
Holiday rentals with a pool in Casselberry
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Casselberry
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for Casselberry rentals with a pool
House rentals with a pool

3 BR/2BA Home w Private Pool~12 min to Airport!
Had a nice stay with family and friends at Alyssa’s place along with 2 dogs. Was so nice to be able to bring out pets along on vacation. The house was clean, beds were comfortable, lots of space. I Spent most of my time out in the pool which was amazing.

Private Pool 4/2 Waterfront Oasis Weekly Discounts
This place was great, nice pool , clean and neat, loaded with kitchen utensils and all you need to cook. The neighborhood was quiet. Overall a good place to stay

Private pool home near Downtown
Great house. Great host. Always attentive and responsive. 2nd stay. Will go for a 3rd

Cozy 4/2, King Beds, Pergola, Hot Tub & Pool
Very nice inside and spacious backyards closed in games for the children and family to do lots of beds I like that you can shut the master door and everybody can still get to the bathroom as a huge thing for me.

Rate Discount~ Pool~Private Country Retreat
In town for a baseball tournament. Location to the fields was great — less than a 10 minute drive! Everything was clean. We enjoyed the pool after a hot day at the field. We appreciated the grill and used it to make some hamburgers and hot dogs. Kitchen was well equipped. Would definitely stay again if we need to be in the area.

Year around Heated Pool 7 min from Airport!
Super nice, pictures do not do it justice. Upgrades clearly done little by little. Pool is amazing, outdoor area great, cozy yet spacious. Would book here again and again. 20 min from Camping World Stadium, 15 min from Downtown Orlando truly accurate, easy in and out from main road and highways.

3,000 Sqft Historic Home With Pool Near Everything
This was the perfect place to stay. This home is beautifully decorated, and such a nice little quiet retreat. I felt like I was staying in a home that was showcased in a magazine. The beds are so comfy and the pool is serene. I had the most relaxing weekend ever, thank you Nicole!

3 bedroom Modern pool home,close to UCF&Boombah
This was my second time renting from Loida, home was exactly as pictured and described. Loida was very responsive to all my questions! She was wonderful and easy to work with. I would absolutely rent again!
Condo rentals with a pool

ORLANDO SUITE@ UNIVERSAL/DISNEY/CONVENTION CENTER
Very convenient

Studio close to Universal Studios + free Netflix
Great Stay,Check In Was Easy You Go Right Up To Room With The Codes They Provide. Room Looks Just Like Picture, Everything Was Clean And Set Up Perfect For A Studio. Everything Is Also Close To Where You Stay.

King Bed Small Studio Disney World Universal
Laura’s place was wonderful for my husband and I. It was our first time to Kissimmee. It is a very short distance from the parks and attractions. It was also close to quality restaurants and convenient gas stations. Laura’s studio was clean and represented what was expected from the photos. This is a very cozy location with pool and hot tub. Laundry and snacks were easily accessible. Overall, it was a wonderful stay and the price was in our budget!

Maria Luz Studio-Huge Terrace/Universal area.
I LOVED THE EXPERIENCE!

VCR2-108 Deluxe New Apartment - Convention Center
We like this apartment very much. it's new and clean, location is also good, whole environment is good. The host reply very fast. will book it again when next time come. only not convenient is that can't stock luggage before check in and after check out.

Modern Studio with Private Terrace near Universal
Great host and beautiful location. Near most of the major attractions and shopping.

LUXURY ONE BEDROOM CONDO NEAR UNIVERSAL
Great stay - very close to Universal and nearby attractions. Fast communication and the pool was a plus. Thank you!

Disney & Epic Free Shuttle, Kitchen
Great area to stay and awesome host!
Home rentals with a private pool

Disney's Championsgate: Private Pool & Arcade Fun!
This property was very nice and matched the photos to a T. The house was spotless & very spacious. The renovated design was modern and the themed rooms were perfectly executed. The only downside was the check-in process at the gate, but after a quick phone call, the issue was resolved. I absolutely loved the space. 10/10.

Minniehaha Castle Retreat
This house was ideal for our weekend. Everything we needed was provided, and the extras pillows, towels, and toiletries were a nice touch. The pool water heater was a great addition, making the water perfect for the time of year ($10 a day was worth it) . We enjoyed our stay and would recommend it to others.

Airy, Stylish Home with Pool Heat Included in Davenport
Had a great stay at Phil's place. The home was perfect for mother's day weekend. My daughter loved the pool. The home was clean! 10/10 recommend.

Visit Disney World from a Sunny Home with a Pool
I can’t say enough good things about this Airbnb – it was absolutely incredible from start to finish. The space was spotless, nicely decorated and had every amenity we could have possibly needed (and then some!). It truly felt like a home away from home, with thoughtful touches throughout that made our stay extra special. The host was communicative welcoming and very helpful!

Family Retreat Near Disney with Pool & Hot Tub!
I really love this place. If I had to change one thing it would have been to be sure that it’s listed as only one bathtub, which wasn’t a big deal cause I’m grandma, but it could be a hassle for others.

Sleeps 20! Near Disney w/ Pool | Twice-as-Nice
Place was nice. It had a lot of amenities that we enjoyed. The game room and pool table was fantastic. Rooms were nice and comfortable. Would definitely stay again.

Amazing 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.

Private Oasis with Pool & Spa- 3400clr
The home was beautiful & exactly as described.
Quick stats about holiday rentals with a pool in Casselberry
Total rentals
60 properties
Nightly prices starting at
$17 NZD before taxes and fees
Total number of reviews
2K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
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- Universal Studios Florida
- Orange County Convention Center
- Universal's Volcano Bay
- Old Town Kissimmee
- Discovery Cove
- Disney's Animal Kingdom Theme Park
- Universal Orlando Resort
- SeaWorld Orlando
- Disney Springs
- Playalinda Beach
- ESPN Wide World of Sports
- Titusville Beach
- Amway Center
- Epcot
- Daytona International Speedway
- Magic Kingdom Park
- Reunion West
- Aquatica
- ChampionsGate Golf Club
- Disney's Hollywood Studios
- Kissimmee Lakefront Park
- Walt Disney World Resort Golf
- Island H2O Water Park
- Blue Spring State Park