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 $181 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 $181 per night (USD)
VRBO
From $89 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 $89 per night (USD)
Expedia
From $271 per night (USD)
VRBO
Lakefront Luxury: Boat Dock, Pet-Friendly, Close to LegoLand, Perfect for Family Fun
Bedrooms:
3
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 $271 per night (USD)
VRBO
From $90 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 $90 per night (USD)
Expedia
$FALL\/WINTER SPECIAL RATES Mid-century Mod w\/ Fireplaces - Downtown Near Legoland$
Click For Pricing
Expedia
FALL\/WINTER SPECIAL RATES Mid-century Mod w\/ Fireplaces - Downtown Near Legoland
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Located in Winter Haven, this handsomely furnished, all-inclusive 2 bedroom/2.5 bathroom townhouse is the ideal home-awa ...
Click For Pricing
Expedia
From $193 per night (USD)
Expedia
Lake Idylwild Delight: Waterfront Lakehouse, Private Dock, Tiki Bar, Kid's Jungle Gym, Near Legoland
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Welcome to SUNRISE ON LAKE IDYLWILD! This home has something special for everyone in your family. This beautifully dec ...
From $193 per night (USD)
Expedia
Click For Pricing
VRBO
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- ...
Click For Pricing
VRBO
From $87 per night (USD)
Expedia
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 $87 per night (USD)
Expedia
From $90 per night (USD)
VRBO
Modern HouseBoat*AceLoca*4Miles*LegoLand*
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Welcome to the SeaRover on Lake Mariam part of the Chain of Lakes! This is a fully furnished newly renovated house boat ...
From $90 per night (USD)
VRBO
From $330 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 $330 per night (USD)
Expedia
From $92 per night (USD)
VRBO
Confidently Clean, Quint & Cozy Apartment
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
This is a unique 2 story antique building that has been completely renovated into 4 small apartments. This property was ...
From $92 per night (USD)
VRBO
From $221 per night (USD)
VRBO
Lake life living 45 mins from most central FL theme parks...
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Older home very spacious 3 bedrooms, 3 baths large back porch looking over the pool as well as Lake Shipp also on the c ...
From $221 per night (USD)
VRBO
From $280 per night (USD)
VRBO
Lakefront Luxury: Boat Dock, Pet-Friendly, Close to LegoLand, Perfect for Family Fun
Bedrooms:
4
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 $280 per night (USD)
VRBO
Click For Pricing
Expedia
3 Bedroom Townhome 431087 by Houzlet
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
One or more photo(s) has been virtually staged. Under Construction. Monthly rent range $1995 to $2295. (Rent varies depe ...
Click For Pricing
Expedia
Click For Pricing
Expedia
4 Bedroom Single_family 430655 by Houzlet
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Brand New Single home in the heart of Winter Haven. Beautiful 4-bedroom, 2 bathrooms with 2 car Garage, never occupied! ...
Click For Pricing
Expedia
From $213 per night (USD)
Expedia
Beautiful 5 Bedroom 3 Bath Home Near Sports Complex with lake access.
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Enjoy your stay in this large, peaceful, historic, fully renovated home. This home consists of 5 bedrooms, 3 bathrooms w ...
From $213 per night (USD)
Expedia
From $92 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 $92 per night (USD)
VRBO
From $85 per night (USD)
Expedia
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 $85 per night (USD)
Expedia
From $159 per night (USD)
VRBO
Winter Haven-Historic property- N Legoland Sleep 4
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to the great property. This historic property was the home of The Red Sox spring training for decades and the so ...
From $159 per night (USD)
VRBO
From $163 per night (USD)
VRBO
Fun and Relaxation in Winter Haven!! 2 Queen Beds,
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Our pet-friendly guest room offers free light breakfast item together with your choice of coffee, tea and juice to start ...
From $163 per night (USD)
VRBO
$*3\/2*GorgeousNEWLakeHome2AceLoc*4mi*LEGOLAND*1724$
From $150 per night (USD)
VRBO
*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 $150 per night (USD)
VRBO
$*3\/2*GorgeousNEWLakeHome2AceLoc*4mi*LEGOLAND*1722$
From $150 per night (USD)
Expedia
*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 $150 per night (USD)
Expedia
From $150 per night (USD)
VRBO
CELEBRATE!! Sun, Fun, Relax- Suite- 2 Queen Beds
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
You’ll find the basic amenities like a microwave and refrigerator in every room. Our suites include a sofa bed and some ...
From $150 per night (USD)
VRBO
From $155 per night (USD)
VRBO
Amazing!!! WINTER HAVEN 2 Queen Beds fun 4 All
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Make the most of your time in Winter Haven with our amenities, which allow you to focus on the people and experiences th ...
From $155 per night (USD)
VRBO
$Spacious Modern 4bd\/2ba Home! Amazing Location$
From $129 per night (USD)
VRBO
Spacious Modern 4bd\/2ba Home! Amazing Location
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Nestled in the Heart of Winter Haven, the Modern Home offers a remarkable fusion of innovation, convenience, and aesth ...
From $129 per night (USD)
VRBO
$Kid & Pet friendly home w\/ Pool and BBQ$
From $175 per night (USD)
Expedia
Kid & Pet friendly home w\/ Pool and BBQ
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Enjoy a delightful stay in our newly Renovated 3BD house for your Winter Haven trip. The unit is equipped with dryer, wa ...
From $175 per night (USD)
Expedia
From $103 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 $103 per night (USD)
VRBO
From $214 per night (USD)
Expedia
Legoland 3 Bedroom Pet Friendly Pool Home
Bedrooms:
4
Bathrooms:
6
Sleeps:
13
Bring the whole family to this great place with lots of room for fun. This home is conveniently located only 2.1 miles f ...
From $214 per night (USD)
Expedia
Click For Pricing
VRBO
Eagle Lake Home < 7 Mi to Legoland!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
A fun-filled family getaway awaits at this lovely Eagle Lake vacation rental! This 3-bedroom, 2-bathroom home provides e ...
Click For Pricing
VRBO
Click For Pricing
VRBO
Lavish Dreams House 5 Miles from Legoland
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Lavish Dreams! This New Modern Construction is furnished with comfortable, King Bed, full kitchen equipped, a ...
Click For Pricing
VRBO
From $89 per night (USD)
VRBO
4.4 miles to Legoland. Conveniently located near large highways and interstates.
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
4.4 miles to Legoland. 36 miles to Disney (43 minutes) Cozy one bed one bath second floor condo. Centrally located. Walk ...
From $89 per night (USD)
VRBO
From $306 per night (USD)
Expedia
Cozy Organic Modern Home- 6 min from Legoland
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Step into this enchanting haven – a spacious retreat, tailor-made for families and friends on the hunt for adventure, re ...
From $306 per night (USD)
Expedia
From $190 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 $190 per night (USD)
VRBO
From $535 per night (USD)
VRBO
The Lakeview Oasis Getaway!
Bedrooms:
5
Bathrooms:
7
Sleeps:
21
Bring your family & friends and enjoy this amazing & relaxing lakefront view property with room for everyone to come tog ...
From $535 per night (USD)
VRBO
From $450 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 $450 per night (USD)
VRBO
From $105 per night (USD)
Expedia
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 $105 per night (USD)
Expedia
$Florida Beachy Breeze 2\/1 Home. No Cleaning Fee!$
From $117 per night (USD)
VRBO
Florida Beachy Breeze 2\/1 Home. No Cleaning Fee!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
This property is a beautifully updated 2/1 home. Property comes equipped with a full kitchen, living room, smart TV, ce ...
From $117 per night (USD)
VRBO
From $63 per night (USD)
Expedia
Nice Private Studio Room — 10 Minutes from the Legoland Park and Downtown
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This private studio room is located a perfect distance from the best places in Winter Haven. It sits a ten minute drive ...
From $63 per night (USD)
Expedia
$Elegant Winter Haven Villa w\/ Dock & Lanai!$
From $462 per night (USD)
VRBO
Elegant Winter Haven Villa w\/ Dock & Lanai!
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Escape to the ‘Water Ski Capital of the World’ at this Winter Haven vacation rental on the Chain of Lakes. This 4-bedroo ...
From $462 per night (USD)
VRBO
From $203 per night (USD)
VRBO
3-Bedroom Lake House Minutes from LegoLand & Peppa Pig Park!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This unique place has a style all its own. From the moment you drive up to the property you will feel the vacation vibes ...
From $203 per night (USD)
VRBO
From $192 per night (USD)
VRBO
Lakefront house for rent
Bedrooms:
3
Bathrooms:
3
Sleeps:
4
Million dollar lake view. Eagles nest in the back yard every year. No pets. No smoking. No children. No parties. Furnish ...
From $192 per night (USD)
VRBO
$*CentralLocated*PrivateKingSuitew\/Bath, Washer&Dryer(Eagle)$
From $95 per night (USD)
Expedia
*CentralLocated*PrivateKingSuitew\/Bath, Washer&Dryer(Eagle)
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Centrally located Modern/Contemporary Spacious Private King Suite that is close to Winter Haven (WH) downtown (2 miles); ...
From $95 per night (USD)
Expedia
From $155 per night (USD)
VRBO
Winter Haven Abode Near Lakes & Attractions
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
Enjoy a relaxing escape to Winter Haven when you book this charming vacation rental home, complete with 2 bedrooms, 1.5 ...
From $155 per night (USD)
VRBO
$A spacious gem w\/private lake front access, boating, restaurants, bars and more!$
Click For Pricing
Expedia
A spacious gem w\/private lake front access, boating, restaurants, bars and more!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to your winter haven!! A rare find on the chain of lakes - Lake Howard. This lake front house opens up to a spa ...
Click For Pricing
Expedia
$Lovely Lakefront Home w\/ Grill: 7 Mi to Legoland!$
From $146 per night (USD)
VRBO
Lovely Lakefront Home w\/ Grill: 7 Mi to Legoland!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Living up to its city name, this elegant 3-bedroom, 3-bathroom Winter Haven home features the perfect haven for escaping ...
From $146 per night (USD)
VRBO
Click For Pricing
Expedia
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 ...
Click For Pricing
Expedia
Click For Pricing
VRBO
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 ...
Click For Pricing
VRBO
From $80 per night (USD)
Expedia
TRAVELLING PROFESSIONALS ONLY - 3.3 miles to Winter Haven Hospital!
Bedrooms:
2
Bathrooms:
2
Sleeps:
1
This home is your home away from home. Quiet, clean, full paint job, all new furnishings, Roku TV in both bedrooms, Quee ...
From $80 per night (USD)
Expedia
Click For Pricing
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 ...
Click For Pricing
VRBO
$Luxury Home w\/ Lanai, Billiards, 6min to Legoland$
From $225 per night (USD)
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 ...
From $225 per night (USD)
Expedia
From $80 per night (USD)
VRBO
Cute & Cozy 1 bedroom guesthouse located in Winter Haven FL
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The guesthouse Cute & Cozy is separate yet, it is adjacent to the main house (owner lives) and has its own entrance. L ...
From $80 per night (USD)
VRBO
Click For Pricing
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 ...
Click For Pricing
Expedia
Click For Pricing
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 ...
Click For Pricing
VRBO
Click For Pricing
VRBO
Beautiful 2bedroom near LEGoLAND
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Forget your worries in this spacious and serene space. This home is in a nice peaceful neighborhood near winter haven h ...
Click For Pricing
VRBO
From $90 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 $90 per night (USD)
VRBO
Click For Pricing
Expedia
Quiet and cozy 55 plus community .
Bedrooms:
2
Bathrooms:
3
Sleeps:
2
Great home in a 55 plus community setting. There are many areas of the home to enjoy. Sitting in the carport, soaking in ...
Click For Pricing
Expedia
From $275 per night (USD)
VRBO
Our Camp at Lake Cannon
Bedrooms:
2
Bathrooms:
2
Sleeps:
12
Unbeatable Sunsets - relax @ the lake. Sleeps a Crowd Comfortably We pack in a lot of sleep space. Bunk room includes t ...
From $275 per night (USD)
VRBO
From $180 per night (USD)
VRBO
341 NEW Legoland Sherman's Antiques Lake Silver
Bedrooms:
1
Bathrooms:
3
Sleeps:
10
Summary: 这个是一个完全新装修的房源，有3个卧室，5张床，可以容纳10个人入住。周边环境非常便利，距离LEGOLAND 6英里，距离Sherman's Antiques 2.5英里，，距离Walmart就更近了，走路就可以去Lake ...
From $180 per night (USD)
VRBO
From $218 per night (USD)
VRBO
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 $218 per night (USD)
VRBO
$Spacious Winter Haven Home w\/ Pool Near Legoland!$
Click For Pricing
Expedia
Spacious 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 ...
Click For Pricing
Expedia
From $160 per night (USD)
VRBO
Vrbo Property
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 $160 per night (USD)
VRBO
Click For Pricing
Expedia
2 Bedroom 644905 by Houzlet
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Embrace Lake Life and Unwind on the Waterfront Your Lakefront Oasis Awaits: Nestled directly on the picturesque Lake M ...
Click For Pricing
Expedia
Click For Pricing
VRBO
Palm Frond Place | House in Winter Haven with a game room, pool, and in-home gym
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Palm Frond Place Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
Click For Pricing
VRBO
From $138 per night (USD)
Expedia
Cozy 1 BR Apt on Lake Howard with Lanai Patio, Dock & Kayaks
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Nestled along the tranquil shores of Lake Howard, this cozy studio apartment retreat offers breathtaking water views, mo ...
From $138 per night (USD)
Expedia
Click For Pricing
Expedia
New Listing! Close to Legoland! Sleeps 6 - 3 Beds
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Welcome to our modern 3 bedroom home, the perfect vacation rental for a group of 6. Your stay here promises relaxation a ...
Click For Pricing
Expedia
Click For Pricing
Expedia
Two Connected Houses, 6 Bedrooms, Sleeps 12, Close to Legoland! Pet Friendly!
Bedrooms:
2
Bathrooms:
6
Sleeps:
12
Experience the ultimate getaway. A unique rental with two connected 3-bedroom homes, perfect for a group of 12. With 6 c ...
Click For Pricing
Expedia
$Lakefront condo\n55+ community$
From $147 per night (USD)
VRBO
Lakefront condo\n55+ community
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Fully furnished. Bring only your clothing. Pool, shuffle board and dock for fishing. Sunroom included. Covered parking. ...
From $147 per night (USD)
VRBO
From $395 per night (USD)
Expedia
Lakefront Winter Haven Retreat: Hot Tub & Patio!
Bedrooms:
4
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 $395 per night (USD)
Expedia
From $92 per night (USD)
VRBO
Winter Haven Vacation Rental ~ 1 Mi to Downtown!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Encompassed by downtown attractions, sprawling lakes, and world-class theme parks, this 1-bed, 1-bath vacation rental in ...
From $92 per night (USD)
VRBO
From $118 per night (USD)
Expedia
Cute & Pet Friendly! Near Legoland!
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
xplore the enchanting Greater Winter Haven at our charming home offering an adorable outdoor space, pet and family-frien ...
From $118 per night (USD)
Expedia
$Lakefront 2 story 4\/2 bungalo with huge yard.$
From $189 per night (USD)
VRBO
Lakefront 2 story 4\/2 bungalo with huge yard.
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Property Description fully renovated lake front property with big back porch and yard flowing to the lake. The house has ...
From $189 per night (USD)
VRBO
From $416 per night (USD)
VRBO
Lake View, Game Room, 10 minutes to Legoland - Perfect for Large Families!
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
Welcome to The Elby, a fully renovated 1940's lake home with spacious rooms, modern amenities, and indoor and outdoor ga ...
From $416 per night (USD)
VRBO
$Large 3\/1 Near DownTown and Dining$
From $150 per night (USD)
VRBO
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 $150 per night (USD)
VRBO
$5 Bedroom Chain of Lakes Home w\/AC Pet Friendly$
Click For Pricing
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 ...
Click For Pricing
VRBO
$Beautiful Spacious 2bd w\/patio near LEGOLAND$
From $125 per night (USD)
VRBO
Beautiful Spacious 2bd w\/patio near LEGOLAND
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
At this property you will find this area quiet in a peaceful neighborhood with a large backyard for family gatherings o ...
From $125 per night (USD)
VRBO
From $98 per night (USD)
VRBO
Vintage Love Studio
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Come and souk up the uniqueness and custom build of this vintage place, turned into a luxurious oasis. This is a cozy st ...
From $98 per night (USD)
VRBO
Click For Pricing
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 ...
Click For Pricing
VRBO
From $242 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 $242 per night (USD)
Expedia
$Florida Beachy Palms 2\/1 Home. No Cleaning Fee!$
From $117 per night (USD)
VRBO
Florida Beachy Palms 2\/1 Home. No Cleaning Fee!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
This property is a beautifully updated 2/1 home. Property comes equipped with a full kitchen, living room, smart TV, ce ...
From $117 per night (USD)
VRBO
Click For Pricing
VRBO
Tiffany's Luxury Vacation Home Near Legoland FL
Bedrooms:
0
Bathrooms:
1
Sleeps:
2
Located in Ruby Lake, a gated community, this 2869 Sq ft spectacular home is in 'Show Place' condition. This home has 4 ...
Click For Pricing
VRBO
From $192 per night (USD)
VRBO
Modern heated pool (salted) home 15min to Legoland
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
About this space Welcome to Lakeside Landing! Get away from the hustle of the city to a tranquil getaway in Winter Have ...
From $192 per night (USD)
VRBO
From $199 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 $199 per night (USD)
VRBO
From $120 per night (USD)
VRBO
Updated 2 Bedroom Condo On Lake Lulu
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Conveniently locate in Winter Haven one mile from Lego Land and Shopping. Two bed rooms, updated kitchen, balcony, commo ...
From $120 per night (USD)
VRBO
From $180 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 $180 per night (USD)
Expedia
Click For Pricing
Expedia
Private Entrance Suite in Cypress Gardens near Legoland
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Guest Suite with completely separate entrance and full bath in safe, quiet neighborhood in the Cypress Gardens area of W ...
Click For Pricing
Expedia
$Everything is Awesome at this Lego Themed Pool House 4\/2, 1 Mile From Legoland$
Click For Pricing
VRBO
Everything is Awesome at this Lego Themed Pool House 4\/2, 1 Mile From Legoland
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
The Lego House, where everything is awesome, thousands of Lego pieces for you to play, it is the AWESOMEST house, with L ...
Click For Pricing
VRBO
From $441 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 $441 per night (USD)
VRBO
Click For Pricing
Expedia
Vibrant Lakeside retreat centrally located
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Vibrant Lakeside oasis. A water enthusiasts' paradise! Stunning views of the Lake Buckeye the moment you step through th ...
Click For Pricing
Expedia
From $289 per night (USD)
VRBO
★Spacious 4-bedroom 2-bath Abode Close to All★
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
This beautiful family-friendly home is ideally located near all of central Florida's attractions. Only a few minutes fro ...
From $289 per night (USD)
VRBO
$View Container 5*Centrally Located*Private Bed\/Bath$
From $90 per night (USD)
Expedia
View Container 5*Centrally Located*Private Bed\/Bath
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
WELCOME! Lake Mariam Container Home sits on 2.6 acres of Lakefront Property. If hospitality & peace is what you want, ou ...
From $90 per night (USD)
Expedia
From $165 per night (USD)
VRBO
A lakeside sunset delight near Disney, Universal, Sea World, Busch, LegoLand
Bedrooms:
3
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 $165 per night (USD)
VRBO
From $150 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 $150 per night (USD)
Expedia
From $241 per night (USD)
VRBO
Charming Lakefront Pool Home - 5 Min to Legoland!
Bedrooms:
3
Bathrooms:
4
Sleeps:
7
Our 4 bedroom, 3 bath home is also lakefront, making it a perfect spot for large groups to travel together. Enjoy your e ...
From $241 per night (USD)
VRBO
From $447 per night (USD)
VRBO
Perfect Vacation on the Chain of Lakes with a Pool!
Bedrooms:
5
Bathrooms:
5
Sleeps:
14
Escape to paradise on the Chain of Lakes! The Lake House at 1443 S. Lake Roy Drive welcomes you to a 5,000 square foot r ...
From $447 per night (USD)
VRBO
From $158 per night (USD)
VRBO
Bright Waterfront Home on Winter Haven's Lake Jessie
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
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 $158 per night (USD)
VRBO
From $110 per night (USD)
VRBO
Welcome Snowbirds, Sunbirds welcome you! Newly Renovated
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Spacious 3 bedroom 2 bath family home awaiting your arrival! Amenities include: Cable, AC, WiFi, and Computer with Fax ...
From $110 per night (USD)
VRBO
From $94 per night (USD)
VRBO
Farm House Stay 5 Miles to Legoland!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Welcome to our farm! This is a great place to come get away from those cold winters! You can come relax after a long day ...
From $94 per night (USD)
VRBO
From $145 per night (USD)
VRBO
LEGOLAND Wonderful 2 Queen Beds-bring pet.FUN-SUN
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
After you’ve soaked up the central Florida lifestyle, you can relax on a comfortable bed made up with premium linens and ...
From $145 per night (USD)
VRBO
From $63 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 $63 per night (USD)
VRBO
From $199 per night (USD)
VRBO
Lake Rochelle Rental Lakefront
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Huge, fenced yard with quaint 3/2 trilevel house overlooking Lake Rochelle in Northeast Winter Haven. Just minutes fro ...
From $199 per night (USD)
VRBO

Search Your Destination Now!

Winter Haven Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 152 Rentals