Vacation rentals with a pool in Winter Park

Find and book unique homes with a pool on Airbnb

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Popular amenities for Winter Park rentals with a pool

House rentals with a pool

Superhost
Home in Orlando
4.84 out of 5 average rating, 306 reviews

King Bed | Grill | Pets | Central Location!

SianoahRating, 5 stars3 weeks ago
This Airbnb is definitely one we will keep in rotation. With an elderly in-law, we needed a place with a fourth bedroom. The bonus was the pool and we took full advantage of that just to relax and enjoy. Everything we needed was close by and easy to get to. All in all the hosts home felt like home. We hope to stay again in the future.
Top guest favorite
Home in Kissimmee
4.87 out of 5 average rating, 241 reviews

3 bedroom Villa in Kissimmee

JenniferRating, 5 stars3 weeks ago
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.
Guest favorite
Home in Casselberry
4.87 out of 5 average rating, 101 reviews

Cozy 4/2, King Beds, Pergola, Hot Tub & Pool

BeverlyRating, 5 stars1 week ago
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.
Top guest favorite
Home in Minneola
4.98 out of 5 average rating, 130 reviews

Pool + Heated spa Family friendly King suite Oasis

VivianRating, 5 stars1 week ago
What an amazing 2 weeks with family!! Don’t hesitate to book this GEM of a home! It’s beautiful, peaceful (on a culdesac) SUPER QUIET at night, great spots to eat at the waterfront and all around Minneola in general. We had an issue with warming the spa and both were very responsive, ordered the part and within 2 days its was perfect. This house had EVERY amenity you would need and then some…games indoor and outdoor, kids books, fire pit, swing, blankets to cozy up on couch, dog bowls, leashes, toys etc. They truly make you feel like it’s home. We can’t rave about it enough!! We were only a short half hour drive away from Disney also. Our 2 small dogs absolutely LOVED chasing lizards and frogs around the pool area! We would LOVE to come back if they would have us! Thank you again for being such great hosts! All you do to make your guests feel comfortable at home does NOT go unnoticed! Until next time beautiful Clermont/Minneola!!! šŸ’•
Top guest favorite
Home in Minneola
4.98 out of 5 average rating, 162 reviews

Spacious Getaway ~ Heated LED Pool & Ping Pong

LaTishaRating, 5 stars2 weeks ago
We had a great stay. The residence was beautiful and came with everything we needed. Our 4 and 1 year old enjoyed the toys provided. The pool was private and relaxing. Neighborhood very quiet with kind neighbors. Thank you for everything ā¤ļø
Guest favorite
Home in Orlando
4.88 out of 5 average rating, 202 reviews

Pool-Jacuzzi & Palm Trees/ 8 Universal/ 15 Disney

JoyceRating, 5 stars4 weeks ago
We where in Orlando to go to my granddaughters graduation & this home just made it a perfect vacation - so comfortable - & clean & the pool & outside area was amazing !!
Superhost
Home in Orlando
4.86 out of 5 average rating, 195 reviews

Year around Heated Pool 7 min from Airport!

JoseRating, 5 stars1 week ago
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.
Guest favorite
Home in Four Corners
4.96 out of 5 average rating, 178 reviews

Luxurious Golf Front Oasis: Pool, Spa, View&Cinema

KaylaRating, 5 stars3 weeks ago
We had such a great time staying at Michael’s place! Our five teenagers were never bored with all of the fun amenities! The kids had a great time with the karaoke machine, arcade games and outdoor area! My husband and I love coffee, so we really appreciated the coffee bar and supplies that were provided. The house was beautiful and Michael was extremely responsive. We would stay again!

Condo rentals with a pool

Superhost
Condo in Florida Center
4.87 out of 5 average rating, 103 reviews

Luxury Condo On I-Drive & One Mile from Universal

Jose EduardoRating, 5 stars1 week ago
We had an absolutely wonderful stay at Mike's place in Orlando! From the moment we booked, Mike was an exceptional host - incredibly communicative, friendly, and always quick to respond to any questions we had. We couldn't have asked for a better experience. We would highly recommend his place to anyone visiting Orlando and will definitely be back on our next trip!
Guest favorite
Condo in Florida Center
4.9 out of 5 average rating, 111 reviews

Studio near Universal Studios with great view

KinjalRating, 5 stars4 days ago
The apartment BNB was really great and exactly as described with all basic amenities provided. Super close, walkable distance, to a variety of restaurants with different cuisines. Universal Studios is a close 10 mins drive/uber ride away. The studio feels super cozy, the view from the balcony is also very nice. Laundry room is right next to the unit which was very convenient. Hosts are quick to respond to any messages/questions you may have. Enjoyed my time at this Airbnb!
Guest favorite
Condo in Orlando
4.92 out of 5 average rating, 101 reviews

Location,Location 3bd 2bth near parks conv.ct/Int.

LucindaRating, 5 stars1 week ago
Working with Isabela, was easy. The place was perfect for our needs. Beautiful, easy access to local attractions. Would highly recommend.
Guest favorite
Condo in Kissimmee
4.97 out of 5 average rating, 144 reviews

202_Magical and Cozy 2BR minutes from Disney

ChristopherRating, 5 stars1 week ago
perfect in every way.
Guest favorite
Condo in Florida Center
4.88 out of 5 average rating, 225 reviews

Maria Luz Studio-Huge Terrace/Universal area.

LisaRating, 5 stars2 weeks ago
Fantastic and Wonderful! This place has by far been the best!
Guest favorite
Condo in Orlando
4.94 out of 5 average rating, 148 reviews

VCR2-108 Deluxe New Apartment - Convention Center

GuoRating, 5 stars1 week ago
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.
Guest favorite
Condo in Kissimmee
4.93 out of 5 average rating, 196 reviews

3150-303 Resort Pool View Disney Universal Orlando

TrinityRating, 5 stars1 week ago
The place was clean and the host had excellent communication.
Guest favorite
Condo in Florida Center
4.85 out of 5 average rating, 487 reviews

Modern Studio with Private Terrace near Universal

VernishaRating, 5 stars1 day ago
She was amazing! And sooo nice! We will definitely visit again!

Home rentals with a private pool

Villa in Four Corners
4.33 out of 5 average rating, 3 reviews

Disney's Championsgate: Private Pool & Arcade Fun!

AurianaRating, 5 stars6 months ago
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.
Superhost
Home in Davenport
4.95 out of 5 average rating, 115 reviews

Airy, Stylish Home with Pool Heat Included in Davenport

RachelRating, 5 stars1 month ago
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.
Villa in Kissimmee
4.79 out of 5 average rating, 251 reviews

Visit Disney World from a Sunny Home with a Pool

ClaudiaRating, 5 stars1 month ago
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!
Guest favorite
Villa in Kissimmee
4.92 out of 5 average rating, 50 reviews

Family Retreat Near Disney with Pool & Hot Tub!

JenniferRating, 5 stars1 week ago
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
Home in Davenport
4.83 out of 5 average rating, 48 reviews

Sleeps 16! Pool + Arcade | Orlando Resort Retreat

MindyRating, 5 stars2 weeks ago
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.
Villa in Four Corners

Elegant 9-Bedroom Villa Close to Disney!

TimRating, 5 stars19 months ago
Very clean will book again!
Home in Kissimmee

Private Oasis with Pool & Spa- 3400clr

TarahRating, 5 stars1 week ago
The home was beautiful & exactly as described.
Home in Kissimmee
4.38 out of 5 average rating, 8 reviews

Vacation Resort Home Right Outside of Disney World

VictoriaRating, 5 stars8 months ago
We evacuated our coastal home ahead of a hurricane and found this pet-friendly rental to be exactly what we needed. The house was fun, which helped lift our spirits during a difficult time. However, the real highlight was the hosts, who were incredibly accommodating and gracious, making an extremely stressful situation much easier to manage.

Quick stats about vacation rentals with a pool in Winter Park

  • Total rentals

    110 properties

  • Total number of reviews

    3.6K reviews

  • Family-friendly rentals

    50 properties are a good fit for families

  • Pet-friendly rentals

    40 properties allow pets

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wifi availability

    110 properties include access to wifi

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Orange County
  5. Winter Park
  6. Rentals with pools