
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.
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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.

Quiet Place, convenient to everything!
The home is as described. Nice and Clean. Quiet neighborhood. Highly Recommend!!!!

3 bedroom Villa in Kissimmee
I cannot say enough good things about Raymond & our stay. I travel a lot for my son’s lacrosse team & this was our favorite Airbnb so far! Raymond is very responsive & kind! I hope it’s available to book next year when we return.

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

Gated community XL pool Home 2500sq/f
Heidy’s house was wonderful! Very clean and well stocked. The pool and backyard were very peaceful, we spent a lot of our time out on the patio. The master king bed was super comfortable! Heidy left us some cold water in the fridge which was needed upon arrival, June is very hot in Florida! Would 100 percent recommend!

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.

BBQ Grill | Wi-Fi | Pool Access | 20 Min Disney
Wonderful hosts, had a great experience. I would definitely revisit if the opportunity comes again.
Apartment rentals with a pool

3191-103 Resort Lake View Disney Universal Orlando
I can’t say enough great things about our stay with Fonti! Traveling with my triplets can be a challenge, but this Airbnb made everything seamless and comfortable from the moment we arrived. The space was cozy, clean, and just right for a family—plenty of room for the kids to spread out and feel at home. The real highlight for my little ones was the pool and water park! They spent hours splashing, laughing, and making memories that they’ll be talking about for a long time. It was such a joy to see them so happy and entertained in a safe, fun environment. Fonti was an exceptional host—kind, communicative, and incredibly accommodating. When I realized I needed to extend our stay, he made it happen quickly and without any hassle. That flexibility made a world of difference and allowed us to enjoy one more night of relaxation and fun. Highly recommend this spot to any families

Fantastic 3BR Condo close to OCCC & Epic Universe!
Very comfortable, in a great location - close to amenities and easy for Uber to find. Dennis was super helpful and responded in minutes.

Maria Luz Studio-Huge Terrace/Universal area.
Fantastic and Wonderful! This place has by far been the best!

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.

Disney & Epic Free Shuttle, Kitchen
Great area to stay and awesome host!

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!

Full-Service Gated Resort, Disney, Universal, MCO!
Thank you AJ and Nicole had a wonderful time this weekend definitely recommend
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.

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!
This home is just at pictured. Has everything you’ll need. Grill and propane being available on site were a very nice bonus. Hot tub and heated pool were fantastic after walking all day. Host was amazing and communication was very quick. Highly recommend this place and location

Sleeps 16! Pool + Arcade | Orlando Resort Retreat
Pictures shown is exactly how the place looks. Felt secure in the neighborhood. Plenty of amenities. Pool and hot tub was a plus. Game room was also a plus for the little ones.

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.

Wr001or (1stfororlando)
Quick stats about holiday rentals with a pool in Casselberry
Total rentals
60 properties
Nightly prices starting at
₹866 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