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 $149 per night (USD)
VRBO
Lakefront Tiny Cottage 4 Miles to LEGOLAND.
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Welcome to Modern Tiny Home Cottage on Lake Mariam, a cozy lakefront retreat located on a private 3-acre property in Win ...
From $149 per night (USD)
VRBO
From $107 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 $107 per night (USD)
Expedia
From $360 per night (USD)
VRBO
Lakefront Family Retreat | Private Dock, Tiki Bar & Kayaks | Near Legoland
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to Sunrise on Lake Idylwild Your perfect lakeside getaway awaits on the beautiful Chain of Lakes in Winter Hav ...
From $360 per night (USD)
VRBO
From $281 per night (USD)
Expedia
3BR/2BA Lake Mariam Home Near LEGOLAND with Kitchen & Laundry_1722
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Welcome to 3BR 2BA Modern Spacious Lake Home 4 Miles to LEGOLAND, a comfortable vacation home located on a peaceful 3-ac ...
From $281 per night (USD)
Expedia
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VRBO
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 ...
Click For Pricing
VRBO
From $148 per night (USD)
Expedia
The Russell Lake House
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This is a Cabana. It has 2 sets of bunk beds (4 total beds). Approx 400 sq. Ft. . Includes a bathroom with sink, toilet ...
From $148 per night (USD)
Expedia
From $408 per night (USD)
VRBO
Hook, Line & Leisure: Lakefront Gem w/ Porch!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
2,384 Sq Ft | Dedicated Office | Yard w/ Fruit Trees Experience Winter Haven’s authentic, diverse neighborhood vibe in ...
From $408 per night (USD)
VRBO
From $277 per night (USD)
Expedia
3BR/2BA Lake Mariam Home Near LEGOLAND with Kitchen & Laundry_1724
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to 3BR 2BA Modern Spacious Lake Home 4 Miles to LEGOLAND, a comfortable vacation home located on a peaceful 3-ac ...
From $277 per night (USD)
Expedia
From $182 per night (USD)
VRBO
Private King Suite with W/D near LEGOLAND & Winter Haven Hospital
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Enjoy a comfortable private king suite in a convenient Winter Haven location near Downtown Winter Haven, Winter Haven Ho ...
From $182 per night (USD)
VRBO
From $527 per night (USD)
Expedia
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 $527 per night (USD)
Expedia
From $301 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 $301 per night (USD)
VRBO
From $210 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 $210 per night (USD)
Expedia
From $563 per night (USD)
VRBO
Lanai & Pool: Elegant Villa in Winter Haven!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
WFH Friendly | Lake Access On-Site | 5,100 Sq Ft Escape to the ‘Water Ski Capital of the World’ at this Winter Haven vac ...
From $563 per night (USD)
VRBO
From $326 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 $326 per night (USD)
Expedia
From $695 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 $695 per night (USD)
VRBO
From $109 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 $109 per night (USD)
Expedia
From $360 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 $360 per night (USD)
VRBO
From $302 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 $302 per night (USD)
VRBO
From $169 per night (USD)
VRBO
Luxury StayComfy at WinterHeaven
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Have fun with the whole family at this two bedroom stylish place. Enjoy two comfy queen beds and a sofa-bed, tv 50'' wi ...
From $169 per night (USD)
VRBO
From $163 per night (USD)
Expedia
3 Bedroom Cozy Home with the Perfect Patio
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to our family-friendly home! Just a 5-minute walk to the nearest lake and a short 15-minute drive from Legoland, ...
From $163 per night (USD)
Expedia
From $505 per night (USD)
VRBO
Historic Manor, sleeps 10+, 5 Bedroom, huge yard, lake, fishing, parks, events
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Experience a piece of history in this peaceful, tastefully renovated 1910 Manor. This fully furnished home features five ...
From $505 per night (USD)
VRBO
From $521 per night (USD)
VRBO
Lake View, Game Room, 10 minutes to Legoland - Perfect for Large Families!
Bedrooms:
4
Bathrooms:
4
Sleeps:
11
Welcome to The Elby, a fully renovated 1940's lake home with spacious rooms, modern amenities, and indoor and outdoor ga ...
From $521 per night (USD)
VRBO
From $428 per night (USD)
VRBO
Lakefront Winter Haven Retreat: Hot Tub & Patio!
Bedrooms:
3
Bathrooms:
4
Sleeps:
22
Located just steps away from the pristine waters of the Chain of Lakes, this stunning 4-bedroom, 3.5-bathroom vacation r ...
From $428 per night (USD)
VRBO
From $130 per night (USD)
Expedia
Winter Haven Apt: 1 Mi to Polk State College!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Close to Polk State College, this convenient, vibrant vacation rental is great for prospective students and alumni, visi ...
From $130 per night (USD)
Expedia
From $112 per night (USD)
VRBO
Studio Apartment in Winter Haven, FL
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to our studio apartment, a perfect retreat for solo travelers or couples seeking a comfortable and convenient pl ...
From $112 per night (USD)
VRBO
From $420 per night (USD)
Expedia
Large Family Home, Legoland, Pet Friendly, 7 Beds
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Nestled near Lake Howard in Winter Haven, this elegant 4BR-2BA retreat offers a perfect blend of comfort, style, and con ...
From $420 per night (USD)
Expedia
From $274 per night (USD)
VRBO
Lakefront 3 story 5/3 bungalo with huge yard, great views, a firepit and a dock.
Bedrooms:
3
Bathrooms:
5
Sleeps:
6
Property Description fully renovated lake front property with big back porch and yard flowing to the lake. The house has ...
From $274 per night (USD)
VRBO
From $305 per night (USD)
Expedia
Peaceful Lakeside Retreat
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Tranquility awaits you at this beautiful lakefront home. We invite you to enjoy the best of Florida indoor/outdoor livi ...
From $305 per night (USD)
Expedia
From $212 per night (USD)
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 ...
From $212 per night (USD)
VRBO
From $153 per night (USD)
VRBO
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 $153 per night (USD)
VRBO
From $235 per night (USD)
VRBO
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 $235 per night (USD)
VRBO
From $228 per night (USD)
Expedia
Family Fun Haven: 3 Bed/2 Bath/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 $228 per night (USD)
Expedia
From $316 per night (USD)
VRBO
Lake House with Private Pool, Beach & 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 $316 per night (USD)
VRBO
From $130 per night (USD)
Expedia
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 $130 per night (USD)
Expedia
From $336 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 $336 per night (USD)
VRBO
From $307 per night (USD)
Expedia
3 bedroom cabin, 15 minutes to Legoland, lake view
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape to this cozy 3-bedroom, 2-bath lakeview cabin in the heart of Winter Haven. Surrounded by mature trees and peacef ...
From $307 per night (USD)
Expedia
From $169 per night (USD)
VRBO
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 $169 per night (USD)
VRBO
From $319 per night (USD)
Expedia
Getaway Clubhouse 5 mil Legoland & .5 mil Downtown
Bedrooms:
2
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 $319 per night (USD)
Expedia
From $282 per night (USD)
VRBO
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
Bedrooms:
1
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 $282 per night (USD)
VRBO
From $183 per night (USD)
Expedia
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)
Expedia
From $294 per night (USD)
VRBO
Cozy Bungalow - 5 mi Legoland & 0.5 mi Dwntwn
Bedrooms:
1
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 $294 per night (USD)
VRBO
From $306 per night (USD)
Expedia
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 $306 per night (USD)
Expedia
From $160 per night (USD)
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 ...
From $160 per night (USD)
VRBO
From $193 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 $193 per night (USD)
Expedia
From $246 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 $246 per night (USD)
VRBO
From $259 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 $259 per night (USD)
Expedia
From $303 per night (USD)
VRBO
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 $303 per night (USD)
VRBO
From $655 per night (USD)
Expedia
Lakeside Adventure Retreat | Heated Pool, Game Room & Private Dock | Optional 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 $655 per night (USD)
Expedia
From $98 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 $98 per night (USD)
VRBO
From $397 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 $397 per night (USD)
Expedia
From $167 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 $167 per night (USD)
VRBO
From $245 per night (USD)
Expedia
Modern Comfort, Pet Friendly, 2 King Beds
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Welcome to the Chain of Lakes Cottage, your refined retreat in the heart of Winter Haven. This elegantly restored cottag ...
From $245 per night (USD)
Expedia
From $234 per night (USD)
VRBO
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 $234 per night (USD)
VRBO
From $158 per night (USD)
Expedia
Waterfront Condo | Pool & Dock | Near Legoland | 2BR, Sleeps 4
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 $158 per night (USD)
Expedia
From $371 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 $371 per night (USD)
VRBO
From $375 per night (USD)
Expedia
Serene, Cozy, Lakefront Home with boat dock and Large Screened in porch!
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
Cozy meets calm at this quaint lakefront home. We invite you to relax under the large, covered, screened in back porch ...
From $375 per night (USD)
Expedia
From $209 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 $209 per night (USD)
VRBO
From $303 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 $303 per night (USD)
VRBO
From $142 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 $142 per night (USD)
VRBO
From $138 per night (USD)
VRBO
1-bedroom Apartment C near Hospitals/Legoland/Chain of Lakes
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Welcome to our charming two-story antique building, beautifully restored and transformed into four cozy apartments . Thi ...
From $138 per night (USD)
VRBO
From $151 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 $151 per night (USD)
VRBO
From $216 per night (USD)
Expedia
Charming and Cozy Winter Haven Oasis
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This fabulous 1-bedroom apartment in Winter Haven is perfect for your escape. The bedroom features a cozy queen bed, and ...
From $216 per night (USD)
Expedia
From $134 per night (USD)
VRBO
Holiday Inn Winter Haven King Studio
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Stay in the heart of Winter Haven, just minutes from LEGOLAND® Florida Resort and local attractions. Enjoy these perks: ...
From $134 per night (USD)
VRBO
From $140 per night (USD)
VRBO
Holiday Inn Winter Haven 2 Queen Studio
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Stay in the heart of Winter Haven, just minutes from LEGOLAND® Florida Resort and local attractions. Enjoy these perks: ...
From $140 per night (USD)
VRBO
From $687 per night (USD)
VRBO
Family & Sports Team Oasis Near Legoland & Parks
Bedrooms:
3
Bathrooms:
6
Sleeps:
16
🛏️ Sleeping Arrangements: Two fully equipped homes with multiple bedrooms combined sleep 16+ guests comfortably. Cribs, ...
From $687 per night (USD)
VRBO
From $172 per night (USD)
Expedia
Charming Lakeside Cottage
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Escape to our cozy lakeside cottage, featuring a dock that’s perfect for watching sunrises, fishing, and launching your ...
From $172 per night (USD)
Expedia
From $446 per night (USD)
VRBO
Vibrant 3-Bedroom Escape in Lovely Winter Haven Featuring Refreshing A/C
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Step into this charming 3-bedroom retreat where comfort, style, and character come together beautifully. This inviting W ...
From $446 per night (USD)
VRBO
From $289 per night (USD)
VRBO
Winter Haven Comfort Retreat
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Welcome to Winter Haven Comfort Retreat- a cozy and comfortable stay designed for families, contractors, and extended gu ...
From $289 per night (USD)
VRBO
From $292 per night (USD)
VRBO
Florida Chill Sunshine by Day, Fire Pit Nights — 3BR with AC in Winter Haven
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Step into this charming 3-bedroom retreat where comfort, style, and character come together beautifully. This inviting W ...
From $292 per night (USD)
VRBO
From $378 per night (USD)
Expedia
Marvelous 3BR/3BA Winter Haven Home — Minutes to Legoland!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Experience the magic of Winter Haven in this beautifully appointed 3-bedroom home with 3 bathrooms, perfectly situated j ...
From $378 per night (USD)
Expedia
From $343 per night (USD)
VRBO
Ultimate Family Getaway: 4BR Home with Pool & Games
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
-Accommodations Master bedroom with Queen bed Kids’ room with Full-over-Full bunk beds Semi-private suite with Queen be ...
From $343 per night (USD)
VRBO
From $512 per night (USD)
Expedia
Legoland & Lakes Pool Home w/ Private Suite
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
1 Mi to Downtown | 5 Mi to LEGOLAND | Private Pool | Pet Friendly Enjoy space, privacy, and easy indoor-outdoor living ...
From $512 per night (USD)
Expedia
From $483 per night (USD)
VRBO
Lakefront Heated Pool Home w/ Hot Tub, Dock & Sunset Views Near LEGOLAND
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Lakefront Living Designed for Gathering and Connection Sunset Haven is a private lakefront home on Lake Howard, part of ...
From $483 per night (USD)
VRBO
From $190 per night (USD)
Expedia
Cozy 1 bedroom home in Winter Haven perfect for your getaway.
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Unwind in Winter Haven at this delightful cozy home. The space features one bedroom, full bathroom with a refreshing ...
From $190 per night (USD)
Expedia
From $379 per night (USD)
VRBO
Cozy 3br 2ba Winter Haven Getaway Chain of Lakes Downtown
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Located in Winter Haven, this terrific house offers a comfortable retreat for guests. With three bedrooms featuring two ...
From $379 per night (USD)
VRBO
From $102 per night (USD)
Expedia
Remote workers 1bed w/full kitchen & living room
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Enjoy a peaceful stay in this modern and beautifully designed guest suite located in Winter Haven, Florida. This private ...
From $102 per night (USD)
Expedia
From $468 per night (USD)
VRBO
White Door House!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Experience a peaceful and spacious Central Florida getaway in this family-friendly 4-bedroom home that comfortably sleep ...
From $468 per night (USD)
VRBO
From $341 per night (USD)
Expedia
Cozy 3 bedroom house in a beautiful Winter Haven area near Legoland and Boktower
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Enjoy a peaceful stay at this 3 bedroom house in Winter Haven. Master bedroom includes comfortable king bed and futon so ...
From $341 per night (USD)
Expedia
From $286 per night (USD)
VRBO
Work, Play or Recharge:3BR Pool Home near Legoland
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Welcome to your modern retreat! This beautifullly decorated, newly remodeled 3BR, 2BA single story home offers the perfe ...
From $286 per night (USD)
VRBO
From $1087 per night (USD)
Expedia
Lake, Pool, HotTub, Game Room, 8 Beds, Sleeps 17
Bedrooms:
3
Bathrooms:
4
Sleeps:
16
Ultimate Lakefront Escape on Lake Howard | Pool • Game Room • Legoland • Sleeps 17 Welcome to your private lakefront re ...
From $1087 per night (USD)
Expedia
$\Chalet\ lake house/walking path/fenced yard/dock$
From $243 per night (USD)
VRBO
\"Chalet\" lake house/walking path/fenced yard/dock
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
"Ski in/Ski out" comes to Winter Haven, Florida style. Enjoy a super cozy and thoughtfully appointed "ski chalet" for yo ...
From $243 per night (USD)
VRBO
From $229 per night (USD)
Expedia
Walk to Winter Haven Hospital: Convenient Apt
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Healthcare Workers Welcome | WFH Friendly | On-Site Laundry Whether it's work or play that brings you to town, you'll f ...
From $229 per night (USD)
Expedia
From $196 per night (USD)
VRBO
Your Winter Haven Oasis Awaits 3-bedroom house near Legoland in Winter Haven
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to your ultimate Sunshine State getaway! Perfectly nestled in the heart of Winter Haven, Florida,. This bright a ...
From $196 per night (USD)
VRBO
From $118 per night (USD)
VRBO
Roomy 3-bedroom house Near Lake Howard & Downtown Winter Haven
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Make yourself at home in this 3-bedroom Winter Haven house. The space features one queen bed and two king beds, offering ...
From $118 per night (USD)
VRBO
From $295 per night (USD)
VRBO
Fabulous house just a few minutes away from LEGOLAND and Peppa Pig Park
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Your cozy getaway awaits in Winter Haven at this welcoming house. With three bedrooms featuring a king bed, a queen bed, ...
From $295 per night (USD)
VRBO
From $324 per night (USD)
Expedia
On the beautiful shores of Lake Conine connected by the 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 $324 per night (USD)
Expedia
From $353 per night (USD)
VRBO
Lake Hamilton Oasis - Pool • Dock • Sunrise Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to your Lake Hamilton sunrise oasis! This waterfront home is designed for relaxed weekend escapes, where mornin ...
From $353 per night (USD)
VRBO
From $425 per night (USD)
VRBO
Lakefront house with Boat Dock and Hot tub on the Winter Haven Chain of Lakes
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Bring your boat and explore the famous Chain of Lakes in Winter Haven Florida. This nearly new home, built in 2023, feat ...
From $425 per night (USD)
VRBO
From $259 per night (USD)
VRBO
Winter Haven 5BR Family Retreat- Near LEGOLAND + Disney, Family-Friendly
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Welcome to Your Winter Haven Family Retreat Make yourself at home in this spacious 5-bedroom, 3-bathroom Winter Haven r ...
From $259 per night (USD)
VRBO

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Results: 89 Rentals