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.

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Guest favorite

Guest suite in Orlando

4.99 out of 5 average rating, 123 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!

Oct 12 – 19

€ 101 per night

Guest favorite

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

Sep 18 – 25

€ 102 per night

Guest favorite

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.

Jun 22 – 29

€ 112 per night

Guest favorite

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.

Dec 26 – Jan 2

€ 135 per night

Guest favorite

Home in Mount Dora

4.94 out of 5 average rating, 109 reviews

Modern Farmhouse & Pool in Mount Dora by Lake Ola

This recently renovated farmhouse cottage is the perfect “home away from home” to retreat w/ family & friends. Enjoy waking up to the beautifully updated kitchen w/ farm sink, catching the sunset over Lake Ola while refreshing in the pool, sipping your morning coffee on the large back porch. Only a few minute drive to downtown Mount Dora filled w/renown restaurants & boutiques . Close to Rock & Wekiva Springs, Sydonie Mansion & other wedding venues & easy commute to theme parks and beaches!

Aug 9 – 16

€ 191 per night

Guest favorite

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}

Jan 12 – 19

€ 259 per night

Guest favorite

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.

Jul 11 – 18

€ 121 per night

Guest favorite

Guesthouse in Mount Dora

4.9 out of 5 average rating, 705 reviews

Key West cottage of Mt Dora

Cozy little cottage located in the gardens of the main house. It has a full kitchen. 1 bath with a jacuzzi tub.. Queen size bed and a couch for a 3rd person. THE LOCATION is 3 MILES between Mount Dora ,Tavares & Eustis a short drive or bike ride to all location. I’m 2.5 blocks off Lake Shore Dr. to beautiful Lake Dora. FRESH eggs from the Easter egg hens for your use ( When available) The eggs they lay are pink, green and blue. They will need to be washed before use..

Jan 27 – Feb 3

€ 146 per night

Guest favorite

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.

Oct 10 – 17

€ 166 per night

Guest favorite

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.

Oct 14 – 21

€ 110 per night

Guest favorite

Guest suite in Orlando

4.99 out of 5 average rating, 339 reviews

Sunny Resort Style - Pool & central location ☀️

Resort Style Vacation with much more Privacy ? You found the right place! :-) From our family to you, we are welcoming you into your modern & efficient Airbnb Guest suite! :-) Located a very short commute to some of the world's most famous tourist attraction, Disney & Universal studio & to an amazing oasis style backyard offered to you! We want to make sure that your stay to our home will be memorable and we want to see you again :-)

Oct 1 – 8

€ 140 per night

Guest favorite

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.

Oct 6 – 13

€ 118 per night

Vacation 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 favorite

Home in Clermont

4.86 out of 5 average rating, 117 reviews

Cozy Family Home near Disney

Jul 28 – Aug 4

€ 161 per night

Superhost

Home in Orlando

4.91 out of 5 average rating, 117 reviews

Lakefront presidential suite / resort pool

May 14 – 21

€ 154 per night

Superhost

Home in Davenport

4.87 out of 5 average rating, 135 reviews

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

Oct 18 – 25

€ 137 per night

Guest favorite

Home in Clermont

4.86 out of 5 average rating, 126 reviews

Our Poolhome by the Mouse house with Game Room.

Dec 15 – 22

€ 209 per night

Guest favorite

Home in Clermont

4.9 out of 5 average rating, 117 reviews

Stylish Villa Private Pool-SPA Near Parks Disney!

Oct 13 – 20

€ 182 per night

Guest favorite

Home in Kissimmee

4.9 out of 5 average rating, 158 reviews

Huge pool 4/2 close to Disney!

May 16 – 23

€ 155 per night

Superhost

Home in Kissimmee

4.79 out of 5 average rating, 256 reviews

3 bedroom Orlando Florida pool home

Dec 14 – 21

€ 135 per night

Guest favorite

Home in Clermont

4.89 out of 5 average rating, 106 reviews

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

Aug 4 – 11

€ 170 per night

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Condo rentals with a pool

Guest favorite

Condo in Orlando

4.81 out of 5 average rating, 342 reviews

Luxury Apt on I-Drive & view of Universal Orlando

Oct 17 – 24

€ 96 per night

Guest favorite

Condo in Kissimmee

4.96 out of 5 average rating, 136 reviews

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

May 1 – 8

€ 115 per night

Guest favorite

Condo in Kissimmee

4.94 out of 5 average rating, 186 reviews

Lakeview Escape close to Disney&retail therapy

Oct 3 – 10

€ 128 per night

Guest favorite

Condo in Kissimmee

4.92 out of 5 average rating, 263 reviews

Beautiful Beach Style Condo minutes from Disney

Oct 14 – 21

€ 124 per night

Guest favorite

Condo in Kissimmee

4.94 out of 5 average rating, 159 reviews

Like Home Family Getaway

Dec 5 – 12

€ 110 per night

Guest favorite

Condo in Kissimmee

4.94 out of 5 average rating, 158 reviews

Affordable condo 3 miles from Disney and Golf!

Jan 9 – 16

€ 148 per night

Guest favorite

Condo in Orlando

4.87 out of 5 average rating, 167 reviews

Beautiful Lakeview ★ 1 Mile to Disney ★ 1BDR/2BA

May 21 – 28

€ 127 per night

Guest favorite

Condo in Orlando

4.86 out of 5 average rating, 199 reviews

Airbnb's Choice- Best at Blue Heron- Stunning View

Jul 27 – Aug 3

€ 161 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

Aug 22 – 29

€ 174 per night

Guest favorite

Townhouse in Kissimmee

4.88 out of 5 average rating, 128 reviews

Stellar Five Bedroom Townhome Under Ten Minutes to Disney

Nov 3 – 10

€ 386 per night

Guest favorite

Home in Davenport

4.97 out of 5 average rating, 97 reviews

Airy, Stylish Home with Pool Heat Included in Davenport

Feb 9 – 16

€ 282 per night

Guest favorite

Villa in Kissimmee

5.0 out of 5 average rating, 13 reviews

Family Retreat Near Disney with Pool & Hot Tub!

Mar 16 – 23

€ 385 per night

Villa in Kissimmee

4.79 out of 5 average rating, 223 reviews

Visit Disney World from a Sunny Home with a Pool

Dec 9 – 16

€ 216 per night

Home in Davenport

4.61 out of 5 average rating, 23 reviews

Solterra Resort 7br Family Home Pool Near Disney

Aug 28 – Sep 4

€ 285 per night

Home in Davenport

4.75 out of 5 average rating, 4 reviews

Luxurious 8br Palms Villa Pool Home-Champions Gate

Jun 21 – 28

€ 492 per night

Villa in Davenport

4.67 out of 5 average rating, 6 reviews

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

Sep 11 – 18

€ 744 per night

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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
180 reviews

Vacation rentals with a pool in Winter Garden

Top-rated rentals with a pool in Winter Garden

Vacation 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 Davenport

Home in Clermont

Home in Clermont

Home in Kissimmee

Home in Kissimmee

Home in Clermont

Condo rentals with a pool

Condo in Orlando

Condo in Kissimmee

Condo in Kissimmee

Condo in Kissimmee

Condo in Kissimmee

Condo in Kissimmee

Condo in Orlando

Condo in Orlando

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 vacation 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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