Pet-friendly holiday rentals in Winter Haven

Find and book unique pet-friendly homes on Airbnb

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Popular amenities for Winter Haven pet-friendly home rentals

Pet-friendly house rentals

Guest favourite
Home in Winter Haven
5 out of 5 average rating, 9 reviews

Bright Home Near Legoland & Lake

GomezRating, 5 stars4 weeks ago
Very easy process. I really like the flexibility. Very clean and organized place. I love it and will definitely recommend it to anyone. Thank you so much 🙏🏽
Top guest favourite
Home in Auburndale
4.95 out of 5 average rating, 57 reviews

Encanto At Auburndale

MattRating, 5 stars1 week ago
This is always our go to place in Auburndale when in town for the weekend. It is always super clean, and it makes it easy to sit back and relax.
Superhost
Home in Winter Haven
4.77 out of 5 average rating, 13 reviews

Winter Haven Hideaway

JessicaRating, 5 stars1 month ago
Great stay for our yearly tournament. The extra living room was perfect for my elderly grandmother and the screened in back porch was great for enjoying outside and behind covered.
Top guest favourite
Home in Winter Haven
4.97 out of 5 average rating, 71 reviews

Kid-friendly Home w/ Pool & BBQ

DeidreRating, 5 stars1 week ago
The house is exactly as pictured. Beds were comfortable and the hosue/pool & was clean. We would definitely recommend staying here!
Superhost
Home in Haines City
4.84 out of 5 average rating, 51 reviews

Stunning 4BR home w/Pool

TyraRating, 5 starstoday
Me and my family had an amazing time here !! It was spacious , the pool was great , and we felt right at home ! I would recommend this air bnb to anybody I know visiting Orlando Florida. It was a quick drive to EPCOT Walt Disney world. I hope to come back soon !
Top guest favourite
Home in Winter Haven
4.95 out of 5 average rating, 98 reviews

Lakefront Home on the Winter Haven Chain O’Lakes!

SeanRating, 5 stars4 weeks ago
We had an amazing stay at this beautiful property right on Lake Roy. The views of the water were absolutely stunning, and we loved having direct access to the lake—it made for the most peaceful mornings and relaxing evenings. The home was spotless, well-equipped, and clearly cared for with love. Whether we were sipping coffee on the dock, kayaking, or just unwinding inside, everything about our stay was seamless and serene. Our hosts were responsive and welcoming, making the experience even better. Highly recommend for anyone looking for a quiet, scenic escape in Florida!
Guest favourite
Home in Winter Haven
4.93 out of 5 average rating, 42 reviews

Arcade+Pingpong + 10 guests + 11 mil to Lego Land!

LaShayiaRating, 5 stars3 weeks ago
Our stay here was amazing! Nathaly was very responsive to all messages and the house was spectacular and spotless 👌 The decor was nice and free of clutter, very spacious. I will definitely book here again when I visit Winterhaven, Florida 😊 Five stars well deserved 🌟🌟🌟🌟🌟
Guest favourite
Home in Winter Haven
4.94 out of 5 average rating, 17 reviews

Fresh & Modern 3BR Home

BernadetteRating, 5 stars1 month ago
i had a great stay!! The place was exactly as described, well laid out and comfortable. The host is very proactive and very responsive. This is my second time staying at this home, as Im in the Orlando area frequently, it will become a space that I look for each time.

Pet-friendly home rentals with a pool

Guest favourite
Townhouse in Haines City
4.95 out of 5 average rating, 41 reviews

Modern townhouse Balmoral Resort

AlettaRating, 5 stars1 month ago
Raychelle was a very responsive host and was friendly which we appreciated. The home is beautiful and set up as described. We felt welcomed and at home. There are lots of restaurants and grocery stores etc in the area so that was nice as well.
Superhost
Home in Haines City
4.78 out of 5 average rating, 94 reviews

Luxurious 3BR: Pool, Golf Views, Disney, Legoland

BeatrizRating, 5 starstoday
I recommend this place. The communication was excellent. The location was also excellent, and the house met the description.
Guest favourite
Guest suite in Winter Haven
4.86 out of 5 average rating, 76 reviews

The Treehouse at Camellia Grove - Winter Haven

RobertRating, 5 stars2 months ago
My girlfriend and I stayed with Martha and Joe and had an amazing time on the farm. We travel often for work and this is by far our favorite AirBnb we’ve stayed in for a while! The treehouse is very cozy and feels like a home. The pool and views from the back yard are stunning. We would definitely stay here again!
Guest favourite
Home in Haines City
4.94 out of 5 average rating, 17 reviews

A beautiful cozy home with heating pool

JohnRating, 5 stars1 month ago
We had a wonderful stay. The host was very accommodating to anything we needed. He is a great host and we will definitely be returning.
Top guest favourite
Home in Davenport
5 out of 5 average rating, 77 reviews

Family Getaway with Pool Near Disney/Parks/Shops

RachelRating, 5 stars1 week ago
The stay at Orvie’s place was excellent. Very kid friendly, would highly recommend for a family stay. The location was very convenient, and the home had everything we needed. Communication with the host was good and check-in went smoothly.
Guest favourite
Villa in Davenport
4.91 out of 5 average rating, 105 reviews

Modern Coastal Farm House/Pool+Jacuzzi/near Disney

EdRating, 5 stars1 week ago
My family really enjoyed our vacation. Stay at this location. It was very, very clean well appointed and exactly as advertised. What was the best part of all was the host who took care of? Everything answered all questions and made sure that we were very much right at home that was fantastic. If you need room to spread out for your family or room to relax, there are plenty of places in this house. The pool and hot tub worked perfectly and everything simply was great. We really enjoyed this. Thank you very much. We will see you again.
Top guest favourite
Home in Davenport
4.98 out of 5 average rating, 173 reviews

House near Disney-Universal w/pool, game room @EV…

JennyRating, 5 stars2 weeks ago
Our family had a wonderful stay at Ana’s property. The house was just what we needed for our family of four. The pool was a highlight! Ana was incredibly responsive and we felt right at home. The house is about 20 minutes to Disney and 35 minutes to Universal. My only tiny complaint was that the WiFi was very slow and spotty, but not a huge deal. Otherwise, I would highly recommend this house to anyone traveling to the Orlando area!
Top guest favourite
Home in Auburndale
5 out of 5 average rating, 25 reviews

Little Castle on the canal on lake Arietta

LisaRating, 5 stars1 month ago
The house was even more spacious than expected. Easy to find, super safe-feeling and quiet neighborhood. The house was incredibly clean and well-organized, and was more stocked with essentials than any other house I’ve stayed in with my family.

Private, pet-friendly home rentals

Top guest favourite
Cottage in Davenport
4.99 out of 5 average rating, 97 reviews

Classic Cottage in country setting

JesicaRating, 5 stars2 weeks ago
The cottage felt like home away from home. Quiet safe area and convenient location. Very clean home you’d never guess they allow pets. Large fenced yard which my fur babies loved. 30 minutes with some traffic to WDW parks. We stayed 8 nights and it’s very comfortable for 4 adult. Will definitely check availability for our next trip to FL. Communication with Host very easy and prompt. Definitely recommend.
Guest favourite
Guest suite in Winter Haven
5 out of 5 average rating, 18 reviews

Cozy Family Vacation Villa

LaurenRating, 5 stars1 week ago
the house was well stocked with all kinds of things. the kitchenette had lots of water which is nice. William is an amazing chef and I would suggest taking him up on it if he offers to cook for you! He made us some really delicious and filling meals while we with him!
Guest favourite
Home in Winter Haven
5 out of 5 average rating, 7 reviews

Travelers Haven

JaredRating, 5 stars2 months ago
We had a great, week long, stay! Extremely clean. Host communicated quickly and accurately. Neighborhood is clean and quiet. We absolutely loved it.
Guest favourite
Home in Winter Haven
4.95 out of 5 average rating, 58 reviews

Book Summer Vaca!, Legoland, Pet Friendly, 7 Beds

RachelRating, 5 stars2 weeks ago
Spacious, clean, and thoughtful amenities (basket of snacks and water bottles, toiletries). Large fenced yard. Very responsive host. I highly recommend. We stayed here for a 2 day volleyball tournament.
Guest favourite
Guest house in Winter Haven
4.9 out of 5 average rating, 29 reviews

Grand Room

KaylaRating, 5 stars3 weeks ago
This place is so nice! Very clean, and super close to Legoland! If you are looking at the listings with “The Block”….don’t go there. That place is very run down. Mara’s place was immaculate. The communication is very nice and quick. So glad we stayed here.
Top guest favourite
Home in Davenport
4.96 out of 5 average rating, 54 reviews

Spectacular Condo 2Bed/2Bath Close to Disney

ArianneRating, 5 stars2 days ago
Beautiful condo. The kids loved the water park and lazy river. Can’t wait for my next Disney trip and book the same condo.
Superhost
Tiny home in Winter Haven
4.85 out of 5 average rating, 55 reviews

Tiny Paradise

AnitaRating, 5 stars2 months ago
The place was very cute, cozy and especially clean. It’s small but it was just enough for me and hubby. I would definitely go back if in the area.
Guest favourite
Home in Winter Haven
4.88 out of 5 average rating, 17 reviews

3b2ba/master suite/pet friendly/6 mi. to LegoLand!

KeithRating, 5 stars3 months ago
Very nice home! Pictures are accurate and the home is very clean. Host was very responsive to communication.

Quick stats about holiday rentals that are pet-friendly in Winter Haven

  • Total rentals

    140 properties

  • Nightly prices starting at

    ₹1,727 before taxes and fees

  • Total number of reviews

    6.9K reviews

  • Family-friendly rentals

    100 properties are a good fit for families

  • Rentals with a pool

    40 properties have a pool

  • Rentals with dedicated workspaces

    90 properties have a dedicated workspace

Destinations to explore