House vacation rentals in Windsor Hills, Four Corners

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Popular amenities for Windsor Hills, Four Corners house rentals

House rentals with a pool

Guest favorite

Home in Kissimmee

4.91 out of 5 average rating, 45 reviews

Luxury Poolside Escape: 3BR, 2BA w/ Large Driveway

PollakRating, 5 stars3 weeks ago
I had an incredible experience at this Airbnb! The place was clean, cozy, and had everything I needed. The location was perfect, and my host was super friendly and helpful. I loved the outdoor space for relaxing. I can’t wait to go back for another amazing stay! Highly recommend!
Guest favorite

Home in Davenport

4.91 out of 5 average rating, 124 reviews

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

JenniferRating, 5 stars1 week 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.
Superhost

Home in Davenport

4.82 out of 5 average rating, 11 reviews

Splash & Play ~ Poolside Bliss ~ 15 Mins to Disney

TerrellRating, 5 stars3 weeks ago
Amazing and beautiful house. Everything was up to par and some more
Superhost

Home in Davenport

4.83 out of 5 average rating, 18 reviews

Beautiful stylish Home in Davenport

JasmineRating, 5 stars5 months ago
The home was perfect, it was clean, private and fun. I enjoyed the spacious pool area and speakers to play music. We also enjoyed playing pool the neighborhood is quiet and a gated community. I would definitely return again!
Guest favorite

Home in Davenport

5 out of 5 average rating, 7 reviews

Casa El Paraiso pool house w| 5 bedrooms.

SamuelRating, 5 stars1 month ago
Henry and Jaileen were accommodating and had the place well prepared for our stay
Guest favorite

Home in Clermont

4.92 out of 5 average rating, 142 reviews

Stylish Villa Private Pool-SPA Near Parks Disney!

SamanthaRating, 5 stars3 weeks ago
Bringing my family of 5 this house gave us plenty of room to get away from each other when needed. Also had things to bring us together and enjoy our time.
Superhost

Home in Kissimmee

4.82 out of 5 average rating, 114 reviews

Pool House in Kissimmee

KuntaRating, 5 stars3 weeks ago
this my second year in a row at the Florida classic and I love this air bnb..I'm getting it again next year...it's safe and peaceful.. and the price is amazing..next year will make the 3rd time i stayed there i love it
Guest favorite

Home in Davenport

4.94 out of 5 average rating, 16 reviews

Carrera retreat

RoseRating, 5 stars3 weeks ago
Thank you for helping me on my amazing family trip . We felt right at home . kids enjoyed the pool every day after you turned on the heater “thanks for coming in such short notice by the way” Amazing home already looking for next trip to book it ! .

Weekly house rentals

Superhost

Home in Kissimmee

4.83 out of 5 average rating, 12 reviews

SUPER VILLA - 7BDR|5.5BAs POOL & THEME ROOMs!

NieceyRating, 5 stars6 days ago
Place was beautiful, Justin was amazing very friendly and fast in responding one of the best properties we have stayed in the area!!!!
Guest favorite

Home in Kissimmee

4.95 out of 5 average rating, 20 reviews

9001-WW 5 Bedroom ALL Suites Pool Home

PatriciaRating, 5 stars2 months ago
Beautiful home, very welcoming, and cozy home to be in. This home was just as nice in person than the pictures. 10/10 stay and would recommend this nice home.
Superhost

Home in Davenport

5 out of 5 average rating, 3 reviews

2024 Brand NEW 10Bdrms/7Bath At Windsor Island

BrianRating, 5 stars1 month ago
the house was beautiful my family liked the kikitchen and the dining 🍽
Guest favorite

Home in Clermont

4.97 out of 5 average rating, 174 reviews

Caribe Villa Brisa- Disney is only 6 miles away!

JeriRating, 5 stars3 weeks ago
We love staying here as it is so relaxing but within so many good restaurants and things to do. The house is clean and beautiful. We spent most of time in the pool and spa. This is our second time staying here because we like it so much! Randy and Barb are great and so responsive!
Superhost

Home in Kissimmee

4.9 out of 5 average rating, 120 reviews

5BD Windsor Westside Private Pool (WW 9025)

ShirleyRating, 5 stars1 month ago
Nice space for a group of 5 adults
Superhost

Home in Kissimmee

4.89 out of 5 average rating, 131 reviews

6BR Disney Vacation Home w\2 Suites Pool + Hot Tub

BruceRating, 5 stars1 month ago
We had a really nice stay at Troys house. Troy has everything a group needs for their stay. The place was very clean. The home is well laid out for large groups. And the community center is a really nice benefit. I highly recommend choosing this home for your visit to Orlando.
Guest favorite

Home in Davenport

5 out of 5 average rating, 6 reviews

BRAND NEW 2024 10Bedrms/Sleeps22 At Windsor Island

NancyRating, 5 stars1 month ago
The house was incredible for our family vacation! It was very clean and we had a great time during our stay. The host was responsive and helpful with any question I had. Highly recommended staying here. It was close to nearby grocery stores and fast food, convenient location! The resort had great amenities such as pool and mini golf, something for everyone!
Guest favorite

Home in Davenport

5 out of 5 average rating, 79 reviews

5 ⭐️Gorgeous*Gated*15 Min.Disney*Wi-Fi*GameRoom

AnimeshRating, 5 stars1 month ago
We stayed at Eric's place for a week during our Disney vacation in Orlando. The place was exactly as described and was very spacious and clean. The pool was clean and we enjoyed swimming on couple of days when we were not visiting the parks. The kitchen was well stocked and had all needed appliances and utensils. The house is in a gated community and is peaceful and safe. Disney parks are about 20-30 mins drive and there are plenty of grocery stores and restaurants nearby. Eric provided all the instructions beforehand and there was no issues checking in. Overall it's a great place to stay and would recommend it to anyone visiting Orlando.

Private house rentals

Guest favorite

Home in Davenport

4.78 out of 5 average rating, 45 reviews

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

JasmineRating, 5 stars3 weeks 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 favorite

Home in Kissimmee

5 out of 5 average rating, 7 reviews

3840 Supreme Trendy Place

JulenRating, 5 stars1 month ago
Bruna has been incredibly responsive for our stay. No issues whatsoever, thanks a ton.
Guest favorite

Home in Kissimmee

4.88 out of 5 average rating, 25 reviews

Pelican House

GeoffRating, 5 stars8 months ago
Had a great month long stay. Took a daily walk on the walkway throughout the community. The home is set up nicely and the lanai is a great place to sit outside with a pet.
Superhost

Home in Kissimmee

5 out of 5 average rating, 4 reviews

Wow House PLUS Apartment*Pool*Near Disney*GolfView

FrancisRating, 5 stars36 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.
Superhost

Home in Kissimmee

4.81 out of 5 average rating, 101 reviews

Luxury vacation house near Disney World

LincolnRating, 5 stars3 weeks ago
Host is very reasonable, very communicative. Great place for big groups. Definitely recommend.
Superhost

Home in Davenport

4.6 out of 5 average rating, 43 reviews

Entire House Davenport My Dream House

HectorRating, 5 stars4 months ago
An excellent, very cozy place to spend a vacation both inside and outside the hotel. Very nice, excellent place. I hope to visit this place again and find it available. Thank you very much.
Guest favorite

Home in Kissimmee

5 out of 5 average rating, 24 reviews

Stylish Lakefront Cottage w/Huge South Facing Pool

CarrieRating, 5 stars20 months ago
This was a beautiful place to stay. Close to all the Disney parks and Universal Studios. The gated community is very quiet and peaceful. Sitting out by the pool, or in the hot tub was the best. Great location with tons of restaurants and Wal-Mart close by. Charles & Jo were wonderful host and very responsive. Checked in during the stay just to make sure everything was going well and we didn’t need anything. I would definitely stay here again next time I was in the area. Thanks Charles & Jo for a wonderful Disney experience!
Superhost

Home in Four Corners

4.82 out of 5 average rating, 141 reviews

Lux 7 Bdr~Private Pool ~Golf at Champions Gate

AidaRating, 5 stars1 month ago
Great hosts! Spacious and clean house. Everything was perfect! We had a wonderful time with the family. We had to rescheduled twice because of the hurricane and every time the communication was great!

Quick stats about house rentals in Windsor Hills, Four Corners

  • Total rentals

    340 properties

  • Nightly prices starting at

    $70 before taxes and fees

  • Total number of reviews

    8.1K reviews

  • Family-friendly rentals

    330 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with a pool

    340 properties have a pool

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Osceola County
  5. Four Corners
  6. Windsor Hills
  7. House rentals