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Pet-friendly vacation 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 home rentals with a pool

Guest favorite
Home in Orlando
4.88 out of 5 average rating, 118 reviews

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

Jordan MatthewRating, 5 stars2 weeks ago
Great place to stay at. Lots to do. Host was helpful
Superhost
Home in Davenport
4.6 out of 5 average rating, 10 reviews

Cozy & modern home 4 bed/3 bath/private pool

BetsyRating, 5 stars1 week ago
We just left after staying for 12 days and it definitely felt right at home. Monique was always very responsive and even came to bring a pack and play and high chair for my grandson. Any concern I had, it was answered and taken care of. I would recommend this place.
Guest favorite
Home in Davenport
4.89 out of 5 average rating, 61 reviews

Modern/Luxe Vacation, close 2 Disney, Heated Pool

HarryRating, 5 stars2 months ago
We thoroughly enjoyed our stay at this house. It had everything we needed. The pool was great and heated to our preferred temperature. Our host could not have been any better. He always responded to our questions and concerns within a short period of time. The one downside of the location was the traffic noise. Very noisy. Other than that it was a wonderful trip.
Guest favorite
Home in Davenport
5 out of 5 average rating, 12 reviews

4/2 home with Pool, BBQ, Playground near Disney

ShirleenRating, 5 stars1 month ago
Our stay here was great! The home is big and beautiful, the yard is spacious and great for dogs and kids. We had so much fun playing games in the outdoor room and watching movies at night. The kitchen had a bunch of pots and pans easy to cook meals. We would definitely stay again. Thank you for having us!
Superhost
Home in Davenport
4.81 out of 5 average rating, 180 reviews

4BR-2KingMasters-SpaHeat-Private Pool-Remodeled

LaylaRating, 5 stars2 weeks ago
Tetyana’s place was very clean, welcoming, and felt like home away from home. It was conveniently located near Disney and easy to access. The bed was very comfortable and I slept like a baby. The master bath was a great way to unwind and relax after walking over 10,000 steps at the Disney parks. We LOVED the jacuzzi/pool combo and how secluded it was. Very quiet neighborhood, responsive host, and easy check-in. We’ll be back. :)
Superhost
Townhouse in Kissimmee
4.81 out of 5 average rating, 134 reviews

T7674O/Windsor Hills Resort/3Bedrm/2miles Disney

MiriamRating, 5 stars1 week ago
Had a great stay! Perfect location, we enjoyed the community pool! Host responded fast when I had questions and the place was extremely cute! Pictures match exactly!
Superhost
Home in Orlando
4.66 out of 5 average rating, 44 reviews

Lovely Pool Home, Pets considered. Orlando 1744

MikaelaRating, 5 stars4 months ago
Place was clean and well located for our purposes. House is spacious enough for 2 adult couples and a child. Came with plenty of cooking supplies, plates, glasses, and utensils. Despite the description, basic linens and cleaning supplies such as laundry pods, dishwasher detergent, washcloths and soap were provided. Would stay again. About 12 minutes to the USTA National campus for our tennis friends!
Guest favorite
Home in Davenport
4.83 out of 5 average rating, 101 reviews

Family Home Gated 10 Beds Pool Disney 7 miles.

SamanthaRating, 5 stars1 week ago
Great stay! The place was clean, comfortable, and exactly as described. Roy was very responsive and made check-in super easy. Would definitely recommend and stay again!

Pet-friendly home rentals with a hot tub

Guest favorite
Townhouse in Kissimmee
4.86 out of 5 average rating, 131 reviews

Disney Vacation 8 miles to Disney World

GelsisRating, 5 stars6 days ago
Ashley is very friendly and very helpful, thank you for having me
Top guest favorite
Home in Auburndale
4.94 out of 5 average rating, 157 reviews

Lake Whistler Beach House with lakefront pool

ToddRating, 5 stars1 month ago
Can't say enough great things about Jonathan and his place! We loved staying there, felt right at home, we were there with 5 kids and there was always something fun for them to do, swimming in the pool and hot tub, s'mores by the fire, pool, air hockey, pacman was a hit, basketball, and lots of games, books and movies to choose from. There was plenty of space to spread out and feel comfortable and Jonathan added so many thoughtful touches to our stay - greeting us with an Apple Pie on the kitchen counter, a bowl of chocolates in the entry way and plenty of coffee. The kitchen was fully stocked with everything we needed, there were plenty of towels for showers and swimming, life jackets were supplied. The kids said they wanted to move there : ). Need I say more? haha
Superhost
Townhouse in Kissimmee
4.68 out of 5 average rating, 28 reviews

Beautiful 3-Bedroom Townhouse with a Hot Tub.

JessicaRating, 5 stars1 month ago
Family and I had a great time at Ivy’s place. Area was quiet and home was clean. We especially loved how close it was to Disney World. Will definitely plan to stay at Ivy’s place again next time we are up in the area.
Top guest favorite
Home in Clermont
4.88 out of 5 average rating, 96 reviews

4-Bedroom, 3 bath with private spa and pool.

LuzRating, 5 stars2 weeks ago
Tamika was a fabulous host! Best we have ever had. Extremely friendly, flexible and very responsive. Her home is absolutely beautiful and just as welcoming as the host. Everything was extremely clean. It exceeded our expectations for our family weekend. Will definitely stay again and recommend to friends and family.
Top guest favorite
Villa in Kissimmee
4.91 out of 5 average rating, 151 reviews

Relax & Play :Luxury Villa Near Disney w/ Pool&Spa

KarenRating, 5 stars2 days ago
Chuck's house is located close to everything but still quiet enough to enjoy the pool and spa. The house has everything you'll ever need and is absolutely beautiful. Chuck is very responsive to messages and very helpful. I can't wait to return.
Guest favorite
Townhouse in Kissimmee
4.86 out of 5 average rating, 223 reviews

Resort-Living at a Bohemian Retreat with Hot Tub

MarkiyaRating, 5 stars1 month ago
such a great stay! host was extremely responsive and kind, the home was beautiful and in a great location. super close to disney and other fun things!
Superhost
Guesthouse in Winter Haven
4.8 out of 5 average rating, 87 reviews

Cozy guest house w/ fenced yard and hot tub

JermaineRating, 5 stars2 days ago
I would love to say my stay here was prefect this was one of my greatest host ever definitely will be going back!!!!
Top guest favorite
Villa in Davenport
4.91 out of 5 average rating, 185 reviews

Beautiful villa home near Disney

LisaRating, 5 stars3 weeks ago
We had a great experience with David's home. It was clean, comfortable, beautifully designed, and very accommodating. They really thought of everything!! The house was super clean, beds were comfortable, plenty of bathrooms, pool area was spacious. David was very responsive, if I asked a question he answered right away. I would highly recommend this house!! It was in a gated community with plenty to do near by, without all the disney traffic. However, if you wanted to go to Disney, Universal or Sea World they were not that far away at all. Would highly recommend!!

Pet-friendly house rentals

Superhost
Home in Davenport
4.75 out of 5 average rating, 16 reviews

Wheelchair accessible, Weekly Discounts, Yes Dogs!

ShawnRating, 5 stars9 months ago
Hello, Me and my family, came to visit Florida for a family gathering. I was pleased with the house I rented from Franka. The house was family friendly spacious and very clean. The host was very polite, responsive to any concerns I had. I really enjoyed the game room it has over 60 games of pure fun. Close to the store for all your shopping needs. Also the house came with more than enough space so everyone had there own space. I am in a wheelchair and I was able to move around the house and wasn't restricted on where I could go. The pool lift was a plus . I will definitely going back to stay there if you're looking for a wheelchair accessible home I would definitely recommend this house. Thanks again
Top guest favorite
Home in Plant City
4.99 out of 5 average rating, 527 reviews

The Strawberry Field Stilt House

TransitoRating, 5 stars2 weeks ago
The Strawberry Guesthouse was clean and very charming. The property is serene and beautifully decorated. As a host, Joseph is attentive and effortless to coordinate with. I must schedule a longer reservation next time! I will be back!
Guest favorite
Home in Davenport
4.89 out of 5 average rating, 35 reviews

2321-WI 5 Bd ALL Suites, Game Room + Pool & SPA

KatieRating, 5 stars1 month ago
lots of things to do, love that we had the hot tub & im glad that I planned to heat the pool for our march trip. having a bathroom in every room was helpful too when you have 5 kids ! we hope to return soon.
Superhost
Home in Kissimmee
4.89 out of 5 average rating, 28 reviews

Pelican House

WilliamRating, 5 stars2 weeks ago
We stayed at the Pelican House for three whole months. This home worked well for our extended stay because of its proximity to restaurants, groceries and Disney World! The neighborhood was quiet pretty much every night and having the open green space in the back was really nice, especially when the Sandhill Cranes came by in the mornings. They were awesome to watch. Donna was very responsive to any questions or concerns we had during the stay. She would reply within 10 minutes usually. The biggest benefit for us was proximity to Disney World. We could leave the house and be at the parks within 15-20 minutes most days. Traffic coming back from Disney was typically a challenge, though I feel the whole area in Kissimmee would be the same. All in all, we would absolutely stay at the Pelican house again for any future long-term stay in that area. It worked great for our needs this trip! Thanks Donna!!
Superhost
Home in Kissimmee
4.82 out of 5 average rating, 90 reviews

Great Lake View - Pet Friendly

JitendraRating, 5 stars2 weeks ago
Overall good experience with family and kids. Nice back view for pleasant morning. Host was responsive and place was clean. My only suggestion would be to have some stocks in kitchen like paper kitchen rolls etc. I would strongly recommend this place.
Superhost
Home in Haines City
5 out of 5 average rating, 5 reviews

Lake House 3BR 2BA, Boat slip, Pets, (king bed)

LarryRating, 5 stars5 months ago
Very accommodating of our request and always there to answer questions. Loved our time there and only wish we could have stayed longer. Even though we are local, will definitely be back again for some time away from home. Very much worth it. Great space for travelers with dogs.
Guest favorite
Home in Davenport
4.89 out of 5 average rating, 9 reviews

Huge Mansion 5Bed4BaHeated Pool, Pet Friendly

TyreeRating, 5 stars1 week ago
One of the best homes I’ve Rented! 10/10 highly Recommended. Everything was as described, Very Spacious, everything was brand new and ready to use! The Host was awesome , great communication and clear instructions! I will most definitely be Renting again! Thank you 🙌🏾
Guest favorite
Home in Orlando
4.84 out of 5 average rating, 58 reviews

Unique &Cozy 3/2, Disney, Universal minutes away!

AnnemarieRating, 5 stars1 month ago
This was our second time staying at David's place. It is just the right location for visits to Disney and Universal and there are enough restaurants and stores nearby. The house is very comfortable, even our dog felt right at home! Plus there is a great dog park not too far away. The street is very quiet and the backyard is peaceful. We'll be back again!

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

  • Total rentals

    140 properties

  • Nightly prices starting at

    ﺩ.ﺇ73 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

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