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Vacation Rentals in Winter Haven, Florida

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about Winter Haven

Winter Haven, Florida Vacation Rentals and Tourism

While Florida beaches preoccupy most tourists, the state’s many lakes ensure just as much summer fun! For a lakeside getaway with a distinctly Florida vibe, check out Winter haven vacation rentals. A Winter Haven, Florida vacation can be defined by many things, but you’ll probably spend some time by the water. There’s no escaping the lakes near your Winter Haven rental – you’ll be vacationing to a decidedly water-based community.

There’s a lot more than just lake recreation to keep you entertained in your Winter Haven vacation rental however. Cypress Gardens Adventure Park, the Fantasy of Flight vintage aircraft museum, and the Bok Sanctuary are some reasons that Winter Haven vacation rentals have such a strong draw. The restaurants in and around Winter Haven lodging are quite the treat as well, whether you’re looking for casual or gourmet dining.

It certainly can’t hurt to take a look at the Winter Haven vacation homes listed here. And once you stay in one, you’ll quickly learn why so many people are proud to call Winter Haven condos, homes, and cabins their permanent homes.

Winter Haven Vacation Rental Deals

If you are planning a trip to Winter Haven, don’t let your budget get in the way of staying in a nice, roomy place—stay in a cheap Winter Haven rental home. Choose from a wide variety of money saving Winter Haven houses, spacious and luxurious villas, and sizable – but reasonably priced – town homes. Because we accommodate the size of any budget as well as the size of any group, we're positive that you'll find a low-cost Winter Haven vacation rental perfect for your next vacation. Just be sure you get a chance to enjoy a fun day away from your Winter Haven lodging.

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Check out more areas which feature homes, villas, cabins, cottages, or condos.

Winter Haven things to do

 

River Ventures

I was visiting family in Tampa and seeing a manatee was on my bucket list for the trip. My aunt found River Ventures and we took the 9:15am tour on a Sunday...read more

 

Legoland Florida

We have a 4 year old who loves Legos, and a 40 something dad that does too. After looking at a number of theme parks online, we narrowed our choices down to...read more

 

Grape Expectations

Two for ones until 7pm on weekdays. Friendly bartenders. A bit of an older crowd but I actually prefer that most of the time. I'll be back.read more

 

Theatre Winter Haven

As someone that has seen several shows here, as well as performed in 3 myself...I can say without a doubt that Theatre Winter Haven is one of the best...read more

 

Circle B Bar Reserve

I've been coming here for numerous years now, but never left my review. This place has grown into a very popular outdoor park with new activities,...read more

 

Legoland Water Park

I loved this place, and more importantly my daughter did too. It's not very big, but there is enough to keep one there for hours, as we learned firsthand....read more

 

Jerney's Hookah Venue & Bar

Overall this is one of the better hookah bars I've ever been to. It has a very classy look; and when I mean classy, I mean it's pretty nice for a hookah...read more

 

Orlando Balloon Rides

This was a great experience! My wife and I loved every minute of it. The staff were super cool and playful. They asked us to help load and unload the bag...read more

 

Southern Dunes Golf Country Club

Great course, a little pricey! $109 on a Wednesday? The greens are in great shape and will challenge your putting. The greens are verrrrry fast and have a...read more

 

Legoland

Had a great time with my friends and their kids. This place is best for kids 5 or 6 years old up until 12. My friends had a 2 and a half year old and he...read more

 

Wright Step School of Dance the

The Wright Step is a great dance school - if your little one is hoping to go into dance professionally or is extremely passionate about dance. The...read more

 

Safe Aim Firearms Training

Classroom & Range time gets you certificate for concealed weapons permit. NRA licensed instructors are very knowledgeable but yet manage to take technical...read more

 

Habitat Health and Fitness

Excellent group workout atmosphere. The trainers are knowledgable, the people are friendly, and sessions accommodate every level of fitness. No need to...read more

 

Florida Cypress Gardens

Cypress Gardens is wonderful. Worth visiting. Now part of Legoland which is awesome.read more

 

Genesis Zoology Ctr

I am going to assume that everything they are saying is the truth, and that this place is rescuing animals and releasing them/rehoming them and only keeping...read more

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DEAL!! Lakehouse Vacation Home in Winter Haven Florida
Winter Haven House Rental Picture
  • House Rental Deals and Discounts free night valued at USD $150
  • bedrooms 3
  • community Lake Daisy Estates
  • rental type House
  • owner badgeowner badge
  • sleeps 10
  • baths
  • rates (USD) $125 - $175 /nt
    $900 - $1,225 /wk
    $2,300 - $2,500 /mth
 
 
 
 
 

16 reviews write a review

Lake Ashton Community
Winter Haven Condo Rental Picture
  • bedrooms 2
  • community Lake Ashton
  • rental type Condo
  • sleeps 4
  • baths 2
  • rates (USD) $2,400 /mth
 
 
 
 
 

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1 bedroom vacation rental
Winter Haven Apartment Rental Picture
  • bedrooms 1
  • community
  • rental type Apartment
  • sleeps 2
  • baths 1
  • rates (USD) $305 - $315 /wk
    $1,065 - $1,075 /mth
 
 
 
 
 

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Huge Winter Haven Orlando Area On Lake!
Winter Haven Condo Rental Picture
  • bedrooms 2
  • community
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $1,399 - $2,399 /mth
 
 
 
 
 

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Beautiful Pool Home on Ski Lake
Winter Haven House Rental Picture
  • bedrooms 4
  • community
  • rental type House
  • owner badgeowner badge
  • sleeps 12
  • baths 4
  • rates (USD) $1,200 - $1,600 /wk
 
 
 
 
 

24 reviews write a review

Lake Guest House
Winter Haven House Rental Picture
  • bedrooms 1
  • community
  • rental type House
  • sleeps 2
  • baths 1
  • rates (USD) $350 - $500 /wk
    $900 - $1,200 /mth
 
 
 
 
 

2 reviews write a review

4070 Lake Marianna Dr lakefront
Winter Haven House Rental Picture
  • bedrooms 3
  • community Auburndale
  • rental type House
  • owner badgeowner badge
  • sleeps 5
  • baths 3
  • rates (USD) $1,000 /wk
    $3,000 /mth
 
 
 
 
 

2 reviews write a review

Stay in Fabulous Lake Ashton Gated Adult Community
Winter Haven House Rental Picture
  • bedrooms 3
  • community Lake Ashton
  • rental type House
  • sleeps 4
  • baths 2
  • rates (USD) $1,500 - $2,500 /mth
 
 
 
 
 

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Lake Howard Waterfront Lake House Winter Haven Fl
Winter Haven House Rental Picture
  • bedrooms 2
  • community
  • rental type House
  • sleeps 4
  • baths
  • rates (USD) $600 - $900 /wk
    $1,000 - $2,000 /mth
 
 
 
 
 

1 reviews write a review

Winter Haven Lake Lulu Orlando Area Condo
Winter Haven Condo Rental Picture
  • bedrooms 1
  • community Park Lake
  • rental type Condo
  • sleeps 3
  • baths 1
  • rates (USD) $1,199 - $1,899 /mth
 
 
 
 
 

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Relax In Winter Haven Orlando Screened Porch!
Winter Haven Condo Rental Picture
  • bedrooms 1
  • community Park Lake
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $1,199 - $1,899 /mth
 
 
 
 
 

2 reviews write a review

Private, tropical getaway near Legoland & Disney
Winter Haven Apartment Rental Picture
  • bedrooms 1
  • community Winter Haven
  • rental type Apartment
  • sleeps 2
  • baths 1
  • rates (USD) $400 /wk
    $1,250 /mth
 
 
 
 
 

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Beautiful Lake Ashton Golf Club - 3 BR 2 Bath Villa
Winter Haven House Rental Picture
  • bedrooms 3
  • community Lake Ashton
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $2,400 - $3,000 /mth
 
 
 
 
 

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Lake Rochelle Rental (Lakefront)
Winter Haven House Rental Picture
  • bedrooms 3
  • community Rochelle Gardens
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD) $2,200 /mth
 
 
 
 
 

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Affordable Winter Haven Orlando Area
Winter Haven Condo Rental Picture
  • bedrooms 1
  • community Park Lake
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $1,199 - $1,899 /mth
 
 
 
 
 

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Relaxation In WInter Haven Orlando Area
Winter Haven Condo Rental Picture
  • bedrooms 1
  • community Park Lake
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $1,199 - $1,899 /mth
 
 
 
 
 

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Winter Haven/Central FL/Winterset
Winter Haven Condo Rental Picture
  • bedrooms 2
  • community Garden Villas
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $1,295 - $2,195 /mth
 
 
 
 
 

6 reviews write a review

Moon's Fish Camp
Winter Haven House Rental Picture
  • bedrooms 2
  • community
  • rental type House
  • sleeps 4
  • baths 2
  • rates (USD) $150 - $200 /nt
    $700 - $900 /wk
    $2,600 - $3,000 /mth
 
 
 
 
 

1 reviews write a review

Winter Haven Apartment Rental
Winter Haven Apartment Rental Picture
  • bedrooms 3
  • community
  • rental type Apartment
  • sleeps 8
  • baths 2
  • rates (USD) $520 - $530 /wk
    $1,550 - $1,560 /mth
 
 
 
 
 

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Winter Haven Two Bedroom Rental
Winter Haven Apartment Rental Picture
  • bedrooms 2
  • community
  • rental type Apartment
  • sleeps 4
  • baths 1
  • rates (USD) $385 - $395 /wk
    $1,350 - $1,360 /mth
 
 
 
 
 

1 reviews write a review

New Listing! Immaculate 4BR Winter Haven Home in a Gated Community, Ideally Located Close to Lego Land & Disney! - Handicap Accessible
Winter Haven House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 8
  • baths 3
  • rates (USD) $110 - $150 /nt
    $750 - $1,000 /wk
    $3,300 - $4,500 /mth
 
 
 
 
 

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10 minutes to lego land 45 minutes to hard rock casino
Winter Haven Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD) $200 - $250 /nt
    $1,000 /wk
    $3,000 /mth
 
 
 
 
 

3 reviews write a review

**LAST MINUTE AUGUST MID WEEK SPECIAL**FANTASTIC CONDO NEAR LEGOLAND
Winter Haven Townhome Rental Picture
  • bedrooms 2
  • rental type Townhome
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $115 /nt
 
 
 
 
 

26 reviews write a review

Chain Of Lakes Pool Home With Beach And Boat House
Winter Haven House Rental Picture
  • bedrooms 5
  • rental type House
  • owner badgeowner badge
  • sleeps 18
  • baths 5
  • rates (USD) $250 - $500 /nt
    $1,750 - $2,300 /wk
    $6,600 - $9,000 /mth
 
 
 
 
 

13 reviews write a review

Affordable Winter Get Away. Apartment. Clean & Comfy & Quiet
Winter Haven Apartment Rental Picture
  • bedrooms 2
  • rental type Apartment
  • sleeps 4
  • baths
  • rates (USD) $887 /mth
 
 
 
 
 

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