Pet-friendly Vacation Rentals in Winter Haven

Just 5 miles from LEGOLAND, this pet-friendly apartment in Greater Winter Haven, Florida, offers convenient access to historic downtown and the scenic Chain of Lakes, with nearby nature trails perfect for outdoor enthusiasts.
This 3-bedroom, 2-bathroom apartment comfortably sleeps 6 guests and features air conditioning, a fully-equipped kitchen with a dishwasher, and an outdoor patio for enjoying the Florida weather.

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.

Enjoy a prime Winter Haven location, just 1 mile from Downtown and 3 miles from Legoland Florida, with numerous lakes nearby for outdoor fun.
This pet-friendly apartment accommodates up to 7 guests with 3 bedrooms, 2 bathrooms, and features a fully equipped kitchen, in-unit washer/dryer, and a backyard with a BBQ grill.

Enjoy outdoor Florida living with a private swimming pool and BBQ grill at this pet-friendly 4-bedroom house, conveniently located just minutes from Downtown Winter Haven and a short 15-minute drive to Legoland.
This spacious, modern home accommodates up to 10 guests and features a fully equipped kitchen, high-speed Wi-Fi, and a unique semi-private studio with its own kitchenette, offering comfort and flexibility for families and groups traveling with pets.

Just 1 mile from Legoland Florida Resort, this spacious family-friendly apartment in Winter Haven is perfect for your next getaway.
This pet-friendly apartment features 4 bedrooms, 2 bathrooms, and a guest capacity of 14, with a kitchen including a fridge, freezer, microwave, and dishwasher, plus air conditioning and a swimming pool.

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.

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 a completely remodeled 3-bedroom apartment, conveniently located just 2.1 miles from Legoland, offering a pet-friendly stay with brand new leather reclining couches and smart TVs in every room.
This spacious apartment accommodates up to 12 guests and features elegant porcelain ceramic tile flooring throughout, with two bathrooms providing both a full tile shower and a relaxing bathtub for your comfort.

Enjoy exclusive private waterfront access and a dedicated entrance for ultimate privacy in this pet-friendly apartment located in a secluded area of Central Florida, just a short drive from local attractions.
This dog-friendly apartment comfortably accommodates up to 4 guests with a queen bed, futon, and portable cot, featuring a well-stocked kitchenette, air conditioning, and a fenced backyard perfect for pets and children.

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.

Located in Eagle Lake, this apartment is just 10 miles from Legoland and 45 miles from Walt Disney World, offering a peaceful retreat with excellent user and location ratings.
This spacious, pet-friendly apartment features 5 bedrooms, 2 bathrooms, and accommodates up to 10 guests, boasting a full kitchen, air conditioning, parking, and a cozy fireplace, ideal for extended stays.

Just minutes from Legoland, this pet-friendly Winter Haven apartment offers an excellent base for exploring Orlando and Tampa attractions, including Disney World and Universal Studios.
This 3-bedroom apartment comfortably sleeps up to 8 guests and features a fenced backyard, a fully stocked kitchen, and provided bikes for local exploration, making it an ideal choice for families and their pets.

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.

This pet-friendly apartment in Winter Haven offers a peaceful family-friendly retreat, conveniently located approximately 15 miles from Legoland and within 40 miles of Disney World.
Enjoy a relaxing stay with amenities like air conditioning, a swimming pool, and a kitchen equipped with a fridge and microwave, perfect for Snowbirds, Travel Nurses, and business travelers seeking mid-term stays with pets allowed.

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.

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.

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.

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.

Centrally located in Winter Haven, this apartment is just two minutes from downtown and within walking distance to scenic Lake Howard.
This pet-friendly apartment offers a private bedroom with a King size bed, a fully equipped kitchen, and on-site laundry, making it ideal for travelers with pets exploring local attractions like Legoland, which is a ten-minute drive away.

Enjoy effortless indoor-outdoor living in this spacious 4-bedroom, 3-bathroom apartment located just 1 mile from Downtown Winter Haven's dining and entertainment, and a 5-mile drive to Legoland Florida Resort, offering a perfect pet-friendly getaway near the Chain of Lakes.
This expansive 2970 square foot apartment accommodates up to 10 guests and features a detached pool house suite, two living areas, a screened-in lanai with a pool, a fenced backyard, a foosball table, and a dedicated workspace, making it ideal for multi-generational groups and families traveling with pets.

Just 5 miles from LEGOLAND Florida Resort, this spacious 4-bedroom apartment in Winter Haven offers pet-friendly accommodations perfect for families and groups of up to 8 guests.
Enjoy convenient access to Orlando and Tampa, both about 45 minutes away, and explore nearby cultural attractions like Theatre Winter Haven and local shopping centers, making this a great base for your Florida adventures.

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.

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.

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.

Directly on Lake Hamilton, this pet-friendly house offers lakefront access and is conveniently located just 5 miles from both Disney and Legoland.
This spacious accommodation features 5 bedrooms, a fully equipped kitchen, a kitchenette, air conditioning, free WiFi, and a terrace with garden views, ensuring a comfortable stay for up to 23 guests.

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.

Just 1.8 miles from Legoland Florida, this pet-friendly apartment in Winter Haven offers convenient access to downtown attractions and free private parking.
This 1000 sq ft apartment welcomes pets and features a fully equipped kitchen, air conditioning, and a terrace for a comfortable stay for up to 7 guests.

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.

Located in a tranquil golf community in Haines City, Florida, this pet-friendly apartment is just a short drive to LEGOLAND Florida and ChampionsGate Golf Club.
This 1400 square feet apartment features 3 bedrooms, 2 bathrooms, a private swimming pool, and accommodates up to 9 guests, making it ideal for families traveling with their pets.

Lakefront property on 3 acres in Winter Haven offers abundant privacy and direct access to Lake Mariam, conveniently located just 2 miles from downtown and the hospital, and 4 miles from LEGOLAND & Peppa Pig Theme Park.
This pet-friendly apartment welcomes families with 3 bedrooms, 2 bathrooms, and a guest capacity of 7, featuring a full kitchen, laundry, and kid-friendly amenities, plus private dock access for boat guests.

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.

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 spacious 3-bedroom, 2-bathroom modern lake home in Winter Haven is located just 4.4 miles from Legoland Florida and Swanns Railroad Station.
This pet-friendly house offers 1210 square feet of living space with air conditioning, free Wifi, and a fully equipped kitchen, perfect for families and accommodating up to 15 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 apartment in Eagle Lake is conveniently located just 10 miles from Legoland, Legoland Waterpark, and Peppa Pig theme parks, and close to downtown Winter Haven's shops and restaurants.
Offering space for up to 10 guests, this apartment boasts three bedrooms, a fully stocked kitchen with brand new appliances, and an extensive game room featuring a pool table, foosball, and ping pong for endless entertainment.