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 $424 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 $424 per night (USD)
VRBO
$Winter Haven Home w\/ Pool Near Legoland!$
From $205 per night (USD)
Expedia
Winter Haven Home w\/ Pool Near Legoland!
Bedrooms:
2
Bathrooms:
5
Sleeps:
8
Discover your next family getaway at 'Little Haven!' The modern 3-bedroom, 2-bathroom property provides a comfortable oa ...
From $205 per night (USD)
Expedia
From $101 per night (USD)
VRBO
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)
VRBO
From $375 per night (USD)
Expedia
Adult-Only Love Hotel with Mermaid Pool
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Explore a world of pleasures at our adult-only love hotel, which features four themed bedroom options*, each designed to ...
From $375 per night (USD)
Expedia
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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 ...
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VRBO
From $185 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 $185 per night (USD)
Expedia
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VRBO
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 ...
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VRBO
$The Lake Alfred Citrus Wood Guest Cabin\n\n$
From $131 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 $131 per night (USD)
Expedia
$The Exclusive Tatman Evergreen Suite\n\n$
From $102 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 $102 per night (USD)
VRBO
$THE SIGNATURE ORANGE GROVE SUITE\n\n$
From $120 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 $120 per night (USD)
Expedia
$Lakefront 2 story 4\/2 bungalo with huge yard.$
From $223 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 $223 per night (USD)
VRBO
From $385 per night (USD)
Expedia
Peaceful Lakeside Retreat
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Tranquility awaits you at this beautiful lakefront home. We invite you to enjoy the best of Florida indoor/outdoor livi ...
From $385 per night (USD)
Expedia
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VRBO
Best sunsets in Winter Haven. Lakefront home 5 minutes from downtown!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Enjoy the best sunset in Winter Haven on a hammock, then drive 3 mins for dinner downtown. You can't beat this slice of ...
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VRBO
$Comfortable bedroom and house to stay in w\/ swimming pool.$
From $144 per night (USD)
Expedia
Comfortable bedroom and house to stay in w\/ swimming pool.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The bedroom i am renting is very comfortable, has tv, dresser, bistro table and chairs, floor lamp, two night stands wit ...
From $144 per night (USD)
Expedia
From $702 per night (USD)
VRBO
Lake-Walk2LEGOLAND-Heated SaltWtr Pool-Putting Green-Beach-Fire Pit-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 $702 per night (USD)
VRBO
From $237 per night (USD)
Expedia
Carefree Cove on Lake Connie - With Hot Tub! 15 mins to Legoland
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Nestled on the shores of Winter Haven's Lake Connie, this charming 3-bedroom promises a tranquil escape. This cozy lake ...
From $237 per night (USD)
Expedia
From $251 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 $251 per night (USD)
VRBO
From $287 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 $287 per night (USD)
Expedia
From $399 per night (USD)
VRBO
Legoland Poolside Paradise
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Nestled in the heart of Central Florida, our charming retreat offers the perfect blend of relaxation and adventure. With ...
From $399 per night (USD)
VRBO
From $280 per night (USD)
VRBO
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)
VRBO
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VRBO
Cozy 3 bedroom central hideaway
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Enjoy quick and easy self check in with lock box system. Beautiful, quiet and secure community. Enjoy spacious and elega ...
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VRBO
$3br\/2ba Haven away from home w\/master suite, 6 mi. to Legoland & pet-friendly!$
From $174 per night (USD)
Expedia
3br\/2ba Haven away from home w\/master suite, 6 mi. to Legoland & pet-friendly!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Location, Location, Location ! Bring the whole family to this spacious home with lots of room for fun! Centrally locate ...
From $174 per night (USD)
Expedia
From $2335 per night (USD)
VRBO
341 Legoland Sherman's Antiques Lake Silver
Bedrooms:
1
Bathrooms:
3
Sleeps:
10
Summary: Welcome to our charming home located in a peaceful neighborhood, perfect for families and small groups. This co ...
From $2335 per night (USD)
VRBO
From $235 per night (USD)
Expedia
Lake House on the LEGOLAND Chain-of-Lakes with Private Pool, Beach and Boat Dock
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Stay comfortably in Central Florida at this 4-bedroom Lakefront Home on the Lego Land Chain-of-Lakes! With two Master Su ...
From $235 per night (USD)
Expedia
From $150 per night (USD)
VRBO
Family-Friendly Haven near Downtown - Fast Wifi
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
Summary: Escape to our inviting 3-bedroom, 1-bath Family-Friendly Retreat near downtown Winter Haven, FL—a haven for fam ...
From $150 per night (USD)
VRBO
$Cozy Winter Haven Escape | Pet-Friendly\/Fenced Lot$
From $161 per night (USD)
Expedia
Cozy Winter Haven Escape | Pet-Friendly\/Fenced Lot
Bedrooms:
1
Bathrooms:
4
Sleeps:
8
Summary: Welcome to Cozy Retreat near Legoland! Our charming 3-bedroom, 1-bath home offers a pullout sofa bed, a fully s ...
From $161 per night (USD)
Expedia
From $207 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 $207 per night (USD)
VRBO
From $231 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 $231 per night (USD)
Expedia
From $149 per night (USD)
VRBO
Tiny Paradise
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This Winter Haven studio boasts 1 inviting bedroom with a full bed. The space is equipped with essentials like WiFi, hea ...
From $149 per night (USD)
VRBO
From $112 per night (USD)
Expedia
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)
Expedia
From $206 per night (USD)
VRBO
- HIDDEN GEM - Spacious, minimal and clean! Legoland + Disney
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Consider this house your home away from home while you visit Florida! This fantastic property boasts 4 bedrooms, inclu ...
From $206 per night (USD)
VRBO
From $227 per night (USD)
Expedia
15 minutes to Legoland- Serene Lakeside Cottage Retreat
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to your serene escape in Winter Haven, just minutes away from the excitement of Legoland! This enchanting 3-bedr ...
From $227 per night (USD)
Expedia
From $182 per night (USD)
VRBO
Cozy house in peaceful Lake Alfred with AC, WiFi very secluded.
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Experience Lake Alfred like a local in this welcoming 1-bedroom house. With amenities like AC, coffee and WiFi, guests c ...
From $182 per night (USD)
VRBO
$4 Bedrm Central Home w\/Gameroom\n\n$
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Expedia
4 Bedrm Central Home w\/Gameroom\n\n
Bedrooms:
2
Bathrooms:
4
Sleeps:
15
Welcome to this charming house in Winter Haven. This superb property boasts 4 queen beds spread across 4 cozy bedrooms, ...
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Expedia
$4 Bedroom, Legoland, Pet Friendly, Pool, Gameroom\n\n$
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VRBO
4 Bedroom, Legoland, Pet Friendly, Pool, Gameroom\n\n
Bedrooms:
2
Bathrooms:
4
Sleeps:
15
This enjoyable house in Winter Haven offers 4 cozy bedrooms with a mix of queen, full, twin, and bunk beds. With WiFi, a ...
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VRBO
From $128 per night (USD)
Expedia
Charming 2-bedroom country house with AC, WiFi in Winter Haven
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Escape to this marvelous 2-bedroom Winter Haven country house retreat. With a cozy full bed and a comfy twin bed, guests ...
From $128 per night (USD)
Expedia
From $328 per night (USD)
VRBO
Getaway Clubhouse 5 mil Legoland & .5 mil Downtown
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Enjoy a relaxing stay in this spacious and comfortable home, perfect for families or groups. The open layout of the livi ...
From $328 per night (USD)
VRBO
From $285 per night (USD)
Expedia
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
Bedrooms:
3
Bathrooms:
2
Sleeps:
8
This delightful lake-life inspired cottage includes 2 bedrooms and 1 ½ baths, a fooseball table, and easily sleeps 7 gue ...
From $285 per night (USD)
Expedia
From $183 per night (USD)
VRBO
The Unique cozy studio
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Super comfortable! Modern clean fully functioning. centrally located in Winter Haven. 1/2 mile to downtown, less than 4 ...
From $183 per night (USD)
VRBO
From $165 per night (USD)
Expedia
Cozy Bungalow - 5 mi Legoland & 0.5 mi Dwntwn
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This cozy bungalow includes 3 bedrooms and 1 ½ baths, and it sleeps up to 8 guests comfortably! Located approximately ...
From $165 per night (USD)
Expedia
From $322 per night (USD)
VRBO
The Old Haven - An Enduring Piece of Nostalgia
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
This charming home was built in 1908 and is located 45 minutes from Tampa/Orlando. Fully furnished, this space is perfe ...
From $322 per night (USD)
VRBO
From $346 per night (USD)
Expedia
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 $346 per night (USD)
Expedia
From $220 per night (USD)
VRBO
Westwood Cottage- 3 BDRM, Perfect for Families!
Bedrooms:
1
Bathrooms:
4
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 $220 per night (USD)
VRBO
From $94 per night (USD)
Expedia
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 $94 per night (USD)
Expedia
$Enchanting Room w\/ Lego Themes, Mini Golf & Outdoor Pool$
From $465 per night (USD)
VRBO
Enchanting Room w\/ Lego Themes, Mini Golf & Outdoor Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
This listing is for a room within a hotel. ✦ Your room is 398 sq. ft, equipped with complimentary toiletries, TV. ✦ Da ...
From $465 per night (USD)
VRBO
From $570 per night (USD)
Expedia
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 $570 per night (USD)
Expedia
From $930 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 $930 per night (USD)
VRBO
From $1140 per night (USD)
Expedia
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 $1140 per night (USD)
Expedia
From $74 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 $74 per night (USD)
VRBO
From $912 per night (USD)
Expedia
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 $912 per night (USD)
Expedia
From $559 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 $559 per night (USD)
VRBO
From $456 per night (USD)
Expedia
Adventure Filled Resort Perfect for Family Getaway | Fun Pools!
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 $456 per night (USD)
Expedia
From $897 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 $897 per night (USD)
VRBO
From $734 per night (USD)
Expedia
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 $734 per night (USD)
Expedia
From $1119 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 $1119 per night (USD)
VRBO
From $1099 per night (USD)
Expedia
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 $1099 per night (USD)
Expedia
From $448 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 $448 per night (USD)
VRBO
From $557 per night (USD)
Expedia
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 $557 per night (USD)
Expedia
$Family Dream Room with Playgrounds Galore | 2 Adventure Theme Rooms w\/ Pool$
From $896 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 $896 per night (USD)
VRBO
$Colorful Room w\/ Waterpark & Lego Fun! Free Parkin$
From $450 per night (USD)
Expedia
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 $450 per night (USD)
Expedia
From $367 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 $367 per night (USD)
VRBO
From $392 per night (USD)
Expedia
5 BR home with large patio, pool & outdoor family fun - 7 mins to LEGOLAND!
Bedrooms:
2
Bathrooms:
5
Sleeps:
12
We accommodate late check-out and early check-in requests whenever possible. This spacious five-bedroom home sleeps 10 ...
From $392 per night (USD)
Expedia
From $203 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 $203 per night (USD)
VRBO
From $337 per night (USD)
Expedia
Serene, Cozy, Lakefront home
Bedrooms:
2
Bathrooms:
1
Sleeps:
7
Cozy meets calm at this quaint lakefront home. We are located on the Chain of Lakes in Winter Haven, where the waterfr ...
From $337 per night (USD)
Expedia
From $535 per night (USD)
VRBO
15% Off Florida Summer Vacation Rentals
Bedrooms:
4
Bathrooms:
6
Sleeps:
14
Escape to Emerald Anchor Escape, a spacious 6-bedroom lakefront retreat in Winter Haven, designed for the ultimate famil ...
From $535 per night (USD)
VRBO
From $197 per night (USD)
Expedia
Large Relaxing Home | Heated Pool+Ping Pong+Games!
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Enjoy the perfect blend of relaxation and entertainment in this newly renovated home, just 10 minutes from Legoland and ...
From $197 per night (USD)
Expedia
From $224 per night (USD)
VRBO
Spacious 5-bedroom house with WiFi, AC in welcoming Winter Haven
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
The Winter Haven home features five welcoming bedrooms, complete with two double beds and five single beds. It also incl ...
From $224 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
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VRBO
Cozy 1-Bedroom Retreat Near Downtown & Legoland
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to your perfect getaway! This charming one-bedroom unit offers all the essentials for a comfortable stay. The un ...
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VRBO
From $158 per night (USD)
Expedia
4 Mi to Legoland: Newly Built Home in Winter Haven
Bedrooms:
2
Bathrooms:
5
Sleeps:
8
3 Mi to Peppa Pig Theme Park | Families Welcome | Remote-Work Friendly Fill your next getaway with magical moments at t ...
From $158 per night (USD)
Expedia
From $284 per night (USD)
VRBO
Riverwood Circle
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Welcome to Riverwood Circle! A charming modern 2 story and 4 bedroom house, nestled in a peaceful winter haven neighborh ...
From $284 per night (USD)
VRBO
From $207 per night (USD)
Expedia
Brand new home located 45 minutes from Disney World & 5 minutes from Legoland.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Consider this house your home away from home while you visit Winter Haven. This amazing property boasts 3 bedrooms - one ...
From $207 per night (USD)
Expedia
$1\/1 condo located on Lk Lulu. 7 minutes from Legoland. access to hwy 27, 17 & I4$
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VRBO
1\/1 condo located on Lk Lulu. 7 minutes from Legoland. access to hwy 27, 17 & I4
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This 1-bedroom condo is perfect for your escape to Winter Haven. The bedroom features a cozy king bed, and the bathroom ...
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VRBO
From $337 per night (USD)
Expedia
Winter Haven Hideaway
Bedrooms:
2
Bathrooms:
6
Sleeps:
8
Welcome to your perfect Winter Haven Florida getaway near Legoland & Chain of Lakes! This spacious 3-bedroom, 2-bathroom ...
From $337 per night (USD)
Expedia
$8 Mi to Legoland: Winter Haven Home w\/ Lanai!$
From $93 per night (USD)
VRBO
8 Mi to Legoland: Winter Haven Home w\/ Lanai!
Bedrooms:
2
Bathrooms:
4
Sleeps:
5
Pet-Friendly Private Yard | Central Location | Families Welcome Experience the best of Winter Haven when you stay at th ...
From $93 per night (USD)
VRBO
Click For Pricing
Expedia
Epic Lakeside Resort – 2 Homes on 2 Acres with 800' of Waterfront
Bedrooms:
7
Bathrooms:
8
Sleeps:
20
Enjoy a wonderful family get away or corporate retreat at these premier waterfront HOMES on the famous Chain of (19) Lak ...
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Expedia
From $249 per night (USD)
VRBO
2-bedroom, 2-bath unit offers a family-friendly retreat just mins from LEGOLAND.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Modern 2BR/2BA Apartment – Perfect for LEGOLAND Getaways Welcome to your brand-new 2024 luxury apartment, conveniently ...
From $249 per night (USD)
VRBO
From $251 per night (USD)
Expedia
2-bedroom, 2-bath unit offers a family-friendly retreat just mins from LEGOLAND.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Modern 2BR/2BA Apartment – Perfect for LEGOLAND Getaways Welcome to your brand-new 2024 luxury apartment, conveniently ...
From $251 per night (USD)
Expedia
From $183 per night (USD)
VRBO
Charming Winter Haven Legoland Retreat with 3-bedrooms, close to Lakes
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Experience Winter Haven like a local in this 3-bedroom house. The bedrooms feature 2 queen beds and 2 twin bed, perfect ...
From $183 per night (USD)
VRBO
From $197 per night (USD)
Expedia
9 Mi to Legoland: Cozy Apartment in Winter Haven!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Dog Friendly w/ Fee | Gas Grill | Fenced Yard | 3 Mi to Town Retreat to Central Florida and book this 1-bedroom, 1-bath ...
From $197 per night (USD)
Expedia
From $96 per night (USD)
VRBO
Cozy 2-bedroom apartment in charming Winter Haven with WiFi, AC
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Get ready to relax in this 2-bedroom apartment in Winter Haven. This nice property features 1 queen bed and 2 twin beds, ...
From $96 per night (USD)
VRBO
From $98 per night (USD)
Expedia
🏖️⭐️GREAT VALUE ⭐️near Legoland🏖️Clean and cozy waterfront apt
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Relax with your family at this beautiful, peaceful 1b1b waterfront apartment. Retreat to Central Florida perfect for cou ...
From $98 per night (USD)
Expedia
From $145 per night (USD)
VRBO
Cozy Grand Room 1-bedroom apartment with WiFi, AC in charming Winter Haven
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Your home away from home in Winter Haven with 1 bedroom. This cozy apartment features a queen bed and a full bed, perfec ...
From $145 per night (USD)
VRBO
Click For Pricing
Expedia
A slice of paradise in central FL
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Experience luxurious resort living in this fully remodeled 2-bedroom, 2-bathroom home within the prestigious Country Clu ...
Click For Pricing
Expedia
From $246 per night (USD)
VRBO
4 Mi to Legoland: Poolside Paradise!
Bedrooms:
3
Bathrooms:
5
Sleeps:
5
Near Restaurants | Dedicated Space for Remote Work | BBQ Ready | Day Trips to Disney Looking to escape the cold weather ...
From $246 per night (USD)
VRBO
$6 Mi to Legoland: Retreat w\/ Pool & Fenced Yard$
From $250 per night (USD)
Expedia
6 Mi to Legoland: Retreat w\/ Pool & Fenced Yard
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Families Welcome | Day Trip to Disney | Game Nights at Home | Prime Location | 2,175 Sq Ft Escape to Florida and settle ...
From $250 per night (USD)
Expedia
From $335 per night (USD)
VRBO
Charming Winter Haven Home. 2 Miles to Legoland with nightly firework show!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
2 MILES to LEGOLAND! 2 bed, 2 bath plus large bonus room or 3rd bedroom. Cozy fireplace in the living room, perfect for ...
From $335 per night (USD)
VRBO
$Lakeside Adventure Retreat w\/ Heated Pool, Fishing Dock, Game Room & Complimentary 1 hr Boat Cruise*$
From $680 per night (USD)
Expedia
Lakeside Adventure Retreat w\/ Heated Pool, Fishing Dock, Game Room & Complimentary 1 hr Boat Cruise*
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
Charming Lakeside Retreat with Modern Comforts in Winter Haven, Florida. Booking this property includes one (1) hour ...
From $680 per night (USD)
Expedia
From $260 per night (USD)
VRBO
Near LegoLand -Family friendly 4 bedroom house with games & Pool in Winter Haven
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Discover the beauty of Winter Haven from this charming 4-bedroom house. With 1 king bed, 2 set of bunk beds (full size b ...
From $260 per night (USD)
VRBO
From $209 per night (USD)
Expedia
Cozy home 3 Bd 2 Bath sleeps 10 people 3 Minutes to Legoland .WiFi, central air.
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Get ready to relax in this modern, and cozy 3-bedroom house in Winter Haven. With 3 queen beds, 3 twin beds and 2 bathr ...
From $209 per night (USD)
Expedia
From $200 per night (USD)
VRBO
Serene Lake Views: Winter Haven Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Pet Friendly w/ Fee | Boating Nearby | Wildlife & Birdwatching On-Site Seeking a respite from the cold? Let your worrie ...
From $200 per night (USD)
VRBO
From $257 per night (USD)
Expedia
Charming 3-bedroom house with Pool in Winter Haven, Blocks from Lego Land
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Discover the beauty of Winter Haven from this 3-bedroom, 2-bathroom house. This marvelous property is located 2.2 miles ...
From $257 per night (USD)
Expedia
From $76 per night (USD)
VRBO
Modern Winter Haven Apartment
Bedrooms:
2
Bathrooms:
2
Sleeps:
2
This 2 bedroom 2 bathroom end unit is fully furnished with a modern flair. Renovated with new roof, energy efficient tan ...
From $76 per night (USD)
VRBO
From $273 per night (USD)
Expedia
Private lakefront retreat
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Hi there! We’re Bryan and Amber — a husband-and-wife duo from Pittsburgh, PA, raising two amazing girls, Madden and Monr ...
From $273 per night (USD)
Expedia
From $165 per night (USD)
VRBO
Luxurious studio with WiFi and AC in wonderful Winter Haven
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to your own private oasis! This charming studio unit has everything you need for a comfortable and convenient st ...
From $165 per night (USD)
VRBO
From $150 per night (USD)
Expedia
Lake Front: Charming 3-bedroom house with WiFi and AC in wonderful Winter Haven
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Your home away from home in Winter Haven with 3 lovely queen bedrooms. This charming house offers AC, WiFi, heating, an ...
From $150 per night (USD)
Expedia
From $196 per night (USD)
VRBO
Summer Specials! Perfect Couple Oasis! Pet Friendly, 2 Beds
Bedrooms:
3
Bathrooms:
6
Sleeps:
5
Nestled within the heart of Winter Haven, Chain of Lakes Cottage offers an enchanting retreat that celebrates the beauty ...
From $196 per night (USD)
VRBO
From $185 per night (USD)
Expedia
Charming 3-bedroom house, 5 min from Legoland & 26 min from Bok tower garden
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Nestled in Winter Haven, this delightful house offers 3 bedrooms with a king, queen, and full bed. With amenities like A ...
From $185 per night (USD)
Expedia

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Results: 198 Rentals