Winter Haven Rentals
From $95 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 $95 per night (USD)VRBO
From $373 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, high defi ...
From $373 per night (USD)VRBO
From $373 per night (USD)VRBO
Pirate Island Hotel: Splashy Pirate Adventure, Playgrounds, Near Legoland
- 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, high defi ...
From $373 per night (USD)VRBO
From $746 per night (USD)VRBO
Playful Stay Perfect for Family Getaway | 2 Units
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 10
This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms. ✦ Each room is ...
From $746 per night (USD)VRBO
From $746 per night (USD)VRBO
2 Pirate Theme Rooms, Legoland Resort, Treasure-Fun Playscape, Near Water Park
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 10
This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms. ✦ Each room is ...
From $746 per night (USD)VRBO
From $80 per night (USD)Expedia
Private Entrance 1 Bd 1.5 Bath Guest Suite in Cypress Gardens near Legoland
- Bedrooms:
- 1
- 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 $80 per night (USD)Expedia
From $718 per night (USD)VRBO
Perfect Family Outing: 2 Themed Rooms Await | Near Lake Dexter
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 10
This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms. ✦ Each room is ...
From $718 per night (USD)VRBO
From $358 per night (USD)VRBO
Kingdom Theme Standard: Fairy-Tale Dreams, Onsite Dining, LEGOLAND Next Door
- 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, high defi ...
From $358 per night (USD)VRBO
From $358 per night (USD)VRBO
Adventure Filled Resort Perfect for Family Getaway | Fun Pools!
- 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, high defi ...
From $358 per night (USD)VRBO
From $534 per night (USD)VRBO
Theme Park at your Door Steps | Near Lake Dexter | Waterpark and Pool Access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 10
This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms. ✦ Each room is ...
From $534 per night (USD)VRBO
From $534 per night (USD)VRBO
LEGOLAND Bungalow Bliss, Family Play Areas, 2 Rooms, Water Park Access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 10
This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms. ✦ Each room is ...
From $534 per night (USD)VRBO
From $718 per night (USD)VRBO
Medieval Dream Stay, Kingdom Themed Room, Onsite LEGO Fun, 2 Rooms
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 10
This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms. ✦ Each room is ...
From $718 per night (USD)VRBO
From $717 per night (USD)VRBO
Adventurer's Dream Room, Legoland Hotel, Mini Golf Excursion, 2 Family Stays
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 10
This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms. ✦ Each room is ...
From $717 per night (USD)VRBO
From $268 per night (USD)VRBO
Theme Park at your Door Steps | Near Lake Dexter | Waterpark and Pool Access
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
This listing is for a room within a hotel. ✦ Your room is 275 sq. ft, equipped with complimentary toiletries, high defi ...
From $268 per night (USD)VRBO
From $358 per night (USD)VRBO
Adventure Awaits: LEGOLAND Hotel Florida, Creative Dining, Mini Golf Fun
- 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, high defi ...
From $358 per night (USD)VRBO
From $717 per night (USD)VRBO
Family Dream Room with Playgrounds Galore | 2 Adventure Theme Rooms w/ Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 10
This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms. ✦ Each room is ...
From $717 per night (USD)VRBO
From $358 per night (USD)VRBO
Colorful Room w/ Waterpark & Lego Fun! Free Parkin
- 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, high defi ...
From $358 per night (USD)VRBO
From $282 per night (USD)VRBO
Beach Retreat Bungalow: Family Joy, LEGO Surprises, Steps from the Waterpark
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
This listing is for a room within a hotel. ✦ Your room is 275 sq. ft, equipped with complimentary toiletries, high defi ...
From $282 per night (USD)VRBO
From $384 per night (USD)VRBO
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 $384 per night (USD)VRBO
From $181 per night (USD)VRBO
Charming Eagle Lake Getaway: Relax & Unwind Near Scenic Trails & Nature Spots!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Your Perfect Eagle Lake Getaway! Nestled near the heart of Winter Haven, Florida, this cozy retreat is the i ...
From $181 per night (USD)VRBO
From $340 per night (USD)VRBO
Serene, Cozy, Lakefront home
- Bedrooms:
- 2
- Bathrooms:
- 2
- 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 $340 per night (USD)VRBO
From $448 per night (USD)Expedia
Lakefront Retreat at 6BR Escape w/ Heated Pool | Private Dock | Game Room | Kayaks | Deck | Perfect
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 14
Escape to Emerald Anchor – Your Ultimate Lakefront Getaway in Winter Haven! Welcome to Emerald Anchor Escape, a spa ...
From $448 per night (USD)Expedia
From $169 per night (USD)VRBO
Relaxing Retreat with Game Room + Massage Chair+ Fire Pit + Wood Fire Pizza Oven
- 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 $169 per night (USD)VRBO
From $233 per night (USD)VRBO
Playground Access: Winter Haven Getaway w/ Patio!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
3 Mi to Peppa Pig Theme Park | Families Welcome | Remote-Work Friendly Fill your next getaway with magical moments at t ...
From $233 per night (USD)VRBO
From $325 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 $325 per night (USD)VRBO
From $182 per night (USD)Expedia
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 ...
From $182 per night (USD)Expedia
From $194 per night (USD)VRBO
Winter Haven Hideaway
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to your perfect Winter Haven Florida getaway near Legoland & Chain of Lakes! This spacious 3-bedroom, 2-bathroom ...
From $194 per night (USD)VRBO
From $174 per night (USD)VRBO
8 Mi to Legoland: Winter Haven Home w/ Lanai!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Pet-Friendly Private Yard | Central Location | Families Welcome Experience the best of Winter Haven when you stay at th ...
From $174 per night (USD)VRBO
From $229 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 $229 per night (USD)VRBO
From $228 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 $228 per night (USD)Expedia
From $269 per night (USD)VRBO
Charming Winter Haven Legoland Retreat with 3-bedrooms, close to Lakes
- Bedrooms:
- 1
- 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 $269 per night (USD)VRBO
From $154 per night (USD)VRBO
9 Mi to Legoland: Apt w/ Yard in Winter Haven!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Dog Friendly w/ Fee | Gas Gill for Cookouts | Quiet Setting | 3 Mi to Town Retreat to Central Florida and book this 1-b ...
From $154 per night (USD)VRBO
From $100 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 $100 per night (USD)VRBO
From $99 per night (USD)Expedia
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 $99 per night (USD)Expedia
From $244 per night (USD)VRBO
4 Mi to Legoland: Poolside Paradise!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Near Restaurants | Dedicated Space for Remote Work | BBQ Ready | Day Trips to Disney Looking to escape the cold weather ...
From $244 per night (USD)VRBO
From $284 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 $284 per night (USD)Expedia
From $484 per night (USD)VRBO
Lakeside Adventure Retreat w/ Heated Pool, Fishing Dock, Game Room & Optional 1 hr Boat Cruise*
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Charming Lakeside Retreat with Modern Comforts in Winter Haven, Florida Escape to your own private paradise on Lake Ot ...
From $484 per night (USD)VRBO
From $256 per night (USD)Expedia
Near LegoLand -Family friendly 4 bedroom house with games & Pool in Winter Haven
- Bedrooms:
- 2
- 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 $256 per night (USD)Expedia
From $190 per night (USD)VRBO
Cozy home 3 Bd 2 Bath sleeps 10 people 3 Minutes to Legoland .WiFi, central air.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
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 $190 per night (USD)VRBO
From $230 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 $230 per night (USD)VRBO
From $239 per night (USD)VRBO
3-bedroom home with private 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 $239 per night (USD)VRBO
From $97 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 $97 per night (USD)VRBO
From $314 per night (USD)VRBO
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 $314 per night (USD)VRBO
From $165 per night (USD)Expedia
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)Expedia
From $125 per night (USD)VRBO
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 $125 per night (USD)VRBO
From $239 per night (USD)Expedia
Summer Specials! Perfect Couple Oasis! Pet Friendly, 2 Beds
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Nestled within the heart of Winter Haven, Chain of Lakes Cottage offers an enchanting retreat that celebrates the beauty ...
From $239 per night (USD)Expedia
From $697 per night (USD)VRBO
Winter Haven Waterfront Retreat
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Stunning lakefront home combines modern comfort with the serene natural beauty of the chain of lakes. Cook up a feast in ...
From $697 per night (USD)VRBO
From $137 per night (USD)Expedia
Legoland home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
The whole group will enjoy easy access to everything from this centrally located home. We are close to Legoland, Tampa & ...
From $137 per night (USD)Expedia
From $167 per night (USD)VRBO
The Grove House - antique lakefront home on Eagle Lake, Central Florida
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
This unique 108-year-old grove owners manor is located on Eagle Lake and is neighbored by citrus groves. The sizable t ...
From $167 per night (USD)VRBO
From $22 per night (USD)Expedia
MCO TPA LAL Traveling nurse Crashpad
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 16
Hi! This brand new duplex Crash Pad is located in the city center of Winter Haven & is perfect for traveling nurses, fli ...
From $22 per night (USD)Expedia
From $138 per night (USD)VRBO
Charming 1-bedroom guesthouse with pool view WiFi and AC in Winter Haven
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Winter Haven is waiting for you at this 1-bedroom guesthouse with pool view. A pleasant living room with sofa lounge and ...
From $138 per night (USD)VRBO
From $198 per night (USD)Expedia
Charming 3-bedroom 2 bathroom home in brilliant Winter Haven,pet friendly, WiFi
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Located in Winter Haven, enjoy what this 3-bedroom home has to offer. With 2 queen beds and 2 twin beds,guests can relax ...
From $198 per night (USD)Expedia
From $171 per night (USD)VRBO
Charming 3-bedroom house in tranquil Winter Haven w/Lake Access
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Your perfect getaway awaits! This stylish 3BR/2BA home is just minutes from Legoland and sits in a peaceful neighborh ...
From $171 per night (USD)VRBO
From $169 per night (USD)Expedia
2BR Waterfront Condo w/ Pool access, Dock, Patio Views & 3 Miles from LEGOLAND
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to your peaceful getaway on beautiful Lake Lulu! This airy and inviting upstairs 2-bedroom, 2-bathroom condo is ...
From $169 per night (USD)Expedia
From $228 per night (USD)VRBO
Escape to tranquility at this PrivatePool Lakeview getaway on the shores of EL
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to this delightful 2-bedroom PrivatePool Lakeview Eagle Lake house retreat. Unwind in the cozy living room with a ...
From $228 per night (USD)VRBO
From $308 per night (USD)Expedia
Bright Home Near Legoland & Lake
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to this charming 3BR, 2BA home in Winter Haven, perfect for families or groups. With 1,555 sqft of space, an open ...
From $308 per night (USD)Expedia
From $487 per night (USD)VRBO
Family Friendly Lake House W/ Pool Near Legoland
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
At this spacious, upgraded lakefront home, with a sandy beach and private dock, spend your days fishing, floating, and b ...
From $487 per night (USD)VRBO
From $225 per night (USD)Expedia
Serene, Cozy, Lakefront Home with covered porch on the Lake
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Cozy meets calm at this quaint lakefront home. Come relax under the large covered back porch with ample seating and wat ...
From $225 per night (USD)Expedia
From $203 per night (USD)VRBO
1-Bedroom Guest Cottage on Historic Lakefront Estate
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Truly a one of a kind find. A fully furnished private guest house on a large historic estate. The guest house is free st ...
From $203 per night (USD)VRBO
From $183 per night (USD)VRBO
4-bedroom house by LegoLand with WiFi, AC
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to your perfect family getaway—just 7 minutes from LEGOLAND Florida! This spacious 4-bedroom, 2.5-bath home feat ...
From $183 per night (USD)VRBO
From $123 per night (USD)VRBO
Welcoming 2-bedroom lake view house in Winter Haven
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to this house in picturesque Winter Haven. This phenomenal property features 2 queen bedrooms and 2 bathrooms wit ...
From $123 per night (USD)VRBO
From $129 per night (USD)VRBO
Cozy Touch Apartment C near LakeLand & Legoland
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Our lovely 1-bedroom apartment is the perfect retreat for couples, solo travelers, or small families. The spacious bedro ...
From $129 per night (USD)VRBO
From $119 per night (USD)VRBO
Cozy Vintage Apt D near Lakeland/Hospitals/Lakes
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Welcome to Cozy Vintage – a lovingly restored two-story gem where classic character meets modern comfort. Our one-bedroo ...
From $119 per night (USD)VRBO
From $331 per night (USD)Expedia
Discover Little Haven, a 3BR/2BA vacation home in Winter Haven with a heated pool, full amenities, and prime location—just 3 miles to LEGOLAND, 30 miles to Disney, and minutes from lakes, scenic trails, and family attractions.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Little Haven, a family-friendly 3BR/2BA vacation rental in Winter Haven, FL! Just 3 miles from LEGOLAND and 3 ...
From $331 per night (USD)Expedia