Pet-friendly vacation rentals in Winter Haven

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Popular amenities for Winter Haven pet-friendly home rentals

Pet-friendly home rentals with a pool

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 Lakeland
4.93 out of 5 average rating, 59 reviews

2/1 Pool & Pet Friendly Spanish Cottage

NicoleRating, 5 stars1 month ago
Our stay at Marlana’s was great. We have two young boys that were able to play outside and enjoy the pool. Everything was provided down to the small details inside - dishwasher pods, laundry soap, etc. The location to Tigertown was PERFECT. So many awesome parks nearby and a beautiful path along the lake to walk made this stay that much more enjoyable. We’re hoping to book this each year we’re back for Spring Training - hopefully the main house next year!
Guest favorite
Home in Davenport
4.89 out of 5 average rating, 61 reviews

Modern/Luxe Vacation, close 2 Disney, Heated Pool

HarryRating, 5 stars1 month 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 stars2 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
Villa in Davenport
4.79 out of 5 average rating, 14 reviews

Spacious Villa South Facing Pool 20 min to Disney

KathyRating, 5 stars13 months ago
What a gorgeous home! There was so much room! The pool was beautiful! Renay was responsive and accommodating.
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 stars4 days 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!
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, 128 reviews

Disney Vacation 8 miles to Disney World

AndresRating, 5 stars2 weeks ago
Ashley was a great host, her place was great for a family or large group. It was pleasant that it wasn't right on a main road, as it helped keep noise to a minimum, but close enough to a couple of main roads, which made it easy to get groceries or food. I would definitely stay here again!
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
4.78 out of 5 average rating, 27 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 stars1 week 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.
Superhost
Townhouse in Kissimmee
4.89 out of 5 average rating, 245 reviews

RUSTY'S DEN House with Hot Tub 3 miles from Disney

ChuckRating, 5 stars2 weeks ago
Place was as described by host. We had a great stay, was quiet and had everything we were looking for while vacationing in Florida. Would recommend this place to anyone looking for a place to stay while in Kissimmee. It’s a great location close to many things to do in the area and not to mention the resort is great also.
Top guest favorite
Villa in Kissimmee
4.91 out of 5 average rating, 150 reviews

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

BrandyRating, 5 stars3 months ago
Beautiful home, close to attractions, and stocked well with necessities. Chuck was very responsive to any questions during the process and checked in with us to make sure we had what we needed. I would stay here again as we had a wonderful stay on our family trip to Disney.
Guest favorite
Townhouse in Kissimmee
4.86 out of 5 average rating, 222 reviews

Resort-Living at a Bohemian Retreat with Hot Tub

MarkiyaRating, 5 stars3 weeks 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, 86 reviews

Cozy guest house w/ fenced yard and hot tub

BrendaRating, 5 stars1 month ago
Perfect location, as far as ease to stores and restaurants. The pictures of the place were spot on. Very clean and delightful!

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 stars3 days 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, 92 reviews

Classic Cottage in country setting

KiranRating, 5 stars4 days ago
just a wonderful experience. easy, clean & very responsive!
Cottage in Kissimmee
4.83 out of 5 average rating, 193 reviews

Cozy Lakehouse Cottage - 4 Miles to Disney!

CaitlinRating, 5 stars4 days ago
Alisha was a wonderful host! Before our trip my family was in need of a stroller for my twins and when I asked was there any strollers on site, she immediately took action and bought 3 brand new strollers, this was so appreciated!!! My only cons to the home was not a lot of seating for a family of 5 but I’d imagine that is due to the small space. And this home has a gas stove which made me nervous with my little ones. Other than that this home was super close to EVERYTHING, she was super responsive as I had questions upon our arrival. I would definitely stay again!
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 stars2 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 Kissimmee
4.82 out of 5 average rating, 268 reviews

Private Cottage. Only 5 miles from Disney.

SofiaRating, 5 stars4 weeks 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 stars1 week 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, 174 reviews

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

TracyRating, 5 stars2 months ago
Melanie’s Place was a lovely retreat from the cold Canadian weather! Would highly recommend, very friendly and responsive host! We were there 3 weeks and thoroughly enjoyed ourselves!! Lots to do in the area. Great pools on site!!
Guest favorite
Cottage in Kissimmee
4.81 out of 5 average rating, 78 reviews

Chic Cottage near Disney - Lots of Amenities!

MattRating, 5 stars4 days 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

    $20 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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