Winter Haven, Florida Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Winter Haven, Florida on RentalSaver.com!

Winter Haven Rentals

From $248 per night (USD)
VRBO
Awesome Lake House With Private Dock, Canoe, Kayaks, Game-Room, & Lots To Do!!!
Bedrooms:
2
Bathrooms:
3
Sleeps:
11
Awesome lake house, with a private dock, kayaks, a canoe, a game room with foosball, air hockey/small pool table, an arc ...
From $248 per night (USD)
VRBO
From $128 per night (USD)
Expedia
Serenity Retreat, Confidently Clean
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
This is a unique 2 story antique building that has been completely renovated and sectioned into 2 small apartments on t ...
From $128 per night (USD)
Expedia
From $299 per night (USD)
VRBO
Lake Silver Retreat – Waterfront Pet Friendly Home w/ Dock, Kayaks & Legoland-Themed Room!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Lake Silver Retreat III is a home with options ~ you can rent it as a 3 bedroom or a 5 bedroom (some holidays exclusions ...
From $299 per night (USD)
VRBO
From $577 per night (USD)
Expedia
Huge Luxury Lake House on the Chain of Lakes near Legoland!
Bedrooms:
5
Bathrooms:
5
Sleeps:
15
Welcome to your ultimate getaway in Winter Haven! This stunning 5,500 sq. ft. lakeside home offers 5 bedrooms, 5 bathroo ...
From $577 per night (USD)
Expedia
From $228 per night (USD)
VRBO
Bright Waterfront Home on Winter Haven's Lake Jessie
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
900 Lake Jessie is a rare rental find. It's a bright lakefront home on Winter Haven's renowned Chain of Lakes. This newl ...
From $228 per night (USD)
VRBO
From $99 per night (USD)
Expedia
*Modern Tiny Lake Cottage*AceLoc*4miles*LEGOLAND*
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
WELCOME! Lake Mariam Tiny Home sits on 2.6 acres of Lakefront Property. If hospitality & peace is what you want, our spa ...
From $99 per night (USD)
Expedia
From $178 per night (USD)
VRBO
A lakeside sunset delight near Disney, Universal, Sea World, Busch, LegoLand
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Here's the place to kick back, fish and recharge or to enjoy endless attractions Central Florida--Disney, Universal Stud ...
From $178 per night (USD)
VRBO
From $202 per night (USD)
Expedia
Looking for Relaxation?Near Legoland and Disney
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Newly renovated 3 bedroom, 2 bathroom house located in a quiet neighborhood in Lake Alfred, Florida. House has own priva ...
From $202 per night (USD)
Expedia
From $282 per night (USD)
VRBO
Luxury 3BR Lake House on Quiet Private Lake, with Pool and Hot Tub
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
3,800 sq ft Executive Vacation Home on a private lake 5 minutes from Legoland and Peppa Pig, and 40 minutes from DisneyW ...
From $282 per night (USD)
VRBO
From $97 per night (USD)
VRBO
55+ community, Sleeps 6-8, Minimum monthly rental, Pets Considered
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Our home has 2 bdrms the master has a king ized bed and there are two twin beds in the second bdr. There is a comfortabl ...
From $97 per night (USD)
VRBO
From $361 per night (USD)
VRBO
Spacious home, in a quiet neighborhood near LEGOLAND®-just a 12-minute drive
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
In this cozy town of Winter Haven, you'll find a beautiful 4-bedroom house that's just a short 12-minute ride away from ...
From $361 per night (USD)
VRBO
From $656 per night (USD)
Expedia
Luxury Lakefront | Heated Salt Pool, Dock & Kayaks | Home Theatre & EV Charger | Near Theme Parks
Bedrooms:
3
Bathrooms:
6
Sleeps:
13
Come to Lake Hamilton’s luxurious lake house and let the sunsets take your breath away as you relax and enjoy making mem ...
From $656 per night (USD)
Expedia
From $410 per night (USD)
VRBO
LAKE HOUSE WITH PRIVATE Free HEATED POOL & GAME ROOM 4 min FROM LEGOLAND
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
4 Bedroom Lake House on Canal to LEGOLAND’s Lake Eloise on the Chain of Lakes, bring your boat there is a small boat ram ...
From $410 per night (USD)
VRBO
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Expedia
Luxury Home w/ Lanai, Billiards, 6min to Legoland
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
CHECKOUT A FULL VIDEO OF THE PROPERTY: https://youtu.be/K6zlvwkvq-o ★ SPACIOUS 5-STAR LUXURY WINTER HAVEN HOME ★ You ...
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Expedia
From $292 per night (USD)
VRBO
Waterfront Lakehouse, Private Dock, Tiki Bar, Playground, Near Legoland | Lake Idylwild Delight
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to Sunrise on Lake Idylwild Your perfect lakeside getaway awaits on the beautiful Chain of Lakes in Winter Hav ...
From $292 per night (USD)
VRBO
From $234 per night (USD)
VRBO
Lake Rochelle Rental Lakefront
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Huge, fenced yard with quaint 3/2 trilevel house overlooking Lake Rochelle in Northeast Winter Haven. Just minutes fro ...
From $234 per night (USD)
VRBO
From $174 per night (USD)
VRBO
*3/2*GorgeousNEWLakeHome2AceLoc*4mi*LEGOLAND*1722
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
WELCOME! Lake Mariam Vacation Home (1), is part of a duplex that sits on 2.6 acres of Lakefront Property. There is also ...
From $174 per night (USD)
VRBO
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Expedia
Lake Lucerne way villa
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Welcome to Villa Lake Lucerne, located just around 30 minutes from the Disney World Resort and 17 minutes from the LEGO- ...
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Expedia
From $112 per night (USD)
VRBO
Soak up the charm of this cozy, recently remodel studio.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This studio is located minutes from Downtown Winter Haven, one of Florida's oldest towns. The small downtown is packed ...
From $112 per night (USD)
VRBO
From $144 per night (USD)
Expedia
★2/1★Central★Location★☀2-Mile LEGOLAND&Dining☀
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
WELCOME to our Wakulla Vacation Home (1) “Nest” which is a duplex property. We are a family own business & genuinely hop ...
From $144 per night (USD)
Expedia
From $445 per night (USD)
VRBO
Waterfront Winter Haven Home with Dock & Hot Tub!
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Your lakeside paradise awaits at this 4-bedroom, 3-bath Winter Haven vacation rental, perfect for your 'Sunshine State' ...
From $445 per night (USD)
VRBO
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Expedia
Peace & Love Room 5 minutes from Winter Haven Hospital
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Peace & Love Sanitized Private Room with private door entrance and bathroom. Wi-Fi, parking space for a Single person. V ...
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Expedia
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VRBO
PEACE & LOVE ROOM 5 Minutes from Winter Haven Florida
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This room is located 5 minutes from Winter Haven Hospital and is only designed to accommodate women, especially nurses a ...
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VRBO
From $258 per night (USD)
Expedia
3br Modern home w/hot tub>5min from LEGOLAND
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Kick back and relax in this calm, stylish space. Comfortable beds, clean home and spa for relaxing. Private back patio a ...
From $258 per night (USD)
Expedia
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VRBO
Lakeside Cottage in Lake Howard (Winter Haven Chain of Lakes)
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Lakeside Cottage sits on Lake Howard, one of the most popular locations on "The Chain of Lakes" near downtown Winter ...
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VRBO
From $178 per night (USD)
Expedia
Newly Vacation Home with Lake view
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Newly vacation home with lake view in a quiet neighborhood. Come and enjoy beautiful sunrises in this peaceful setting. ...
From $178 per night (USD)
Expedia
From $105 per night (USD)
VRBO
Lake House to be leased with Main house: 2042348
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
23 Miles from Disney world, 35 Miles from Universal Studios. 5 miles from Legoland Theme and Water Park. 20 Min to Bo ...
From $105 per night (USD)
VRBO
From $106 per night (USD)
Expedia
The Russell Lake House
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This is a Cabana. It has 2 sets of bunk beds (4 total beds). Approx 400 sq. Ft. . Includes a bathroom with sink, toilet ...
From $106 per night (USD)
Expedia
From $308 per night (USD)
VRBO
Beautiful Lake Front cottage w/ heated pool & Hot Tub, 23 miles from Disney
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Only 23 miles from Disney world and 35 miles to Universal Studios. 5 miles from Legoland Theme and Water Park. Amazin ...
From $308 per night (USD)
VRBO
From $243 per night (USD)
VRBO
Hook, Line & Leisure: Lakefront Gem w/ Porch!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
2,384 Sq Ft | Dedicated Office | Yard w/ Fruit Trees Living up to its name, Winter Haven delivers an authentic Florida ...
From $243 per night (USD)
VRBO
From $384 per night (USD)
VRBO
Beautiful home located in a gated community only 20 miles from LegoLand!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Beautiful 4 bedroom home in gated community. Private heated pool and hot tub* in an awesome outdoor space. Theater room ...
From $384 per night (USD)
VRBO
From $178 per night (USD)
Expedia
*3/2*GorgeousNEWLakeHome2AceLoc*4mi*LEGOLAND*1724
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
WELCOME! Lake Mariam Vacation Home (2) is part of a duplex built in 2016 that sits on 2.6 acres of Lakefront Property. I ...
From $178 per night (USD)
Expedia
From $1474 per night (USD)
VRBO
Spectacular Waterfront Home in Winter Haven
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
HIGHLIGHTS +Custom built in 2006 +Chef’s kitchen with Viking Professional appliances +Waterfront on 3 sides of the prop ...
From $1474 per night (USD)
VRBO
From $452 per night (USD)
Expedia
Fantastic Water Front Home on the Chain of Lakes
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
We are sharing our dream home with you! This home offers one of the best open layouts in Winter Haven. Great open kitche ...
From $452 per night (USD)
Expedia
From $260 per night (USD)
VRBO
Lake Shipp House with pool and dock on the water
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Fully furnished single story home on Lake Shipp; has boat dock, inground heated swimming pool. Two bedrooms (king & quee ...
From $260 per night (USD)
VRBO
From $172 per night (USD)
VRBO
Bright Cypress Gardens Home Near Legoland!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
A fun-filled family escape awaits at this lovely home in Cypress Gardens! This 3-bedroom, 2-bathroom vacation rental pro ...
From $172 per night (USD)
VRBO
From $212 per night (USD)
VRBO
3/ 2 kid friendly home, only minutes to Legoland.
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Fully furnished, brick gas fireplace for cool nights or winter months. Central heat and air. WiFi and security system. ...
From $212 per night (USD)
VRBO
From $343 per night (USD)
Expedia
Heated Pool Backyard Fun | Kayaks | Boat Dock | Lake Access | Theater Room | EV Charger Theme Parks
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Come to Lake Hamilton’s luxurious lake house and let the sunsets take your breath away as you relax and enjoy making mem ...
From $343 per night (USD)
Expedia
From $517 per night (USD)
VRBO
Lake Silver Retreat – 5BR Lakefront Home w/ Dock, Kayaks & Legoland-Themed Room – Perfect Getaway!
Bedrooms:
3
Bathrooms:
5
Sleeps:
11
Ready for some Lake with a New Dock & Lego fun - Lake Silver Retreat in the Heart of the City will take your breath away ...
From $517 per night (USD)
VRBO
From $438 per night (USD)
Expedia
Cheerful New Construction Home
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Bring the whole family to this great place with lots of room for fun. Winter Haven is the up and coming city. Boasting b ...
From $438 per night (USD)
Expedia
From $385 per night (USD)
VRBO
Heated Pool, Arcade with PS5, 5min from Legoland-Stylish LakeHome
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
One of the very few Stylish stays in Winter haven. Only 5 min to Legoland, 40 min from Busch Gardens, and 40 min from Di ...
From $385 per night (USD)
VRBO
From $456 per night (USD)
Expedia
Lanai & Pool: Elegant Villa in Winter Haven!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
WFH Friendly | Lake Access On-Site | 5,100 Sq Ft Escape to the ‘Water Ski Capital of the World’ at this Winter Haven va ...
From $456 per night (USD)
Expedia
From $516 per night (USD)
VRBO
Lakefront Lego Land Estate
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
Welcome to the Lakefront Legoland Estate, a spacious 5-bedroom, 4-bathroom pool home set directly on Lake Summit, part o ...
From $516 per night (USD)
VRBO
From $402 per night (USD)
Expedia
Eagle Haven Lake House
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Plan a trip to Central Florida and let relaxation greet you at the door of this newly renovated lovely waterfront vacati ...
From $402 per night (USD)
Expedia
From $118 per night (USD)
VRBO
Charming Town House — 10 Minutes from the Legoland Park and Downtown
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This house is located a perfect distance from the best places in Winter Haven. It sits a ten minute drive from the Legol ...
From $118 per night (USD)
VRBO
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Expedia
Modern spacious 2-bedroom Apartment 1 mile from Legoland. 6-month minimum stay.
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Beautiful 2 bedroom apt centrally located in a beautiful and safe neighborhood, only 1 mile from Legoland, restaurants a ...
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Expedia
From $116 per night (USD)
VRBO
Private/Spacious 1BR Central Near LegoLand 2 Miles
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
WELCOME to our Wakulla Vacation Home (2), duplex property. We are a family own business & genuinely hope to tailor our p ...
From $116 per night (USD)
VRBO
From $178 per night (USD)
Expedia
Newly remodeled Lakefront Vacation Home on the Chain of Lakes in Winter Haven
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Newly remodeled Lakefront Vacation Home on the Chain of Lakes right next to Winter Haven Municipal Airport across from B ...
From $178 per night (USD)
Expedia
From $512 per night (USD)
VRBO
An Amazing Mid-Century Modern Experience
Bedrooms:
1
Bathrooms:
4
Sleeps:
6
Welcome to The Gene Leedy House, the life-long residence of iconic architect, Gene Leedy. A founding member of the Saras ...
From $512 per night (USD)
VRBO
From $97 per night (USD)
VRBO
Waterfront Vacation Rental on Lake Mirror!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Situated directly on Lake Mirror, this charming Winter Haven vacation rental is perfect for snowbirds looking to embrace ...
From $97 per night (USD)
VRBO
From $278 per night (USD)
VRBO
Heated Pool and Hot tub-near Legoland, Disney, Theme parks
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Relax in the pool and hot tub after enjoying theme parks such as Busch Gardens, Disney world, and Universal Studios! Leg ...
From $278 per night (USD)
VRBO
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Expedia
Great Family Home Near Legoland
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
About this space Your family will be close to everything when you stay at this centrally-located home near Legoland and ...
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Expedia
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VRBO
Cozy Family Home Near Legoland
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
About this space Relax with the fam after a fun day at LEGOLAND (4.7 miles) or Disney World (36 miles) in our newly reno ...
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VRBO
From $358 per night (USD)
Expedia
Lake Hamilton Hideout
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
This beautiful home provides the perfect setting for a relaxing and rejuvenating vacation in the heart of central Florid ...
From $358 per night (USD)
Expedia
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VRBO
Spacious 3 Bed, 2 Bath Home Near Legoland
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
About this space A gem in the Heart of Winter Haven. This brand new 3 bedroom, 2 bathroom home is fresh, clean and ready ...
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VRBO
From $312 per night (USD)
Expedia
Cheerful 4 Bed, 3 Bath Home with Screened Pool
Bedrooms:
3
Bathrooms:
4
Sleeps:
11
About this space This stylish place to stay is perfect for vacation. With 2 ensuite bedrooms plus 2 additional rooms and ...
From $312 per night (USD)
Expedia
From $250 per night (USD)
VRBO
Newly remodeled Vacation Home with Saltwater Pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This "brand-new" home, built in 2010, totally rebuilt and remodeled in 2022, is located in a gated community in the sout ...
From $250 per night (USD)
VRBO
From $433 per night (USD)
Expedia
Luxury lakehouse with private pool, hot tub, & office - close to Legoland
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
The Luxury Lakehouse Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $433 per night (USD)
Expedia
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VRBO
5 Bedroom Chain of Lakes Home w/AC Pet Friendly
Bedrooms:
2
Bathrooms:
5
Sleeps:
16
Bring the wwireless network kitchen for cooking air conditioner television washing machine supporting facilities free pa ...
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VRBO
From $258 per night (USD)
Expedia
LEGOLAND! Disney, Universal &+! Your Home Away from Home in Winter Haven, FLA!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Winter Haven is a beautiful, charming and friendly city locally known as "Chain of Lakes!" Strategically located between ...
From $258 per night (USD)
Expedia
From $128 per night (USD)
VRBO
Luxury StayComfy at WinterHeaven
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Have fun with the whole family at this two bedroom stylish place. Enjoy two comfy queen beds and a sofa-bed, tv 50'' wi ...
From $128 per night (USD)
VRBO
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Expedia
Modern Waterfront Oasis
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
About this space Welcome to Casa Bella! Inside, the home boasts a sleek and contemporary design, with clean lines and lu ...
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Expedia
From $130 per night (USD)
VRBO
2 bedroom private vacation home in winter haven
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to our family-friendly home! Just a 5-minute walk to the nearest lake and a short 15-minute drive from Legoland, ...
From $130 per night (USD)
VRBO
From $315 per night (USD)
VRBO
Winter Haven Retreat w/ Private Pool!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Run, don't walk, to Winter Haven and experience the ultimate vacation at this charming 3-bedroom, 2-bath home. Ideally l ...
From $315 per night (USD)
VRBO
$Historic, private, updated, 5 Bedroom Plantation Home, lake, fishing, leasure\n$
From $300 per night (USD)
VRBO
Historic, private, updated, 5 Bedroom Plantation Home, lake, fishing, leasure\n
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Enjoy your stay in this Historic, large, peaceful, fully renovated Plantation home. This home consists of 5 bedrooms, 3 ...
From $300 per night (USD)
VRBO
From $256 per night (USD)
Expedia
Large 3/1 Near DownTown and Dining
Bedrooms:
1
Bathrooms:
3
Sleeps:
10
Welcome to our spacious and modern retreat, perfectly situated in the heart of the city. This stylish home is designed ...
From $256 per night (USD)
Expedia
From $298 per night (USD)
VRBO
Stylish Waterfront Lake Wales Home Rental w/ Dock!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Lakefront living doesn’t get much more chic and comfortable than this Lake Wales vacation rental. This 3-bedroom, 2-bath ...
From $298 per night (USD)
VRBO
From $225 per night (USD)
Expedia
Cozy Lakefront Home w/ Pool -7 mins from Legoland
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to Tulum House! Discover true family bliss at our 3-bedroom lakeside retreat in Winter Haven. Dive into the priv ...
From $225 per night (USD)
Expedia
From $521 per night (USD)
VRBO
Lake View, Game Room, 10 minutes to Legoland - Perfect for Large Families!
Bedrooms:
4
Bathrooms:
4
Sleeps:
11
Welcome to The Elby, a fully renovated 1940's lake home with spacious rooms, modern amenities, and indoor and outdoor ga ...
From $521 per night (USD)
VRBO
From $366 per night (USD)
VRBO
Lakefront Winter Haven Retreat: Hot Tub & Patio!
Bedrooms:
3
Bathrooms:
4
Sleeps:
22
Located just steps away from the pristine waters of the Chain of Lakes, this stunning 4-bedroom, 3.5-bathroom vacation r ...
From $366 per night (USD)
VRBO
From $193 per night (USD)
VRBO
Serene Lakefront Escape
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to our 2-bedroom condo boasting panoramic lake views in the esteemed gated community of Winterset. Experience t ...
From $193 per night (USD)
VRBO
From $104 per night (USD)
VRBO
Winter Haven Apt: 1 Mi to Polk State College!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Close to Polk State College, this convenient, vibrant vacation rental is great for prospective students and alumni, visi ...
From $104 per night (USD)
VRBO
From $106 per night (USD)
VRBO
Studio Apartment in Winter Haven, FL
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to our studio apartment, a perfect retreat for solo travelers or couples seeking a comfortable and convenient pl ...
From $106 per night (USD)
VRBO
From $372 per night (USD)
Expedia
Summer Specials! Pet Friendly, 7 Beds, Family Oasis
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Nestled on the west side of Lake Howard in Winter Haven, the Chain of Lakes Villa offers an enchanting retreat that cele ...
From $372 per night (USD)
Expedia
From $190 per night (USD)
VRBO
Winter Haven Home w/ Pool Near Legoland!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Discover your next family getaway at 'Little Haven!' The modern 3-bedroom, 2-bathroom property provides a comfortable oa ...
From $190 per night (USD)
VRBO
From $438 per night (USD)
Expedia
Adult-Only Love Hotel with Mermaid Pool
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Explore a world of pleasures at our adult-only love hotel, which features four themed bedroom options*, each designed to ...
From $438 per night (USD)
Expedia
From $225 per night (USD)
VRBO
Hot Tub & Fire Pit: Lakefront Home on Lake Eloise
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Waterfront Patio | Sunset Views | Voted 3rd Best Staycation in Winter Haven | ~1 Mi to Legoland Situated on an idyllic ...
From $225 per night (USD)
VRBO
$The Lake Alfred Citrus Wood Guest Cabin\n\n$
From $111 per night (USD)
Expedia
The Lake Alfred Citrus Wood Guest Cabin\n\n
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Relax and enjoy this modern beautifully appointed Guesthouse Cabin with an abundance of exceptional privacy and a peacef ...
From $111 per night (USD)
Expedia
$The Exclusive Tatman Evergreen Suite\n\n$
From $84 per night (USD)
VRBO
The Exclusive Tatman Evergreen Suite\n\n
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The Exclusive Tatman Evergreen Deluxe Suite is a stylistic, contemporary modern and beautiful completely private Suite s ...
From $84 per night (USD)
VRBO
From $86 per night (USD)
VRBO
Furnished Condo on the water in Winter Haven, FL
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beautiful 2 bedroom 2 bathroom newly renovated condominium located in the gated community of Winterset with sunset views ...
From $86 per night (USD)
VRBO
From $215 per night (USD)
VRBO
Peaceful Lakeside Retreat
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Tranquility awaits you at this beautiful lakefront home. We invite you to enjoy the best of Florida indoor/outdoor livi ...
From $215 per night (USD)
VRBO
From $235 per night (USD)
Expedia
Best sunsets in Winter Haven. Lakefront home 5 minutes from downtown!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Enjoy the best sunset in Winter Haven on a hammock, then drive 3 mins for dinner downtown. You can't beat this slice of ...
From $235 per night (USD)
Expedia
From $144 per night (USD)
VRBO
Comfortable bedroom and house to stay in w/ swimming pool.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The bedroom i am renting is very comfortable, has tv, dresser, bistro table and chairs, floor lamp, two night stands wit ...
From $144 per night (USD)
VRBO
From $691 per night (USD)
Expedia
Lake-Walk2LEGOLAND-Heated SaltWtr Pool-Putting Green-Beach-Fire Pit-Dock-Sunsets
Bedrooms:
4
Bathrooms:
5
Sleeps:
14
"Most beautiful home we’ve ever stayed at. Thank you for your sweet hospitality!" - Jessica "House felt like a spa!" - ...
From $691 per night (USD)
Expedia
From $260 per night (USD)
VRBO
Carefree Cove on Lake Connie - With Hot Tub! 15 mins to Legoland
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Nestled on the shores of Winter Haven's Lake Connie, this charming 3-bedroom promises a tranquil escape. This cozy lake ...
From $260 per night (USD)
VRBO
From $474 per night (USD)
Expedia
Legoland Poolside Paradise
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Nestled in the heart of Central Florida, our charming retreat offers the perfect blend of relaxation and adventure. With ...
From $474 per night (USD)
Expedia
Click For Pricing
VRBO
Cozy 3 bedroom central hideaway
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Enjoy quick and easy self check in with lock box system. Beautiful, quiet and secure community. Enjoy spacious and elega ...
Click For Pricing
VRBO
From $185 per night (USD)
Expedia
Family Fun Haven: 3 Bed/2 Bath/6 Mi to Legoland/Pet Friendly!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Location, Location, Location ! Bring the whole family to this spacious home with lots of room for fun! Centrally locate ...
From $185 per night (USD)
Expedia
From $305 per night (USD)
VRBO
Lake House on the LEGOLAND Chain-of-Lakes with Private Pool, Beach and Boat Dock
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Stay comfortably in Central Florida at this 4-bedroom Lakefront Home on the Lego Land Chain-of-Lakes! With two Master Su ...
From $305 per night (USD)
VRBO
From $144 per night (USD)
Expedia
Family-Friendly Haven near Downtown - Fast Wifi
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
Summary: Escape to our inviting 3-bedroom, 1-bath Family-Friendly Retreat near downtown Winter Haven, FL—a haven for fam ...
From $144 per night (USD)
Expedia
From $96 per night (USD)
VRBO
Cozy Winter Haven Escape | Pet-Friendly/Fenced Lot
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Summary: Welcome to Cozy Retreat near Legoland! Our charming 3-bedroom, 1-bath home offers a pullout sofa bed, a fully s ...
From $96 per night (USD)
VRBO
From $157 per night (USD)
Expedia
Charming 2-bedroom house with huge yard and firepit in Eagle Lake
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to this charming house in Eagle Lake. This fabulous vacation rental is perfect for guests seeking a pleasant and ...
From $157 per night (USD)
Expedia
From $231 per night (USD)
VRBO
Charming 3-Bedroom House Near Legoland, Lake & Golf!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Discover the beauty of Winter Haven from this 3-bedroom house. close to LEGOLAND! Nestled in the beautiful Neighborhood, ...
From $231 per night (USD)
VRBO
From $88 per night (USD)
Expedia
Tiny Paradise
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This Winter Haven studio boasts 1 inviting bedroom with a full bed. The space is equipped with essentials like WiFi, hea ...
From $88 per night (USD)
Expedia
From $250 per night (USD)
VRBO
Serene Lakeside Cottage Retreat
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Welcome to your serene escape in Winter Haven, just minutes away from the excitement of Legoland! This enchanting 3-bedr ...
From $250 per night (USD)
VRBO
From $173 per night (USD)
Expedia
Cozy house in peaceful Lake Alfred with AC, WiFi very secluded.
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Experience Lake Alfred like a local in this welcoming 1-bedroom house. With amenities like AC, coffee and WiFi, guests c ...
From $173 per night (USD)
Expedia
From $310 per night (USD)
VRBO
Getaway Clubhouse 5 mil Legoland & .5 mil Downtown
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Enjoy a relaxing stay in this spacious and comfortable home, perfect for families or groups. The open layout of the livi ...
From $310 per night (USD)
VRBO
From $280 per night (USD)
Expedia
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
This delightful lake-life inspired cottage includes 2 bedrooms and 1 ½ baths, a fooseball table, and easily sleeps 7 gue ...
From $280 per night (USD)
Expedia
From $169 per night (USD)
VRBO
Cozy Bungalow - 5 mi Legoland & 0.5 mi Dwntwn
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This cozy bungalow includes 3 bedrooms and 1 ½ baths, and it sleeps up to 8 guests comfortably! Located approximately ...
From $169 per night (USD)
VRBO
From $298 per night (USD)
Expedia
The Old Haven - An Enduring Piece of Nostalgia
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
This charming home was built in 1908 and is located 45 minutes from Tampa/Orlando. Fully furnished, this space is perfe ...
From $298 per night (USD)
Expedia

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Results: 164 Rentals