Pet-friendly holiday rentals in Winter Haven

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Popular amenities for Winter Haven pet-friendly home rentals

Pet-friendly house rentals

Superhost
Home in Davenport
4.71 out of 5 average rating, 17 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
Guest favourite
Home in Davenport
4.89 out of 5 average rating, 36 reviews

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

SarahRating, 5 stars1 week ago
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!
Superhost
Home in Kissimmee
4.89 out of 5 average rating, 28 reviews

Pelican House

WilliamRating, 5 stars4 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
4.8 out of 5 average rating, 92 reviews

Great Lake View - Pet Friendly

NormaRating, 5 stars6 days ago
Nice places Really clean
Guest favourite
Home in Kissimmee
4.88 out of 5 average rating, 189 reviews

4BR,PrvtNOTOverlookedPool,FencedYard,GameRM,WiFi

RoxanaRating, 5 stars2 weeks ago
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!!
Guest favourite
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!
Guest favourite
Home in Lakeland
4.89 out of 5 average rating, 27 reviews

Palm Cottage - 3 bedroom Coastal Cottage

VanessaRating, 5 stars1 week ago
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!
Top guest favourite
Home in Kissimmee
4.95 out of 5 average rating, 79 reviews

Spacious Disney Retreat - Sleeps 7 - Pet Friendly

CarmenRating, 5 stars3 weeks ago
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

Guest favourite
Home in Orlando
4.88 out of 5 average rating, 119 reviews

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

OmarRating, 5 stars2 weeks ago
Very nice house we love the pool. Thank you
Guest favourite
Villa in Davenport
5 out of 5 average rating, 21 reviews

Disney Proximity: Luxury 5BD Home

NichelleRating, 5 stars3 weeks ago
We were very pleased with our stay it was comfortable and convenient to all the places we went to visit.
Guest favourite
Home in Lakeland
4.87 out of 5 average rating, 62 reviews

2/1 Pool & Pet Friendly Spanish Cottage

JacquelineRating, 5 stars2 weeks ago
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!
Guest favourite
Home in Davenport
4.81 out of 5 average rating, 32 reviews

4 Bed/3 bath Pool home close to Disney!

DoloresRating, 5 stars10 months ago
The best location for a trip plan to Disney world . under 28 minutes to the parks
Guest favourite
Home in Davenport
4.89 out of 5 average rating, 62 reviews

Modern/Luxe Vacation, close 2 Disney, Heated Pool

Beth-AlisonRating, 5 stars1 month ago
Well appointed and clean. Bed was comfortable, pool was lovely.
Guest favourite
Home in Davenport
5 out of 5 average rating, 12 reviews

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

ShirleenRating, 5 stars2 months 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
Townhouse in Kissimmee
4.81 out of 5 average rating, 135 reviews

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

Brenda Ashley JRating, 5 stars3 weeks ago
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
Superhost
Home in Orlando
4.66 out of 5 average rating, 44 reviews

Lovely Pool Home, Pets considered. Orlando 1744

MikaelaRating, 5 stars5 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!

Private, pet-friendly home rentals

Guest favourite
Guest house in Orlando
4.95 out of 5 average rating, 55 reviews

The SoDo Suite: near Universal & Downtown

KimRating, 5 stars3 weeks ago
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!
Top guest favourite
Guest house in Winter Haven
4.95 out of 5 average rating, 219 reviews

The Paradise Hide Away

KseniaRating, 5 stars3 weeks ago
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!
Superhost
Home in Winter Haven
4.9 out of 5 average rating, 10 reviews

Winter Haven Hideaway

JessicaRating, 5 stars1 week 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.
Guest favourite
Townhouse in Kissimmee
4.94 out of 5 average rating, 31 reviews

Townhouse Near Disney-Sleeps 8, Hot Tub & Pools!

RandyRating, 5 stars1 month ago
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
Guest favourite
Flat in Kissimmee
4.91 out of 5 average rating, 116 reviews

Modern 3 Bedroom Apartment Near the Theme Parks

Cache JillRating, 5 stars6 days ago
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!
Apartment in Kissimmee
4.6 out of 5 average rating, 60 reviews

Brand New 2BR Waterview | Patio | Pool

RoselorRating, 5 stars3 weeks ago
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!
Guest favourite
Home in Orlando
4.91 out of 5 average rating, 210 reviews

★ PRIVATE HOME IN DOWNTOWN ORLANDO ★ RETREAT ★

KimberlyRating, 5 stars2 weeks ago
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!
Guest favourite
Home in Clermont
4.92 out of 5 average rating, 12 reviews

Private backyard-Family & Pet Friendly- Pool Home

JessicaRating, 5 stars2 weeks ago
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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