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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Top guest favorite

Home in Kissimmee

4.92 out of 5 average rating, 139 reviews

Disney Playhouse, Private Pool & Spa, Near Disney

Disney Playhouse – Your Dream Vacation Awaits! Indulge in elegance and comfort at this newly upgraded, pet-friendly retreat. Relax in your private pool & spa within a fully fenced backyard. Unwind in the plush master suite, enjoy Roku TVs in every room, and stay connected with blazing fast 1GB WiFi. The Diner Themed game room features a Marvel electronic pinball machine, pool table, and Wii. Pool heat is optional, hot tub always free! Pets welcome. King Master. Book your luxury getaway today!

Superhost

Home in Clermont

4.84 out of 5 average rating, 224 reviews

Great House w/Heated Pool;Near all Parks!

Welcome to la Casita de todos! This home will be your home away from home, children-friendly, and spacious for the whole family! Dogs under 20 pounds are allowed with a 75 USD fee per pet. HEATED pool with a charge fee of $ 25 USD per day. BBQ grill has an extra charge of $40 USD (for the whole stay, including 1 propane gas and cleaning). After booking and before check-in please let me know if you are bringing a pet or will use the BBQ. Locations nearby: Walmart 0.5 miles. Dollar Tree 0.1 miles.

Guest favorite

Apartment in Kissimmee

4.94 out of 5 average rating, 120 reviews

*KingSizeBed*NrDisney* 100%private*PetsOK

Relax in this 5-star studio, just 15 minutes from Disney, MCO Airport, Downtown, and Universal! Enjoy your private patio, dining under the stars or swaying in the hammock! Take in serene lake views and beautiful sunsets just steps away. With nearby shopping, dining, and local parks, this studio offers the perfect blend of tranquility and easy access to top attractions. Whether you’re here for a Disney vacation or a business trip, this is the ideal retreat for relaxation, comfort, and convenience

Guest favorite

Apartment in Kissimmee

4.94 out of 5 average rating, 16 reviews

3 br Disney area condo with a view & FREE resort!

Hands down the Best value and location for a visit to the parks! This super clean and cozy 3 bedroom, 2 bath condo with a private porch and views of the conservation is just what you were looking for in that perfect vacation in the Orlando/Kissimmee areas! Situated inside beautiful Windsor Palms resort and it's FREE resort amenities and mere minutes from all of the main area attractions, the nice furnishings and linens, private views and attention to detail will get your entire family smiling.

Superhost

Home in Kissimmee

4.79 out of 5 average rating, 102 reviews

View the Disney fireworks from your pool!

Our home is close to Walt Disney World - Shopping - Restaurants . You’ll love the fully stocked granite kitchen, ALL SMART TVs in EVERY room, the views (fireworks), the location, the high ceilings & ceiling fans. Our home is great for couples, families (with kids), and furry friends (pets). Laundry room is INSIDE. The garage is full of games (air hockey, pool & foosball) The pool has a covered lanai with table & chairs for outdoor eating while overlooking our lake with a lighted fountain.

Top guest favorite

Townhouse in Kissimmee

4.99 out of 5 average rating, 102 reviews

Family friendly/Pet friendly Orlando paradise

*PET AND CHILD FRIENDLY* *Long term renters welcome* 2 bedroom 2.5 bath Townhome in gated community! 10 mins to Disney, 20 to seaworld, and 30 to universal studios. Community includes large beautiful heated pool and playground/bbq area. Professional cleaning services after each guest stay. Fully stocked kitchen with Keurig coffee, all dishes, utensils, seasonings etc. All bathrooms fully stocked with toiletries and plenty of extra towels. Patio includes chairs, gas grill, and sitting area.

Superhost

Home in Davenport

4.8 out of 5 average rating, 15 reviews

Modern Legends, Near Disney, kings bed ste

Welcome to your new home away from home! This stunning single-level property boasts an open floor plan that is perfect for relaxing with the family. The cheerful modern decor is sure to brighten your day, and the property is equipped with everything you need for a comfortable stay, including a washer and dryer, and TVs in all bedrooms. This property is located in a gated community that provides free parking, ensuring that you and your family will be safe and secure throughout your stay.

Superhost

Condo in Kissimmee

4.79 out of 5 average rating, 215 reviews

Comfortable Universal Disney Orlando Family Condo

Welcome🌞! This unit is on the second floor! Your much deserved fun vacation away from home starts here 😎! Llocated in the heart 💗 of Walt Disney World and all Kissimmee and Orlando best fun spots 🎢! Includes 2 full size bed. and 1 Full size sofa bed. Just added BIG SMART TVs with Disney+, Netflix, Amazon Video perfect for relaxing after a fun-filled day.✨ 🚗 NEED A CAR? Ask us about our 8-passenger minivan. You can plan your stay and car rental all in one go. Ask us for the link!

Superhost

Home in Kissimmee

4.72 out of 5 average rating, 96 reviews

Southwest facing pool! 5 Miles from Disney.

Enjoy the sunset by your SOUTHWEST facing pool, just 5 miles from Disney. The huge pool area has a conservation & lake view. Enjoy outdoor games or shoot some hoops with the family! Bedroom theming includes 101 Dalmatians (popular with pups AND kids), Harry Potter, Little Mermaid, and Mickey rooms. After a day spent in the parks, wind down with a game of pool or watch a movie in the theatre/game room. Bring your fur baby and the whole family to this spacious and open pet-friendly home!

Top guest favorite

Home in Lakeland

5 out of 5 average rating, 43 reviews

Freshly Updated Luxury Downtown Home

This inviting and cozy luxury retreat is located in the quiet Lake Hunter neighborhood in Lakeland. Our charming home offers a blend of modern comforts and classic Southern charm, making it the perfect base for your trip to Lakeland. Location -8 mins to FSC -10 mins to SEU -10 mins to Publix Field/Detroit Tigers -13 mins to Sun n Fun/Lakeland Linder -45 minutes away from Disney -30 minutes away from Legoland -45 mins to Tampa Int'l Airport -1 hour to Orlando Int'l Airport

Guest favorite

Townhouse in Kissimmee

4.93 out of 5 average rating, 100 reviews

Private Pool-StoreyLakesResort-Near Disney!

This gated community is perfect for your family &friends to create amazing memories! The home has a first floor bedroom (king) &a very PRIVATE LAKEFRONT pool (that can be heated at a reasonable fee). The resort is very lively.... has TONS AND TONS of amenities including a micky shaped pool, lazy river, tiki bar, slides, &kayaking. You are sure to enjoy your ultimate dream vacation! 5miles-Disney, 14 miles-Universal Studios. We provide all basic essentials, too!

Guest favorite

Cottage in Kissimmee

4.98 out of 5 average rating, 113 reviews

1BD Cottage "Limoncello" in Margaritaville

Welcome to your own island-inspired oasis. Our charming cottage is the perfect home base for your next dream Orlando vacation. The unit comes with all the comforts from home but worlds away. Conveniently located minutes from the Disney parks, a state-of-the art water park and newly opened 196,000 square foot shopping and dining district with multiple dining food and beverage options & brand-new movie theater. All Pets Must Be Preapproved :)