Vacation Rentals in Winter Haven, FL
· House in Winter Haven
Awesome Lake House With Private Dock, Canoe, Kayaks, Game-Room, & Lots To Do!!!
3 Beds · 2 baths · Sleeps 11 ·
Hardwood Floor · Workspace · Fireplace ·
From
$198/nightAmenities
Hardwood Floor
Fireplace
Lake
Waterfront
Oven
Dishwasher
In Unit Laundry
Air Conditioning
Other spaces
Workspace, Kitchen
· House in Winter Haven
10% Off Thru 2/28~Lake Silver V~Gorgeous Sunset~Boat Dock~Pristine Lake Water & Close to LegoLand!
3 Beds · 2 baths · Sleeps 7 ·
Workspace · Outdoor Space · Lake ·
From
$256/nightAmenities
Lake
Waterfront
Dishwasher
In Unit Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Workspace, Kitchen
· House in Haven Shores
NEW! Elegant Winter Haven Villa w/ Dock & Lanai!
4 Beds · 5 baths · Sleeps 8 ·
Garden · Walk In Closets · Cable ·
From
$370/nightAmenities
Walk In Closets
Cable
Toiletries
Tv
Microwave
Beach
Central Heat
Assigned Parking
Other spaces
Garden, Balcony, Kitchen
· House in Winter Haven
NEW! Winter Haven Abode Near Lakes & Attractions
2 Beds · 2 baths · Sleeps 7 ·
Toiletries · Walk In Closets · Tv ·
From
$70/nightAmenities
Toiletries
Walk In Closets
Tv
Microwave
Ceiling Fan
Central Heat
Free Parking
Fireplace
Other spaces
Kitchen
· Apartment in Winter Haven
Lake Silver V - Lake House with Dock - Legoland Getaway!
Studio · 3 baths · Sleeps 11 ·
Dishwasher · Air Conditioning · Kitchen ·
From
$378/nightAmenities
Dishwasher
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen
· Apartment in Winter Haven
Lake Silver Retreat lll
Studio · 2 baths · Sleeps 7 ·
Dishwasher · Air Conditioning · Kitchen ·
From
$313/nightAmenities
Dishwasher
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen
· Apartment in Winter Haven
Spacious 4-bedroom 2-bath Abode Close to All
4 Beds · 2 baths · Sleeps 8 ·
On Site Laundry · Assigned Parking · Free Parking ·
From
$371/nightAmenities
On Site Laundry
Assigned Parking
Free Parking
Fireplace
Oven
Dishwasher
In Unit Laundry
Air Conditioning
Other spaces
Workspace, Kitchen
· Apartment in Winter Haven
Winter Haven Abode Near Lakes and Attractions
2 Beds · 2 baths · Sleeps 7 ·
Free Parking · Fireplace · Oven ·
From
$336/nightAmenities
Free Parking
Fireplace
Oven
In Unit Laundry
Furnished
Wifi
Other spaces
Kitchen
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· Apartment in Winter Haven
Lovely Lakefront Home with Grill 7 Mi to Legoland!
3 Beds · 3 baths · Sleeps 8 ·
Free Parking · Fireplace · Outdoor Space ·
From
$277/nightAmenities
Free Parking
Fireplace
Lake
Waterfront
Oven
Dishwasher
In Unit Laundry
Furnished
Other spaces
Kitchen
· Apartment in Winter Haven
Lake Hamilton III Pool and Backyard Oasis with Kayaks Lake Access Theater
Studio · 3 baths · Sleeps 6 ·
Private Pool · Pool · Dishwasher ·
From
$389/nightAmenities
Private Pool
Pool
Dishwasher
Air Conditioning
Furnished
Wifi
Swimming Pool
Other spaces
Kitchen
· Apartment in Haven Shores
Elegant Winter Haven Villa with Dock and Lanai!
4 Beds · 5 baths · Sleeps 8 ·
Beach · Balcony · Free Parking ·
From
$785/nightAmenities
Beach
Free Parking
Fireplace
Pool
Lake
Waterfront
Oven
Dishwasher
Other spaces
Balcony, Kitchen
· Apartment in Winter Haven
625 Avenue M SE
3 Beds · 2 baths · Sleeps 9 ·
On Site Laundry · Assigned Parking · Free Parking ·
From
$84/nightAmenities
On Site Laundry
Assigned Parking
Free Parking
Air Conditioning
Furnished
Wifi
· House in Winter Haven
Private/Spacious 1BR Central Near LegoLand 2 Miles
1 Bed · 1 bath · Sleeps 5 ·
Air Conditioning · Furnished · Wifi ·
From
$130/nightAmenities
Air Conditioning
Furnished
Wifi
Business Center
· House in Winter Haven
Waterfront Winter Haven Home with Dock & Hot Tub!
4 Beds · 3 baths · Sleeps 12 ·
Garden · Cable · Tv ·
From
$250/nightAmenities
Cable
Tv
Microwave
Ceiling Fan
Central Heat
Free Parking
Fireplace
Pool
Other spaces
Garden, Kitchen
· House in Winter Haven
Everything is Awesome at this Lego Themed Pool House 4/2, 1 Mile From Legoland
4 Beds · 2 baths · Sleeps 10 ·
Private Pool · Pool · Oven ·
From
$220/nightAmenities
Private Pool
Pool
Oven
Dishwasher
In Unit Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen
· House in Winter Haven
Lovely Lakefront Home w/ Grill: 7 Mi to Legoland!
3 Beds · 3 baths · Sleeps 8 ·
Toiletries · Garden · Cable ·
From
$175/nightAmenities
Toiletries
Cable
Tv
Microwave
Ceiling Fan
Central Heat
Assigned Parking
Free Parking
Other spaces
Garden, Kitchen
· House in Winter Haven
Cozy home near Cypress Garden and Legoland
3 Beds · 2 baths · Sleeps 6 ·
Dishwasher · Air Conditioning · Kitchen ·
From
$125/nightAmenities
Dishwasher
Air Conditioning
Furnished
Wifi
Garage Parking
Other spaces
Kitchen
· House in Winter Haven
cozy for the family close to Legoland
2 Beds · 1 bath · Sleeps 5 ·
Air Conditioning · Kitchen · Furnished ·
From
$95/nightAmenities
Air Conditioning
Furnished
Other spaces
Kitchen
· House in Winter Haven
Waterfront Winter Haven Home with Dock & Hot Tub!
4 Beds · 3 baths · Sleeps 12 ·
Hot Tub · Central Heat · Private Pool ·
From
$413/nightAmenities
Hot Tub
Central Heat
Private Pool
Fireplace
Pool
Lake
Waterfront
Oven
Other spaces
Kitchen
· House in Tranquility Park
Charming Town House — 10 Minutes from the Legoland Park and Downtown.
2 Beds · 2 baths · Sleeps 6 ·
Balcony · Outdoor Space · Oven ·
From
$127/nightAmenities
Oven
In Unit Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Balcony, Kitchen
· Apartment in Winter Haven
Nice studio walking distance from lake and 10 minutes to Legoland attractions
1 Bed · 1 bath · Sleeps 2 ·
In Unit Laundry · Air Conditioning · Kitchen ·
From
$64/nightAmenities
In Unit Laundry
Air Conditioning
Furnished
Wifi
Business Center
Other spaces
Kitchen
· Apartment in Winter Haven
Modern spacious 2-bedroom Apartment 1 mile from Legoland
2 Beds · 1 bath · Sleeps 5 ·
Ev Charging · Oven · Dishwasher ·
From
$140/nightAmenities
Ev Charging
Oven
Dishwasher
In Unit Laundry
Air Conditioning
Furnished
Wifi
Fitness Center
Other spaces
Kitchen
· Apartment in Winter Haven
Modern HouseBoat*AceLoca*4Miles*LegoLand*
1 Bed · 1 bath · Sleeps 3 ·
Lake · Waterfront · Oven ·
From
$90/nightAmenities
Lake
Waterfront
Oven
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen
· Apartment in Haven Shores
Elegant Winter Haven Villa w/ Dock & Lanai!
4 Beds · 5 baths · Sleeps 8 ·
Walk In Closets · Beach · Balcony ·
From
$459/nightAmenities
Walk In Closets
Beach
Private Pool
On Site Laundry
Fireplace
Pool
Lake
Waterfront
Other spaces
Balcony, Kitchen
· House in Winter Haven
LAKE HOUSE WITH PRIVATE FREE HEATED POOL & GAME ROOM 4 min FROM LEGOLAND
4 Beds · 3 baths · Sleeps 12 ·
Smoking Allowed · Fitness Center · Private Pool ·
From
$300/nightAmenities
Smoking Allowed
Fitness Center
Private Pool
Pool
Lake
Waterfront
Oven
Dishwasher
Other spaces
Kitchen
· House in Winter Haven
Luxury Home w/ Lanai, Billiards, 6min to Legoland
6 Beds · 3 baths · Sleeps 12 ·
High Ceilings · Ceiling Fan · Oven ·
From
$464/nightAmenities
High Ceilings
Ceiling Fan
Oven
Dishwasher
In Unit Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen
· House in Winter Haven
💎Only 1 mile from Legoland🎢 💎Modern spacious apt with Full kitchen 🙂
1 Bed · 1 bath · Sleeps 4 ·
Workspace · Lake · Waterfront ·
From
$95/nightAmenities
Lake
Waterfront
In Unit Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Workspace, Kitchen
· House in Winter Haven
10% Off Thru 2/28~Family Fun Times~Pet Friendly~Foosball~Ping Pong~45 minutes to Disney
3 Beds · 1 bath · Sleeps 9 ·
On Site Laundry · Assigned Parking · Fireplace ·
From
$154/nightAmenities
On Site Laundry
Assigned Parking
Fireplace
Lake
Waterfront
Dishwasher
In Unit Laundry
Air Conditioning
Other spaces
Kitchen
· House in Winter Haven
★Spacious 4-bedroom 2-bath Abode Close to All★
4 Beds · 2 baths · Sleeps 10 ·
Workspace · Oven · Dishwasher ·
From
$297/nightAmenities
Oven
Dishwasher
In Unit Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Workspace, Kitchen
· Apartment in Winter Haven
Cute & Cozy 1 bedroom guesthouse located in Winter Haven FL
1 Bed · 1 bath · Sleeps 2 ·
Workspace · Outdoor Space · In Unit Laundry ·
From
$80/nightAmenities
In Unit Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Workspace, Kitchen
· House in Winter Haven
Charming Lakefront Pool Home - 5 Min to Legoland!
4 Beds · 3 baths · Sleeps 7 ·
Private Pool · Pool · Dishwasher ·
From
$211/nightAmenities
Private Pool
Pool
Dishwasher
In Unit Laundry
Air Conditioning
Furnished
Wifi
Swimming Pool
Other spaces
Kitchen
· Apartment in Winter Haven
*Modern Tiny Lake Cottage*AceLoc*4miles*LEGOLAND*
2 Beds · 1 bath · Sleeps 3 ·
Lake · Waterfront · Oven ·
From
$95/nightAmenities
Lake
Waterfront
Oven
Dishwasher
Air Conditioning
Furnished
Wifi
Business Center
Other spaces
Kitchen
· Hotel in Winter Haven
Hampton Inn Winter Haven
1 Bed · Sleeps 5 ·
Coffee Tea Maker · Heated Indoor Pool · Smoking Allowed ·
From
$93/nightAmenities
Coffee Tea Maker
Heated Indoor Pool
Smoking Allowed
Carpet
On Site Laundry
Assigned Parking
Free Parking
Pool
Other spaces
Workspace
· Hotel in Winter Haven
Holiday Inn Winter Haven, an IHG Hotel
1 Bed · Sleeps 4 ·
Smoking Allowed · Carpet · On Site Laundry ·
From
$90/nightAmenities
Smoking Allowed
Carpet
On Site Laundry
Free Parking
Pool
Air Conditioning
Furnished
Wifi
Other spaces
Workspace
· Hotel in Winter Haven
Travel Inn Winter Haven
1 Bed · Sleeps 10 ·
Carpet · Assigned Parking · Free Parking ·
From
$58/nightAmenities
Carpet
Assigned Parking
Free Parking
Pool
Air Conditioning
Furnished
Wifi
Swimming Pool
Other spaces
Workspace
· Hotel in Winter Haven
Courtyard by Marriott Winter Haven
1 Bed · Sleeps 4 ·
Smoking Allowed · Carpet · On Site Laundry ·
From
$119/nightAmenities
Smoking Allowed
Carpet
On Site Laundry
Free Parking
Fireplace
Pool
Air Conditioning
Furnished
Other spaces
Workspace
· House in Winter Haven
New remodeled 2/2 Lakefront Vacation Home on the Chain of Lakes in Winter Haven
2 Beds · 2 baths · Sleeps 5 ·
Fitness Center · Workspace · Outdoor Space ·
From
$126/nightAmenities
Fitness Center
Lake
Waterfront
Oven
Dishwasher
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Workspace, Kitchen
· Apartment in Winter Haven
Serenity Retreat, Confidently Clean
1 Bed · 1 bath · Sleeps 3 ·
Beach · Balcony · Lake ·
From
$87/nightAmenities
Beach
Lake
Waterfront
In Unit Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Balcony, Kitchen
· House in Winter Haven
★2/1★Central★Location★☀2-Mile LEGOLAND&Dining☀
2 Beds · 1 bath · Sleeps 5 ·
In Unit Laundry · Air Conditioning · Kitchen ·
From
$125/nightAmenities
In Unit Laundry
Air Conditioning
Furnished
Wifi
Business Center
Other spaces
Kitchen
· House in Winter Haven
Florida Oasis, Private Pool, BBQ, 7min to Legoland
3 Beds · 2 baths · Sleeps 8 ·
Ceiling Fan · Private Pool · Outdoor Space ·
From
$267/nightAmenities
Ceiling Fan
Private Pool
Pool
In Unit Laundry
Air Conditioning
Furnished
Wifi
Swimming Pool
Other spaces
Kitchen
· House in Winter Haven
Luxury Lakehouse with Private Pool, Hot Tub, Pool Table, Office & Jetted Tub
3 Beds · 3 baths · Sleeps 7 ·
High Ceilings · Fireplace · Pool ·
From
$300/nightAmenities
High Ceilings
Fireplace
Pool
In Unit Laundry
Air Conditioning
Furnished
Swimming Pool
Other spaces
Kitchen
· Apartment in Winter Haven
Soak up the charm of this cozy, recently remodel studio.
1 Bed · 1 bath · Sleeps 2 ·
Lake · Waterfront · In Unit Laundry ·
From
$81/nightAmenities
Lake
Waterfront
In Unit Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen
· House in Winter Haven
Lake Lucerne way villa
4 Beds · 2 baths · Sleeps 8 ·
Furnished · Wifi · Swimming Pool ·
From
$152/nightAmenities
Furnished
Wifi
Swimming Pool
· House in Winter Haven
*3/2*GorgeousNEWLakeHome2AceLoc*4mi*LEGOLAND*1722
3 Beds · 2 baths · Sleeps 7 ·
Fitness Center · Lake · Waterfront ·
From
$150/nightAmenities
Fitness Center
Lake
Waterfront
Oven
Dishwasher
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Kitchen
· House in Winter Haven
Lake Rochelle Rental (Lakefront)
3 Beds · 3 baths · Sleeps 8 ·
Fitness Center · Outdoor Space · Lake ·
From
$119/nightAmenities
Fitness Center
Lake
Waterfront
Oven
Dishwasher
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Kitchen
· Condo in Winter Haven
Updated 2 Bedroom Condo On Lake Lulu
2 Beds · 1 bath · Sleeps 4 ·
Balcony · Pool · In Unit Laundry ·
From
$120/nightAmenities
Pool
In Unit Laundry
Furnished
Wifi
Swimming Pool
Other spaces
Balcony, Kitchen
· House in Winter Haven
Conveniently located 10 minutes from Legoland!
3 Beds · 2 baths · Sleeps 9 ·
Fitness Center · Workspace · Oven ·
From
$110/nightAmenities
Fitness Center
Oven
Dishwasher
In Unit Laundry
Air Conditioning
Furnished
Wifi
Garage Parking
Other spaces
Workspace, Kitchen
· House in Winter Haven
Welcome Snowbirds, Sunbirds welcome you! Near LEGOLAND
3 Beds · 2 baths · Sleeps 8 ·
Smoking Allowed · Workspace · Outdoor Space ·
From
$150/nightAmenities
Smoking Allowed
Pool
Oven
Dishwasher
In Unit Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Workspace, Kitchen
· House in Winter Haven
Vibrant Lakeside retreat centrally located
3 Beds · 2 baths · Sleeps 6 ·
Lake · Waterfront · In Unit Laundry ·
From
$126/nightAmenities
Lake
Waterfront
In Unit Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen
· House in Downtown Winter Haven
FALL/WINTER SPECIAL RATES Mid-century Mod w/ Fireplaces - Downtown Near Legoland
2 Beds · 3 baths · Sleeps 6 ·
Ski In Ski Out · Carpet · Fitness Center ·
From
$129/nightAmenities
Ski In Ski Out
Carpet
Fitness Center
On Site Laundry
Assigned Parking
Fireplace
Pool
Lake
Other spaces
Workspace, Kitchen
Showing 1 - 50 of 80 results
Updated: March 9, 2023
Learn about vacation rentals in
Winter Haven
Explore 83 vacation rentals near Winter Haven, Florida. Whether you’re a tourist or on a staycation, there’s plenty of things to do and restaurants to try around the city. If you’re looking to take a trip to Winter Haven, you can see photos of Winter Haven vacation rentals, view amenities and features, browse by specific property types, and more. Use our interactive map to find Winter Haven vacation rentals in specific areas. Whether you’re looking for a Winter Haven staycation, weekend getaway, or a long vacation, we’ve got you covered. Use the date filters at the top to select your travel dates and view availability. The lowest vacation rental price in Winter Haven is $58 per night and the highest price is $785 per night.
10 of the vacation rentals near Winter Haven are
apartments or condos. The average bathroom count for this property type is 1. The median price for these vacation
units is $87 per night. There are
currently 5 vacation units under this
price. 62 of the vacation rentals near Winter Haven are houses.
The average bathroom count for a vacation house near Winter Haven is
2. The average price for vacation houses near Winter Haven is $218 per night. There are 35 vacation homes under this price. The most common
amenities for vacation rentals near Winter Haven are: furnished, wifi, and kitchen. To find vacation properties that might be a good option for large groups or families, use our filters for bedroom count, bathroom count and more.
1 bed rentals
19 available
2 bed rentals
16 available
3 bed rentals
25 available
4+ bed rentals
20 available
Getting around Winter Haven
Walking
3/10
Fewer daily needs are within walking distance (unless you’re up for a challenge).
Car
8/10
Commuting is easy with multiple accessible routes and plenty of parking.
Points of interest in Winter Haven
Groceries
3/10
At least one grocery store within a 30-minute walk
Shopping
4/10
Some shops within walking distance
Cafes
2/10
Few or no cafés within walking distance
Restaurants
4/10
Some restaurants within walking distance
Nightlife
2/10
Few or no bars within walking distance
Vacation Rentals in Winter Haven, FL FAQ
How many vacation rentals in Winter Haven are available?
There are currently 83 vacation rentals in Winter Haven available. Our vacation rentals in Winter Haven include nightly rentals, weekend rentals, weekly rentals, and monthly rentals.
Are there any pet friendly vacation rentals in Winter Haven?
Yes, right now there are 17 pet friendly vacation rentals in Winter Haven. A pet friendly vacation rental in Winter Haven means a rental home that is dog friendly or cat friendly. Some pet friendly homes may accommodate other types of pets, as well. Contact the listing agent for any pet related inquiries.
Are there any vacation rentals in Winter Haven with a pool?
Yes there are vacation rentals with a pool available in Winter Haven, FL. View more detailed vacation spots on Vacations by Zumper.
Are there any vacation rentals in Winter Haven with internet access?
As of March 9, 2023, there are vacation rentals with internet access available in Winter Haven, Florida. Check out more enjoyable destinations on Vacations by Zumper.
