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 $184 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 $184 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 $239 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 $239 per night (USD)
VRBO
$Experience the Chain of Lakes from Your Private Lake House Retreat w\/ a Pool!$
From $445 per night (USD)
VRBO
Experience the Chain of Lakes from Your Private Lake House Retreat w\/ 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 $445 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 $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
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 $195 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 $195 per night (USD)
VRBO
From $80 per night (USD)
Expedia
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)
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 $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
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 $199 per night (USD)
VRBO
Luxury 3BR Lake House on Quiet Private Lake, with Pool and Hot Tub
Bedrooms:
5
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 $199 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 $283 per night (USD)
Expedia
★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 $283 per night (USD)
Expedia
$View Container 5*Centrally Located*Private Bed\/Bath$
From $90 per night (USD)
VRBO
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)
VRBO
From $551 per night (USD)
Expedia
Luxury Lakefront Oasis | Heated Pool, Dock & Kayaks | Home Theatre & EV Charger | Near Theme Parks
Bedrooms:
4
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 $551 per night (USD)
Expedia
From $333 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 $333 per night (USD)
VRBO
$Luxury Home w\/ Lanai, Billiards, 6min to Legoland$
From $264 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 $264 per night (USD)
Expedia
From $191 per night (USD)
VRBO
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 $191 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
$*3\/2*GorgeousNEWLakeHome2AceLoc*4mi*LEGOLAND*1722$
From $150 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 $150 per night (USD)
VRBO
Click For Pricing
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- ...
Click For Pricing
Expedia
From $87 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 $87 per night (USD)
VRBO
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
$★2\/1★Central★Location★☀2-Mile LEGOLAND&Dining☀$
From $125 per night (USD)
VRBO
★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 $125 per night (USD)
VRBO
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 $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 $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
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 $473 per night (USD)
Expedia
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 $473 per night (USD)
Expedia
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 $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
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 $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
Click For Pricing
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 ...
Click For Pricing
VRBO
Click For Pricing
Expedia
Peaceful Garden Retreat
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Imagine waking up to a tranquil and restful location near Legoland, Tampa, and all the attractions and theme parks of Or ...
Click For Pricing
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 $99 per night (USD)
VRBO
Charming Home 5 Minutes From Legoland
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Great neighborhood! Peaceful, safe, friendly. Close to Legoland! 5 minute drive (1 mile). Relax and enjoy your time in ...
From $99 per night (USD)
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
From $126 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 $126 per night (USD)
Expedia
From $143 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 $143 per night (USD)
VRBO
$Beautiful Lake Front cottage w\/ heated pool & Hot Tub, 23 miles from Disney$
From $333 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 $333 per night (USD)
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 $140 per night (USD)
Expedia
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 $140 per night (USD)
Expedia
$A spacious gem w\/private lake front access, boating, restaurants, bars and more!$
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 $160 per night (USD)
Expedia
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 $160 per night (USD)
Expedia
From $279 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 $279 per night (USD)
VRBO
$*3\/2*GorgeousNEWLakeHome2AceLoc*4mi*LEGOLAND*1724$
From $150 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 $150 per night (USD)
Expedia
From $795 per night (USD)
VRBO
Spectacular Waterfront Home in Winter Haven
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
HIGHLIGHTS +Custom built in 2006 +Chef’s kitchen with Viking Professional appliances +Waterfront on 3 sides of the prop ...
From $795 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 $356 per night (USD)
VRBO
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 $356 per night (USD)
VRBO
From $185 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 $185 per night (USD)
VRBO
From $100 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 $100 per night (USD)
VRBO
From $88 per night (USD)
Expedia
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 $88 per night (USD)
Expedia
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 $272 per night (USD)
Expedia
Luxury Lakefront Oasis | Heated Pool, Dock & Kayaks | Home Theatre & EV Charger | Near Theme Parks
Bedrooms:
3
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 $272 per night (USD)
Expedia
From $351 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 $351 per night (USD)
VRBO
From $192 per night (USD)
Expedia
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)
Expedia
Click For Pricing
VRBO
A1 Family Getaway
Bedrooms:
2
Bathrooms:
5
Sleeps:
6
Amazing home located in eagle lake FL, 30 minutes away from Disney World and 20 minutes from Disney Land. Very close to ...
Click For Pricing
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
From $333 per night (USD)
VRBO
Heated Pool, Arcade with PS5, 5min from Legoland-Stylish LakeHome
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
One of the very few Luxury stays in Winter haven. Only 5 min to Legoland, 40 min from Busch Gardens, and 40 min from Dis ...
From $333 per night (USD)
VRBO
$Elegant Winter Haven Villa w\/ Dock & Lanai!$
From $369 per night (USD)
Expedia
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 $369 per night (USD)
Expedia
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 $350 per night (USD)
Expedia
Lakefront Lego Land Estate
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
Relax and enjoy the waterfront lifestyle in our beautiful home nestled on Lake Summit in Winter Haven. Located 1 mile ...
From $350 per night (USD)
Expedia
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
Click For Pricing
Expedia
Cozy retirement community with golf course
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Short term rental in 55+ age retirement community. Located in Carefree Country Club, a "Retirement Gem in Central Flori ...
Click For Pricing
Expedia
From $315 per night (USD)
VRBO
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 $315 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
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
$Private\/Spacious 1BR Central Near LegoLand 2 Miles$
From $130 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 $130 per night (USD)
VRBO
From $126 per night (USD)
VRBO
New remodeled Lakefront Vacation Home on the Chain of Lakes in Winter Haven
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
New remodeled Lakefront Vacation Home on the Chain of Lakes right next to Winter Haven Municipal Airport across from Bro ...
From $126 per night (USD)
VRBO
From $135 per night (USD)
VRBO
cozy for the family close to Legoland
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Come to a fully furnished house with a kitchen that's fully equipped and an enclosed gazebo in the back to enjoy the war ...
From $135 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 $128 per night (USD)
VRBO
Perfect Fun House for Theme Parks & Family Fun!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Nestled within easy reach of all the thrills of Florida's amusement parks, from Busch Gardens to Legoland, Disney World, ...
From $128 per night (USD)
VRBO
From $100 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 $100 per night (USD)
Expedia
From $220 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 $220 per night (USD)
VRBO
Click For Pricing
Expedia
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
Expedia
From $211 per night (USD)
VRBO
Central FL Vacation Home - Dog Friendly with no pet fee. 7 minutes to LEGOLand!!
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Welcome to Winter Haven, Florida and welcome to “The Florida House”!! This property offers several amenities that are t ...
From $211 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
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
From $269 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 $269 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
Click For Pricing
Expedia
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
Expedia
From $238 per night (USD)
VRBO
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 $238 per night (USD)
VRBO
$Florida Beachy Palms 2\/1 Home. No Cleaning Fee!$
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
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 $338 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 $338 per night (USD)
Expedia
Click For Pricing
VRBO
Relaxing location To 10 minutes Legoland , 40 minutes Disney word
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Perfect space for relaxing and sleeping, which coffee area, small refrigerator which water and sodas including, amazing ...
Click For Pricing
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
$5 Bedroom Chain of Lakes Home w\/AC Pet Friendly$
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
From $161 per night (USD)
VRBO
Chanti’s Place, Winter Haven. Great Longterm Stay
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Come stay at Chanti's Place for your next stay. Experience a secret hideaway in this stylish, boho-modern designed home. ...
From $161 per night (USD)
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
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

Search Your Destination Now!

Winter Haven Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 155 Rentals