Pet-friendly holiday rentals in Winter Haven

Find and book unique pet-friendly homes on Airbnb

Top-rated pet-friendly home rentals in Winter Haven

Guests agree: these pet-friendly homes are highly rated for location, cleanliness and more.

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Guest favourite

Guest house in Winter Haven

4.95 out of 5 average rating, 202 reviews

The Paradise Hide Away

This is a beautiful and private place newly renovated with private access and parking. It’s a great place to get away and relax with a large and beautiful backyard! Talk to me if you need different check in/out times? Dogs are allowed with permission. There is a $200 fully refundable pet security deposit to cover any damages that may occur since Airbnb doesn’t cover damages caused by pets plus a non refundable pet fee of $50 per pet for every 1-7 day period and must be paid before checking in !

23–30 Nov

£82 per night

Guest favourite

Home in Auburndale

4.95 out of 5 average rating, 136 reviews

three bedroom family house, near legoland

Relax with the whole family at this just renovate house with many amenities. everything new and really clean, is in a central location right next to the highway and many places like beautiful like. You will have a really nice experience. is centrally located to the Tampa and Orlando parks and just 10 miles from Legoland , next to the highway, close to many shops and restaurants, We have a super lake very close, for those who like to fish or ride a jet ski or boat,southeastern university 7.9 mi

19–26 Jun

£130 per night

Guest favourite

Guest house in Lakeland

4.94 out of 5 average rating, 143 reviews

Cozy Studio + Secluded Courtyard, SEU, FSC, dwntwn

Enjoy your stay in Lakeland in our cozy, newly remodeled studio! It is centrally located in Lakeland and a short drive from downtown, Florida Southern College (1.4 miles) Southeastern University (1 mile) It comes fully equipped with everything you will need to enjoy a relaxing or adventurous stay! Cook a dinner for two in the cozy modern kitchen! Enjoy a glass of wine in the warm lit courtyard to cap the night! Parking is just a few steps down the pathway through the courtyard from your door!

29 Aug – 5 Sept

£103 per night

Guest favourite

Home in Lakeland

4.96 out of 5 average rating, 115 reviews

Cute, Historic District Home - GREAT LOCATION

Enjoy a stylish experience at this centrally-located place 5 mins from downtown Lakeland, 8 mins from I-4, 40 mins from Tampa and Orlando (Disney World/Universal), 1 hour from several beaches including Clearwater. 🐕 Pet friendly but you MUST include your pets in the reservation Nearby places of interest: - Downtown Lakeland - Southeastern University and Florida Southern College - RP Funding Center - Lakeland Linder International Airport - Polk Theatre - Circle B Nature Reserve - and more!

5–12 Sept

£120 per night

Guest favourite

Cottage in Lake Wales

4.88 out of 5 average rating, 107 reviews

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

Welcome to the Little TOA, Central Florida's fishing, hunting and winter get away. The house sits just off the Kissimmee River which is part of the Kissimmee chain of lakes, connecting Lake Hatchineha and Kissimmee. This will be a great spot for you and your buddies or family for a short weekend trip or an extended stay. Come see old Florida, the area holds many things to occupy your vacation time. *Your pet is welcome, please let me know ahead of time. There is a one time fee for pets.

6–13 Oct

£126 per night

Guest favourite

Farm stay in Lakeland

4.95 out of 5 average rating, 111 reviews

The Barn at Crews Lake Ranch, near Tampa & Disney

Situated on a 240-acre working ranch with a private lake, this 1-bed, 1-bath modern farmhouse sleeps 4 and offers fishing and nature walks! The 725 sq. ft. cottage-style home includes an open floor plan with full kitchen, washer/dryer and two 250 sq. ft. porches, perfect for coffee or a glass of wine. The home boasts a relaxed, cozy atmosphere in a rustic setting. This private ranch estate will create a memorable stay for your Central Florida getaway. Pets welcome for a small fee!

13–20 Apr

£161 per night

Guest favourite

Cottage in Lakeland

4.92 out of 5 average rating, 157 reviews

Florida Southern, Cozy Cottage

This beautiful little cottage has it all. Everything has been newly renovated, all new furnishings, smart home equipped, new appliances and more. Have a cup of coffee on the back porch and enjoy the beautiful landscape while you listed to the birds singing their early morning songs. All rooms are furnished with the nicest linens and mattresses for your comfort. Also, all rooms have 50" or larger smart TV's with the ability to stream your favorite shows and movies.

19–26 May

£157 per night

Guest favourite

Home in Winter Haven

4.9 out of 5 average rating, 154 reviews

Hidden Haven Lakehouse Pool by Legoland

Relax in style in this 96 year old custom built home.Tall ceilings,large rooms and wood floors throughout.With an extra large swimming pool overlooking Little Lake Otis this outdoor area is second to none.Less than 2 miles from Legoland,Chain of Lakes Fieldhouse,and Downtown Winter Haven. It is possible that days may be available and not listed on the calendar. This is to give ample time for cleaning. Feel free to ask for additional availability and shorter stays.

20–27 Jun

£175 per night

Guest favourite

Home in Winter Haven

4.94 out of 5 average rating, 144 reviews

Cozy Family Home Near Legoland

Relax with the fam after a fun day at LEGOLAND (4.1 miles) or Disney World (36 miles) in our cozy home complete with a well-stocked kitchen, fully-fenced backyard, and comfortable beds. Spend a day on the famous Chain of Lakes (24 canal-connected lakes), catch a free ski show on Lake Silver, wander downtown to shop, or toast a pint at Union Taproom. Winter Haven is centrally located between Tampa and Orlando with plenty of fun nearby for the whole family.

11–18 Apr

£143 per night

Guest favourite

Flat in Winter Haven

4.91 out of 5 average rating, 113 reviews

Quint & Cozy, Confidently Clean Apartment

This is a unique 2 story antique building that has been completely renovated into 4 small apartments. This property was designed with the porpoise of offering our guest an oasis of peace, tranquility; geared towards meditation and relaxation. Though we are located only few minutes from restaurants, stores, hospitals, universities and much more, once you turn into our street, you will notice the quiet and serine atmosphere of the neighborhood.

9–16 Aug

£96 per night

Guest favourite

Home in Auburndale

4.94 out of 5 average rating, 146 reviews

Lake Whistler Beach House with lakefront pool

The Lake house is a resort with Paddle boards/Kayaks at no cost to our guests. Enjoy the entire yard and non-public lake with a private beach which offers you fishing and water sports (jet skis are additional). The main house has a pool table,air hockey and live darts! Also there is a BBQ, 4 TV's, cable, internet, movie library and washer/dryer, Pool and pool Jacuzzi. Small fenced back yard for pets (pet fee required).

6–13 Aug

£353 per night

Guest favourite

Guest suite in Winter Haven

4.96 out of 5 average rating, 257 reviews

Horse Farm on a Beautiful Lake

Small Thoroughbred Race Horse Farm on a beautiful lake. Fishing available on site. New dock just finished with plenty of benches for fishing, picnicking, or just dreaming. There is a Swimming pool right out your door, horse paddocks and patio overlooking the lake for hanging out or quiet time. Please note price is for studio (sleeps 3 or more with sofa beds)

6–13 Dec

£102 per night