Pet-friendly vacation 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 favorite

Guesthouse 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 !

Jan 18 – 25

ﺩ.ﺇ274 per night

Guest favorite

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

Jun 18 – 25

ﺩ.ﺇ431 per night

Guest favorite

Home in Lakeland

4.96 out of 5 average rating, 116 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!

Jun 26 – Jul 3

ﺩ.ﺇ509 per night

Guest favorite

Cottage in Lake Wales

4.88 out of 5 average rating, 109 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.

Apr 26 – May 3

ﺩ.ﺇ481 per night

Guest favorite

Guesthouse in Lakeland

4.94 out of 5 average rating, 145 reviews

Modern Studio + Secluded Courtyard, SEU, FSC,dntwn

Enjoy your stay in Lakeland in our cozy, 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!

Aug 2 – 9

ﺩ.ﺇ390 per night

Guest favorite

Home in Lakeland

4.86 out of 5 average rating, 109 reviews

Hollingsworth Pool Home

This artistic, craftsman-style pool home is regally situated on a red brick street in Lakeland's beloved Lake Morton Historic District. Centrally located, with Lake Hollingsworth just 2 blocks away, the Hollingsworth House is also walking distance to Cob & Pen, Concord Coffee, and the trendy Dixieland neighborhood where you can shop at antique and boutique shops. The large pool is surrounded by 8 foot privacy fence and a fully-fenced in backyard. Free driveway parking.

Nov 15 – 22

ﺩ.ﺇ706 per night

Guest favorite

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.

Sep 25 – Oct 2

ﺩ.ﺇ685 per night

Guest favorite

Home in Winter Haven

4.94 out of 5 average rating, 145 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.

Oct 9 – 16

ﺩ.ﺇ481 per night

Guest favorite

Apartment in Winter Haven

4.91 out of 5 average rating, 114 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.

Jun 22 – 29

ﺩ.ﺇ371 per night

Guest favorite

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).

Aug 16 – 23

ﺩ.ﺇ1,346 per night

Guest favorite

Home in Winter Haven

4.98 out of 5 average rating, 99 reviews

Spectacular Waterfront Home in Winter Haven

Have a wonderful family get away at this premier waterfront home on the famous Chain of (19) Lakes! Separate yourself from the crowd at this beautiful Cypress Gardens home set on an acre with lush tropical foliage and surrounded by 3 sides of water. 2 private docks, the "New Florida Pool," 2 hot tubs, fire pit and many more amenities. Enjoy relaxed luxury at its finest.

Jun 24 – Jul 1

ﺩ.ﺇ2,748 per night

Guest favorite

Guest suite in Winter Haven

4.96 out of 5 average rating, 258 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)

Mar 7 – 14

ﺩ.ﺇ419 per night