Search for vacation rentals in Winter Haven.

Whether it's vacation home rentals, apartments, condos, or cabins/cottages, we have you covered -- search for rental properties in the entire Winter Haven area to find the perfect spot for your vacay.

Reggie Rd
	Reggie Rd Winter Haven, FL $2,030 Vacation Rentals, Unknown Welcome to your ideal rental opportunity in Winter Haven, FL! This property offers a comfortable living space that is perfect for anyone looking to enjoy the vibrant lifestyle of this charming......

301 Avenue G SE
	301 Avenue G SE Winter Haven, FL $1,600 Vacation Rentals, Unknown HOUSE FOR RENT (3 BEDROOMS / 2 BATHS , CARPORT PLUS DETACHED GARAGE TENANT will pay for utilities, (electr., garb, landscaping, etc...) SMALL DOG OK CLEAN CRIMINAL RECORDS NO DRUGS, NO SMOKERS, NO......

750 26th St NW
	750 26th St NW Winter Haven, FL $1,299 Vacation Rentals, Unknown This inviting 2 bedroom, 1 bathroom house is conveniently located off Ave G NW, just minutes from Recker Hwy and a variety of shopping and dining destinations. Inside, the home offers tile flooring......

4202 Roberta Dr
	4202 Roberta Dr Winter Haven, FL $2,235 Vacation Rentals, Unknown Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare professional......

361 Honey Bell Rd
	361 Honey Bell Rd Winter Haven, FL $1,850 Vacation Rentals, Unknown 361 Honey Bell Rd, Winter Haven, FL 33880 Welcome to this spacious and modern 4-bedroom, 2-bathroom home offering 1,751 sq. ft. of comfortable living space. Built in 2019, this property features an......

429 Kensington View Dr
	429 Kensington View Dr Winter Haven, FL $2,049 Vacation Rentals, Unknown 15 DAYS OF CHEER-Live, Lease, and Celebrate Here! Sign by Dec. 15th and get $250 Off Move-In Fees. Limited-time holiday welcome offer! Discover spacious homes for rent at Kensington View in Winter......

834 Cinnamon Dr
	834 Cinnamon Dr Winter Haven, FL $1,985 Vacation Rentals, Unknown 3 Bedroom Pet-Friendly Home in WINTER HAVEN, FL with Main Street Renewal Welcome to your dream home! Step inside this pet-friendly home featuring modern finishings and a layout designed with......

3766 Fieldstone Cir
	3766 Fieldstone Cir Winter Haven, FL $2,075 Vacation Rentals, Unknown Please note, our homes are available on a first-come, first-serve basis and are not reserved until the holding fee agreement is signed and the holding fee is paid by the primary applicant. This......

2640 Pine Pl
	2640 Pine Pl Winter Haven, FL $1,695 Vacation Rentals, Unknown Welcome to 2640 Pine Pl, a stunning 3-bedroom, 2.5-bath retreat that perfectly blends modern style with serene waterfront living. Start your mornings with peaceful water views right from your......

2580 Pine Pl
	2580 Pine Pl Winter Haven, FL $1,695 Vacation Rentals, Unknown Experience the beauty of 2580 Pine Pl, a gorgeous 3-bedroom, 2.5-bath home offering effortless style and breathtaking waterfront tranquility. Enjoy stunning backyard water views that enhance......

1599 Lemon Ave
	1599 Lemon Ave Winter Haven, FL $2,249 Vacation Rentals, Unknown Coming soon - this home is currently being enjoyed by another resident but will be available soon. This home is professionally managed by Tricon, dedicated to creating exceptional rental......

26 The Village Blvd
	26 The Village Blvd Winter Haven, FL $2,605 Vacation Rentals, Unknown We make Pre-Leasing easy! Apply now and, once you're approved, take this home off the market by paying a Pre-Lease Hold Fee; ask your Leasing Professional for more information. Once the home is......

2880 Whispering Trails Dr
	2880 Whispering Trails Dr Winter Haven, FL $1,795 Vacation Rentals, Unknown Winter Haven, FL - House - $1,795.00 Available December 2025 APPLY TODAY FOR FREE!! Welcome home to a lovely 3 bedroom, 2 bathroom home with a 2 car garage, perfectly positioned in the vibrant......

4510 Rapallo Ave
	4510 Rapallo Ave Winter Haven, FL $2,295 Vacation Rentals, Unknown Minimum Deposit $2295. Monthly Rent $2295. Available NOW! *Showings are not confirmed until you speak directly with the Property Manager and a mutually agreed upon showing day/time has been......

2658 Pine Pl
	2658 Pine Pl Winter Haven, FL $1,795 Vacation Rentals, Unknown Discover the perfect combination of style, comfort, and relaxation at 2541 Pine Place in Winter Haven, FL. This beautifully designed 3-bedroom, 2.5-bath home sits in a tranquil community and offers......

1010 4th St SE
	1010 4th St SE Winter Haven, FL $1,400 Vacation Rentals, Unknown This bright and airy apartment offers ample room for you and your family. With three bedrooms and two bathrooms, there's plenty of space for everyone. The open floor plan and generous square......

4262 Roberta Dr
	4262 Roberta Dr Winter Haven, FL $1,849 Vacation Rentals, Unknown Coming soon - this home is currently being enjoyed by another resident but will be available soon. This home is professionally managed by Tricon, dedicated to creating exceptional rental......

2587 Pine Pl
	2587 Pine Pl Winter Haven, FL $1,695 Vacation Rentals, Unknown Discover 2587 Pine Pl, a gorgeous 3-bedroom, 2.5-bath home offering the perfect blend of comfort, style, and peaceful waterfront living. Wake up to serene water views right in your backyardan ideal......

2581 Pine Pl
	2581 Pine Pl Winter Haven, FL $1,695 Vacation Rentals, Unknown Experience the beauty of waterfront living at 2581 Pine Pl, a stunning 3-bedroom, 2.5-bath home that blends modern style with peaceful serenity. Wake up each day to calming water views from your......

2765 Sycamore St
	2765 Sycamore St Winter Haven, FL $1,595 Vacation Rentals, Unknown Discover this stunning 3-bedroom, 2.5-bath Winter Haven home that seamlessly blends style, comfort, and convenience. Step into a bright, open floor plan with a fresh contemporary kitchen, spacious......

2653 Pine Pl
	2653 Pine Pl Winter Haven, FL $1,725 Vacation Rentals, Unknown Welcome to 2653 Pine Pl, a charming and stylish 3-bedroom, 2.5-bath home offering the ideal blend of comfort, modern finishes, and calming water views. Enjoy peaceful mornings and relaxing evenings......

4510 Papallo Ave
	4510 Papallo Ave Winter Haven, FL $2,295 Vacation Rentals, Unknown Minimum Deposit $2295. Monthly Rent $2295. Available NOW! *Showings are not confirmed until you speak directly with the Property Manager and a mutually agreed upon showing day/time has been......

5776 Royal Hills Cir
	5776 Royal Hills Cir Winter Haven, FL $2,000 Vacation Rentals, Unknown Beautiful 3-bedroom, 2-bathroom house with a family room, granite countertops in the kitchen, master suite with jacuzzi, 2-car garage, enclosed patio with vinyl fencing, freshly painted, close to......

171 Kings Pond Ave
	171 Kings Pond Ave Winter Haven, FL (Contact seller for price) Vacation Rentals, Unknown Winter Haven, FL - House - $1,795.00 Available November 2025 APPLY TODAY FOR FREE!! Experience comfort, privacy, and convenience in Winter Haven! This charming 3-bedroom, 2-bathroom home offers a......

1761 Elbert Acres Ct NE
	1761 Elbert Acres Ct NE Winter Haven, FL (Contact seller for price) Vacation Rentals, Unknown Adoor does not advertise on Craigslist or Facebook Marketplace. Apply today and take advantage of flexible lease terms starting at just 9 months! Discover this inviting 3-bedroom, 2-bathroom......

208 Southern Breeze Loop
	208 Southern Breeze Loop Winter Haven, FL (Contact seller for price) Vacation Rentals, Unknown We make Pre-Leasing easy! Apply now and, once you're approved, take this home off the market by paying a Pre-Lease Hold Fee; ask your Leasing Professional for more information. Once the home is......

1349 Lucerne Loop Rd NE
	1349 Lucerne Loop Rd NE Winter Haven, FL (Contact seller for price) Vacation Rentals, Unknown LEASING SPECIAL Get 1/2 off your first full month's rent if you move in by 11/30/2025! MOVE IN READY! For more details and to apply, visit verticalre. com or give us a call to schedule a tour with......

3134 Whispering Trails St
	3134 Whispering Trails St Winter Haven, FL (Contact seller for price) Vacation Rentals, Unknown We make Pre-Leasing easy! Apply now and, once you're approved, take this home off the market by paying a Pre-Lease Hold Fee; ask your Leasing Professional for more information. Once the home is......

1900 Manor Cir SE
	1900 Manor Cir SE Winter Haven, FL (Contact seller for price) Vacation Rentals, Unknown Newly Remodeled 3BR/2BA Home + Bonus Room Winter Haven Beautifully updated home on a spacious 0.38-acre corner lot featuring 3 bedrooms, 2 baths, and a versatile bonus room perfect for an office or......

3319 Fox Ridge Dr
	3319 Fox Ridge Dr Winter Haven, FL (Contact seller for price) Vacation Rentals, Unknown Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare professional......