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 $185 per night (USD)
VRBO
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 $185 per night (USD)
VRBO
From $392 per night (USD)
Expedia
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 $392 per night (USD)
Expedia
From $280 per night (USD)
VRBO
Roe Family Lake House on Lake McLeod - Close to Legoland
Bedrooms:
1
Bathrooms:
2
Sleeps:
7
We can't wait for you to enjoy our fully renovated, family friendly lake house. It's a happy home that provides a wonder ...
From $280 per night (USD)
VRBO
From $323 per night (USD)
Expedia
Disney Castle Cove - Private Pool & Community Boat Ramp close to Legoland
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Discover the perfect vacation rental: a Disney-themed 4-bedroom, 2-bath home just 34 miles from Disney World Resort. Enj ...
From $323 per night (USD)
Expedia
From $568 per night (USD)
VRBO
Legoland's Luxury Estate
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
This peaceful neighborhood is located less than 5 minutes away from Legoland! A great vacation spot for the whole family ...
From $568 per night (USD)
VRBO
From $254 per night (USD)
VRBO
Charming 2-bedroom house, with AC, WiFi in superb Winter Haven, LEGOLAND CITY
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Winter Haven/LEGOLAND CITY is waiting for you at this 2-bedroom house. This beautiful property features 1 king bed and 1 ...
From $254 per night (USD)
VRBO
From $1270 per night (USD)
VRBO
Perfect Family Outing: 2 Themed Rooms Await | Near Lake Dexter
Bedrooms:
2
Bathrooms:
2
Sleeps:
10
Enjoy a lively, LEGO-filled adventure! Steps from Lake Dexter and 11 miles away from Historic Bok Tower Gardens perfect ...
From $1270 per night (USD)
VRBO
From $785 per night (USD)
VRBO
Kingdom Theme Standard: Fairy-Tale Dreams, Onsite Dining, LEGOLAND Next Door
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
Enjoy a lively, LEGO-filled adventure! Steps from Lake Dexter and 11 miles away from Historic Bok Tower Gardens perfect ...
From $785 per night (USD)
VRBO
From $636 per night (USD)
VRBO
Adventure Filled Resort Perfect for Family Getaway | Free Onsite Parking
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
Enjoy a lively, LEGO-filled adventure! Steps from Lake Dexter and 11 miles away from Historic Bok Tower Gardens perfect ...
From $636 per night (USD)
VRBO
From $1276 per night (USD)
VRBO
Theme Park at your Door Steps | Near Lake Dexter | Waterpark and Pool Access
Bedrooms:
2
Bathrooms:
2
Sleeps:
10
Enjoy a lively, LEGO-filled adventure! Steps from Lake Dexter and 11 miles away from Historic Bok Tower Gardens perfect ...
From $1276 per night (USD)
VRBO
From $1038 per night (USD)
VRBO
LEGOLAND Bungalow Bliss, Family Play Areas, 2 Rooms, Water Park Access
Bedrooms:
2
Bathrooms:
2
Sleeps:
10
Enjoy a lively, LEGO-filled adventure! Steps from Lake Dexter and 11 miles away from Historic Bok Tower Gardens perfect ...
From $1038 per night (USD)
VRBO
From $1569 per night (USD)
VRBO
Medieval Dream Stay, Kingdom Themed Room, Onsite LEGO Fun, 2 Rooms
Bedrooms:
2
Bathrooms:
2
Sleeps:
10
Enjoy a lively, LEGO-filled adventure! Steps from Lake Dexter and 11 miles away from Historic Bok Tower Gardens perfect ...
From $1569 per night (USD)
VRBO
From $1588 per night (USD)
VRBO
Adventurer's Dream Room, Legoland Hotel, Mini Golf Excursion, 2 Family Stays
Bedrooms:
2
Bathrooms:
2
Sleeps:
10
Enjoy a lively, LEGO-filled adventure! Steps from Lake Dexter and 11 miles away from Historic Bok Tower Gardens perfect ...
From $1588 per night (USD)
VRBO
From $638 per night (USD)
VRBO
Theme Park at your Door Steps | Near Lake Dexter | Waterpark and Pool Access
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
Enjoy a lively, LEGO-filled adventure! Steps from Lake Dexter and 11 miles away from Historic Bok Tower Gardens perfect ...
From $638 per night (USD)
VRBO
From $795 per night (USD)
VRBO
Adventure Awaits: LEGOLAND Hotel Florida, Creative Dining, Mini Golf Fun
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
Enjoy a lively, LEGO-filled adventure! Steps from Lake Dexter and 11 miles away from Historic Bok Tower Gardens perfect ...
From $795 per night (USD)
VRBO
$Family Dream Room with Playgrounds Galore | 2 Adventure Theme Rooms w\/ Pool$
From $1286 per night (USD)
VRBO
Family Dream Room with Playgrounds Galore | 2 Adventure Theme Rooms w\/ Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
10
Enjoy a lively, LEGO-filled adventure! Steps from Lake Dexter and 11 miles away from Historic Bok Tower Gardens perfect ...
From $1286 per night (USD)
VRBO
$Colorful Room w\/ Waterpark & Lego Fun! Free Parkin$
From $642 per night (USD)
VRBO
Colorful Room w\/ Waterpark & Lego Fun! Free Parkin
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
Enjoy a lively, LEGO-filled adventure! Steps from Lake Dexter and 11 miles away from Historic Bok Tower Gardens perfect ...
From $642 per night (USD)
VRBO
From $518 per night (USD)
VRBO
Beach Retreat Bungalow: Family Joy, LEGO Surprises, Steps from the Waterpark
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
Enjoy a lively, LEGO-filled adventure! Steps from Lake Dexter and 11 miles away from Historic Bok Tower Gardens perfect ...
From $518 per night (USD)
VRBO
From $390 per night (USD)
VRBO
Great get away for the entire family. Enjoy theme parks and great restaurants.
Bedrooms:
3
Bathrooms:
5
Sleeps:
14
Get transported to a galaxy far, far away! Even if you are not a Star Wars fan, this home offers all the space to launch ...
From $390 per night (USD)
VRBO
From $109 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 $109 per night (USD)
VRBO
From $196 per night (USD)
VRBO
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 $196 per night (USD)
VRBO
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
$Beautiful Lake Front cottage w\/ heated pool & Hot Tub, 23 miles from Disney$
From $378 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 $378 per night (USD)
VRBO
From $83 per night (USD)
VRBO
55+ community, Sleeps 6-8, Minimum monthly rental, Pets Considered
Bedrooms:
2
Bathrooms:
4
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 $83 per night (USD)
VRBO
From $234 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 $234 per night (USD)
VRBO
From $566 per night (USD)
VRBO
Huge Luxury Lake House on the Chain of Lakes - near Legoland!
Bedrooms:
5
Bathrooms:
5
Sleeps:
15
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 $566 per night (USD)
VRBO
From $218 per night (USD)
VRBO
Bright Waterfront Home on Winter Haven's Lake Jessie
Bedrooms:
3
Bathrooms:
3
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 $218 per night (USD)
VRBO
$3\/ 2 kid friendly home, only minutes to Legoland.$
From $204 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 $204 per night (USD)
VRBO
From $984 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 $984 per night (USD)
VRBO
From $115 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 $115 per night (USD)
VRBO
From $172 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 $172 per night (USD)
VRBO
Click For Pricing
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 ...
Click For Pricing
Expedia
From $496 per night (USD)
VRBO
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 $496 per night (USD)
VRBO
Click For Pricing
Expedia
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
Expedia
From $314 per night (USD)
VRBO
Adult-Only Love Hotel with Mermaid Pool
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
(All guests must be 18+ years of age.) Adult-only love hotel with k*nk dungeon equipment & mermaid pool with deep plung ...
From $314 per night (USD)
VRBO
From $224 per night (USD)
Expedia
Legoland on The Lake Gem!Close to Disney! All you need in one place! Cozy&Lovely
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This cozy apartment is in the heart of Winter Haven! It is at a short distance from Legoland park, only 3.6 mi and 13 mi ...
From $224 per night (USD)
Expedia
$The Exclusive Tatman Evergreen Suite\n\n$
From $120 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 $120 per night (USD)
VRBO
$THE SIGNATURE ORANGE GROVE SUITE\n\n$
From $100 per night (USD)
Expedia
THE SIGNATURE ORANGE GROVE SUITE\n\n
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Wooded views with serene & complete privacy ,ultra modern private large master bedroom suite with Tuscany Stone private ...
From $100 per night (USD)
Expedia
From $411 per night (USD)
VRBO
Legoland Family & Pet Friendly Pool Home
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Nice quiet neighborhood with large saltwater pool, four spacious bedrooms, two living areas, updated stainless appliance ...
From $411 per night (USD)
VRBO
From $280 per night (USD)
Expedia
On The Chain Connected By Chain Of Lakes
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Spacious and completely renovated 2000 sq ft home! It features a lovely back patio with fire pit and both screened and ...
From $280 per night (USD)
Expedia
From $367 per night (USD)
VRBO
Charming Eagle Lake Getaway: Relax & Unwind Near Scenic Trails & Nature Spots!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to Your Perfect Eagle Lake Getaway! Nestled near the heart of Winter Haven, Florida, this cozy retreat is the i ...
From $367 per night (USD)
VRBO
From $284 per night (USD)
Expedia
Game Garage + Relaxing Couches and beds + Kids Play room and more
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Newly renovated bathrooms and kitchens. Recline on the leather couches inside or sit by the bonfire outside. Super comfy ...
From $284 per night (USD)
Expedia
From $416 per night (USD)
VRBO
Live Oak Oasis - Getaway Close to Legoland! Sleeps 8 Guests, Fenced yard, Games
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Bring the whole family to this great place with lots of room for fun. Experience the perfect family getaway in this spac ...
From $416 per night (USD)
VRBO
From $236 per night (USD)
Expedia
Westwood Cottage- 3 BDRM, Perfect for Families!
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Spend a memorable family fun-filled getaway at this comfortable home in Winter Haven! The 3-bedroom, 1-bath home has ame ...
From $236 per night (USD)
Expedia
$Enchanting Room w\/ Lego Themes, Mini Golf & Outdoor Pool$
From $642 per night (USD)
VRBO
Enchanting Room w\/ Lego Themes, Mini Golf & Outdoor Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
Enjoy a lively, LEGO-filled adventure! Steps from Lake Dexter and 11 miles away from Historic Bok Tower Gardens perfect ...
From $642 per night (USD)
VRBO
From $794 per night (USD)
VRBO
Pirate Island Hotel: Splashy Pirate Adventure, Playgrounds, Near Legoland
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
Enjoy a lively, LEGO-filled adventure! Steps from Lake Dexter and 11 miles away from Historic Bok Tower Gardens perfect ...
From $794 per night (USD)
VRBO
From $1284 per night (USD)
VRBO
Playful Stay Perfect for Family Getaway | 2 Units
Bedrooms:
2
Bathrooms:
2
Sleeps:
10
Enjoy a lively, LEGO-filled adventure! Steps from Lake Dexter and 11 miles away from Historic Bok Tower Gardens perfect ...
From $1284 per night (USD)
VRBO
From $1585 per night (USD)
VRBO
2 Pirate Theme Rooms, Legoland Resort, Treasure-Fun Playscape, Near Water Park
Bedrooms:
2
Bathrooms:
2
Sleeps:
10
Enjoy a lively, LEGO-filled adventure! Steps from Lake Dexter and 11 miles away from Historic Bok Tower Gardens perfect ...
From $1585 per night (USD)
VRBO
From $1125 per night (USD)
VRBO
Adventurer's Dream Room, Legoland Hotel, Mini Golf Excursion, 2 Family Stays
Bedrooms:
2
Bathrooms:
2
Sleeps:
10
Enjoy a lively, LEGO-filled adventure! Steps from Lake Dexter and 11 miles away from Historic Bok Tower Gardens perfect ...
From $1125 per night (USD)
VRBO
$Family Dream Room with Playgrounds Galore | 2 Adventure Theme Rooms w\/ Pool$
From $915 per night (USD)
VRBO
Family Dream Room with Playgrounds Galore | 2 Adventure Theme Rooms w\/ Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
10
Enjoy a lively, LEGO-filled adventure! Steps from Lake Dexter and 11 miles away from Historic Bok Tower Gardens perfect ...
From $915 per night (USD)
VRBO
From $420 per night (USD)
VRBO
Beach Retreat Bungalow: Family Joy, LEGO Surprises, Steps from the Waterpark
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
Enjoy a lively, LEGO-filled adventure! Steps from Lake Dexter and 11 miles away from Historic Bok Tower Gardens perfect ...
From $420 per night (USD)
VRBO
From $515 per night (USD)
VRBO
Theme Park at your Door Steps | Near Lake Dexter | Waterpark and Pool Access
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
Enjoy a lively, LEGO-filled adventure! Steps from Lake Dexter and 11 miles away from Historic Bok Tower Gardens perfect ...
From $515 per night (USD)
VRBO
From $561 per night (USD)
VRBO
Adventure Awaits: LEGOLAND Hotel Florida, Creative Dining, Mini Golf Fun
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
Enjoy a lively, LEGO-filled adventure! Steps from Lake Dexter and 11 miles away from Historic Bok Tower Gardens perfect ...
From $561 per night (USD)
VRBO
$Colorful Room w\/ Waterpark & Lego Fun! Free Parkin$
From $455 per night (USD)
VRBO
Colorful Room w\/ Waterpark & Lego Fun! Free Parkin
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
Enjoy a lively, LEGO-filled adventure! Steps from Lake Dexter and 11 miles away from Historic Bok Tower Gardens perfect ...
From $455 per night (USD)
VRBO
From $76 per night (USD)
VRBO
Private Entrance 1 Bd 1.5 Bath Guest Suite in Cypress Gardens near Legoland
Bedrooms:
2
Bathrooms:
1
Sleeps:
5
1 bedroom, 1.5 bath In-law Guest Suite with private entrance in safe, quiet neighborhood in the Cypress Gardens area of ...
From $76 per night (USD)
VRBO
From $290 per night (USD)
Expedia
Charming 3-bedroom house in fantastic Winter Haven with WiFi, AC, Community Pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Located in Winter Haven, enjoy what this 3-bedroom house has to offer. With 2 queen beds and 1 twin bed, guests can rela ...
From $290 per night (USD)
Expedia
From $112 per night (USD)
VRBO
Cozy Legoland Guest House with Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
Private Guest House wt Pool Close to Legoland! Only 3 miles from Legoland, 30 miles from Disney, and 2 miles from Chain ...
From $112 per night (USD)
VRBO
From $289 per night (USD)
Expedia
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 $289 per night (USD)
Expedia
From $271 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 $271 per night (USD)
VRBO
From $336 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 $336 per night (USD)
Expedia
$Private\/Spacious 1BR Central Near LegoLand 2 Miles$
From $183 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 $183 per night (USD)
VRBO
From $184 per night (USD)
Expedia
New remodeled Lakefront Vacation Home on the Chain of Lakes in Winter Haven
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
New remodeled Lakefront Vacation Home on the Chain of Lakes right next to Winter Haven Municipal Airport across from Bro ...
From $184 per night (USD)
Expedia
From $429 per night (USD)
VRBO
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 $429 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 $199 per night (USD)
VRBO
Bright Cypress Gardens Home Near Legoland!
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
A fun-filled family escape awaits at this lovely home in Cypress Gardens! This 3-bedroom, 2-bathroom vacation rental pro ...
From $199 per night (USD)
VRBO
From $362 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 $362 per night (USD)
Expedia
From $406 per night (USD)
VRBO
Heated Pool, Arcade with PS5, 5min from Legoland-Stylish LakeHome
Bedrooms:
3
Bathrooms:
5
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 $406 per night (USD)
VRBO
Click For Pricing
Expedia
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
Expedia
From $663 per night (USD)
VRBO
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 $663 per night (USD)
VRBO
From $408 per night (USD)
Expedia
LAKE HOUSE WITH PRIVATE Free HEATED POOL & GAME ROOM 4 min FROM LEGOLAND
Bedrooms:
3
Bathrooms:
5
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 $408 per night (USD)
Expedia
Click For Pricing
VRBO
Peaceful Garden Retreat
Bedrooms:
2
Bathrooms:
4
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
VRBO
$★2\/1★Central★Location★☀2-Mile LEGOLAND&Dining☀$
From $133 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 $133 per night (USD)
Expedia
$Winter Haven Retreat w\/ Private Pool!$
From $301 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 $301 per night (USD)
VRBO
Click For Pricing
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 ...
Click For Pricing
Expedia
From $212 per night (USD)
VRBO
Family-Friendly Eagle Lake Home, 7 Mi to Legoland!
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Treat your family to a fun-packed Sunshine State getaway at this 3-bedroom, 2-bath Eagle Lake vacation rental! Nestled i ...
From $212 per night (USD)
VRBO
From $101 per night (USD)
Expedia
2 Bedroom 1.5 bath home in 55+ age community in Winter Haven FL
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
You must be over 55+ age so you can rent this property. 2 people are only allowed to this property with guest able to st ...
From $101 per night (USD)
Expedia
$Stylish Waterfront Lake Wales Home Rental w\/ Dock!$
From $318 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 $318 per night (USD)
VRBO
$Glass Haven: Serene Getaway 7 min from Legoland!\n\n\n\n\n$
Click For Pricing
Expedia
Glass Haven: Serene Getaway 7 min from Legoland!\n\n\n\n\n
Bedrooms:
3
Bathrooms:
2
Sleeps:
7
Come relax with your whole family in this peaceful home! Our 2 bedroom 2.5 bathroom home is very spacious and can accomm ...
Click For Pricing
Expedia
$Cozy Lakefront Home w\/ Pool -7 mins from Legoland$
From $252 per night (USD)
VRBO
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 $252 per night (USD)
VRBO
From $149 per night (USD)
Expedia
Cozy house in peaceful Lake Alfred with AC, WiFi
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Experience Lake Alfred like a local in this welcoming 1-bedroom house. With amenities like AC, a hair dryer, and WiFi, g ...
From $149 per night (USD)
Expedia
$The Lake Alfred Citrus Wood Guest Cabin\n\n$
From $149 per night (USD)
VRBO
The Lake Alfred Citrus Wood Guest Cabin\n\n
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Relax and enjoy this modern beautifully appointed Guesthouse Cabin with an abundance of exceptional privacy and a peacef ...
From $149 per night (USD)
VRBO
From $241 per night (USD)
Expedia
Hot Tub & Fire Pit: Lakefront Home on Lake Eloise
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Waterfront Patio | Sunset Views | Fishing & Birdwatching On-Site | ~1 Mi to Legoland Situated on an idyllic peninsula s ...
From $241 per night (USD)
Expedia
From $816 per night (USD)
VRBO
Walk to LEGOLAND- Heated Pool- Putting Green- Beach- Fire Pit- Boat Dock-Sunsets
Bedrooms:
5
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 $816 per night (USD)
VRBO
$Legoland Poolside Paradise - 3 BR\/2BA w\/ Pool - 1 Mile from Legoland!$
From $336 per night (USD)
Expedia
Legoland Poolside Paradise - 3 BR\/2BA w\/ Pool - 1 Mile from Legoland!
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 $336 per night (USD)
Expedia
From $90 per night (USD)
VRBO
Cozy Haven Apartment
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Escape to a brilliant corporate apartment in Winter Haven. This charming 1-bedroom retreat features a cozy queen bed and ...
From $90 per night (USD)
VRBO
From $466 per night (USD)
Expedia
FRESHLY REMODELED – 5BR in Winter Haven – Only 7 Minutes to LEGOLAND!
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
This freshly remodeled spacious 5-bedroom home comfortably sleeps 10 guests and is designed with family fun and relaxati ...
From $466 per night (USD)
Expedia
From $464 per night (USD)
VRBO
You'll find all the newest upgraded services at our room !!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Guests at the Holiday Inn Winter Haven can start the day with a workout in the 24-hour fitness center or enjoy a refresh ...
From $464 per night (USD)
VRBO
From $374 per night (USD)
VRBO
Welcome to our Lake Wales Hotel in Central Florida, check out our .
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Relax in our large guest rooms that feature a 50-inch LCD HDTV, microwave, mini fridge and a well-lit desk with an ergon ...
From $374 per night (USD)
VRBO
$Luxury Style home w\/ fire pit \nnear LakeHoward \n20min to LEGOLAND! \nPet-Friendly$
From $175 per night (USD)
VRBO
Luxury Style home w\/ fire pit \nnear LakeHoward \n20min to LEGOLAND! \nPet-Friendly
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
Welcome to LuxStay! The Luxurious Way!! Here is our fully Remodeled Home!! We have styled designed this home perfectly f ...
From $175 per night (USD)
VRBO
From $305 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 $305 per night (USD)
VRBO
Click For Pricing
VRBO
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
VRBO

Search Your Destination Now!

Winter Haven Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 191 Rentals