends you’re staying with, but haven’t met yet. We are happy to interact, but also happy to remain out of sight to ensure your privacy. We live in the master (on OTHER SIDE w/own bath) when not traveling and we DO use kitchen. Everything else is exclusive to you! You get plenty of space & PRIVACY. Photos represent YOUR space (we use kitchen too, but rest is exclusive) If you’re not comfortable with on-site host w/kitchen usage, we aren’t right choice.

16–23 Jun

$215 NZD per night

Guest favourite

Guest suite in Orlando

4.99 out of 5 average rating, 243 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

$295 NZD per night

Guest favourite

Condo in Kissimmee

4.94 out of 5 average rating, 109 reviews

Cheery 2BR Condo w/zero entry pool near Disney

Ideal location 15 minutes from Disney yet removed from the melee! **New Dishwasher** Second floor condo with fully equipped kitchen in gated community. Free WIFI and parking. Everything you need to have a magical Orlando holiday! King master bedroom, 2 twin beds in second bedroom, a queen sofa bed in living room. Private screened balcony facing lake to enjoy a tranquil moment. Community zero-entry pool, fitness center, game room, sports courts. Smoke and pet free.

14–21 Oct

$196 NZD per night

Superhost

Apartment in Maitland

4.81 out of 5 average rating, 262 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.

8–15 Sep

$140 NZD per night

Guest favourite

Guesthouse 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.

5–12 Aug

$209 NZD 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

Wi-Fi

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

29 Jul – 5 Aug

$286 NZD 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

$217 NZD per night

Guest favourite

Home in Clermont

4.86 out of 5 average rating, 126 reviews

Our Poolhome by the Mouse house with Game Room.

15–22 Dec

$372 NZD 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 Jul

$370 NZD per night

Guest favourite

Home in Clermont

4.9 out of 5 average rating, 117 reviews

Stylish Villa Private Pool-SPA Near Parks Disney!

13–20 Oct

$324 NZD per night

Superhost

Home in Kissimmee

4.79 out of 5 average rating, 256 reviews

3 bedroom Orlando Florida pool home

10–17 Dec

$243 NZD per night

Guest favourite

Home in Kissimmee

4.92 out of 5 average rating, 125 reviews

South Facing Pool Home! 5 Miles from Disney

10–17 May

$291 NZD per night

Guest favourite

Home in Davenport

4.95 out of 5 average rating, 161 reviews

DOLPHIN COVE NEAR DISNEY

20–27 Jan

$302 NZD per night

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Condo rentals with a pool

Guest favourite

Condo in Davenport

4.91 out of 5 average rating, 209 reviews

3/2 King Bed Apartment near Disney Universal

5–12 May

$195 NZD per night

Guest favourite

Condo in Kissimmee

4.94 out of 5 average rating, 186 reviews

Lakeview Escape close to Disney&retail therapy

3–10 Oct

$229 NZD per night

Guest favourite

Condo in Kissimmee

4.96 out of 5 average rating, 136 reviews

55B-DISNEY-STAR ISLAND, 1 BR DELUX-TENNIS/POOL/SPA

1–8 May

$204 NZD per night

Guest favourite

Condo in Kissimmee

4.94 out of 5 average rating, 159 reviews

Like Home Family Getaway

5–12 Dec

$196 NZD per night

Guest favourite

Condo in Kissimmee

4.92 out of 5 average rating, 263 reviews

Beautiful Beach Style Condo minutes from Disney

6–13 Oct

$221 NZD per night

Guest favourite

Condo in Orlando

4.81 out of 5 average rating, 342 reviews

Luxury Apt on I-Drive & view of Universal Orlando

17–24 Oct

$170 NZD per night

Guest favourite

Condo in Orlando

4.9 out of 5 average rating, 128 reviews

[Lake View, Modern Decor, 1 Mile to Disney!]

28 May – 4 Jun

$283 NZD per night

Guest favourite

Condo in Kissimmee

4.94 out of 5 average rating, 158 reviews

Affordable condo 3 miles from Disney and Golf!

12–19 Aug

$266 NZD 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

22–29 Aug

$312 NZD 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

3–10 Nov

$685 NZD 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

22–29 Mar

$667 NZD per night

Guest favourite

Villa in Kissimmee

5.0 out of 5 average rating, 13 reviews

Family Retreat Near Disney with Pool & Hot Tub!

26 Nov – 3 Dec

$698 NZD per night

Villa in Kissimmee

4.79 out of 5 average rating, 223 reviews

Visit Disney World from a Sunny Home with a Pool

9–16 Dec

$385 NZD per night

Home in Davenport

4.61 out of 5 average rating, 23 reviews

Solterra Resort 7br Family Home Pool Near Disney

14–21 Nov

$552 NZD per night

Home in Davenport

4.75 out of 5 average rating, 4 reviews

Luxurious 8br Palms Villa Pool Home-Champions Gate

11–18 Dec

$930 NZD per night

Villa in Davenport

4.67 out of 5 average rating, 6 reviews

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

26 Oct – 2 Nov

$1,448 NZD 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, Wi-Fi and Pool
Wi-Fi availability
20 properties include access to Wi-Fi
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 Davenport

Home in Clermont

Home in Mount Dora

Home in Clermont

Home in Kissimmee

Home in Kissimmee

Home in Davenport

Condo rentals with a pool

Condo in Davenport

Condo in Kissimmee

Condo in Kissimmee

Condo in Kissimmee

Condo in Kissimmee

Condo in Orlando

Condo in Orlando

Condo in Kissimmee

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

Wi-Fi availability

Family-friendly rentals

Total number of reviews

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