Here are Winter Haven listings for rentals and roommates -- find yourself a whole new living arrangement by choosing from apartments, homes for rent, and other rooms for rent.

1517 Wallace Manor Ave
	1517 Wallace Manor Ave Winter Haven, FL $1,850 Vacation Rentals, Unknown  NEW! APPLY TODAY FOR FREE!! This one has been upgraded to luxury vinyl flooring and fresh paint! Make an appointment today to come and see this beautiful 4 bedroom, 2 bath home in Winter Haven! Enjoy......

1005 Harold Pass
	1005 Harold Pass Winter Haven, FL $2,200 Vacation Rentals, Unknown # Better-than-new home with new upgrades and extra large backyard - easy access to schools, swimming pool and park # / Why This Home Is Better Than New / Unlike many of the newer builds in the......

609 Avenue G SE
	609 Avenue G SE Winter Haven, FL $1,399 Vacation Rentals, Unknown Welcome to your new home! This 2-bedroom, 1-bathroom unit offers approximately 875 sq ft of living space, designed for practical and efficient living. Step inside to a functional layout with......

329 Gretna Ln
	329 Gretna Ln Winter Haven, FL $1,795 Vacation Rentals, Unknown All Bridge Homes listings are pet-friendly and offer easy self-toursschedule yours today! This home comes with high-speed internet at an exclusive group rate. This service includes 24/7 premium......

606 Holt Cir
	606 Holt Cir Winter Haven, FL $1,700 Vacation Rentals, Unknown This 3 bedroom, 2 bathroom home brings a fun mix of comfort and flexibility, featuring a bonus room that's ready to become whatever you need next a home office, gaming room, craft space, or an......

548 Lake Dexter Blvd
	548 Lake Dexter Blvd Winter Haven, FL $1,578 Vacation Rentals, Unknown Home Description: This Adorable 3 bedroom 2 bathroom home in S.E. Winter Haven with a community swimming pool, playground, fishing dock and boat ramp that leads to Lake Dexter. This home features......

3365 Costello Cir
	3365 Costello Cir Winter Haven, FL $2,975 Vacation Rentals, Unknown New home builded in 2024, only 1 owner and occupied for a few months only, amazing lake on the back patio, 2 floors, 5 bed and 3 baths, attached garage, great family oriented community, with pool,......

147 Avenue E SW
	147 Avenue E SW Winter Haven, FL $997 Vacation Rentals, Unknown AWESOME CONTEMPORARY HOUSE WITH AN AMAZING KITCHEN WITH GRANITE COUNTERTOP, TILE IN ALL HOUSE, APPLIANCES INCLUDED, YOU GOT TO COME AND SEE IT TODAY For more properties like this visit Affordable......

1018 Sunshine Way SW
	1018 Sunshine Way SW Winter Haven, FL $1,485 Vacation Rentals, Unknown One or more photo(s) has been virtually staged. Check out this beautifully refreshed 2-bedroom, 2-bath rental home! This property features vaulted ceilings, a freshly painted interior, and tile......

1063 Michelangelo Ln
	1063 Michelangelo Ln Winter Haven, FL $2,150 Vacation Rentals, Unknown Immaculate home still feels like brand new construction! 4 bedroom 2 bath home in the Estates of Lake Florence. This home is ideally located in Winter Haven minutes from HWY 17, near I-4 and SR 60,......

422 22nd St SW
	422 22nd St SW Winter Haven, FL $1,600 Vacation Rentals, Unknown FOR RENT - 3 Bedroom/1 Bath Single Family Home - Very clean cement block home. The home comes with beautiful ceiling fans, nice light fixtures, a range, and a refrigerator. It also features two......

5320 Laurel Oak Dr
	5320 Laurel Oak Dr Winter Haven, FL $1,650 Vacation Rentals, Unknown This welcoming 3 bedroom, 2 bathroom home in the Winter Haven Oaks 55+ community blends comfort, convenience, and an upbeat, easygoing lifestyle. The layout offers three flexible bedrooms along......

1787 Lakehill Dr
	1787 Lakehill Dr Winter Haven, FL $4,500 Vacation Rentals, Unknown Beautiful 4-bedroom/3.5-bathroom home with additional bonus room ideal for an office, den, gym, or play room in the prestigious Woodpointe community of SE Winter Haven! Elegant custom and designer......

1993 Sarah St
	1993 Sarah St Winter Haven, FL $2,050 Vacation Rentals, Unknown Welcome to this spacious, modern 4-bedroom, 2-bathroom one-story home in the sought-after Peace Creek Reserve community! Perfectly positioned near Hwy 27, this prime location offers quick access to......

1030 Corso Dr
	1030 Corso Dr Winter Haven, FL $2,175 Vacation Rentals, Unknown This gorgeous 4-bedroom, 2.5-bathroom home located in Villamar, is loaded with space and comes with all new stainless appliances as well as a spacious two-car garage. The location doesn't get any......

3304 White Indigo
	3304 White Indigo Winter Haven, FL $1,750 Vacation Rentals, Unknown AVAILABLE: NOW Pets: OK 1 Small only (up to 35 lbs.) (Dangerous Pets are not permitted, Pit Bulls, etc.) EASY TO VIEW AT A CONVENIENT TIME SAVE MONEY ON THE APPLICATION FEES: We recommend that you......

330 Royal Palm Way
	330 Royal Palm Way Winter Haven, FL $2,400 Vacation Rentals, Unknown Be one of the first to move into these recently built, energy-efficient homes, LOADED with the best finishes. If you have pets, not only do we allow them, but we have homes available that include a......

611 Avenue G SE
	611 Avenue G SE Winter Haven, FL $1,399 Vacation Rentals, Unknown Step into your new home! This 2-bedroom, 1-bathroom unit offers approximately 875 sq ft of well-utilized living space, with a layout that balances functionality and comfort for everyday living. The......

578 Squires Grove Dr
	578 Squires Grove Dr Winter Haven, FL $1,895 Vacation Rentals, Unknown APPLY TODAY FOR FREE! Built in 2020 this 3 bedroom, 2 bath is located in Winter Haven. Beautifully appointed with a 2 car garage, stainless steel appliances, ceramic tile flooring, smart home......

1816 Galloway Ter
	1816 Galloway Ter Winter Haven, FL $2,300 Vacation Rentals, Unknown This home offers 4 spacious bedrooms and 2 baths. The Master Bath is equipped with double vanity sinks and has been upgraded with a spacious 5ft shower! The home offers high ceilings with an open......

331 Columbo St
	331 Columbo St Winter Haven, FL $2,295 Vacation Rentals, Unknown We are currently making final preparations for this home to be available. We make Pre-Leasing easy! Apply now and, once you're approved, take this home off the market by paying a Pre-Lease Hold......

632 Vittorio Dr
	632 Vittorio Dr Winter Haven, FL $2,095 Vacation Rentals, Unknown This gorgeous 4-bedroom, 2-bathroom home is loaded with space and comes with all stainless appliances as well as a spacious two-car garage. The location doesn't get any better than this as its......

187 Emanuelle Dr
	187 Emanuelle Dr Winter Haven, FL $2,000 Vacation Rentals, Unknown The property will be ready for renting on June 1 2026 This amazing 3-bedroom, 2-bathroom property is just minutes from LEGOLAND and Cypress Gardens Blvd, filled with restaurants and supermarkets.......

2115 Kings Xing SW
	2115 Kings Xing SW Winter Haven, FL $1,000 Vacation Rentals, Unknown Property is located within a quiet community Close to all shopping (with a Publix 2 miles away) Shared office with 2 computers Close to State Road 540...

106 Jace Way
	106 Jace Way Winter Haven, FL $1,999 Vacation Rentals, Unknown Step inside to a bright and open floor plan featuring plenty of natural light. Perfect for relaxing or entertaining. The kitchen is the centerpiece of the home, complete with: -Stainless steel......

5608 Lake Fox Cir
	5608 Lake Fox Cir Winter Haven, FL $2,400 Vacation Rentals, Unknown This 3-bedroom, 2-bathroom home spans a generous 1490 square feet, offering ample space for relaxation and entertainment. The open floor plan invites natural light through the living areas. The......

2721 Whispering Trails Dr
	2721 Whispering Trails Dr Winter Haven, FL $1,800 Vacation Rentals, Unknown ForRent BY OWNER To View call (8 63- 412- 9 319) Beautiful 2 Story House. 4 Bedrooms, 3 Baths, 2150 sq. ft. of Living area. Soaring Ceilings in The Great Room with an Overlooking Loft. Large Eat in......

669 Reggie Rd
	669 Reggie Rd Winter Haven, FL $2,100 Vacation Rentals, Unknown Spacious 4-bedroom home for rent in Winter Haven, FL, located in the highly desirable Peace Creek Reserve community! This beautifully and well-maintained home offering 2.5 bathrooms and 1,933 sq ft......

3050 Laurel Oak Ln
	3050 Laurel Oak Ln Winter Haven, FL $2,095 Vacation Rentals, Unknown This gorgeous 4-bedroom, 2-bathroom home is loaded with space and comes with stainless appliances as well as a spacious two-car garage. The location doesn't get any better than this as its walking......

803 26th St NW
	803 26th St NW Winter Haven, FL $1,700 Vacation Rentals, Unknown This charming 3-bedroom, 2-bathroom home 4 minutes driving from lake, offers 974 square feet of comfortable living space perfect for families with 2 to 3 kids or anyone looking for a cozy yet......