
Pet-friendly holiday rentals in Winter Haven
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Top-rated pet-friendly home rentals in Winter Haven
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Pet-friendly house rentals

Wheelchair accessible, Weekly Discounts, Yes Dogs!
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

2321-WI 5 Bd ALL Suites, Game Room + Pool & SPA
Great place, very clean. Clear instructions, easy to find. Really appreciated the high chair. We loved the pool and appreciated the pool fence. Comfy beds, clean kitchen. Great access to amenities. Highly recommend!

Pelican House
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!!

Great Lake View - Pet Friendly
Nice places Really clean

4BR,PrvtNOTOverlookedPool,FencedYard,GameRM,WiFi
The location was great! I had 2 teens and a 4 year old and it was great for everyone ! The Walmart being 5 mins away was extremely helpful!!

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

Palm Cottage - 3 bedroom Coastal Cottage
Cozy Cottage! It had an old charm on the outside & a new updated charm on the inside. It felt very homie & the rocking chairs on the front porch was delightful. The kitchen is fully equipped, however there is no dining room table but we made do. The back yard is big but not very private, yet neighborhood is super calm & quiet. Overall we had a pleasant stay!

Spacious Disney Retreat - Sleeps 7 - Pet Friendly
The house is beautiful inside. Jeremy was proactive when I had an issue and was quick to find a solution. I definitely will be booking here again next time. My stay here felt very comfortable and enjoyable.
Pet-friendly home rentals with a pool

3 BR/2BA Home w Private Pool~12 min to Airport!
Very nice house we love the pool. Thank you

Disney Proximity: Luxury 5BD Home
We were very pleased with our stay it was comfortable and convenient to all the places we went to visit.

2/1 Pool & Pet Friendly Spanish Cottage
Marlana was such a pleasure to communicate with. Prior to booking, I spoke with her co-host quite a bit. He answered all of my questions. The home had comfortable beds (2 bedrooms with one bed each), a fully functioning kitchen, a nice living room, and an enclosed patio with a beautiful pool. There is hotel travel-size shampoo & conditioner in the bathroom. If you need a bigger size like my girls and I do - we have long hair, bring that & body wash along. There were plenty of towels and a washer & dryer too! This was the perfect stay for my daughter's college graduation from SEU. Marlana was so helpful with every message and request. I would definitely rent from her again!

4 Bed/3 bath Pool home close to Disney!
The best location for a trip plan to Disney world . under 28 minutes to the parks

Modern/Luxe Vacation, close 2 Disney, Heated Pool
Well appointed and clean. Bed was comfortable, pool was lovely.

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

T7674O/Windsor Hills Resort/3Bedrm/2miles Disney
It was a pleasure staying at Michael's place, the condo was exactly as it was described in the listing and I always felt like Michael and cohosts were just a message away if we needed anything, they were excellent at providing clear detailed instructions for check in and check out and always there if we needed anything. This was our first trip to Florida and our first ever accommodation booking, and we will definitely be back again. With 3 kids and 3 adults, this condo was spacious and nobody felt on top of each other. Gated community, felt safe and was quiet and peaceful; the clubhouse was a plus !! fun times at the pool and a store for quick refreshments. we will be back again!! thank you

Lovely Pool Home, Pets considered. Orlando 1744
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!
Private, pet-friendly home rentals

The SoDo Suite: near Universal & Downtown
Amanda and Dan's place was perfect for us. We have a large (70 lb) dog, so their "any size dog" policy was key. There's a fenced area on the property to let her out, and the place included a nice bathroom (with towels and essential toiletries), kitchen, two bedrooms, and a cute living room. The neighborhood is nice, and it's a short walk to an Einstein's bagels. Amanda and Dan were also understanding and kind after a problem we caused. Highly recommend booking with them!

The Paradise Hide Away
Kelley is a great host! This was our second time staying at his bungalow, and it was a pleasure both times. The place is clean, it is in a great location, Kelley is very friendly and helpful. 10/10 would recommend!

Winter Haven Hideaway
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.

Townhouse Near Disney-Sleeps 8, Hot Tub & Pools!
My family enjoyed our week stay! Best sleep we’ve had in months. Clean space. Large eating area for entire family. Loved it . Booking agai this summer for sure

Modern 3 Bedroom Apartment Near the Theme Parks
Felt right at home. Cozy stay for a bigger family and a dog! Linens were clean, house was tidy and the dining table with 6 chairs was a plus. We stayed in and cooked our meals, bring your favorite knife and seasonings, but the bare essentials are there. Host was friendly and communicative. Surrounding area was great for walks, even tried the gym. Community pool, Tennis court and sand volleyball available. Overall, a no fuss home-y stay! Thank you for the hospitality!

Brand New 2BR Waterview | Patio | Pool
We had an amazing stay! The place was spotless, beautifully decorated, and exactly as described. The host was incredibly welcoming and responsive, making everything super easy. The location was perfect. We’d absolutely stay here again and highly recommend it to anyone visiting the area!

★ PRIVATE HOME IN DOWNTOWN ORLANDO ★ RETREAT ★
We decided to stay here because of the photos (very beautiful and hilarious!) and the location is perfect. The house is very comfy, cozy, and just as expected (except we couldn't find the dinosaur costume.... womp womp). The patio is an awesome place to relax. We liked that there is a dedicated workspace so we could work remotely during our stay. Everything we needed was provided and the shower products are high quality. The host is amazingly friendly and quick to respond. Overall, everything was perfect, and we enjoyed our stay. 5/5 would stay here again! Thank you!

Private backyard-Family & Pet Friendly- Pool Home
Our stay was wonderful we had a great time, the home was very inviting, comfortable and clean, the host was also great. This place did not disappoint the view in the back was also beautiful. We would definitely book with Robert again in the future. His home was very relaxing, accomdated all our needs and we all were happy with our experience.
Quick stats about holiday rentals that are pet-friendly in Winter Haven
Total rentals
140 properties
Nightly prices starting at
£15 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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- Universal Studios Florida
- Orange County Convention Center
- Universal's Volcano Bay
- Old Town Kissimmee
- Discovery Cove
- Reunion Resort Golf Courses - Palmer & Watson
- Disney's Animal Kingdom Theme Park
- SeaWorld Orlando
- Disney Springs
- Busch Gardens Tampa Bay
- ESPN Wide World of Sports
- Amalie Arena
- Universal Orlando Resort
- Raymond James Stadium
- Reunion West
- Amway Center
- Kissimmee Lakefront Park
- ChampionsGate Golf Club
- Epcot
- Disney's Hollywood Studios
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- Magic Kingdom Park
- Tampa Theatre
- Curtis Hixon Waterfront Park