Pet-friendly Vacation Rentals in Winter Haven

Just a 12-minute drive from LEGOLAND Florida and Peppa Pig Theme Park, this pet-friendly apartment is conveniently located near Chain of Lakes Park and Circle B Bar Reserve in Winter Haven.
This spacious 4-bedroom apartment welcomes pets and offers a fully stocked kitchen, free WiFi, and an outdoor fire pit, perfect for families exploring the nearby theme parks and natural attractions.

Enjoy a pet-friendly vacation in Haines City at this spacious 2000 sq ft house, located 9.3 miles from Swanns Railroad Station and 14 miles from Legoland Florida.
This family-friendly accommodation offers a private heated pool and jacuzzi, a fully equipped kitchen, and an indoor play area, ensuring a comfortable stay for you and your furry companions.

Enjoy a pet-friendly apartment in Winter Haven, Florida, conveniently located within 50 miles of Orlando and Tampa attractions and coastal beaches.
This spacious 3-bedroom, 2-bathroom apartment accommodates up to 8 guests and features a fenced backyard with an in-ground pool, a grill, and a video game area, making it ideal for families and pet owners.

Experience the ultimate family getaway at this expansive 8-bedroom villa, a premier pet-friendly destination located in Davenport's Champions Gate Resort, just 9 miles from Walt Disney World.
This spacious accommodation boasts a private south-facing pool and spa, a Hollywood-style movie theater, and a full game room, offering ample entertainment for your group of 16, with the added benefit of full access to the Champions Gate Oasis Clubhouse amenities.

Enjoy a serene lakefront setting in Winter Haven, Florida, this historic manor is just a 10-minute drive from Legoland and within easy reach of Orlando and Tampa theme parks.
This spacious, pet-friendly apartment boasts 5 bedrooms, 3 bathrooms, and accommodates up to 10 guests, featuring a fully-equipped kitchen, a private patio, backyard with lake views, and high-speed Wi-Fi.

This 6-bedroom apartment in Haines City's gated Calabay Parc at Tower Lake community is a pet-friendly option, located approximately 25-30 miles from Walt Disney World and 35 miles from Universal Studios.
Enjoy a private screened-in pool and jacuzzi, a game zone with a pool table and foosball, and a master suite with a spa-style soaking tub in this spacious 2710 square foot home accommodating up to 12 guests, with a 24-hour on-site host available for assistance.

Just 500 feet from LEGOLAND Florida Resort and Peppa Pig Theme Park, this 2-bedroom, 2-bathroom apartment offers a prime location in Winter Haven with resort-style amenities and is pet-friendly.
This brand-new 2024 luxury complex features a fully equipped kitchen, in-unit laundry, a heated swimming pool, and is conveniently located for day trips to Walt Disney World and Universal Studios Orlando.

This pet-friendly house in Davenport is located 16 miles from Legoland Florida and 29 miles from Orlando International Airport, offering a prime spot for family vacations.
With 3410 square feet, this spacious villa features eight bedrooms, a private pool, a hot tub, and an outdoor barbecue area, ensuring a comfortable and entertaining stay for you and your pets.

Just three houses from Lake Howard, Chain of Lakes Villa in Winter Haven offers peek-a-boo water views and direct access to a scenic trail connecting to the South Chain of Lakes for boating, with Legoland just a 15-minute drive away.
This 4-bedroom, 2-bathroom apartment welcomes pets and features a private, fenced backyard, a fully equipped kitchen, and ample parking for up to 4 vehicles, making it an ideal pet-friendly stay.

Just 500 feet from Legoland Florida, this centrally located Winter Haven apartment is a perfect pet-friendly choice for families and business travelers.
This apartment accommodates up to 4 guests with a queen bed and a pull-out couch, offering a fully equipped kitchen, on-site laundry, and private parking for a convenient stay.

Directly on Lake Eloise via a private canal, this pet-friendly apartment in Winter Haven's Cypress Inlet district offers easy access to Legoland, Disney World, and SeaWorld, all within a short drive.
This 2-bedroom, 2-bath apartment features a full kitchen with a dishwasher, air conditioning, a swimming pool, and a garden, making it an excellent choice for families and dog-friendly vacations near Florida's famous Chain of Lakes.

This historic 100-year-old custom-built apartment is located less than 2 miles from Legoland, Chain of Lakes Fieldhouse, and Downtown Winter Haven, offering easy access to dining, shopping, and major highways.
Enjoy a pet-friendly stay with exclusive use of amenities including an extra-large swimming pool with a view of Little Lake Otis, a garden, and ample space for up to 6 guests.

Centrally located in Winter Haven, this apartment offers convenient access to Downtown Winter Haven, less than 1 mile away, and Legoland, just 4 miles away.
This dog-friendly apartment features a fully fenced, spacious backyard, making it ideal for families traveling with pets, and comfortably accommodates up to 7 guests with 3 bedrooms and 2 bathrooms.

This pet-friendly house in Winter Haven offers ample space for large groups and is conveniently located 6.1 miles from Legoland Florida, with fishing activities available nearby.
Boasting 5 bedrooms and 3 bathrooms, this spacious 450 square foot home features a fully equipped kitchen, air conditioning, free WiFi, and an indoor play area, making it ideal for families and sports teams traveling with pets.

Enjoy a fantastic family getaway at this pet-friendly apartment in Winter Haven, just a 20-minute drive from LEGOLAND and 50 minutes from the Disney Parks.
This spacious 3-bedroom, 2-bathroom apartment accommodates up to 7 guests and features a private swimming pool, a fully equipped kitchen, complimentary Wi-Fi, and baby-proofing for added convenience.

Perfectly situated, this pet-friendly guest suite is only 1.2 miles from Downtown Winter Haven and 1.4 miles from Winter Haven Hospital.
This modern, private 1-bedroom guest suite accommodates 2 guests and features a full-size sleeper sofa, a kitchen area, a screened-in porch, and is just 4.7 miles from LEGOLAND Florida Resort.

Enjoy a pet-friendly apartment vacation in Winter Haven, conveniently located just 4.7 miles from Legoland and a short 6-minute drive to numerous shopping plazas.
This spacious 3-bedroom, 2-bathroom apartment accommodates up to 6 guests and features a fully equipped kitchen with a dishwasher and access to a community pool.

Enjoy unique boathouse access with canal-side seating and a picnic table in this pet-friendly efficiency unit located in a residential community of Winter Haven, just a short drive from the chain of lakes.
This dog-friendly accommodation offers a kitchenette with a cooktop, fridge, and microwave, a private full-size bathroom, and sleeping arrangements for up to two guests, with small dogs allowed with pre-approval and a fee.

Directly on the Chain of Lakes in Winter Haven, this apartment offers exceptional access to water skiing and water sports, and is a short drive to LEGOLAND and Universal Studios.
This pet-friendly apartment boasts 3,300 sq ft with a game room, kayaks, paddle boards, and a hot tub, comfortably accommodating up to 22 guests.

Just 3 houses from Lake Howard, this pet-friendly apartment is in a quiet Winter Haven neighborhood, offering peek-a-boo water views and direct access to a scenic walking/biking trail connecting to the South Chain of Lakes.
This newly renovated, single-level 1800 sq ft apartment accommodates up to 12 guests with 4 bedrooms and 2 bathrooms, featuring a fully stocked kitchen, a private fenced backyard, and ample parking, all just 15 miles from Legoland.

This pet-friendly cottage in Lake Hamilton offers a lakeside escape, located just 7.2 miles from Legoland Florida and 7.9 miles from Swanns Railroad Station.
Enjoy a fully equipped kitchen, air conditioning, and outdoor seating in this 100 square feet accommodation, perfect for a family of 9.

Located in Winter Haven, this private resort offers direct access to a terrace and is just 3 miles from Legoland Florida and 4.8 miles from Swanns Railroad Station.
This pet-friendly house features a private swimming pool and a fully equipped kitchen, perfect for families or groups of up to 23 guests.

Just minutes from LEGOLAND® Florida, this pet-friendly apartment in Eagle Lake offers exceptional proximity to theme parks and local attractions like Indigo's Family Fun Center.
This 1800 sq ft apartment accommodates up to 10 guests with three bedrooms, a game room featuring a pool table and foosball, and an outdoor patio with grilling facilities, making it ideal for families and groups traveling with pets.

Centrally located in Winter Haven, this newly renovated, stylish tri-level apartment offers a prime destination just 5 miles from Legoland and 40 miles from Busch Gardens and Disney.
This pet-friendly apartment boasts 3 bedrooms, 2 bathrooms, and accommodates up to 7 guests with amenities like a private terrace, air conditioning, a swimming pool, and an in-home theater.

Experience a pet-friendly apartment on the award-winning Southern Dunes Golf & Country Club in Haines City, offering lake views and convenient access to LEGOLAND (14 miles) and Walt Disney World (21 miles).
This 3-bedroom, 2-bathroom apartment accommodates up to 6 guests and features a heated swimming pool, terrace, garden, and is within walking distance to Walmart and grocery stores, making it ideal for families and pet owners.

This waterfront house in Winter Haven offers a peaceful escape, located just 1.4 miles from Legoland Florida and near historical railroad stations.
Enjoy a spacious 3200 square foot home with a swimming pool, garden, and terrace, perfect for a pet-friendly family vacation with a guest capacity of 23.

This pet-friendly apartment in Winter Haven is conveniently located 1 mile from Polk State College and within 10 miles of historical railroad stations like Phosmico and Swanns, with Legoland Florida just 4.4 miles away.
Enjoy a comfortable stay in this 540 sq ft apartment that welcomes pets, features air conditioning, complimentary WiFi, a full kitchen, and a private balcony, perfect for accommodating up to 3 guests.

This pet-friendly apartment in Eagle Lake is located near downtown Winter Haven, just a 10-minute drive to Legoland and Peppa Pig theme parks, and approximately 20 miles from the Country Club of Winter Haven.
Enjoy a spacious 3-bedroom apartment that accommodates up to 8 guests, featuring a dedicated game room with a pool table, foosball, and ping pong, plus a full kitchen and a terrace or balcony.

Just 1.8 miles from Legoland Florida, this pet-friendly house in Winter Haven offers a comfortable stay with two bedrooms and one bathroom.
This dog-friendly accommodation features air conditioning, free WiFi, and a kitchenette, perfect for families with a guest capacity of nine.

Just 5 miles from Legoland and within an hour of Orlando's major theme parks, this pet-friendly apartment in Winter Haven offers a prime location for family fun.
This apartment boasts 3 bedrooms, accommodates 6 guests, and features a Jacuzzi, garden, and fully equipped kitchen, ensuring a comfortable and convenient stay for you and your pets.

Just 0.5 miles from LEGOLAND Florida, this first-floor apartment in Winter Haven offers a convenient and pet-friendly escape for families.
This 1280 sq ft apartment sleeps 6 and features resort-style amenities including a heated pool, fitness center, and a dog park, making it ideal for a comfortable, self-sufficient stay.

Conveniently located in a quiet Winter Haven neighborhood, this apartment is just 8.7 miles from Legoland Florida Resort and within 5 miles of the Chain of Lakes Complex and Downtown Winter Haven.
This pet-friendly apartment features 3 bedrooms, 2 bathrooms, and sleeps up to 7 guests with a well-equipped kitchen, screened-in patio, and a private master ensuite, making it ideal for families and dog-friendly vacations.

Just 130 steps from LEGOLAND Florida theme park, this resort in Winter Haven offers unique, pet-friendly village-style bungalows and themed hotel rooms near Lake Dexter.
Enjoy family-friendly amenities including zero-entry heated outdoor pools, in-room treasure hunts with LEGO prizes, and a convenient shuttle service, making it an ideal spot for travelers with pets looking for fun near Historic Bok Tower Gardens, 11 miles away.

Conveniently located in Winter Haven, Florida, this apartment is just 5 minutes from Winter Haven Hospital and 4 minutes from downtown.
This pet-friendly apartment offers 2 bedrooms, sleeps up to 6 guests, and features a full kitchen, air conditioning, and a 50-inch TV with streaming services, with Legoland just 14 minutes away.

Conveniently located in Davenport, this pet-friendly house is situated 18 to 20 miles from major Disney attractions like Animal Kingdom and Blizzard Beach, and 18 miles from Legoland Florida.
This spacious 2160 sq ft house offers 4 bedrooms, 3 bathrooms, a full kitchen with a dishwasher, air conditioning, a private swimming pool, and a garden, making it ideal for families and their pets.

Directly across from Lake Howard boat ramp, this pet-friendly apartment is only a 10-minute drive to Legoland and offers boat parking.
This spacious 2300 sq ft apartment accommodates up to 6 guests and features a fenced backyard with a pergola, outdoor fireplace, and on-site recreational activities like kayaks and bicycles.