Pet-friendly Vacation Rentals in Winter Haven

This pet-friendly apartment in Dundee sits on a lake, offering a scenic escape just 6 miles from LEGOLAND® Florida and 43 miles from Orlando International Airport.
Enjoy comfortable air-conditioned accommodations with complimentary WiFi and a seasonal outdoor swimming pool, perfect for families of up to 4, with motor boating and swimming opportunities nearby.

This lakefront house in Winterset, Winter Haven, is conveniently located just 1.7 miles from Legoland Florida, offering a prime location with scenic lake views and proximity to historical landmarks like Swann's Railroad Station, 9 miles away.
Enjoy this pet-friendly accommodation with 2 bedrooms, 2 bathrooms, and a guest capacity of 11, featuring a full kitchen with a fridge, microwave oven, and dishwasher, plus a relaxing jacuzzi, spa, tennis court, and ample parking for a comfortable stay.

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.

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.

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.

Just 2 miles from Legoland Florida Resort, this pet-friendly apartment offers 4 bedrooms and 2 bathrooms, accommodating up to 5 guests and featuring a full kitchen with a fridge, microwave, and dishwasher.
Enjoy a comfortable stay with air conditioning and parking, perfect for families looking to explore Winter Haven's chain of lakes and downtown dining, knowing your pets are welcome.

Enjoy a pet-friendly condo in Winter Haven, conveniently located just 500 feet from local shopping and diverse dining options, and a short drive to Central Florida's popular tourist attractions.
This 3-bedroom, 2-bathroom apartment comfortably accommodates up to 4 guests and features a fully equipped kitchen, spacious living area, and fast Wi-Fi, making it an ideal retreat for families and business travelers.

Centrally located in downtown Winter Haven, this apartment offers convenient access to shops and dining, just a short walk from local attractions.
This pet-friendly apartment features an on-site arcade machine and fast WiFi, perfect for families or groups of up to five guests, with two queen beds and a dedicated workspace.

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.

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.

Enjoy a pet-friendly apartment stay in Dundee, Florida, conveniently located just 6 miles from Legoland Florida and 14 miles from Swanns Railroad Station (Historical).
This dog-friendly accommodation offers 150 square feet of space, air conditioning, complimentary WiFi, and a seasonal outdoor swimming pool for your enjoyment.

This spacious lake home in Cypress Gardens is located just 4.4 miles from Legoland Florida and 4.9 miles from Swanns Railroad Station, offering a pet-friendly retreat with free WiFi and parking.
Featuring 3 bedrooms and 2 bathrooms across 1650 square feet, this house comfortably accommodates up to 13 guests and includes a fully equipped kitchen and air conditioning for a pleasant stay.

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.

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 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.

Located just 1.5 miles from Polk State College, this pet-friendly apartment offers convenient access to Lake Elbert for outdoor recreation and is a short drive to Legoland Florida Resort.
This 1-bedroom, 1-bathroom apartment accommodates up to 2 guests and features a full kitchen, air conditioning, and a covered balcony with an outdoor dining area, making it ideal for travelers with pets.

Just 5 minutes from Indigo's Family Fun Center and Theatre Winter Haven, this pet-friendly apartment offers a prime location for exploring Winter Haven with easy access to major attractions.
This spacious 6-bedroom, 3-bathroom apartment comfortably accommodates up to 16 guests, featuring a fully equipped kitchen, air conditioning, complimentary Wi-Fi, and a private garden with outdoor furniture and a terrace, making it an ideal choice for families and dog-friendly vacations.

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.

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.

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.

This pet-friendly apartment in Haines City is located within the exclusive Balmoral Resort, offering 24/7 security and full amenity access, just 26 miles from LEGOLAND Florida and 36 miles from Walt Disney World.
Boasting 2540 square feet, this dog-friendly accommodation features 4 bedrooms, 5 bathrooms, a private screened pool with lake views, and access to a resort-style pool, water park, and fitness center.

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.

Directly on the shores of Lake Hamilton, this 5-bedroom, 2-bathroom apartment offers stunning lake views and is conveniently located just minutes from Legoland, dining, golf, and shopping, with Disney and Orlando attractions a short drive away.
This pet-friendly retreat features a fully equipped kitchen, Smart TVs, fast WiFi, and ample on-site parking for multiple vehicles, boats, and trailers, ensuring a comfortable stay for large families and groups of up to 12 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.

Enjoy prime waterfront living on Eagle Lake, just a 15-minute drive from LEGOLAND® Florida and within easy reach of Orlando's theme parks.
This newly renovated, pet-friendly 4-bedroom, 2-bathroom apartment offers 1690 square feet of modern living space, accommodating up to 8 guests with a fully equipped kitchen and an outdoor deck perfect for enjoying lake views.

Lakefront living awaits in this 3-bedroom, 2-bathroom apartment in Winter Haven, conveniently located just 4 miles from LEGOLAND and within an hour's drive of major Orlando attractions.
This modern, pet-friendly apartment offers 1190 square feet of comfortable space for up to 6 guests, featuring a full kitchen, air conditioning, and a garden, with nearby access to The Circle B Bar Reserve and shopping centers.

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.

Directly on the Winter Haven Chain of Lakes, this pet-friendly apartment is located just 5 miles from LEGOLAND Florida Resort and 35 miles from Orlando theme parks.
This spacious, recently updated apartment offers 3 bedrooms, sleeps 6 guests, and features a large screened-in lanai, a fully equipped kitchen, and a covered patio with outdoor dining, making it ideal for families and dog-friendly vacations.

This pet-friendly house in Winter Haven is located in a residential area, offering easy access to local attractions and amenities, with a fully fenced backyard perfect for your pets.
Enjoy a vacation with your family and pets in this 4-bedroom, 2-bathroom house featuring an outdoor entertainment hub with a jacuzzi and pool, plus indoor fun like foosball and air hockey, accommodating up to 10 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 just 0.5 miles from Legoland and close to downtown Winter Haven, this pet-friendly apartment offers a prime spot for family fun and exploration.
This spacious 3-bedroom apartment accommodates up to 7 guests with a fully equipped kitchen, including a high chair and children's dinnerware, plus comprehensive baby amenities for a comfortable stay with your dog-friendly family.

Explore Central Florida from this pet-friendly apartment, located less than 60 miles from Walt Disney World Resort and Universal Orlando Resort, and within 90 miles of Busch Gardens Tampa Bay.
This apartment welcomes pets and offers a fenced yard, a dog door, and comfortable accommodations for up to 5 guests, featuring a fully equipped kitchen and outdoor seating.