
House vacation rentals in Longwood
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Top-rated house rentals in Longwood
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Popular amenities for Longwood house rentals
House rentals with a pool

Private pool home near Downtown
This is instantly become my favorite Airbnb. Such a wonderful and beautiful experience. It’s an absolutely fantastic location while also enjoying the aspect of privacy. This will definitely be my go to anytime that I have to come into Orlando!

The Shire -Private Pool & Hot Tub, Close to parks!
Monica was very responsive when we had an issue with one of the bathrooms and got it promptly fixed! We have stayed at this house previously and love the location and amenities. We will be back!

Gated community XL pool Home 2500sq/f
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.

Pool-Jacuzzi & Palm Trees/ 8 Universal/ 15 Disney
This home was clean and conveniently located near a ton of things to do, paces to eat, and a short drive to Disney.

Stylish Villa Private Pool-SPA Near Parks Disney!
Guillermo was an amazing host with a beautiful location. 10/10 would visit again.

Country Pool home on 2 acres-30 minutes to Disney
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.

Pool House in Kissimmee
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.

4BR-2KingMasters-SpaHeat-Private Pool-Remodeled
Tetyana’s place was very clean, welcoming, and felt like home away from home. It was conveniently located near Disney and easy to access. The bed was very comfortable and I slept like a baby. The master bath was a great way to unwind and relax after walking over 10,000 steps at the Disney parks. We LOVED the jacuzzi/pool combo and how secluded it was. Very quiet neighborhood, responsive host, and easy check-in. We’ll be back. :)
Weekly house rentals

Pet-Friendly Bungalow Near Downtown Orlando
Megan was really attentive and great to book with! The house felt very comfortable, like I was staying at a good friend’s house for a few days. I loved being so close to downtown and really appreciated the pet friendly hospitality as well!

969T-Single Storey House 20 min from Disney 4 bed
Tatiana is an excellent professional, friendly, and attentive to all requirements. The house is spacious, bright and with all the details to spend a comfortable and pleasant stay Nothing negative to mention, quite the contrary

9001-WW 5 Bedroom ALL Suites Pool Home
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.

5BD Windsor Westside Private Pool (WW 9025)
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

3/2 Family Home, climatized Pool and Sunset Views
Our host Ana was very helpful and would always respond quickly to any questions I had. I had a great experience.

BRAND NEW 10Bedrms/Sleeps22 At Windsor Island
Our stay was fantastic!! Close to all the parks, but with all the amenities here, you can enjoy your entire stay within the community! Perfect for large groups with kids! Game space upstairs is awesome! Would love to stay here again when we are in the area. Highly recommend!

Spacious 4 bedroom single story home
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.

5 ⭐️Gorgeous*Gated*15 Min.Disney*Wi-Fi*GameRoom
Excellent space. Close to Disney and other dining options. Nice, gated community. Will recommend!
Private house rentals

Central Florida Pool Home.
We truly enjoyed our stay at Jim's. It is a very nice house and well worth the money! Yoburt the cat is awesome company and a great host! Will go back again if we need a place to stay.

Jas Vacation Home
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.

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

Pelican House
We stayed at the Pelican House for three whole months. This home worked well for our extended stay because of its proximity to restaurants, groceries and Disney World! The neighborhood was quiet pretty much every night and having the open green space in the back was really nice, especially when the Sandhill Cranes came by in the mornings. They were awesome to watch. Donna was very responsive to any questions or concerns we had during the stay. She would reply within 10 minutes usually. The biggest benefit for us was proximity to Disney World. We could leave the house and be at the parks within 15-20 minutes most days. Traffic coming back from Disney was typically a challenge, though I feel the whole area in Kissimmee would be the same. All in all, we would absolutely stay at the Pelican house again for any future long-term stay in that area. It worked great for our needs this trip! Thanks Donna!!

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

Quiet Home Near the Springs
Glenn was nothing but friendly and responsive the entire time we needed something. His home was cute and what we needed for a good nights rest. A cute living area, small kitchen with the basics and a clean bedroom with a comfy bed. Very simple instructions to gain entry and for check out as well. As guests, the best we can do is be amenable and make sure we follow suit.

Villa with Guest House & Pool-Patio
We were in town for my son’s wedding this past week. We had a variety of family - both old and young - that we were trying to please. This place checked all the boxes we were looking for - spacious, clean, easy to get in and out, great pool and outside area (perfect for relaxing during the day). Lots of little touches as well - soap, shampoo, plenty of towels and extra linens, we even found some sunscreen one afternoon for the pool. We had a great stay and Jose was extremely helpful along the way. Definitely will stay here again in the future as we come back to FL to visit my son and new daughter-in-law! Thank you!

318 BD - Disney Dream House
Edney was an amazing host! His communication was quick and helpful, ensuring we had everything we needed for a comfortable stay. The house was breathtaking – extremely clean, spacious, and thoughtfully designed with every detail in mind. It far exceeded our expectations! We highly recommend staying here and would gladly return in the future. Thank you, Edney, for making our stay unforgettable!
Quick stats about house rentals in Longwood
Total rentals
60 properties
Nightly prices starting at
$10 before taxes and fees
Total number of reviews
2.8K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
10 properties have a pool
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- Universal Studios Florida
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- Reunion Resort Golf Courses - Palmer & Watson
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- Disney's Animal Kingdom Theme Park
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- SeaWorld Orlando
- ESPN Wide World of Sports
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- Amway Center
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- Epcot
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