Holiday rentals with a pool in Winter Park

Find and book unique homes with a pool on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Winter Park rentals with a pool

House rentals with a pool

Guest favourite
Home in Orlando
4.88 out of 5 average rating, 123 reviews

3 BR/2BA Home w Private Pool~12 min to Airport!

DerekRating, 5 stars1 week ago
Alyssa was a great host, easy to communicate with & fast responding. Place was well kept, spacious & peaceful. Had a great stay, thanks!
Guest favourite
Home in Orlando
4.92 out of 5 average rating, 61 reviews

Villa Pilar | KingBed • Outdoor Kitchen & Dining

VanessaRating, 5 stars2 months ago
Very Comfortable House in a very quiet neighborhood. The Patio is very nice and peaceful .
Top guest favourite
Home in Sanford
4.99 out of 5 average rating, 141 reviews

The Cypress House

LaurenRating, 5 stars5 days ago
All I can say is wow to this cute little oasis!! So fun and relaxing just make sure to bring bug spray. Totally worth every bite for the relaxing trip.
Guest favourite
Home in Orlando
4.96 out of 5 average rating, 103 reviews

Private Pool 4/2 Waterfront Oasis Weekly Discounts

TerryRating, 5 stars6 days ago
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
Top guest favourite
Home in Minneola
4.98 out of 5 average rating, 128 reviews

Pool + Heated spa Family friendly King suite Oasis

JohnRating, 5 stars2 weeks ago
House, yard and pool were exactly what what we were looking for! Thank you to our hosts!
Top guest favourite
Home in Clarcona
4.96 out of 5 average rating, 108 reviews

BBQ Grill | Wi-Fi | Pool Access | 20 Min Disney

BillRating, 5 stars1 day ago
Wonderful hosts, had a great experience. I would definitely revisit if the opportunity comes again.
Superhost
Home in Orlando
4.87 out of 5 average rating, 193 reviews

Year around Heated Pool 7 min from Airport!

SoreeRating, 5 stars3 days ago
We stayed here right after our cruise before heading home, and it was perfect! Only about 10 minutes from the airport, so super convenient. I saw someone mention the neighborhood in a review, but honestly, once you walk into the house, it’s a total wow. The remodel looks amazing! The heated pool in the backyard was a huge hit our kids loved it, and the adults did too. There’s even a Bluetooth speaker in the bathroom, which my teenage niece thought was so cool. The house was super clean, modern, and really comfy. We had such a fun time. Thanks for a great stay!
Top guest favourite
Home in Kissimmee
4.99 out of 5 average rating, 102 reviews

Traveler's Dream - King Bed, Pool, Games, Disney+

AndrewRating, 5 stars6 days ago
We enjoyed our stay at Jimmy and Via’s place! It was the perfect size for our family and it had everything we needed. We greatly appreciated the privacy of the pool area and it was very quiet. Their house was also extremely clean and they were very responsive to any questions we had. Thank you, Jimmy and Via!

Apartment rentals with a pool

Superhost
Apartment in Orlando
4.87 out of 5 average rating, 102 reviews

Luxury Condo On I-Drive & One Mile from Universal

JustinRating, 5 stars1 month ago
Wonderful and beautiful place amazing area clear instructions will definitely be staying when I return
Guest favourite
Apartment in Orlando
4.89 out of 5 average rating, 131 reviews

Studio close to Universal Studios + free Netflix

TerryRating, 5 stars2 weeks ago
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.
Guest favourite
Apartment in Orlando
4.87 out of 5 average rating, 223 reviews

Maria Luz Studio-Huge Terrace/Universal area.

ElizabethRating, 5 stars3 weeks ago
I LOVED THE EXPERIENCE!
Guest favourite
Apartment in Kissimmee
4.93 out of 5 average rating, 195 reviews

3150-303 Resort Pool View Disney Universal Orlando

FrankRating, 5 stars2 weeks ago
Me and my family had a great experience with Fonti. Beautiful place and lots to do around the area. I will absolutely be staying again with my family on our next trip to Florida!
Guest favourite
Apartment in Orlando
4.8 out of 5 average rating, 117 reviews

Suites at Lake Buena Vista close Disney Springs

JoelRating, 5 stars2 months ago
This location is wonderful. Across the street is several restaurants and some shops. It is limited distance from Disney springs that you have shopping and dining with a 10 min drive at most. Parking is plentiful and easy to walk in and get right to the room.
Guest favourite
Apartment in Orlando
4.85 out of 5 average rating, 483 reviews

Modern Studio with Private Terrace near Universal

AshantiRating, 5 stars1 week ago
Nicoleta’s place was beautiful and well maintained. She was very helpful with accommodating our check out time and left very clear instructions for check in and check out. We enjoyed our stay and will be back again!!!
Top guest favourite
Apartment in Orlando
5 out of 5 average rating, 141 reviews

Disney & Epic Free Shuttle, Kitchen

EleanorRating, 5 stars1 week ago
We enjoyed our stay at Ryan’s place! The place was pristine and just as pictured. I loved the extra towels, blankets, and stocked coffee station. Ryan was communicative (without being annoying) and was extremely accommodating! We didn’t use the shuttle service for the parks, since we had a vehicle, so I can’t comment on that. My kids enjoyed late night swims after days at Universal Studios and Epic Universe, which were both about a 20-minute drive from the place. I would definitely recommend this place to anyone who will be visiting Disney or Universal Studios!
Top guest favourite
Apartment in Kissimmee
4.98 out of 5 average rating, 135 reviews

Condo on the top floor with lake view near Disney!

IwonaRating, 5 stars2 weeks ago
We’ve stayed at several rentals in Orlando before, and this one has definitely been our favorite. The apartment was spotless, very well equipped, and had everything we needed. The location is excellent, very safe and quiet, and close to everything we needed. We really enjoyed the peaceful view over the lake to the pool area behind it. The pool with the lazy river was nice and added to the relaxing atmosphere. Joanne was very quick to respond and helpful throughout our stay. Would absolutely come back.

Home rentals with a private pool

Villa in Four Corners

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.
Villa in Kissimmee

Disney Dreams Luxury Home Private Water Park

CorlesaRating, 5 stars47 months ago
The home was very nice. It accommodated our family extremely well. The post was accurate and it definitely felt like a Home away from Home! We were also able to get responses from the Host in a timely manner. I would stay at this property again!
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 stars2 weeks 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 favourite
Villa in Kissimmee
4.92 out of 5 average rating, 49 reviews

Family Retreat Near Disney with Pool & Hot Tub!

KimRating, 5 stars4 days ago
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.
Home in Kissimmee
4.83 out of 5 average rating, 18 reviews

Sleeps 25! Resort Home near Parks | Coconut Breeze

ShanaRating, 5 stars1 week ago
Excellent space. Looks exactly like the pictures and was very well stocked!
Villa in Davenport
4.67 out of 5 average rating, 6 reviews

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

CraigRating, 5 stars48 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 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 holiday 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