Pet-friendly Vacation Rentals in Winter Haven

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.

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.

Enjoy unforgettable sunsets over Lake Howard at this pet-friendly apartment, conveniently located less than a mile from Winter Haven Hospital and a short walk to downtown Winter Haven.
This fully furnished 1-bedroom, 1-bathroom apartment accommodates two guests and features air conditioning, a kitchen, and onsite laundry facilities available for an additional fee, providing a peaceful retreat with easy access to local attractions.

Just 1 mile from Polk State College and a short walk to Lake Elbert, this 2nd-floor apartment in Winter Haven offers a prime location for students and families, with Legoland Florida Resort and Cypress Gardens just 5 miles away and multiple golf courses within 5 miles.
This pet-friendly apartment features a covered balcony with outdoor dining, a full kitchen, and driveway parking for two vehicles, making it an ideal choice for travelers with pets.

Conveniently located just a few blocks from downtown Winter Haven's restaurants and bars, this pet-friendly apartment offers easy access to attractions like Legoland and Bok Tower Gardens.
This 1450 sq ft apartment features 3 bedrooms and 2 bathrooms, comfortably sleeping up to 8 guests with amenities like a full kitchen, air conditioning, and a garden, making it a perfect dog-friendly choice for exploring the area's lakes and sports facilities.

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 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 just 6 miles from Legoland and Peppa Pig Park, this Winter Haven apartment offers easy access to major Orlando attractions and airports.
This pet-friendly apartment comfortably accommodates up to 7 guests with 3 bedrooms, 2 bathrooms, and a fully equipped kitchen featuring a microwave in every room, plus premium Wi-Fi and parking for two cars.

Directly on Lake Howard, this apartment offers a prime location on the Winter Haven Chain-of-Lakes, just 1 mile from downtown Winter Haven and a short drive to LEGOLAND, making it an ideal pet-friendly escape.
This one-bedroom apartment accommodates up to three guests and features a full kitchen, air conditioning, and direct lake access with shared kayaks and paddleboards, perfect for active travelers with 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.

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 is located in a quiet district of Winter Haven, offering a peaceful retreat close to the renowned chain of lakes and LEGOLAND Florida.
With a guest capacity of 12, this apartment features 4 bedrooms, 2 bathrooms, air conditioning, and a full kitchen, providing a comfortable and welcoming environment for family vacations.

Enjoy a pet-friendly apartment in Winter Haven, conveniently located just 1 mile from Indigo's Family Fun Center and Eagle Ridge Mall.
This one-bedroom apartment accommodates up to four guests and features a king bed, a jetted bathtub, a futon in the office area, and essential amenities like WiFi and air conditioning.

Just 10 miles from LEGOLAND® Florida and 40 miles from Disney World, this pet-friendly apartment in Winter Haven offers convenient access to major theme parks and the city's 50 lakes.
This 3-bedroom apartment accommodates up to 6 guests, featuring a full kitchen with a microwave and dishwasher, air conditioning, a swimming pool, and parking, making it ideal for travelers with pets.

Direct lake access to the beautiful Chain of Lakes makes this pet-friendly apartment an ideal getaway in Winter Haven, situated in a quiet neighborhood only a 5-10 minute drive from local attractions and medical centers.
This 800 sq ft apartment features two bedrooms, one bathroom, accommodates up to five guests, and offers a fully equipped kitchen, air conditioning, and a private, fenced backyard perfect for your pets.

Centrally located in Winter Haven, this pet-friendly apartment is just a 2-minute drive to downtown and a short walk to scenic Lake Howard.
This dog-friendly apartment features a full kitchen, air conditioning, and two dedicated parking spaces, perfect for travelers with pets visiting Winter Haven.

Enjoy a pet-friendly vacation in Cypress Gardens at this 1730 square foot house, conveniently located just 3.4 miles from Legoland Florida and near historical railroad stations.
This dog-friendly house offers 3 bedrooms, 2 bathrooms, a private swimming pool, a garden, and an indoor play area, ensuring a fun-filled stay for families and their pets.

Just 2 miles from Legoland, this pet-friendly apartment in Cypress Gardens offers convenient access to local dining and entertainment.
This fully equipped 3-bedroom apartment accommodates up to 6 guests and features a large screened patio with a swimming pool, perfect for family gatherings and creating new memories.

Just 500 feet from downtown Winter Haven and Lake Howard, this pet-friendly apartment offers excellent access to numerous restaurants and is only a 12-minute drive to Legoland.
This 3-bedroom apartment accommodates up to 6 guests with 2 queen and 2 twin beds, featuring a full kitchen with a microwave and dishwasher, air conditioning, and on-site parking, making it ideal for families and outdoor enthusiasts.

Just 20 miles from Walt Disney World and 30 miles from Universal Studios, this Haines City apartment offers a prime location for theme park adventures.
This spacious, pet-friendly apartment boasts 2,880 square feet with four bedrooms, a fenced backyard, and a game room, ensuring a comfortable stay for up to 10 guests.

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.

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 peaceful waterfront living on Lake Florence in this spacious 3200 sq ft apartment, conveniently located just minutes from LEGOLAND Florida and downtown Winter Haven's shops and dining.
This pet-friendly apartment offers 5 bedrooms, 3 bathrooms, and accommodates up to 12 guests, featuring a heated swimming pool and a garden for your enjoyment.

Located just 3.8 miles from Swanns Railroad Station (Historical) and 3.9 miles from Legoland Florida, this pet-friendly house in Winter Haven offers convenient access to local attractions.
This spacious 2970 square foot house welcomes up to 19 guests with 4 bedrooms, 3 bathrooms, air conditioning, a full kitchen, and a swimming pool, making it ideal for families and dog-friendly vacations.

This pet-friendly apartment in Haines City is located within the gated Southern Dunes Golf & Country Club, just a short walk to Walmart and CVS, and only 20 miles from LEGOLAND® Florida.
This spacious 1800 sq ft apartment comfortably accommodates up to 9 guests with 4 bedrooms and 3 bathrooms, featuring a full kitchen with a fridge, microwave, and dishwasher, air conditioning, a swimming pool, terrace, garden, and parking.

This pet-friendly apartment is conveniently located within walking distance of Winter Haven's city center, just a mile from Polk State College and a moderate drive from Disney's Animal Kingdom Theme Park and Disney's Hollywood Studios.
Enjoy this dog-friendly accommodation with complimentary Wi-Fi, air conditioning, and free parking, perfect for a 2-guest stay with your furry companions.

Centrally located in Haines City, this resort offers convenient access to major Orlando theme parks, including LEGOLAND® Florida, just a short drive away.
This pet-friendly resort features a spacious 2-bedroom, 2-bath townhouse with a fully equipped kitchen, air conditioning, and a swimming pool, perfect for families of up to 5 people and offering on-site dining at the bar & grill.

Conveniently located in Winter Haven, this pet-friendly apartment is just 3.3 miles from Swanns Railroad Station and 8.2 miles from Legoland Florida, offering easy access to attractions and transportation.
This 650 square feet apartment features air conditioning, a kitchenette with a fridge and microwave, a private balcony, and garden space, comfortably accommodating up to 7 guests with complimentary parking and free Wifi.

Just 0.5 miles from LEGOLAND Florida and Peppa Pig Theme Park, this first-floor apartment in Winter Haven offers a prime location for family fun and is a pet-friendly destination.
This 1280 sq ft, 2-bedroom, 2-bathroom apartment comfortably accommodates up to 6 guests and features a fully equipped kitchen, in-unit laundry, and access to resort-style amenities including a heated pool and dog park.

Enjoy picturesque views of Lake Howard from this pet-friendly apartment, conveniently located just minutes from downtown Winter Haven and Legoland.
This spacious 4-bedroom apartment accommodates up to 8 guests and features a private dock, a charcoal grill, and a loft with a King bed and projector for an ultimate entertainment experience.

Enjoy a unique lakeside apartment in Winter Haven, Florida, just 2.5 miles from Legoland and 3.5 miles from downtown.
This pet-friendly apartment accommodates up to 6 guests and features a private pool, a grill, and seasonal fruit for a memorable stay.

Directly across from Eagle Lake, this apartment offers stunning lake views and is just 7.3 miles from Legoland and 4.1 miles from Downtown Winter Haven.
This pet-friendly apartment comfortably accommodates up to 7 guests with 3 bedrooms and 2 bathrooms, featuring a well-equipped kitchen, air conditioning, a garden, and an outdoor patio with a hammock and BBQ grill, perfect for family memories and remote work.

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.

This pet-friendly resort in Haines City offers a 3-bedroom, single-story home with a private pool and game room, located just minutes from LEGOLAND® Florida.
Enjoy 1820 square feet of living space, an ultra-modern kitchen, and free Wi-Fi, with optional access to Balmoral Resort's heated community pool, making it ideal for families and their pets.

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.

Directly on the renowned Southern Dunes Golf Course in Haines City, this apartment offers panoramic golf course views and is a short drive to Walt Disney World and Universal Studios.
This pet-friendly apartment features a 1540 sq ft layout with 4 bedrooms and 2 bathrooms, comfortably sleeping 8 guests with a private south-facing pool, air conditioning, and a fully equipped kitchen.