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House holiday rentals in Winter Garden

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Popular amenities for house rentals in Winter Garden

House rentals with a pool

Top guest favourite
Home in Orlando
5 out of 5 average rating, 121 reviews

Private pool home near Downtown

FrankRating, 5 stars1 week ago
Kyle was a very responsive and friendly host. We especially noted the little details and home amenities of the place. Light switches were labeled, which was a great help. The location is in walking distance to some of Orlando’s very best restaurants. Fantastic stay overall!
Guest favourite
Home in Davenport
4.91 out of 5 average rating, 124 reviews

The Shire -Private Pool & Hot Tub, Close to parks!

JenniferRating, 5 stars3 months ago
This home has such a great layout. Monica was a wonderful and attentive host. This location is close to everything Orlando has to offer. The pool and hot tub were lovely. This home looked even better in person. The beds and pillows were so comfortable. We cannot wait to come back.
Guest favourite
Home in Lake Mary
4.89 out of 5 average rating, 252 reviews

Gated community XL pool Home 2500sq/f

KatieRating, 5 stars1 week ago
Heidy and her husband Michael were absolutely wonderful hosts while we were visiting Lake Mary. We loved the Sanford area and all the recommendations Heidy gave us. Their home is beautiful, clean, cozy and the backyard is an absolute dream. Our girls loved the pool. It is “cannon ball approved” by my 10 yo. My husband accidentally left the garage door open when we left for Universal for the day, but Michael was notified and kindly went and closed it and checked on the house for us. We loved having them close by. They were so sweet and helpful. We had the best time on our vacation and can’t wait to visit again.
Guest favourite
Home in Orlando
4.87 out of 5 average rating, 197 reviews

Pool-Jacuzzi & Palm Trees/ 8 Universal/ 15 Disney

JenniferRating, 5 stars1 week ago
Our host was very nice. House was clean and cute. Only issue we had was the 2nd bathroom being outside. Other than that we had a great stay. Very close to shopping and restaurants!
Top guest favourite
Home in Clermont
4.92 out of 5 average rating, 144 reviews

Stylish Villa Private Pool-SPA Near Parks Disney!

TyreseRating, 5 stars3 months ago
Guillermo was an amazing host with a beautiful location. 10/10 would visit again.
Guest favourite
Home in Apopka
4.87 out of 5 average rating, 138 reviews

Country Pool home on 2 acres-30 minutes to Disney

LindaRating, 5 stars1 week ago
This was the perfect location for our family! The kids enjoyed the pool and swings. We enjoyed everything about the home. We would definitely book this home again.
Superhost
Home in Kissimmee
4.82 out of 5 average rating, 116 reviews

Pool House in Kissimmee

DouglasRating, 5 stars2 weeks ago
Everything was great. We came down to see our granddaughters on spring break. Usually don’t want to swim,this time they did. Wish I would have spent the money to heat the pool. They enjoyed playing pool and wanted to play air hockey but no puck but amazon took care of that. The master on one end and other bedrooms on the opposite end was a big plus for we got up earlier so we didn’t wake them. Would definitely recommend and would love to come back next year.
Guest favourite
Home in Davenport
4.95 out of 5 average rating, 22 reviews

Retreat Race

VeronicaRating, 5 stars1 week ago
Beautiful, spacious and clean home. Great stay. Hope to be back in the future.

Weekly house rentals

Top guest favourite
Home in Orlando
4.94 out of 5 average rating, 31 reviews

Pet-Friendly Bungalow Near Downtown Orlando

StephanieRating, 5 stars3 weeks ago
Megan's place was everything we needed. We felt right at home and my dog was very happy with the house and the backyard. Totally fenced in yard was safe and secure for my fur baby and the neighborhood was super quiet and cute. Megan was very responsive if I had any questions and the instructions to get in were super easy. I am so very pleased with the comfort of the beds and how wonderful the space was. I will definitely be staying here again hopefully soon. If you need a safe, pet friendly place to stay close to just about everything this is the place for you and your pets. Highly recommend!!!!! 5 stars from me and my 4 legged friend.
Guest favourite
Home in Davenport
4.78 out of 5 average rating, 46 reviews

969T-Single Storey House 20 min from Disney 4 bed

JasmineRating, 5 stars4 months ago
Loved this property, it had everything we needed for a thanksgiving weekend. Publix was 8 mins away, very large driveway. And they supplied the bathrooms with plenty of tissue paper. A lot to do on the property such as fire pit and game room
Guest favourite
Home in Kissimmee
4.95 out of 5 average rating, 21 reviews

9001-WW 5 Bedroom ALL Suites Pool Home

AmberRating, 5 stars3 months ago
Found this air b&b last minute and late due to having to leaving our precious air b&b. Magic was very helpful and responsive on such short notice. I’m so thankful we found this place my kids absolutely loved it and they will remember it forever! It was very clean. They were also very accommodating. Had an issue with the dishwasher but it was quickly fixed. We absolutely loved it, thank you again!! You made our vacation amazing. Perfect house for our Disney Christmas surprise. We will be back.
Superhost
Home in Kissimmee
4.9 out of 5 average rating, 123 reviews

5BD Windsor Westside Private Pool (WW 9025)

LydiaRating, 5 stars1 month ago
Jose is very friendly and respond most of the time within 15 minutes. Easy to talk to. We loved the place. We were already familiar with the subdivision and the area. We were with 6 and had plenty of rooms and bathrooms
Superhost
Home in Kissimmee
4.77 out of 5 average rating, 141 reviews

3/2 Family Home, climatized Pool and Sunset Views

DerekRating, 5 stars2 weeks ago
The house was very clean and in a nice area. It was a great place to come back and relax after the day’s activities. The view through the back door was excellent too!
Guest favourite
Home in Davenport
4.92 out of 5 average rating, 12 reviews

BRAND NEW 10Bedrms/Sleeps22 At Windsor Island

KelsiRating, 5 stars2 weeks ago
Bruce’s place was great. We had a family of 11. There were enough rooms for everyone, and the place matched the pictures. This was our first time staying at a resort, and it was worth it. The only problem we had was the long lines getting into the resort(they could use a second entrance, but it did not impact our overall stay! We had questions for Bruce, and each time he answered in a timely manner!
Guest favourite
Home in Winter Springs
5 out of 5 average rating, 6 reviews

Spacious 4 bedroom single story home

RobertRating, 5 stars6 days ago
This home is one the most wonderful place we’ve stayed in. Lovely kitchen complete with so many items to cook a family dinner. Beautiful lanai with comfortable seating and lovely plants. And the back garden is beautiful as well with many flowering plants this time of year. Ronald was very accommodating by solving all the minor problems. Loved our stay here.
Guest favourite
Home in Davenport
4.91 out of 5 average rating, 11 reviews

Spacious 4BR Near All Florida Attractions!

BlandineRating, 5 stars3 months ago
Evening was as depicted, we really enjoyed the home and the area is really quiet and really close to everything ! Thank you again Michelle for a seamless journey and we will definitely book again !

Private house rentals

Top guest favourite
Home in Auburndale
4.94 out of 5 average rating, 156 reviews

Lake Whistler Beach House with lakefront pool

ToddRating, 5 stars2 weeks ago
Can't say enough great things about Jonathan and his place! We loved staying there, felt right at home, we were there with 5 kids and there was always something fun for them to do, swimming in the pool and hot tub, s'mores by the fire, pool, air hockey, pacman was a hit, basketball, and lots of games, books and movies to choose from. There was plenty of space to spread out and feel comfortable and Jonathan added so many thoughtful touches to our stay - greeting us with an Apple Pie on the kitchen counter, a bowl of chocolates in the entry way and plenty of coffee. The kitchen was fully stocked with everything we needed, there were plenty of towels for showers and swimming, life jackets were supplied. The kids said they wanted to move there : ). Need I say more? haha
Superhost
Home in Four Corners
4.77 out of 5 average rating, 97 reviews

Jas Vacation Home

CarmenRating, 5 stars3 months ago
Great place for my family to spend Christmas together. The place had enough space, quite, easy access, and mostly the kitchen space was more than enough to cook a holiday dinner.
Guest favourite
Home in Orlando
4.86 out of 5 average rating, 56 reviews

Private luxury home w additional Suite on 0.6 acre

IgnatiosRating, 5 stars1 month ago
My family and I travel all around the world. This is by far one of the best Airbnb we have ever stayed at truly a home away from home. The house is excellent. The host is amazing. Always willing to help in whatever way he can. Thank you very much for a wonderful stay.We will definitely stay with you again.
Guest favourite
Home in Davenport
4.89 out of 5 average rating, 153 reviews

Private Haven: Free Pool Heat & BBQ/5Bedroom/4.5Ba

NataliaRating, 5 stars1 month ago
Pam’s place was lovely and a perfect place for our vacation. The heated pool was very appreciated, and there were plenty of towels, blankets, soap, dishes, blankets etc. The house was exactly as pictured and very spacious. Pam was very helpful with instructions and checked in regularly. We had no issues during our stay but we felt if anything did occur Pam would have been responsive which was nice to know. We would definitely recommend this place and would stay again if we came back to Orlando.
Superhost
Home in Kissimmee
4.89 out of 5 average rating, 27 reviews

Pelican House

JessicaRating, 5 stars3 months ago
Our family had a great stay at The Pelican House. Donna was very responsive and friendly. The house matched its description. Very clean, comfy beds and close to all the parks. Thank you for the outstanding stay.
Superhost
Home in Kissimmee
5 out of 5 average rating, 4 reviews

Sleeps 10 * House + Apt *Pool*Near Disney*GolfView

FrancisRating, 5 stars40 months ago
Walk in the door of the main house and first thing is “wow.” Spaciousness and high ceilings and the view all the way through to the back windows of the golf course was impressive. Neighborhood very walkable and safe Little traffic within the complex for kids. Nice to have easy driveway parking right out front for unloading. Plenty of space to fit my people. Nicely decorated and not full of a bunch of bling on end tables and shelves that the kids would run into and break. I was not just clean but had a sense of clean, design-wise, with the modern but comfy furniture, giant kitchen island, table surfaces… all that and, again, the spaciousness gives you the ability to breathe! But it still had a homey feel – way better than a hotel setting where we would have all been on top of each other. The cute coffee station was a really nice touch with everything you needed right there in one spot off the kitchen. Because the house is set back on the property it was like a real get-away, and with the guest house, my parents were able to have their privacy and we could have ours – when we needed it. The guest house is exactly what they needed. Separated from main house it is perfect for the grandparents to spend alone time with the kids for a while. But it’s also like a real house by itself! Very open and comfortable – and a great view of the action in the pool and courtyard. Pool is just big enough to enjoy and with the protective fence, you don’t really have to worry about the kids running around in the yard – that was also a nice touch. And even though there’s a Wa Wa right outside the complex gate, for quick lunches and coffee – and gas – we discovered an area ChampionsGate, a suburban community with all the restaurants and shops and places to do errands. About a 5-10 minute drive. Lastly, I really liked the big walk-in shower, and my partner absolutely loved the big tub – all that in the en suite bathroom off the master bedroom. It was out of the way and private –  like our own a retreat spot.
Guest favourite
Home in Clermont
5 out of 5 average rating, 9 reviews

Sunset Cove at Champions! Book this very private

TamiRating, 5 stars3 weeks ago
This lovely home was exactly as described. Located near the end of a gated street, but within 20 minutes of many restaurants. It also had the best selection of kitchen supplies and the nicest washer & dryer I’ve ever seen in a rental. Sue was a pleasure to work with!! We hope to return next year.
Guest favourite
Home in Apopka
4.94 out of 5 average rating, 189 reviews

Quiet Home Near the Springs

KaylaRating, 5 stars1 week ago
Glenn's place was great! It was extremely clean and all the essentials were available. We loved the swing on the porch and the quality linens. The kiddo said "5 stars!"

Quick stats about house rentals in Winter Garden

  • Total rentals

    70 properties

  • Total number of reviews

    2.8K reviews

  • Family-friendly rentals

    30 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with a pool

    10 properties have a pool

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

Destinations to explore

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