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 $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
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 $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
From $126 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 $126 per night (USD)
VRBO
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 $187 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 $187 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 $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
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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 ...
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VRBO
From $211 per night (USD)
Expedia
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)
Expedia
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 $94 per night (USD)
Expedia
Cozy cottage. 6 Miles to Legoland. Pet Friendly! Fenced yard.
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
This cozy and inviting home is centrally located close to Legoland and a short drive to Disney and Tampa. With ample spa ...
From $94 per night (USD)
Expedia
From $125 per night (USD)
VRBO
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 $125 per night (USD)
VRBO
From $260 per night (USD)
Expedia
Adult-Only love hotel with mermaid pool.
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Daydream. Fantasize. And then indulge in what an idyllic retreat can look like for you. Comfortable linens to ease into ...
From $260 per night (USD)
Expedia
$The Exclusive Tatman Evergreen Suite\n\n$
From $89 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 $89 per night (USD)
VRBO
$THE SIGNATURE ORANGE GROVE SUITE\n\n$
From $89 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 $89 per night (USD)
Expedia
From $283 per night (USD)
VRBO
Legoland Winter Haven Pool Home
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Nice quiet neighborhood with large pool, four spacious bedrooms, two living areas, updated stainless appliances, private ...
From $283 per night (USD)
VRBO
From $190 per night (USD)
Expedia
Family-Friendly Winter Haven Home 9 Mi to Legoland
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Treat your family to a fun-filled getaway with this recently renovated vacation rental in Winter Haven as your home base ...
From $190 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
$Private\/Spacious 1BR Central Near LegoLand 2 Miles$
From $130 per night (USD)
Expedia
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)
Expedia
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 $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
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 $333 per night (USD)
Expedia
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)
Expedia
From $350 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 $350 per night (USD)
VRBO
From $100 per night (USD)
Expedia
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)
Expedia
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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 $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
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VRBO
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 ...
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VRBO
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
$★2\/1★Central★Location★☀2-Mile LEGOLAND&Dining☀$
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 $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
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Expedia
Stunning Lakefront - Heated Pool, Firepit, & Grill
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Brilliantly Blue Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
Click For Pricing
Expedia
Click For Pricing
VRBO
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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VRBO
$The Lake Alfred Citrus Wood Guest Cabin\n\n$
From $99 per night (USD)
Expedia
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 $99 per night (USD)
Expedia
From $217 per night (USD)
VRBO
Waterfront Winter Haven Studio on Lake Eloise!
Bedrooms:
1
Bathrooms:
0
Sleeps:
4
Situated on an idyllic peninsula surrounded by the calm waters of Lake Eloise, this 1-bathroom studio vacation rental in ...
From $217 per night (USD)
VRBO
From $172 per night (USD)
Expedia
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 $172 per night (USD)
Expedia
From $166 per night (USD)
VRBO
Relax with the whole family at this peaceful place.
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Retreat to the central Florida with your family or friends book this 4 bedroom 2 bath vacation rental. This home feature ...
From $166 per night (USD)
VRBO
From $59 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 $59 per night (USD)
Expedia
$Stylish Waterfront Lake Wales Home Rental w\/ Dock!$
From $242 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 $242 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
$Winter Haven Retreat w\/ Private Pool!$
From $217 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 $217 per night (USD)
VRBO
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Expedia
3 Bedroom 644960 by Houzlet
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Create Unforgettable Lake Memories in Comfort Embrace Lake Living: Create cherished memories by the lake at this invit ...
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Expedia
From $88 per night (USD)
VRBO
Winterset Lakeview Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
We invite you to Stay and Play at our Updated 2 Bedroom Condo with an all around Lake View located in the Prestigious Ga ...
From $88 per night (USD)
VRBO
$Cozy Lakefront Home w\/ Pool -7 mins from Legoland$
From $185 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 $185 per night (USD)
Expedia
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VRBO
Winter Haven Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Charming 3/2 home with no HOA! This single family home is conveniently located in the heart of Winter Haven. It sits on ...
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VRBO
From $414 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 $414 per night (USD)
VRBO
From $334 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 $334 per night (USD)
VRBO
$Luxury Style home w\/ fire pit \nnear LakeHoward \n20min to LEGOLAND! \nPet-Friendly$
From $143 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 $143 per night (USD)
VRBO
From $269 per night (USD)
VRBO
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)
VRBO
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
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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

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Winter Haven Rentals

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Results: 155 Rentals