Vacation Rentals & Homes in Winter Haven Florida
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We have many choices for Winter Haven Vacation Rentals, Homes and Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities they have to offer for your visit to Florida.
Lake Hamilton Hideout
Winter Haven Private vacation home 
10.0
This beautiful home provides the perfect setting for a relaxing and rejuvenating vacation in the heart of central Florida. As soon as you step inside, you will be greeted by a bright and spacious living spaces, complete with comfortable furnishings and modern amenities. The large windows throughout the house provide views of Lake Hamilton. Located .......read more
4 Bedroom(s)
2 Bath(s) Sleeps 8
Lakefront Vacation Home on the Chain of Lakes in Winter Haven
Winter Haven Private vacation home 9.6
New remodeled Lakefront Vacation Home on the Chain of Lakes right next to Winter Haven Municipal Airport across from Brown's Seaplane base. Come and enjoy the beautiful sunrises over the lake.
The house offers wonderful lake views from almost every room with 2 bedrooms, 2 bathrooms (2nd bathroom in the garage), large living room with sleepe.......read more
2 Bedroom(s)
2 Bath(s) Sleeps 5
Bright Waterfront Home on Winter Haven's Lake Jessie
Winter Haven Private vacation home 10.0
900 Lake Jessie is a rare rental find. It's a bright lakefront home on Winter Haven's renowned Chain of Lakes. This newly renovated, spacious, single story home on Lake Jessie is well equipped, so you can relax and have fun. The home is fully furnished including towels, bedding, kitchenware and laundry. It can accommodate 10 people. Waterski/barefo.......read more
4 Bedroom(s)
3 Bath(s) Sleeps 10
Newly remodeled Vacation Home with Saltwater Pool
Winter Haven Private vacation home 9.6
This "brand-new" home, built in 2010, totally rebuilt and remodeled in 2022, is located in a gated community in the south of Winter Haven, next to Legoland, and features everything you need for a relaxing vacation. Enjoy the sunsets over Round Lake as you sit out in the nice, large, screened pool area with a 14x28 saltwater pool and relax under the.......read more
3 Bedroom(s)
2 Bath(s) Sleeps 6
Luxury 3BR Lake House on Quiet Private Lake, with Pool and Hot Tub
Winter Haven Private vacation home 9.6
3,800 sq ft Executive Vacation Home on a private lake 5 minutes from Legoland and Peppa Pig, and 40 minutes from DisneyWorld, Orlando, Fl. Three large bedrooms, two with king size beds and all with en suite bathrooms, plus living room, family room, dining room, large laundry room, screened pool and hot tub, screened outdoor dining room and BBQ area.......read more
3 Bedroom(s)
5 Bath(s) Sleeps 6
Spacious home, in a quiet neighborhood near LEGOLAND®-just a 12-minute drive
Winter Haven Private vacation home 9.2
This beautiful family-friendly home is ideally located near all of central Florida's attractions. Only a few minutes from Polk Pkwy/I-4, Legoland, Peppa Pig Park, and Bok Tower Gardens. Easy commute to Disney, Orlando, and Tampa. Close to shopping and restaurants. Located in a safe and quiet community.
This home has two living and dining are.......read more
4 Bedroom(s)
2 Bath(s) Sleeps 10
Luxury Lakefront Retreat | Heated Salt Pool, Dock & Kayaks | Home Theatre & EV Charger
Winter Haven Private vacation home 9.6
Come to Lake Hamilton’s luxurious lake house and let the sunsets take your breath away as you relax and enjoy making memories at our gorgeous Mediterranean home! No detail has been missed with a gorgeous lanai, outdoor kitchen and heated pool to share with family & friends! The kitchen is full of natural light with three skylights that stream in.......read more
6 Bedroom(s)
4 Bath(s) Sleeps 13
Private pool lake house with game room—just 4 minutes from LEGOLAND
WINTER HAVEN Private vacation home 10.0
4 Bedroom Lake House on Canal to LEGOLAND’s Lake Eloise on the Chain of Lakes, bring your jet skis- there is a small boat ramp across the canal to launch or head to the Marina just a few miles down the road and rent a pontoon boat for the day. Large solor heated/cooled inground pool w/ 55” tv WITH SOUNDBAR on the large pool patio for the family.......read more
4 Bedroom(s)
3 Bath(s) Sleeps 12
Lakefront Family Retreat | Private Dock, Tiki Bar & Kayaks | Near Legoland
Winter Haven Private vacation home 10.0
Welcome to SUNRISE ON LAKE IDYLWILD! This gorgeous newly renovated and beautifully decorated lake house is located on the Chain of Lakes at Lake Idylwild and is the very definition of lake living. Lake Idylwild connects with 18 of the Chain of Lakes with its own private dock. This stunning lake house offers spacious outdoor areas with beautiful .......read more
3 Bedroom(s)
2 Bath(s) Sleeps 7
Lake Rochelle Rental Lakefront
Winter Haven Private vacation home 10.0
Huge, fenced yard with quaint 3/2 trilevel
house overlooking Lake Rochelle in Northeast Winter Haven. Just
minutes from LegoLand Florida and U.S. 27 and approx. forty minutes
to Disney/Universal/Sea World, our lakehouse is designed to get away
from it all. No smoking please. Great bird watching, fishing, and
boating. Very serene .......read more
3 Bedroom(s)
3 Bath(s) Sleeps 8
Family-Friendly 2BR Near LEGOLAND with Parking
Winter Haven Private vacation home 8.6
WELCOME to our Wakulla Vacation Home (1) “Nest” which is a duplex property. We are a family own business & genuinely hope to tailor our properties to meet our Guest needs. We adhere to a 3 Core Property Standards that we expect; so, you'll always arrive to a home that is Safe, Clean and Guest Ready!
This property is centrally located, 2.......read more
2 Bedroom(s)
1 Bath(s) Sleeps 5
TRAVELLING PROFESSIONALS ONLY - 3.3 miles to Winter Haven Hospital!
WINTER HAVEN Private vacation home
This home is your home away from home. Quiet, clean, full paint job, all new furnishings, Roku TV in both bedrooms, Queen size beds, dresser with mirror, beautiful desk space with desk lamps.2 bedside tables with lamps in each bedroom, bed linens, towels and wash rags, Private full SKY bathroom for each bedroom, Dove body wash and shampoo provided,.......read more
2 Bedroom(s)
2 Bath(s) Sleeps 1
Luxury StayComfy at WinterHeaven
Winter Haven Private vacation home 8.6
Have fun with the whole family at this two bedroom stylish place. Enjoy two comfy queen beds and a sofa-bed, tv 50'' with streaming and channels. Coffee station, all utensils, and appliances. Welcome refreshment, kids coloring books, washer and dryer. Well located at Winter Heaven, Florida. Only five minutes from Winter Heaven hospital, 14 minutes.......read more
2 Bedroom(s)
1 Bath(s) Sleeps 6
Hook, Line & Leisure: Lakefront Gem w/ Porch!
Winter Haven Private vacation home 9.6
Living up to its city name, this elegant 3-bedroom, 3-bathroom Winter Haven home features the perfect haven for escaping to the warmth. Complete with a welcoming atmosphere and a lakefront yard, this vacation rental is optimized for relaxation and fun. Go fishing on Lake Maude, spend a day at Disney World, and visit the largest LEGOLAND in the worl.......read more
3 Bedroom(s)
3 Bath(s) Sleeps 8
Beautiful home located in a gated community only 20 miles from LegoLand!
Winter Haven Private vacation home 10.0
7 year old home in gated community , private pool, heated with heated hot tub all screened in with a awesome outdoor space. theater room, minutes from winter haven, 2 lakes within a mile for boating and fishing needs, 40 min from Tampa and 50 min from Disneyworld. We can turn pool heater on but it is a addition 300 a week. But hot tub is free to p.......read more
4 Bedroom(s)
3 Bath(s) Sleeps 8
3BR/2BA Lake Mariam Home Near LEGOLAND with Kitchen & Laundry_1724
Winter Haven Private vacation home 9.4
WELCOME! Lake Mariam Vacation Home (2) is part of a duplex built in 2016 that sits on 2.6 acres of Lakefront Property. If hospitality & quality sleeping accommodation is what you want, our space focuses on that & much more. Rejuvenate from a day of Adventure or Business in our Lakefront property home. ONLY 4 miles from LEGOLAND. Famous Orlando attr.......read more
3 Bedroom(s)
2 Bath(s) Sleeps 6
Fantastic Water Front Home on the Chain of Lakes
Winter Haven Private vacation home 10.0
We are sharing our dream home with you! This home offers one of the best open layouts in Winter Haven. Great open kitchen with granite counter tops, stainless steel appliances, and numerous appliances. The large TV room features a Samsung smart 65" TV that connects to the Lanai/Pool area. A must see to believe! .......read more
4 Bedroom(s)
3 Bath(s) Sleeps 12
Luxury Lakefront Retreat | Heated Pool, Theater & Private Dock | Near Legoland | EV Charger
Winter Haven Private vacation home 9.8
Come to Lake Hamilton’s luxurious lake house and let the sunsets take your breath away as you relax and enjoy making memories at our gorgeous Mediterranean home! No detail has been missed with gorgeous travertine tile and crown moulding throughout the home. The kitchen is full of natural light with three skylights that stream in the Florida suns.......read more
3 Bedroom(s)
3 Bath(s) Sleeps 6
Huge Luxury Lake House on the Chain of Lakes near Legoland!
Winter Haven Private vacation home 9.8
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 retreat, boasting 5 bedrooms and 5 baths spread across two spacious stories. Nestled in the heart of Central Florida, this luxurious home promises warmth, tranquility, and special moments with your loved ones.
Conveniently l.......read more
5 Bedroom(s)
5 Bath(s) Sleeps 14
3 Bedroom Cozy Home with the Perfect Patio
Winter Haven Private vacation home 9.6
Welcome to our family-friendly home! Just a 5-minute walk to the nearest lake and a short 15-minute drive from Legoland, our charming retreat offers 3 bedrooms, 2 bathrooms, a spacious kitchen, and a cozy living room. Fuel up with complimentary coffee from our bar before exploring the nearby attractions. Unwind on the oversized porch, perfect for o.......read more
2 Bedroom(s)
2 Bath(s) Sleeps 6
Winter Haven Retreat w/ Private Pool!
Winter Haven Private vacation home 9.2
Run, don't walk, to Winter Haven and experience the ultimate vacation at this charming 3-bedroom, 2-bath home. Ideally located, this vacation rental offers easy access to top attractions, like LEGOLAND, Walt Disney World, and Universal Studios. After a day of fun, return home to relax in the cozy living room or take a dip in the pool. With comforta.......read more
3 Bedroom(s)
2 Bath(s) Sleeps 6
Cute & Cozy 1 bedroom guesthouse located in Winter Haven FL
Winter Haven Guest house 10.0
The guesthouse Cute & Cozy is separate yet, it is adjacent to the main house (owner lives) and has its own entrance. Located in central Florida, Winter Haven is between Orlando and Tampa; 3 miles from Legoland, 5-10 minute walk from shopping and restaurants on Cypress Gardens Blvd. The Cute & Cozy is also in a great location for Florida's amazi.......read more
1 Bedroom(s)
1 Bath(s) Sleeps 2
Lanai & Pool: Elegant Villa in Winter Haven!
Winter Haven Villa 9.4
Escape to the ‘Water Ski Capital of the World’ at this Winter Haven vacation rental on the Chain of Lakes. This 4-bedroom, 4.5-bathroom, Chateaux-style home offers imported double French doors that open to a grand marble entry, brass light fixtures, a crystal dining room chandelier, and a floating spiral staircase to make your stay unique. Enjo.......read more
4 Bedroom(s)
5 Bath(s) Sleeps 8
Lakefront Lego Land Estate
Winter Haven Private vacation home 9.8
Relax and enjoy the waterfront lifestyle in our beautiful home nestled on Lake Summit in Winter Haven.
Located 1 mile from Legoland and 3 miles from downtown, you will be a short drive away from all the attractions, restaurants, and bars Winter Haven has to offer. This is a perfect location for exploring all of Winter Haven, Lakeland, Tampa.......read more
4 Bedroom(s)
3 Bath(s) Sleeps 8
3BR/2BA Lake Mariam Home Near LEGOLAND with Kitchen & Laundry_1722
Winter Haven Private vacation home 9.2
WELCOME! Lake Mariam Vacation Home (1), is part of a duplex that sits on 2.6 acres of Lakefront Property. There is also a Tiny Home located the duplex, behind this property; but every guest has a lot privacy and there is NO interaction.
If hospitality & quality sleeping accommodation is what you want, our space focuses on that & much more. .......read more
3 Bedroom(s)
2 Bath(s) Sleeps 7
Historic, sleeps 10+, 5 Bedroom, huge yard, lake, fishing, parks, events
Winter Haven Private vacation home 9.8
Enjoy your stay in this large, peaceful, historic, fully renovated home. This home consists of 5 bedrooms, 3 bathrooms with modern kitchen, new AC, and more! All rooms are fully furnished for your comfort. Includes a Private large yard, in a country like setting but has many amenities in walking distance. Lake access with docks and boat launch acro.......read more
5 Bedroom(s)
3 Bath(s) Sleeps 10
Waterfront Winter Haven Home with Dock & Hot Tub!
Winter Haven Private vacation home 10.0
Your lakeside paradise awaits at this 4-bedroom, 3-bath Winter Haven vacation rental, perfect for your 'Sunshine State' getaway! The home features luxury amenities, including a 26-foot dock, swimming pool, hot tub, gazebo bar, and game room! Spend each day water skiing on Lake Lulu, toasting cocktails on the dock bar, or jumping in the pool! If tha.......read more
4 Bedroom(s)
3 Bath(s) Sleeps 12
Legoland 3 Bedroom Pet Friendly Pool Home
Winter Haven Private vacation home 7.6
Bring the whole family to this great place with lots of room for fun. This home is conveniently located only 2.1 miles from Legoland! Completely remodeled home with new soft close cabinets with granite counter tops to porcelain ceramic tile throughout. Every room has smart tvs so you can stream your favorite streaming service. The home has two bath.......read more
6 Bedroom(s)
4 Bath(s) Sleeps 13
Private Spacious 1BR Near LEGOLAND 2 Miles
Winter Haven Private vacation home 8.8
WELCOME to our Wakulla Vacation Home (2), duplex property. We are a family own business & genuinely hope to tailor our properties to meet our Guest needs. We adhere to a 3 Core Property Standards that we expect; so, you'll always arrive to a home that is Safe, Clean and Guest Ready! This property is centrally located, 2 mi to dtwn Winter Haven and .......read more
1 Bedroom(s)
1 Bath(s) Sleeps 5
Lake House to be leased with Main house: 2042348
Winter Haven Private vacation home
23 Miles from Disney world, 35 Miles from Universal Studios. 5 miles from Legoland Theme and Water Park. Amazing lake front home. Bring your boat and enjoy skiing, boating and fishing from pier. Lake Hamilton is large lake chain with 2,184 total acres.
This is a 1 Bed 1 Bath property with Bed: 1 King Bed & Living Room: 1 Queen Pullout Cou.......read more
1 Bedroom(s)
1 Bath(s) Sleeps 4
Waterfront Vacation Rental on Lake Mirror!
Winter Haven Private vacation home 10.0
Situated directly on Lake Mirror, this charming Winter Haven vacation rental is perfect for snowbirds looking to embrace lake life and experience endless water sport recreation! Whether you spend your days fishing off the dock, exploring the lake, or watching local wildlife, you’ll love having this 2-bedroom, 2-bath abode as your home away from h.......read more
2 Bedroom(s)
2 Bath(s) Sleeps 5
Minutes to Legoland. Heated Pool and Private Hot Tub. Relaxation Awaits!
Winter Haven Private vacation home 10.0
Relax in the pool and hot tub after enjoying theme parks such as Busch Gardens, Disney world, and Universal Studios! LegoLand is 1 mile away! Lego bedroom for kids. Centrally Located in the middle of Florida allows beach trips to both east & west coast. air conditioned garage has been turned into a game room pool table, air hockey and a actual miss.......read more
4 Bedroom(s)
2 Bath(s) Sleeps 8
Spectacular Waterfront Home in Winter Haven
Winter Haven Private vacation home 10.0
HIGHLIGHTS
+Custom built in 2006
+Chef’s kitchen with Viking Professional appliances
+Waterfront on 3 sides of the property!
+2 docks with boat cleats - bring your boat!
+Beautifully manicured grounds - all new lakeside landscaping
+Screen enclosed Florida Pool with hot tub
+Additional waterfront above ground hot tub
+Wes.......read more
4 Bedroom(s)
4 Bath(s) Sleeps 10
Cozy Lakefront Home w/ Pool -7 mins from Legoland
Winter Haven Private vacation home 8.4
Discover family bliss at our 3-bedroom lakeside retreat in Winter Haven. Dive into the private pool, fire up the grill for al fresco feasts, and unwind in the Tulum-inspired luxury of your cozy abode. With a wealth of family-friendly activities nearby, from Legoland to lakeside strolls, this safe and quiet neighborhood is your gateway to cherished .......read more
3 Bedroom(s)
2 Bath(s) Sleeps 8
Private King Suite with W/D near LEGOLAND & Winter Haven Hospital
Winter Haven Apartment 8.4
Centrally located Modern/Contemporary Spacious Private King Suite that is close to Winter Haven (WH) downtown (2 miles); WH Hospital (2 miles) & LEGOLAND (6 miles). It is perfect for couples+1 kid, solo adventure, or business travelers. This Spacious Private King Suite has a private bathroom (walk-in shower); memory foam King bed; Loveseat Sofa Bed.......read more
1 Bedroom(s)
1 Bath(s) Sleeps 3
Cozy Lakeside Cottage near Legoland, Winter Haven! Florida vacation ready!
Winter Haven Cottage 10.0
This lakeside cottage has a peaceful view of Eagle Lake. Close to Legoland resort and an easy drive to many central Florida destinations including Disney World parks, other Orlando destinations, Bok Singing Tower, Tampa beaches, etc. Local community events include free waterski shows and great restaurants. Amenities include high speed internet.......read more
2 Bedroom(s)
2 Bath(s) Sleeps 6