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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.
Top guest favorite
Townhouse in Kissimmee
4.95 out of 5 average rating, 56 reviews

9027-WW Beautiful 5 Bedroom Pool Home

ShakiraRating, 5 stars3 weeks ago
Very clean home, close to all Disney parks. Street parking was a bit annoying, but it was a good thing we had a garage. Smart TV’s in every room. Overall a great stay and would stay again
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
Guest favorite
Home in Davenport
4.84 out of 5 average rating, 32 reviews

Solterra discount slps 18/7 bdm/GR/pool/spa5485

SamanthaRating, 5 stars1 month ago
The house is brilliant. We had 11 adults and a 5 month old baby. We all flew in at different times, to different airports but access was easy for everyone. we had been given the details by the host prior to our arrival. Susan is a great host, very communicative but not intrusive. Every detail was taken care of. Passes at the gate, information about the activities and much more. I would highly recommend this AirBnB to anyone. Having a large family, it was great for space but also playing games and spending time together. We had family visit, who live in Florida, which was also easy. Susan was very helpful when my father in law couldnt be located, after visiting us. Thank you Susan, we will be back
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!!!!

Pet-friendly cottage rentals

Superhost
Cottage in Four Corners
4.67 out of 5 average rating, 30 reviews

10% OFF | Charming 2BR Cottage with Private Pool

BrittanyRating, 5 stars1 week ago
Good place to stay close to Disney. Dennis responds very quickly, great communication
Top guest favorite
Cottage in Davenport
4.99 out of 5 average rating, 93 reviews

Classic Cottage in country setting

MattRating, 5 stars3 days ago
We enjoyed our stay! We were grateful to be able to have our dog with us. The yard was huge and completely fenced. The house was super clean and decorated beautifully. Quiet neighborhood. Nice, private fire pit area! we enjoyed a fire at night. Carport was nice to park the car under too! Great experience ! Highly recommend.
Top guest favorite
Cottage in Lake Wales
4.89 out of 5 average rating, 123 reviews

The "Little ‘Toa" Ideal for short & long stays!

ShannonRating, 5 stars3 weeks ago
This was our 2nd stay at Tyler's and we've already told him we can't wait to book again for next yeat.
Superhost
Cottage in Clermont
4.96 out of 5 average rating, 46 reviews

Lilac Loft- Lake, Pool, Pickle Ball, Disney, FUN!

JustinRating, 5 stars6 months ago
We did rent this place because in the description it does say it has a heated pool unfortunately we came at the end of October and the pool wasn’t heated yet so we wasn’t able to swim
Superhost
Cottage in Kissimmee
4.83 out of 5 average rating, 269 reviews

Private Cottage. Only 5 miles from Disney.

SofiaRating, 5 stars1 month ago
Very lovely tiny-home, it was adorable and completely comfortable! Great deal, although it was way closer to Disney, the drive to Universal was only about 25-30 minutes :)
Guest favorite
Cottage in Winter Haven
4.85 out of 5 average rating, 112 reviews

7 - Country Cottage 2bed/1bath - Unit 9

NathanRating, 5 stars2 weeks ago
Perfect for family trip to Legoland and Natural Encounters tour. Really loved eating dinner out on the front porch overlooking the inlet.
Top guest favorite
Cottage in Kissimmee
4.98 out of 5 average rating, 176 reviews

2/2 Condo with Patio- Epic Universe, Magic Kingdom

GenevieveRating, 5 stars1 week ago
We really enjoyed our stay at this appartment. Melanie responded quickly to our messages and the place is perfect for a small family. We appreciated the proximity to a big Walmart (13 minutes walk). We also enjoyed the many pools available, the mini golf and the gym (24h). Nice little spot also to sit outside and enjoy the view. It is also very close to Disney sites (about 15 minutes), and we often used the free shuttle. We will certainly come back to this place when we return to Disney or Universal.
Guest favorite
Cottage in Kissimmee
4.8 out of 5 average rating, 80 reviews

Chic Cottage near Disney - Lots of Amenities!

MattRating, 5 stars1 week ago
Hernan’s home was cozy and the development was very peaceful. Any questions we had were quickly answered and Hernan made sure to do whatever he could to make the stay as enjoyable as possible! Development pools and clubhouses were clean and comfortable. We were traveling with our small child, and Hernan made sure that we had what we needed ahead of time. No complaints about noise or disruption from the neighbors. Very decent location, close to stores, theme parks and local attractions. Definitely bookmarking this one for future trips!

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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