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Vacation rentals with a pool in Osceola County

Find and book unique homes with a pool on Airbnb

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Popular amenities for Osceola County rentals with a pool

House rentals with a pool

Superhost

Home in Kissimmee

4.79 out of 5 average rating, 184 reviews

4 Bedroom House Heated Pool 20 min From All Parks

DannielleRating, 5 stars3 weeks ago
Beautiful pool, very clean, comfortable beds! Only note is bringing your own towels, pillows, and blankets. There just isn't enough.
Guest favorite

Home in Kissimmee

4.9 out of 5 average rating, 185 reviews

Cozy Home with private pool in Kissimmee/Orlando

Niki-LynnRating, 5 stars1 week ago
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 🖤
Guest favorite

Home in Kissimmee

4.97 out of 5 average rating, 288 reviews

Upscale Contemporary Waterfront 3/2 Heated Pool

RobertRating, 5 stars1 week ago
stay was perfect. located fairly close to MCO. loved all the Latin food options
Superhost

Home in Kissimmee

4.82 out of 5 average rating, 110 reviews

Beautiful Vacation Home With Private Pool.

KristenRating, 5 stars4 days ago
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!
Guest favorite

Home in Kissimmee

4.86 out of 5 average rating, 150 reviews

Private 3BR PoolHome, WiFi,GameRM, AppleTV, ROKU

RobertaRating, 5 stars2 weeks ago
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!
Guest favorite

Home in Kissimmee

4.88 out of 5 average rating, 149 reviews

15 mi to Disney, KING Bed,Heated Pool & Fire Pit

MarcosRating, 5 stars4 days ago
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
Guest favorite

Home in Kissimmee

4.91 out of 5 average rating, 315 reviews

Family Home minutes from Disney!

PeterRating, 5 stars1 week ago
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.
Guest favorite

Home in Haines City

4.89 out of 5 average rating, 156 reviews

Southern Dunes Villa - Pool - Golf - near Disney

CarolineRating, 5 stars2 weeks ago
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

Guest favorite

Condo in Kissimmee

4.8 out of 5 average rating, 275 reviews

Renewed Disney Family Condo Universal Orlando

FernandaRating, 5 stars2 days ago
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! 🙏🏻☺️
Guest favorite

Condo in Kissimmee

4.9 out of 5 average rating, 118 reviews

NEW APT WITH WATER PARK AND NEAR DISNEY

BrynnRating, 5 stars1 month ago
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.
Guest favorite

Condo in Kissimmee

4.97 out of 5 average rating, 178 reviews

Welcome to our Son Shine condo ....

Nick and PaulinaRating, 5 stars2 days ago
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!
Guest favorite

Condo in Kissimmee

4.85 out of 5 average rating, 131 reviews

Magic Disney home/kissimmee3

RamseyRating, 5 stars1 month ago
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!
Guest favorite

Condo in Kissimmee

4.95 out of 5 average rating, 105 reviews

Stylish condo 7 miles to Disney.

NicRating, 5 stars3 weeks ago
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!
Guest favorite

Condo in Kissimmee

4.92 out of 5 average rating, 210 reviews

Lakeview Escape close to Disney&retail therapy

RubanaRating, 5 stars2 weeks ago
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.
Guest favorite

Condo in Kissimmee

4.84 out of 5 average rating, 114 reviews

Windsor Hills Resort - Why go to a hotel?

ChristopherRating, 5 stars7 months ago
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!
Guest favorite

Condo in Kissimmee

4.98 out of 5 average rating, 169 reviews

Modern Apartment with lake view Close to Disney

ShirleyRating, 5 stars4 days ago
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

KeppenRating, 5 stars1 month ago
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 reviews

Visit Disney World from a Sunny Home with a Pool

AndrewRating, 5 stars2 months ago
A beautiful villa that had everything we needed. A fantastic stay.
Guest favorite

Villa in Kissimmee

4.93 out of 5 average rating, 29 reviews

Family Retreat Near Disney with Pool & Hot Tub!

KatieRating, 5 stars1 week ago
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!
Guest favorite

Townhouse in Kissimmee

4.83 out of 5 average rating, 214 reviews

Beach House with Private Pool and Clubhouse near Disney

MariaRating, 5 stars3 weeks ago
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!
Guest favorite

Home in Kissimmee

4.93 out of 5 average rating, 14 reviews

Resort Home Near Disney with Pool & Game Room

Heather Tothany RhRating, 5 stars6 days ago
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!
Guest favorite

Townhouse in Kissimmee

4.89 out of 5 average rating, 131 reviews

Stellar Five Bedroom Townhome Under Ten Minutes to Disney

StephenieRating, 5 stars1 month ago
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 reviews

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

CraigRating, 5 stars40 months ago
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 reviews

Luxurious 8br Palms Villa Pool Home-Champions Gate

AunastashiaRating, 5 stars19 months ago
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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