Vacation rentals with a pool in Osceola County
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Top-rated rentals with a pool in Osceola County
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
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Popular amenities for Osceola County rentals with a pool
House rentals with a pool
Home in Kissimmee
4.79 out of 5 average rating, 184 reviews4 Bedroom House Heated Pool 20 min From All Parks
Beautiful pool, very clean, comfortable beds! Only note is bringing your own towels, pillows, and blankets. There just isn't enough.
Home in Kissimmee
4.9 out of 5 average rating, 185 reviewsCozy Home with private pool in Kissimmee/Orlando
Yirlen’s home had everything and more that we needed. So thoughtful with the added details, from the Garage with the BBQ and spot to hang out to the numerous fluffy blankets to kitchen appliances. We felt safe and had a great time bonding in the home. Thanks Again Yirlen 🖤
Home in Kissimmee
4.97 out of 5 average rating, 288 reviewsUpscale Contemporary Waterfront 3/2 Heated Pool
stay was perfect. located fairly close to MCO. loved all the Latin food options
Home in Kissimmee
4.82 out of 5 average rating, 110 reviewsBeautiful Vacation Home With Private Pool.
Me and my husband loved staying here! We celebrated our honeymoon in Kissimmee and going to the beach! Extremely nice location and would love to stay again! No issues finding it at all and the pool was great!
Home in Kissimmee
4.86 out of 5 average rating, 150 reviewsPrivate 3BR PoolHome, WiFi,GameRM, AppleTV, ROKU
Our visit to Tetyana's house was based upon our leaving the St.Pete/Tampa area for Hurrican Milton. Her house was a great place. We were safe inland and the house was comforting. Tetyana was very responsive. She checked in with us when we arrived to be sure that we were settled. She was very understanding when we told her that most of our party had traveled further north and therefore were not staying with us. She initiated an additional day for our stay when we told her that our house was still without power. She couldn't have been a better host. Thank you so very much Tetyana!
Home in Kissimmee
4.88 out of 5 average rating, 149 reviews15 mi to Disney, KING Bed,Heated Pool & Fire Pit
Love ❤️ the home. I am extremely grateful for the hospitality. Thank you for sharing your home with us. We will be coming back I promise
Home in Kissimmee
4.91 out of 5 average rating, 315 reviewsFamily Home minutes from Disney!
Juan's house was very clean and is kid friendly with the large fenced in yard and screened patio. If I could give 10 stars I would and will be coming back in the future.
Home in Haines City
4.89 out of 5 average rating, 156 reviewsSouthern Dunes Villa - Pool - Golf - near Disney
This was our second stay in this very comfortable, well equipped home. We love the location, and the pool is a real highlight. Unfortunately, this trip coincided with Hurricane Milton and Danielle was wonderfully responsive and could not have been more helpful when we were stranded due to cancelled flights. Lovely people and a lovely home! We will return, just maybe outside of Hurricane season.
Condo rentals with a pool
Condo in Kissimmee
4.8 out of 5 average rating, 275 reviewsRenewed Disney Family Condo Universal Orlando
The apartment was in a great area and easy location, and safe! The place inside was exactly how is described, and very clean, peaceful and private. The beds are super comfortable and everything was ready to use and working as expected. We didn’t had an enough time to use the pool, but it looked like very pleasant. The communication and instructions with Sara was quickly and clear. She was very supportive and kind all the time. I deeply recommend the place to stay and have a good time in Orlando area. Thank you again, Sara and team! 🙏🏻☺️
Condo in Kissimmee
4.9 out of 5 average rating, 118 reviewsNEW APT WITH WATER PARK AND NEAR DISNEY
We loved staying here for a weekend getaway! The condo was very clean and exactly what we needed for the three of us. Super convenient location for both Disney and Universal. Ivan was super responsive to our requests as well as answering our questions about the local weather! Would highly recommend for anyone looking for a fun getaway in Florida, as we would definitely book again.
Condo in Kissimmee
4.97 out of 5 average rating, 178 reviewsWelcome to our Son Shine condo ....
We had a really lovely stay at Laurie’s condo! It was absolutely perfect for our two little guys (5 and 1.5) who settled right in as soon as we arrived! What really stood out to me was the thoughtful communication from Laurie’s end with some check-in tips knowing we would arrive in the late evening. When travelling with young kids, these are the things that truly make a difference. The condo was fully equipped with everything we needed and more! It was VERY clean, bright and spacious. We spent 7 lovely days and could have spent much much longer! Thank you to Laurie for welcoming us so warmly and creating such a comfortable space to recharge after busy days! Everything was perfect!
Condo in Kissimmee
4.85 out of 5 average rating, 131 reviewsMagic Disney home/kissimmee3
The perfect place for a staycation! The theming of the house was perfect for our family. Close to the theme parks, restaurants and grocery stores. Would stay stay again!
Condo in Kissimmee
4.95 out of 5 average rating, 105 reviewsStylish condo 7 miles to Disney.
Great place to stay, located just a few miles from the major attractions and easy to get to with a car. Perhaps a little more dated than it looks from the photos but was very clean and tidy and everything you need is supplied, from bathroom towels to pool towels, a starter kit of essentials (toilet rolls, washing machine tablets, teabags, coffee, creamer etc. ) and a range of kitchen utensils and cookware. Overall a homely place with all you need for a great break and located near enough to everything you will want to do. Great communication throughout, easy to find and flexible checkin all made the experience that little better. Thanks Oton and team, hope to be back again one day!
Condo in Kissimmee
4.92 out of 5 average rating, 210 reviewsLakeview Escape close to Disney&retail therapy
Thank you for making us feel comfortable in your lovely place. We were very comfortable and decorated well. It was well equipped with all essentials. Kid friendly. We would definitely stay here again. Thank you for being great hosts.
Condo in Kissimmee
4.84 out of 5 average rating, 114 reviewsWindsor Hills Resort - Why go to a hotel?
We really enjoyed our stay. Had no problems checking in. We actually had a friend of ours come over, simple process we called Margie and within 20 minutes she had them registered and was able to visit. Very quiet, friendly and peaceful community. Thanks!
Condo in Kissimmee
4.98 out of 5 average rating, 169 reviewsModern Apartment with lake view Close to Disney
We had a wonderful time at Carol’s. It was beautiful, spotless, and the location was great just what we were looking for. We had a hiccup in our travel plans and we checked in very late and she was still available for us to communicate with she’s a fantastic host. We will definitely be returning to her lovely home. Thank you!!
Home rentals with a private pool
Home in Haines City
New Listing! Minniehaha Castle Retreat
This place was absolutely perfect. It was big enough for each of us to have our own space as well as our dog. It has a homey feel and I didn’t feel like I was staying in a museum. The host was promptly responsive and helpful when we had to book an extra night.
Villa in Kissimmee
4.79 out of 5 average rating, 236 reviewsVisit Disney World from a Sunny Home with a Pool
A beautiful villa that had everything we needed. A fantastic stay.
Villa in Kissimmee
4.93 out of 5 average rating, 29 reviewsFamily Retreat Near Disney with Pool & Hot Tub!
Super clean place (and we are picky) and comfy beds, which were much appreciated after long days at Disney! Kids loved their themed rooms, the arcade games, and the infinity game table. Hot tub was awesome! Publix nearby for easy pick up on the way in. Host was super responsive! All the different apps, companies, and guidebook were a bit confusing for what we needed to access for certain things (door code, QR code for entering the neighborhood, communicating before the trip, etc.) However, it’s always better to have more info than less!
Townhouse in Kissimmee
4.83 out of 5 average rating, 214 reviewsBeach House with Private Pool and Clubhouse near Disney
We had a wonderful stay at Jader’s place. It was exactly what my family of five needed. The location is perfect. Everything about the house was amazing. We would absolutely stay here again!
Home in Kissimmee
4.93 out of 5 average rating, 14 reviewsResort Home Near Disney with Pool & Game Room
THE best Airbnb I’ve ever stayed at! The only thing that was disappointing was the hot tub not working. I would definitely book again with overmoon!
Townhouse in Kissimmee
4.89 out of 5 average rating, 131 reviewsStellar Five Bedroom Townhome Under Ten Minutes to Disney
We loved staying at Hermon’s vacation rental. It was exactly what we needed: perfect location with plenty of parking for all of us who drove. The amenities were great and we loved the pool. We would definitely stay there again!
Villa in Davenport
4.67 out of 5 average rating, 6 reviewsAmazing Dream Solterra Villa -Disney/club/pool/spa
They house is exactly like described and had a lot of room. The cleaning could be a bit better, but they apparently had a very short turn-around. Be prepared to have parties going on around you. They do not enforce the noise ordinance at midnight like they should. We were not their to party, so this did have an affect on some of our guests. Overall, it was a pleasant stay. Edward is a super host for a reason. He always returned my emails and texts. When we needed something he was sure to get it to us. He made us feel comfortable about this purchase from the very beginning.
Home in Davenport
4.75 out of 5 average rating, 4 reviewsLuxurious 8br Palms Villa Pool Home-Champions Gate
Great place for large group plenty of space big kitchen for family to move around and cook. Kids enjoyed the pool they could slept in it if we allowed it . Overall great retail with good amenities in neighborhood
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