Discover a selection of 1,000 vacation rentals in Winter Haven, FL that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $88 per night, and houses and villas are popular options for a stay in Winter Haven. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Winter Haven
Destination guide

Wonderful times in Winter Haven

Let Winter Haven vacation rentals welcome you to this year-round destination. Let your imagination run wild in LEGOLAND Florida Resort or go wild in the water in one of Winter Haven’s 50 lakes. Catch the community theater bug by taking in a show at the Theatre Winter Haven. If you’re really looking for some retail therapy, step back in time and explore the many antiques stores that call Winter Haven home. However you want to spend your vacation, Winter Haven is sure to have something to satisfy everyone.

Things to do

Theme park and theater thrills in Winter Haven

Adults and children alike will love LEGOLAND Florida Resort! This 150-acre theme park is dedicated to family-friendly fun and will delight children of all ages. Make a splash in the adjoining water park for an additional fee, and cool off in the Floridian sun. After a day of fun in the sun, returning to the Winter Haven vacation rentals will always be welcome; but how about an evening at the theater? Theatre Winter Haven is locally renowned for its top-quality community theater. The program will, of course, depend on when you visit, but you’re guaranteed a great evening.


Wild water and amazing antiques in Winter Haven

Winter Haven is also known as “The Chain of Lakes City” and for good reason. After getting settled in Winter Haven vacation rentals, break out your bathing suit and head for one of the city’s 50 lakes! Flyboarding is one of the area’s popular water pursuits and you can book a lesson with companies operating from different lakes. Want something a bit more sedate on the water? Charter a boat and spend an afternoon bobbing on the waves while bass fishing. On land, eagle-eyed antiques enthusiasts will love browsing for souvenirs and gifts in the many antiques stores here.


It’s not called Winter Haven for nothing!

If you’re looking for year-round sunshine and warm temperatures, Winter Haven is the perfect place for you. July through August see average highs in the low 90s but also a lot of rain owing to the humid, subtropical Floridian climate. For those looking to avoid the rain, come to Winter Haven from October through May as these are by far the driest months. Winters see average highs in the high 40s so you can expect to get your fill of this town’s average 242 days of sunshine.

Natural features

Love the lakes in Winter Haven

Located between Tampa and Orlando within the Central Florida Highlands, Winter Haven is not your typical Floridian beach-side community. You’ll see flatland with rolling hills all around you, as well as the lakes this city is so famous for. The lakes are full of wildlife, and nature lovers may be able to spot bald eagles and alligators as well as the bass. To get a real sense of the natural world, sit back and relax on a guided river tour and learn all about the birds and creatures that call Winter Haven home.

How to get there

Transportation to and around Winter Haven

Fly into Tampa Intl. Airport (TPA), the closest airport, located 49 mi (78.9 km) from the city center. If you're unable to find a flight that fits your schedule, you could book a flight to Tampa, FL (TPF-Peter O. Knight), which is 44.4 mi (71.5 km) away.

If you're traveling by train, the main station serving the city is Winter Haven Station.

What are the top vacation rentals in or near Winter Haven?

Whether you're searching for a cozy escape for you and your sweetie or someplace roomy to fit the family, you'll find some top vacation rentals in and around Winter Haven. Here are a couple to start you off:

  • "Luxury Villa 5 Bedroom 4 Bath Full Sun Private Pool And Spa" is a guest favorite. Around 19 miles from Winter Haven, it has 5 bedrooms and lots of useful amenities, including a separate dining area and games.
  • Alternatively, make a booking at "Gorgeous - Gated - Spacious Modern". Located around 20 miles from the heart of Winter Haven, it has 4 bedrooms and features free toiletries and a theme park.

For even more great options, use the search bar at the top of the page to find the perfect Winter Haven vacation rental for you.

What are the best tiny house vacation rentals in or near Winter Haven?

For a different kind of experience, book one of Vrbo's tiny house rentals in Winter Haven. Do be warned though — after you've experienced the tiny house lifestyle, the urge to move into one of these mini digs will be hard to resist!

  • Take a few days off to recharge your batteries at "Close To Everything In Law Suite And Tiny House". Located in Lake Wales, a dishwasher and free toiletries are included here.
  • "Lovely And Cozy Tiny House" comes with plenty of conveniences, such as WiFi and a TV. Located in Lakeland, you'll be able to live large in this small but nicely designed abode.

What are the top-rated vacation rentals for weekend getaways in or near Winter Haven?

Get away from the rat race at one of our weekend getaways in or near Winter Haven. Whether you'd like to hang out with friends or spend quality time with the family, there'll be something to suit your style. These top-rated options are hard to beat:

  • Get comfortable at "15 Min To Disney World. Top Rated Clean Home In A Prime Location Pool". Located about 20 miles to the north of Winter Haven, this cozy escape has everything you need for a relaxing stay, including a private pool and an iron and ironing board.
  • Otherwise, make new memories with loved ones at "Luxury 5 - Bed Golf Course Villa With Private Pool And Spa And Games Room", which is around 20 miles to the north of Winter Haven. You'll have use of shopping, a water park and more here.

Can I find studio apartments for rent in and around Winter Haven?

You certainly can. If you're looking for a small but stylish stay, you can't go wrong with a studio apartment. These compact properties exude charm and are often conveniently placed in the center of town. We suggest the following options in or near Winter Haven:

  • One of our top picks is "Serenity Retreat, Confidently Clean". Lock in a few nights at this popular apartment and you'll have access to free WiFi and a hair dryer.
  • Alternatively, use "View Container 5centrally Locatedprivate Bed" as a base to explore the sights around you. This comfy stay comes with heating, air conditioning and more.

Can I find short term rentals in or near Winter Haven?

Whether you're looking for a compact apartment or a house to fit the entire family, you'll find the perfect place on Vrbo. Treat yourself to a mini break at one of these getaways in or near Winter Haven:

  • Within close reach of central Winter Haven, "3250 Sqft 5br/4ba Luxury Family Home" welcomes short-term guests. When you're not chilling out in your comfortable digs, get out and explore what's around you.
  • Alternatively, spend a couple of relaxing nights at "Regal Palms - Lazy River - Water Slide". This centrally located property makes exploring the sights easy.

What are the best romantic weekend getaways in or near Winter Haven?

Whether spent in a rustic cabin or a luxury condo, a romantic weekend getaway is a perfect way to spice up your love life. Whisk your partner away for a couple of days at one of these sought-after escapes in or near Winter Haven:

  • Sneak away on Friday afternoon for a few passionate nights at "Luxury Villa 5 Bedroom 4 Bath Full Sun Private Pool And Spa". Located roughly 19 miles from Winter Haven, this property comes with plenty of nice touches, including air conditioning and outdoor furniture.
  • Another place where you can enjoy a few magical days together is "Gorgeous - Gated - Spacious Modern". Located 20 miles from Winter Haven, beauty services and winery tours add to the ambiance here.

Are there mansions for rent in or near Winter Haven?

Nothing screams "best vacation evvv-er" like staying in a mansion. Treat your loved ones to a memorable getaway at one of these mansions for rent in and around Winter Haven:

  • Approximately 16 miles to the northeast of Winter Haven is "Fashionable Mansion With Karaoke Studio At Solterra". As well as its awe-inspiring design, you'll be impressed by its first-class amenities, such as a swimming pool and beauty services.
  • With a swimming pool, concierge services and a host of other high-end amenities, "Mythical Mansion | Villa Out Of A Storybook: Treehouse Playrm" will get your team's tick of approval. This opulent home is roughly 16 miles to the northeast of Winter Haven.

What are the best large group vacation rentals in or near Winter Haven?

Big groups mean gigantic fun. They also mean finding someplace that'll easily fit your whole squad. Check out our large group vacation rentals in or around Winter Haven and get everybody together under the one roof:

  • Providing privacy, space and comfort, you'll get everyone's seal of approval at "South Del Rio Cozy Home". Up to 12 people can be accommodated at this escape which has 5 bedrooms, a swimming pool and a kitchen. You'll discover it around 20 miles to the north of Winter Haven.
  • Nothing's more important than being with the people you love, and "Luxurious 5 Bed/5 Bath 3500sf Villa With Private Pool In Highlands Reserve" is the ideal place to do that. Located around 20 miles to the north of Winter Haven, as many as 12 guests can stay in this vacation rental which has 5 bedrooms. A water park and a swimming pool are among the many amenities on offer here.

What are the best houses for rent with a pool in or near Winter Haven?

A pool is often a nonnegotiable when choosing where to spend your vacation, particularly if you're getting away with the kids. Browse these houses with a pool in or near Winter Haven and fill your days with frolicking good fun:

  • Round up your gang and enjoy an unforgettable break at "94 Per Nt Special: Minutes To Disney. Pool House On Golf Course W". There's plenty to love about this retreat apart from its pool, such as a video library and a dining table.
  • Spend laid-back days swimming or just kicking back by the water at "Farm House Stay 5 Miles To Legoland". This property is also a firm favorite and features on-site watersports, childrens activities and more.

Wondering what the weather's like in Winter Haven? It has a humid subtropical climate, with average summertime temperatures ranging from 75 ºF to 90 ºF. If you're chasing a little more inspiration on where to stay in this impressive destination, use the search bar at the top of the page and adjust the filters to check out our entire range of Winter Haven vacation rentals.

What are the best large family vacation rentals in or near Winter Haven?

Whether your idea of the perfect escape is high in the hills or near the beach, you'll have so much more fun if you share it with loved ones. Choose one of these large family vacation rentals in or near Winter Haven and bring the whole gang along:

  • Sleeping as many as 10 guests in 5 bedrooms, "Luxury Villa 5 Bedroom 4 Bath Full Sun Private Pool And Spa" is the ideal place to enjoy some family time. This getaway is 19 miles to the north of Winter Haven and has creature comforts such as a kitchen and a fenced pool.
  • Another popular option is "Gorgeous - Gated - Spacious Modern". This property is 20 miles north of Winter Haven and comes with a kitchen, towels and more. With 4 bedrooms accommodating up to 10 people, there's no need to leave anyone off your guest list.

If you're hoping to visit some family-friendly attractions in the area, you have plenty of choice. LEGOLAND® Florida, Northeast Regional Park and Wing Chun Kung Fu Downtown Lakeland promise lots of fun for young and old.